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Sample records for surface-immobilized phenethyl phenyl

  1. Thermolysis of surface-immobilized phenethyl phenyl ether

    Energy Technology Data Exchange (ETDEWEB)

    Britt, P.F.; Buchanan, A.C. III; Hitsman, V.M.

    1991-01-01

    Our research has focused on modeling the constraints on free-radical reactions that might be imposed in coal as a consequence of its cross-linked macromolecular structure by covalently bonding diphenylalkanes to an inert silica surface. A surface-immobilized phenethyl phenyl ether ({approx}PhCH{sub 2}CH{sub 2}POh, or {approx}PPE-3) has been prepared as a model for ether linkages in lignin by the condensation of p-HOPhCH{sub 2}CH{sub 2}OPh with the surface hydroxyls of a high purity fumed silica. Thermolysis of {approx}PPE-3 at saturation surface coverage at 375{degree}C produces {approx}PhCH = CH{sub 2} and PhOH as the major products which are consistent with the proposed free-radical chain mechanism for the decomposition of fluid-phase phenethyl phenyl ether. However, significant quantities of {approx}PhCH{sub 3} and PhCHO (ca. 18% of the products) are produced indicating the emergence of a new reaction pathway on the surface. The mechanism for the decomposition of {approx}PPE-3 will be discussed in light of this new information. 18 refs., 1 fig.

  2. Thermolysis of phenethyl phenyl ether: A model of ether linkages in low rank coal

    Energy Technology Data Exchange (ETDEWEB)

    Britt, P.F.; Buchanan, A.C. III; Malcolm, E.A.

    1994-09-01

    Currently, an area of interest and frustration for coal chemists has been the direct liquefaction of low rank coal. Although low rank coals are more reactive than bituminous coals, they are more difficult to liquefy and offer lower liquefaction yields under conditions optimized for bituminous coals. Solomon, Serio, and co-workers have shown that: in the pyrolysis and liquefaction of low rank coals, a low temperature cross-linking reaction associated with oxygen functional groups occurs before tar evolution. A variety of pretreatments (demineralization, alkylation, and ion-exchange) have been shown to reduce these retrogressive reactions and increase tar yields, but the actual chemical reactions responsible for these processes have not been defined. In order to gain insight into the thermochemical reactions leading to cross-linking in low rank coal, we have undertaken a study of the pyrolysis of oxygen containing coal model compounds. Solid state NMR studies suggest that the alkyl aryl ether linkage may be present in modest amounts in low rank coal. Therefore, in this paper, we will investigate the thermolysis of phenethyl phenyl ether (PPE) as a model of 0-aryl ether linkages found in low rank coal, lignites, and lignin, an evolutionary precursor of coal. Our results have uncovered a new reaction channel that can account for 25% of the products formed. The impact of reaction conditions, including restricted mass transport, on this new reaction pathway and the role of oxygen functional groups in cross-linking reactions will be investigated.

  3. Identification of a new psychoactive substance in seized material: the synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (Acrylfentanyl)

    DEFF Research Database (Denmark)

    Breindahl, Torben; Kimergård, Andreas; Andreasen, Mette Findal

    2017-01-01

    Among the new psychoactive substances (NPS) that have recently emerged on the market, many of the new synthetic opioids have shown to be particularly harmful. A new synthetic analogue of fentanyl, N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (acrylfentanyl), was identified in powder...... from a seized capsule found at a forensic psychiatric ward in Denmark. Gas chromatography with mass spectrometry (GC-MS) identified a precursor to synthetic fentanyls, N-phenyl-1-(2-phenylethyl)piperidin-4-amine; however, the precursor 1-(2-phenethyl)piperidin-4-one, was not detected. Analysis...... of the electron impact mass spectrum of the main, unknown chromatographic peak (GC) tentatively identified an acryloyl analogue of fentanyl. Further analyses by quadrupole time-of-flight high resolution mass spectrometry (QTOF-MS), matrix-assisted laser ionization Orbitrap mass spectrometry (MALDI...

  4. Synthesis of a Series of Caffeic Acid Phenethyl Amide (CAPA) Fluorinated Derivatives: Comparison of Cytoprotective Effects to Caffeic Acid Phenethyl Ester (CAPE)

    Science.gov (United States)

    2010-06-11

    Synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives: Comparison of cytoprotective effects to caffeic acid phenethyl...to induce genes with the downstream effect of counter- acting oxidative stress.5,6 Caffeic acid phenethyl ester (CAPE), a plant polyphenolic con... synthesis and investigation of catechol ring-fluorinated derivatives of CAPE with regard to cytoprotective ability against oxidative stress in vitro.14

  5. Effect of Betong Watercress and Phenethyl Isothiocyanate on N ...

    African Journals Online (AJOL)

    Purpose: To investigate the effect of Betong watercress and phenethyl isothiocyanate (PEITC) on the N-demethylation of caffeine (CF) in rats. Methods: Male Wistar rats were subjected to 2 phases of experiment. Phase I, they received a single oral dose of CF (10 mg/kg), while in phase II, they were pretreated with the ...

  6. Macrophage migration inhibitory factor covalently complexed with phenethyl isothiocyanate

    OpenAIRE

    Tyndall, Joel D. A.; Lue, Hongqi; Rutledge, Malcolm T.; Bernhagen, Jurgen; Hampton, Mark B.; Wilbanks, Sigurd M.

    2012-01-01

    Macrophage migration inhibitory factor undergoes a localized conformational shift in response to covalent modification by phenethyl isothiocyanate, a natural compound with anti-inflammatory and anticancer properties. The inhibitor sits within a deep hydrophobic pocket and defines a potential target for the development of improved inhibitors.

  7. Caffeic Acid Phenethyl Ester (CAPE) mediated decrease in ...

    African Journals Online (AJOL)

    Background: Caffeic acid phenethyl ester (CAPE) is a phytochemically active component obtained from honeybee hive propolis. CAPE has been reported to show antimitogenic, anticancer, and other beneficial medicinal properties. Many of its activities have been reported to be mediated by inhibiting levels of matrix ...

  8. Chemical and enzymatic synthesis of a library of 2-phenethyl esters and their sensory attributes.

    Science.gov (United States)

    Li, Cheng; Sun, Jingcan; Li, Tianhu; Liu, Shao-Quan; Huang, Dejian

    2014-07-01

    We report a simple enzymatic approach to synthesise phenethyl esters as natural flavouring materials. Chemical and lipase-catalysed esterification reactions between fatty acids of C4-C18 and 2-phenethyl alcohol were studied. Both methods were compared qualitatively and quantitatively by GC-MS/FID. The acid and thermal stabilities of 2-phenethyl esters were excellent and can meet the requirements of food matrices under most processing conditions. Sensory evaluation showed that each 2-phenethyl ester with a different carbon-chain-length fatty acid had unique sensory notes. Moreover, through Lipozyme TL IM-mediated transesterification, valuable 2-phenethyl alcohol-derived esters were synthesised from butter oil and 2-phenethyl alcohol. The influence of several physicochemical parameters (temperature, substrate molar ratio, enzyme loading, shaking speed and time) on the transesterification reaction was investigated to give optimal reaction conditions, leading to a high yield of 80.0%. Copyright © 2014 Elsevier Ltd. All rights reserved.

  9. Aspergillus niger whole-cell catalyzed synthesis of caffeic acid phenethyl ester in ionic liquids.

    Science.gov (United States)

    Rajapriya, Govindaraju; Morya, Vivek Kumar; Mai, Ngoc Lan; Koo, Yoon-Mo

    2018-04-01

    Synthesis of caffeic acid ester essentially requires an efficient esterification process to produce various kinds of medicinally important ester derivatives. In the present study, a comprehensive and comparative analysis of whole-cell catalyzed caffeic acid esters production in ionic liquids (ILs) media was performed. Olive oil induced mycelial mass of halotolerant Aspergillus niger (A.niger) EXF 4321 was freeze dried and used as a catalyst. To ensure maximum solubilization of caffeic acid for highest substrate loading several ILs were screened and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Emim][Tf 2 N]) was found to have the maximum solubility and favoured for enzymatic activity of freeze dried mycelia. The whole-cell catalyzed synthesis of caffeic acid phenethyl ester (CAPE) conditions were optimized and bioconversion up to 84% was achieved at a substrate molar ratio of 1:20 (caffeic acid:2-phenyl ethanol), 30°C for 12h. Results obtained during this study were encouraging and helpful to design a bioreactor system to produce caffeic acid derived esters. Copyright © 2017 Elsevier Inc. All rights reserved.

  10. Terpenoids and phenethyl glucosides from Hyssopus cuspidatus (Labiatae).

    Science.gov (United States)

    Furukawa, Megumi; Makino, Mitsuko; Ohkoshi, Emika; Uchiyama, Taketo; Fujimoto, Yasuo

    2011-12-01

    Monoterpenoids (3 and 4), sesquiterpenoid (2), diterpenoid (1) and four phenethyl glucosides (5-8), together with fourteen known compounds, were isolated from the whole herb of Hyssopus cuspidatus. Their structures were determined by spectroscopic means. The abietane-type diterpenoids (1, 9, 10), rosmarinic acid (15) and salvigenin (17) inhibited leukotriene (LT) C(4) secretion from primary alveolar cells of Wistar rats. Copyright © 2011 Elsevier Ltd. All rights reserved.

  11. Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays

    Directory of Open Access Journals (Sweden)

    Roberta Bernini

    2018-01-01

    Full Text Available Polyphenols are natural compounds showing a variety of health-promoting effects. Unfortunately, due to low lipid solubility, their applications in the pharmaceutical, food, and cosmetic industries are limited. With the aim of obtaining novel lipophilic derivatives, the present study reports the synthesis of a series of phenethyl trifluoroacetate esters containing up to two hydroxyl groups in the aromatic ring. Experimental logP values confirmed a greater lipophilicity of the novel compounds compared to the parent compounds. The radical scavenging capacity of all phenethyl trifluoroacetate esters was evaluated by in vitro assays (ABTS, DPPH and in cultured cells (L6 myoblasts and THP-1 leukemic monocytes using 2′,7′-dichlorodihydrofluorescein diacetate. These data revealed that the esters showed a good antioxidant effect that was strictly dependent on the grade of hydroxylation of the phenyl ring. The lack of toxicity, evaluated by the MTT assay and proliferation curves, makes these trifluoroacetates attractive derivatives for pharmaceutical, food, and cosmetic applications.

  12. Covalent and density-controlled surface immobilization of E-cadherin for adhesion force spectroscopy.

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    Dagmar Fichtner

    Full Text Available E-cadherin is a key cell-cell adhesion molecule but the impact of receptor density and the precise contribution of individual cadherin ectodomains in promoting cell adhesion are only incompletely understood. Investigating these mechanisms would benefit from artificial adhesion substrates carrying different cadherin ectodomains at defined surface density. We therefore developed a quantitative E-cadherin surface immobilization protocol based on the SNAP-tag technique. Extracellular (EC fragments of E-cadherin fused to the SNAP-tag were covalently bound to self-assembled monolayers (SAM of thiols carrying benzylguanine (BG head groups. The adhesive functionality of the different E-cadherin surfaces was then assessed using cell spreading assays and single-cell (SCSF and single-molecule (SMSF force spectroscopy. We demonstrate that an E-cadherin construct containing only the first and second outmost EC domain (E1-2 is not sufficient for mediating cell adhesion and yields only low single cadherin-cadherin adhesion forces. In contrast, a construct containing all five EC domains (E1-5 efficiently promotes cell spreading and generates strong single cadherin and cell adhesion forces. By varying the concentration of BG head groups within the SAM we determined a lateral distance of 5-11 nm for optimal E-cadherin functionality. Integrating the results from SCMS and SMSF experiments furthermore demonstrated that the dissolution of E-cadherin adhesion contacts involves a sequential unbinding of individual cadherin receptors rather than the sudden rupture of larger cadherin receptor clusters. Our method of covalent, oriented and density-controlled E-cadherin immobilization thus provides a novel and versatile platform to study molecular mechanisms underlying cadherin-mediated cell adhesion under defined experimental conditions.

  13. Decolorization of industrial synthetic dyes using engineered Pseudomonas putida cells with surface-immobilized bacterial laccase

    Science.gov (United States)

    2012-01-01

    cell culturing. Conclusions This study demonstrates, for the first time, the methodology by which the engineered P. putida with surface-immobilized laccase was successfully used as regenerable biocatalyst for biodegrading synthetic dyes, thereby opening new perspectives in the use of biocatalysis in industrial dye biotreatment. PMID:22686507

  14. Decolorization of industrial synthetic dyes using engineered Pseudomonas putida cells with surface-immobilized bacterial laccase

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    Wang Wei

    2012-06-01

    via a subsequent 4-h cell culturing. Conclusions This study demonstrates, for the first time, the methodology by which the engineered P. putida with surface-immobilized laccase was successfully used as regenerable biocatalyst for biodegrading synthetic dyes, thereby opening new perspectives in the use of biocatalysis in industrial dye biotreatment.

  15. Surface Immobilization of Human Arginase-1 with an Engineered Ice Nucleation Protein Display System in E. coli.

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    Zhen Zhang

    Full Text Available Ice nucleation protein (INP is frequently used as a surface anchor for protein display in gram-negative bacteria. Here, MalE and TorA signal peptides, and three charged polypeptides, 6×Lys, 6×Glu and 6×Asp, were anchored to the N-terminus of truncated INP (InaK-N to improve its surface display efficiency for human Arginase1 (ARG1. Our results indicated that the TorA signal peptide increased the surface translocation of non-protein fused InaK-N and human ARG1 fused InaK-N (InaK-N/ARG1 by 80.7% and 122.4%, respectively. Comparably, the MalE signal peptide decreased the display efficiencies of both the non-protein fused InaK-N and InaK-N/ARG1. Our results also suggested that the 6×Lys polypeptide significantly increased the surface display efficiency of K6-InaK-N/ARG1 by almost 2-fold, while also practically abolishing the surface translocation of non-protein fused InaK-N, indicating the interesting roles of charged polypeptides in bacteria surface display systems. Cell surface-immobilized K6-InaK-N/ARG1 presented an arginase activity of 10.7 U/OD600 under the optimized conditions of 40°C, pH 10.0 and 1 mM Mn2+, which could convert more than 95% of L-Arginine (L-Arg to L-Ornithine (L-Orn in 16 hours. The engineered InaK-Ns expanded the INP surface display system, which aided in the surface immobilization of human ARG1 in E. coli cells.

  16. Phenethyl ester and amide of Ferulic Acids: Synthesis and bioactivity against P388 Leukemia Murine Cells

    Science.gov (United States)

    Firdaus; Soekamto, N. H.; Seniwati; Islam, M. F.; Sultan

    2018-03-01

    Bioactivity of a compound is closely related to the molecular structure of the compound concerned, its strength being the quantitative relation of the strength of the activity of the group it possesses. The combining of moieties of the active compounds will produce more active compounds. Most phenolic compounds as well as compounds containing moiety phenethyl groups have potential activity as anticancer. Combining phenolic groups and phenethyl groups in a compound will result in compounds having strong anticancer bioactivity. This study aims to combine the feruloyl and phenethyl groups to form esters and amides by synthesize of phenethyl trans-3-(4-hydroxy-3-methoxyphenyl)acrylate (5) and trans-3-(4- hydroxy-3-methoxyphenyl)-N-phenethylacrylamide (6) from ferulic acid with phenethyl alcohol and phenethylamine, and to study their bioactivity as anticancer. The synthesis of both compounds was conducted via indirect reaction, including acetylation, chlorination, esterfication/amidation, and deacetylation. Structures of products were characterized by FTIR and NMR data, and their bioactivity assay of the compounds against P388 Leukemia Murine Cells was conducted by an MTT method. Results showed that the compound 5 was obtained as a yellow gel with the IC50 of 10.79 μg/mL (36.21 μΜ), and the compound 6 was a yellowish solid with a melting point of 118-120°C and the IC50 of 29.14 μg/mL (97.79 μΜ). These compounds were more active than the analog compounds.

  17. Inhibition of excision repair of DNA in u.v.-irradiated Escherichia coli by phenethyl alcohol

    International Nuclear Information System (INIS)

    Tachibana, A.; Yonei, S.

    1985-01-01

    Membrane-specific drugs such as procaine and chlorpromazine have been shown to inhibit excision repair of DNA in u.v.-irradiated E. coli. One possible mechanism is that, if association of DNA with the cell membrane is essential for excision repair, this process may be susceptible to drugs affecting the structure of cell membranes. We examined the effect of phenethyl alcohol, which is a membrane-specific drug and known to dissociate the DNA-membrane complex, on excision repair of DNA in u.v.-irradiated E. coli cells. The cells were irradiated with u.v. light and then held at 30 0 C in buffer (liquid-holding) in the presence or absence of phenethyl alcohol. It was found that phenethyl alcohol inhibits the liquid-holding recovery in both wild-type and recA strains, corresponding to its dissociating action on the DNA-membrane complex. Thus, the association of DNA with cell membrane is an important factor for excision repair in E. coli. Procaine did not show the dissociating effect, suggesting that at least two different mechanisms are responsible for the involvement of cell membrane in excision repair of DNA in E. coli. (author)

  18. Photocatalytic degradation of 2-phenethyl-2-chloroethyl sulfide in liquid and gas phases.

    Science.gov (United States)

    Vorontsov, Alexandre V; Panchenko, Alexander A; Savinov, Evgueni N; Lion, Claude; Smirniotis, Panagiotis G

    2002-12-01

    This work explores the ability of photocatalysis to decontaminate water and air from chemical warfare agent mustard using its simulant 2-phenethyl 2-chloroethyl sulfide (PECES). PECES like mustard slowly dissolves in water with hydrolysis, forming 2-phenethyl 2-hydroxyethyl sulfide (PEHES). Irradiation of TiO2 suspension containing PECES with the unfiltered light of a mercury lamp (lambda > or = 254 nm) decomposed all PECES mostly via photolysis. Reaction under filtered light (lambda > 300 nm) proceeds mainly photocatalytically and requires longer time. Sulfur from starting PECES is completely transformed into sulfuric acid at the end of the reaction. Detected volatile, nonvolatile, surface products, and the suggested scheme of degradation are reported. The main volatile products are styrene and benzaldehyde, nonvolatile--hydroxylated PEHES, surface--2-phenethyl disulfide. Photolysis of PECES produced the same set of volatile products as photocatalysis. Photocatalytic degradation of gaseous PECES in air results in its mineralization but is accompanied by TiO2 deactivation. The highest rate of mineralization with minimum deactivation was observed at about room temperature and a water concentration of 27,500 ppm. No gaseous products except CO2 were detected. The main extracted surface product was styrene. It was concluded that PECES photocatalytic degradation proceeds mainly via C-S bond cleavage and further oxidation of the products. Hydrolysis of the C-S bond was detected only in gas-phase photocatalytic degradation. The quantum efficiency of gas-phase degradation (0.28%) was much higher than that of liquid-phase degradation (0.008%). The results demonstrate the ability of photocatalysis to decontaminate an aqueous and especially an air environment

  19. Synthesis and Biological Activity of Arylspiroborate Salts Derived from Caffeic Acid Phenethyl Ester

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    Martin J. G. Hébert

    2015-01-01

    Full Text Available Two novel boron compounds containing caffeic acid phenethyl ester (CAPE derivatives have been prepared and characterized fully. These new compounds and CAPE have been investigated for potential antioxidant and antimicrobial properties and their ability to inhibit 5-lipoxygenase and whether chelation to boron improves their biological activity. Sodium salt 4 was generally more active than ammonium salt 5 in the biological assays and surpassed the radical scavenging ability of CAPE. Compounds 4 and 5 were more active than CAPE and Zileuton in human polymorphonuclear leukocytes. These results clearly show the effectiveness of the synthesized salts as transporter of CAPE.

  20. Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity

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    Pier Morin

    2017-07-01

    Full Text Available Glioblastoma multiforme (GBM is an aggressive brain tumor that correlates with short patient survival and for which therapeutic options are limited. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE, 1a, have been investigated for their anticancer properties in several types of cancer. To further explore these properties in brain cancer cells, a series of caffeic and ferulic acid esters bearing additional oxygens moieties (OH or OCH3 were designed and synthesized. (CAPE, 1a, but not ferulic acid phenethyl ester (FAPE, 1b, displayed substantial cytotoxicity against two glioma cell lines. Some but not all selected compounds derived from both (CAPE, 1a and (FAPE, 1b also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO, however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Molecular docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds. Overall, this work highlights the relevance of exploring polyphenolic compounds in cancer models and provides additional leads in the development of novel therapeutic strategies in gliomas.

  1. Optimization of lipase-catalyzed synthesis of caffeic acid phenethyl ester in ionic liquids by response surface methodology.

    Science.gov (United States)

    Ha, Sung Ho; Van Anh, Tran; Koo, Yoon-Mo

    2013-06-01

    Lipase-catalyzed caffeic acid phenethyl ester (CAPE) synthesis in ionic liquid, 1-ethyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([Emim][Tf(2)N]), was investigated in this study. The effects of several reaction conditions, including reaction time, reaction temperature, substrate molar ratio of phenethyl alcohol to caffeic acid (CA), and weight ratio of enzyme to CA, on CAPE yield were examined. In a single parameter study, the highest CAPE yield in [Emim][Tf(2)N] was obtained at 70 °C with a substrate molar ratio of 30:1 and weight ratio of enzyme to CA of 15:1. Based on these results, response surface methodology (RSM) with a 3-level-4-factor central composite rotatable design (CCRD) was adopted to evaluate enzymatic synthesis of CAPE in [Emim][Tf(2)N]. The four major factors were reaction time (36-60 h), reaction temperature (65-75 °C), substrate molar ratio of phenethyl alcohol to CA (20:1-40:1), and weight ratio of enzyme to CA (10:1-20:1). A quadratic equation model was used to analyze the experimental data at a 95 % confidence level (p ratio of phenethyl alcohol to CA (27.1:1), and weight ratio of enzyme to CA (17.8:1)] established by our statistical method, whereas the experimental conversion yield was 96.6 ± 2 %.

  2. ED50 G(Na) block predictions for phenyl substituted and unsubstituted n-alkanols.

    Science.gov (United States)

    Kondratiev, A; Hahin, R

    2001-03-15

    To study the role the phenyl group plays in producing local anesthetic block, a sequence of n-alkanols and phenyl-substituted alkanols (phi)-alkanols) were characterized in their ability to block Na channels. The sequence of n-alkanols studied possess 3-5 carbons (propanol-pentanol). The action of phenol and 3-phi-alkanols (benzyl alcohol, phenethyl alcohol, 3-phenyl-1-propanol) were also studied. Na currents (INa) were recorded from single frog skeletal muscle fibers using the Vaseline-gap voltage clamp technique. INas were recorded prior to, during, and following the removal of the solutes in Ringer's solution. All alkanols and phenol acted to block INa in a dose-dependent manner. Effective doses to produce half block (ED50) of INa or Na conductance (GNa) were obtained from dose-response relations for all solutes used. The block of GNa depended on voltage, and could be separated into voltage-dependent and -independent components. Each solute acted to shift GNa-V relations in a depolarized direction and reduce the maximum GNa and slope of the relation. All solutes acted to speed up INa kinetics and cause hyperpolarizing shifts in steady-state inactivation. The magnitude of the kinetic changes increased with dose. Size was an important variable in determining the magnitude of the changes in INa; however, size alone was not sufficient to predict the changes in INa. ED50s for GNa and AP block could be predicted as a function of intrinsic molar volume, hydrogen bond acceptor basicity (beta) and donor acidity (alpha), and polarity (P) of the solutes. The equivalency of ED50 predictions for AP and GNa block can be explained by the fact that AP block arises from channel block and solute-induced changes in INa kinetics. phi-Alkanols were more effective at blocking and inactivating Na channels than their unsubstituted counterparts. Phenyl-substituted alkanols are more likely to interact with the channel than their unsubstituted counterparts.

  3. Possible molecular targets for therapeutic applications of caffeic acid phenethyl ester in inflammation and cancer

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    Ghulam Murtaza

    2015-03-01

    Full Text Available Of the various derivatives of caffeic acid, caffeic acid phenethyl ester (CAPE is a hydrophobic, bioactive polyphenolic ester obtained from propolis extract. The objective in writing this review article was to summarize all published studies on therapeutics of CAPE in inflammation and cancer to extract direction for future research. The possible molecular targets for the action of CAPE, include various transcription factors such as nuclear factor-κB, tissue necrosis factor-α, interleukin-6, cyclooxygenase-2, Nrf2, inducible nitric oxide synthase, nuclear factor of activated T cells, hypoxia-inducible factor-1α, and signal transducers and activators of transcription. Based on the valuable data on its therapeutics in inflammation and cancer, clinical studies of CAPE should also be conducted to explore its toxicities, if any.

  4. Antiviral properties of caffeic acid phenethyl ester and its potential application.

    Science.gov (United States)

    Erdemli, Hacı Kemal; Akyol, Sumeyya; Armutcu, Ferah; Akyol, Omer

    2015-01-01

    Caffeic acid phenethyl ester (CAPE) is found in a variety of plants and well-known the active ingredient of the honeybee propolis. CAPE showed anti-inflammatory, anticarcinogenic, antimitogenic, antiviral, and immunomodulatory properties in several studies. The beneficial effects of CAPE on different health issues attracted scientists to make more studies on CAPE. Specifically, the anti-viral effects of CAPE and its molecular mechanisms may reveal the important properties of virus-induced diseases. CAPE and its targets may have important roles to design new therapeutics and understand the molecular mechanisms of virus-related diseases. In this mini-review, we summarize the antiviral effects of CAPE under the light of medical and chemical literature.

  5. Effect of caffeic acid phenethyl ester on bone formation in the expanded inter-premaxillary suture

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    Kazancioglu HO

    2015-12-01

    Full Text Available Hakki Oguz Kazancioglu,1 Sertac Aksakalli,2 Seref Ezirganli,1 Muhammet Birlik,2 Mukaddes Esrefoglu,3 Ahmet Hüseyin Acar1 1Department of Oral and Maxillofacial Surgery, 2Department of Orthodontics, Faculty of Dentistry, 3Department of Histology, Faculty of Medicine, Bezmialem Vakif University, Istanbul, Turkey Background: Narrow maxilla is a common problem in orthodontics and dentofacial orthopedics. To solve this problem, a procedure called rapid maxillary expansion (RME has been used. However, relapse tendency is a major problem of RME. Although relapse tendency is not clearly understood, various treatment procedures and new application has been investigated. The present study aimed to investigate the possible effectiveness of caffeic acid phenethyl ester (CAPE on new bone formation in rat midpalatal suture after RME.Materials and methods: Twenty male Sprague Dawley rats were used in this study. The animals were randomly divided into two groups as control and CAPE group. In CAPE group, CAPE was administered systemically via intraperitoneal injection. RME procedure was performed on all animals. For this purpose, the springs were placed on the maxillary incisors of rats and activated for 5 days. After then, the springs were removed and replaced with short lengths of rectangular retaining wire for consolidation period of 15 days. At the end of the study, histomorphometric analysis was carried out to assess of new bone formation.Results: New bone formation was significantly greater in CAPE group than the control group (P<0.05. CAPE enhances new bone formation in midpalatal suture after RME.Conclusion: These results show that CAPE may decrease the time needed for retention. Keywords: rapid maxillary expansion, bone formation, caffeic acid phenethyl ester, midpalatal suture, histopathology

  6. 3-Substituted 2-phenyl-indoles

    DEFF Research Database (Denmark)

    Johansson, Karl Henrik; Jørgensen, T.B.; Gloriam, D.E.

    2013-01-01

    -indoles with a variety of substituents at the indole 3-position. Herein we describe the development of optimised and efficient synthetic routes to a series of new 2-phenyl-indole building blocks 3 to 9 and show that these can be used to generate a broad variety of 3-substituted 2-phenyl-indoles of interest to medicinal...

  7. Novel coumarin glycoside and phenethyl vanillate from Notopterygium forbesii and their binding affinities for opioid and dopamine receptors.

    Science.gov (United States)

    Ma, Zhongze; Xu, Wei; Liu-Chen, Lee-Yuan; Lee, David Y W

    2008-03-15

    Bioactivity-guided fractionation of Notopterygium forbesii has resulted in the isolation of one new coumarin glycoside and one new phenethyl vanillate, together with seventeen known compounds. The structures of these compounds were characterized by spectroscopic methods. These compounds were evaluated for their binding affinities to the opioid and dopamine receptors, and falcarindiol showed weak binding affinities to opioid receptors and moderate affinity for D1 receptor (K(i)=192+/-6 nM).

  8. Protective Effects of Intralipid and Caffeic Acid Phenethyl Ester on Nephrotoxicity Caused by Dichlorvos in Rats

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    Muhammet Murat Celik

    2015-01-01

    Full Text Available The protective effects of Caffeic Acid Phenethyl Ester (CAPE and intralipid (IL on nephrotoxicity caused by acute Dichlorvos (D toxicity were investigated in this study. Forty-eight Wistar Albino rats were divided into 7 groups as follows: Control, D, CAPE, intralipid, D + CAPE, D + IL, and D + CAPE + IL. When compared to D group, the oxidative stress index (OSI values were significantly lower in Control, CAPE, and D + IL + CAPE groups. When compared to D + IL + CAPE group, the TOS and OSI values were significantly higher in D group (P<0.05. When mitotic cell counts were assessed in the renal tissues, it was found that mitotic cell count was significantly higher in the D group while it was lower in the D + CAPE, D + IL, and D + IL + CAPE groups when compared to the control group (P<0.05. Also, immune reactivity showed increased apoptosis in D group and low profile of apoptosis in the D + CAPE group when compared to the Control group. The apoptosis level was significantly lower in D + IL + CAPE compared to D group (P<0.05 in the kidneys. As a result, we concluded that Dichlorvos can be used either alone or in combination with CAPE and IL as supportive therapy or as facilitator for the therapeutic effect of the routine treatment in the patients presenting with pesticide poisoning.

  9. Regulatory Effects of Caffeic Acid Phenethyl Ester on Neuroinflammation in Microglial Cells

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    Cheng-Fang Tsai

    2015-03-01

    Full Text Available Microglial activation has been widely demonstrated to mediate inflammatory processes that are crucial in several neurodegenerative disorders. Pharmaceuticals that can deliver direct inhibitory effects on microglia are therefore considered as a potential strategy to counter balance neurodegenerative progression. Caffeic acid phenethyl ester (CAPE, a natural phenol in honeybee propolis, is known to possess antioxidant, anti-inflammatory and anti-microbial properties. Accordingly, the current study intended to probe the effects of CAPE on microglia activation by using in vitro and in vivo models. Western blot and Griess reaction assay revealed CAPE significantly inhibited the expressions of inducible nitric oxide synthase (NOS, cyclooxygenase (COX-2 and the production of nitric oxide (NO. Administration of CAPE resulted in increased expressions of hemeoxygenase (HO-1and erythropoietin (EPO in microglia. The phosphorylated adenosine monophosphate-activated protein kinase (AMPK-α was further found to regulate the anti-inflammatory effects of caffeic acid. In vivo results from immunohistochemistry along with rotarod test also revealed the anti-neuroinflammatory effects of CAPE in microglia activation. The current study has evidenced several possible molecular determinants, AMPKα, EPO, and HO-1, in mediating anti-neuroinflammatory responses in microglial cells.

  10. Early Treatment of radiation-Induced Heart Damage in Rats by Caffeic acid phenethyl Ester

    International Nuclear Information System (INIS)

    Tawfik, S.S.; Mansour, H. H.

    2012-12-01

    The study designed to determine the therapeutic effect of caffeic acid phenethyl ester (CAPE) in minimising radiation-induced injuries in rats. Rats were exposed to 7 Gy γ-rays, 30 minutes later; rats were injected with CAPE (10μmol/ kg body, i.p.) for 7 consecutive days. Rats were sacrificed at 8 and 15 days after starting the experiment. Gamma-irradiation induced significant increase in malonaldehyde (MDA) level and xanthine oxidase (XO) and adenosine deaminase (ADA) activities, and significant decrease in total nitrate/nitrate (NO (x)) level and glutathione peroxidise (Gpx), superoxide dismutase (SOD)and catalase (CAT) activities in heart tissue and augmented activities of lactate dehydrogenase (LDH), creatine phosphokinase (CPK) and aspartate transaminase (AST) in serum. Irradiated rats early treated with CAPE showed significant decrease in MDA, XO and ADA and significant increase in group. Cardiac enzymes were restored. Conclusion, CAPE could exhibits curable effect on gamma irradiation-induced cardiac-oxidative impairment in rats. (Author)

  11. Watercress and Water Quality: The Effect of Phenethyl Isothiocyanate on the Mating Behaviour of Gammarus pulex

    Directory of Open Access Journals (Sweden)

    Melanie J. Dixon

    2011-01-01

    Full Text Available Watercress releases phenethyl isothiocyanate (PEITC upon wounding as a defence against herbivores. PEITC levels released from watercress farms are elevated due to cropping, washing, and processing and are thought to lead to adverse effects on Gammarus pulex in chalk streams. This study elucidates the sublethal effect of PEITC on reproductive behaviour of G. pulex, employing ex situ tests to investigate the disruption of precopular pairing under conditions simulating in situ exposure. Mean time to separation of precopular pairs was 89 ± 6 minutes for watercress wash water (1 g watercress per litre water and 81 ± 15 minutes for pure PEITC (1 μL/L. Re-exposure to watercress wash water to simulate the pulsed operation at a watercress farm did not alter behavioural response. The repeated interruption of reproductive behaviour under in situ conditions would impair long-term reproductive success and could explain in part low abundance of G. pulex downstream of watercress farms.

  12. EFFECTS OF EXERCISE AND CAFFEIC ACID PHENETHYL ESTER AFTER CHRONIC EXERCISE RAT MODEL

    Directory of Open Access Journals (Sweden)

    Ayse Alp

    2011-01-01

    Full Text Available In order to understand whether exercise and caffeic acid phenethyl ester (CAPE has an effect on obesity and weight control, we investigated the effects of CAPE, and exercise on lipid parameters (triglyceride, total cholesterol, HDL-C, LDL-C, and adipokine substances such as leptin and resistin in rats. 40 male rat were randomly assigned into 4 groups. It was determined that CAPE does not have any significant effect on these parameters but that lipid parameters and leptin values in exercise groups decreased considerably, while no significant change occurred in resistin levels. In order to understand whether diet has an effect on exercise, body weights of all animal groups in pre and post-exercise were compared. A significant weight gain was observed (p = 0.005 in all groups. This study concluded that exercise has a considerable effect on leptin and lipid parameters; however, exercise alone was not sufficient for weight control and could be effective in weight control only when accompanied by a restricted diet.

  13. Modulation of Tamoxifen Cytotoxicity by Caffeic Acid Phenethyl Ester in MCF-7 Breast Cancer Cells

    Directory of Open Access Journals (Sweden)

    Tarek K. Motawi

    2016-01-01

    Full Text Available Although Tamoxifen (TAM is one of the most widely used drugs in managing breast cancer, many women still relapse after long-term therapy. Caffeic acid phenethyl ester (CAPE is a polyphenolic compound present in many medicinal plants and in propolis. The present study examined the effect of CAPE on TAM cytotoxicity in MCF-7 cells. MCF-7 cells were treated with different concentrations of TAM and/or CAPE for 48 h. This novel combination exerted synergistic cytotoxic effects against MCF-7 cells via induction of apoptotic machinery with activation of caspases and DNA fragmentation, along with downregulation of Bcl-2 and Beclin 1 expression levels. However, the mammalian microtubule-associated protein light chain LC 3-II level was unchanged. Vascular endothelial growth factor level was also decreased, whereas levels of glutathione and nitric oxide were increased. In conclusion, CAPE augmented TAM cytotoxicity via multiple mechanisms, providing a novel therapeutic approach for breast cancer treatment that can overcome resistance and lower toxicity. This effect provides a rationale for further investigation of this combination.

  14. Phthalate esters reveal skin-sensitizing activity of phenethyl isothiocyanate in mice.

    Science.gov (United States)

    Matsuda, Tomoko; Maruyama, Takashi; Iizuka, Hiromi; Kondo, Ayumi; Tamai, Takuma; Kurohane, Kohta; Imai, Yasuyuki

    2010-06-01

    Phenethyl isothiocyanate (PEITC) is a constituent of edible cruciferous vegetables and has received attention due to its potential cancer chemopreventive activity. Although its protein-binding activity is known, PEITC has not been studied as a contact sensitizer. We previously demonstrated that phthalate esters, including dibutyl phthalate (DBP) and di-n-propyl phthalate (DPP), enhance skin sensitization in a fluorescein isothiocyanate (FITC)-induced contact hypersensitivity mouse model. In this study, we examined whether DBP and DPP enhance skin sensitization to haptens other than FITC. During this study, we tested PEITC as a contact sensitizer. BALB/c mice were epicutaneously sensitized with a suboptimal dose of a hapten with or without a phthalate ester. Sensitization was evaluated as the ear swelling response after a challenge with the respective hapten. DBP and DPP did not enhance the sensitization to two T-helper 1-type (2,4-dinitrofluorobenzene and oxazolone) or three T-helper 2-type (trimellitic anhydride, methylenediphenyl 4,4'-diisocyanate, and tolulene 2,4-diisocyanate) haptens. In contrast, DBP and DPP enhanced the sensitization to two FITC analogues (eosin 5-isothiocyanate and rhodamine B isothiocyanate) as well as to PEITC. Adjuvant effects of DBP and DPP were observed in contact hypersensitivity to haptens other than FITC, including a food ingredient PEITC. Copyright 2010 Elsevier Ltd. All rights reserved.

  15. Caffeic Acid Phenethyl Ester Regulates PPAR’s Levels in Stem Cells-Derived Adipocytes

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    Luca Vanella

    2016-01-01

    Full Text Available Hypertrophic obesity inhibits activation of peroxisome proliferators-activated receptor gamma (PPARγ, considered the key mediator of the fully differentiated and insulin sensitive adipocyte phenotype. We examined the effects of Caffeic Acid Phenethyl Ester (Cape, isolated from propolis, a honeybee hive product, on Adipose Stem Cells (ASCs differentiation to the adipocyte lineage. Finally we tested the effects of Cape on insulin-resistant adipocytes. Quantification of Oil Red O-stained cells showed that lipid droplets decreased following Cape treatment as well as radical oxygen species formation. Additionally, exposure of ASC to high glucose levels decreased adiponectin and increased proinflammatory cytokines mRNA levels, which were reversed by Cape-mediated increase of insulin sensitivity. Cape treatment resulted in decreased triglycerides synthesis and increased beta-oxidation. Exposure of ASCs to Lipopolysaccharide (LPS induced a reduction of PPARγ, an increase of IL-6 levels associated with a well-known stimulation of lipolysis; Cape partially attenuated the LPS-mediated effects. These observations reveal the main role of PPARγ in the adipocyte function and during ASC differentiation. As there is now substantial interest in functional food and nutraceutical products, the observed therapeutic value of Cape in insulin-resistance related diseases should be taken into consideration.

  16. Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate

    Directory of Open Access Journals (Sweden)

    Jian-Kang Jiang

    2002-10-01

    Full Text Available In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction mechanism is proposed for the formation of compounds 4.

  17. The effect of the shape of single, sub-ms voltage pulses on the rates of surface immobilization and hybridization of DNA

    International Nuclear Information System (INIS)

    Cabeca, R; Rodrigues, M; Chu, V; Conde, J P; Prazeres, D M F

    2009-01-01

    Electric fields generated by single square and sinusoidal voltage pulses with amplitudes below 2 V were used to assist the covalent immobilization of single-stranded, thiolated DNA probes, onto a chemically functionalized SiO 2 surface and to assist the specific hybridization of single-stranded DNA targets with immobilized complementary probes. The single-stranded immobilized DNA probes were either covalently immobilized (chemisorption) or electrostatically adsorbed (physisorption) to a chemically functionalized surface. Comparing the speed of electric field assisted immobilization and hybridization with the corresponding control reactions (without electric field), an increase of several orders of magnitude is observed, with the reaction timescaled down from 1 to 2 h to a range between 100 ns and 1 ms. The influence of the shape of the voltage pulse (square versus sinusoidal) and its duration were studied for both immobilization and hybridization reactions. The results show that pulsed electric fields are a useful tool to achieve temporal and spatial control of surface immobilization and hybridization reactions of DNA.

  18. Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analoguesc

    Directory of Open Access Journals (Sweden)

    Mohamed Touaibia

    2012-12-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.

  19. Synthesis and antiradical/antioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analogues.

    Science.gov (United States)

    LeBlanc, Luc M; Paré, Aurélie F; Jean-François, Jacques; Hébert, Martin J G; Surette, Marc E; Touaibia, Mohamed

    2012-12-10

    Caffeic acid phenethyl ester (CAPE) is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl) propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl) acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.

  20. Caffeic acid phenethyl ester decreases acute pneumonitis after irradiation in vitro and in vivo

    Directory of Open Access Journals (Sweden)

    Yang Cheng-Ta

    2005-12-01

    Full Text Available Abstract Background Lung cancer is relatively resistant to radiation treatment and radiation pneumonitis is a major obstacle to increasing the radiation dose. We previously showed that Caffeic acid phenethyl ester (CAPE induces apoptosis and increases radiosensitivity in lung cancer. To determine whether CAPE, an antioxidant and an inhibitor of NF-kappa B, could be a useful adjuvant agent for lung cancer treatment, we examine the effects of CAPE on irradiated normal lung tissue in this study. Methods We compared the effects of CAPE on cytotoxicity and intracellular oxidative stress in normal lung fibroblast and a lung cancer cell line. For in vivo analysis, whole thorax radiation (single dose 10 Gy and 20 Gy was delivered to BALB/c male mice with or without CAPE pretreatment. NF- kappaB activation and the expression levels of acute inflammatory cytokines were evaluated in mice after irradiation. Results The in vitro studies showed that CAPE cause no significant cytotoxicity in normal lung as compared to lung cancer cells. This is probably due to the differential effect on the expression of NF-kappa B between normal and malignant lung cells. The results from in vivo study showed that CAPE treatment decreased the expression of inflammatory cytokines including IL-1 alpha and beta, IL-6, TNF-alpha and TGF- beta, after irradiation. Moreover, histological and immunochemical data revealed that CAPE decreased radiation- induced interstitial pneumonitis and TGF-beta expression. Conclusion This study suggests that CAPE decreases the cascade of inflammatory responses induced by thoracic irradiation without causing toxicity in normal lung tissue. This provides a rationale for combining CAPE and thoracic radiotherapy for lung cancer treatment in further clinical studies.

  1. Caffeic acid phenethyl ester decreases acute pneumonitis after irradiation in vitro and in vivo.

    Science.gov (United States)

    Chen, Miao-Fen; Keng, Peter C; Lin, Paul-Yang; Yang, Cheng-Ta; Liao, Shuen-Kuei; Chen, Wen-Cheng

    2005-12-09

    Lung cancer is relatively resistant to radiation treatment and radiation pneumonitis is a major obstacle to increasing the radiation dose. We previously showed that Caffeic acid phenethyl ester (CAPE) induces apoptosis and increases radiosensitivity in lung cancer. To determine whether CAPE, an antioxidant and an inhibitor of NF-kappa B, could be a useful adjuvant agent for lung cancer treatment, we examine the effects of CAPE on irradiated normal lung tissue in this study. We compared the effects of CAPE on cytotoxicity and intracellular oxidative stress in normal lung fibroblast and a lung cancer cell line. For in vivo analysis, whole thorax radiation (single dose 10 Gy and 20 Gy) was delivered to BALB/c male mice with or without CAPE pretreatment. NF- kappaB activation and the expression levels of acute inflammatory cytokines were evaluated in mice after irradiation. The in vitro studies showed that CAPE cause no significant cytotoxicity in normal lung as compared to lung cancer cells. This is probably due to the differential effect on the expression of NF-kappa B between normal and malignant lung cells. The results from in vivo study showed that CAPE treatment decreased the expression of inflammatory cytokines including IL-1 alpha and beta, IL-6, TNF-alpha and TGF- beta, after irradiation. Moreover, histological and immunochemical data revealed that CAPE decreased radiation- induced interstitial pneumonitis and TGF-beta expression. This study suggests that CAPE decreases the cascade of inflammatory responses induced by thoracic irradiation without causing toxicity in normal lung tissue. This provides a rationale for combining CAPE and thoracic radiotherapy for lung cancer treatment in further clinical studies.

  2. Dietary Phenethyl Isothiocyanate Alters Gene Expression in Human Breast Cancer Cells

    Directory of Open Access Journals (Sweden)

    Young Jin Moon

    2011-01-01

    Full Text Available Phenethyl isothiocyanate (PEITC, a component in cruciferous vegetables, can block chemical carcinogenesis in animal models. Our objective was to determine the effect of treatment with PEITC on gene expression changes in MCF-7 human breast cancer cells in order to evaluate potential mechanisms involved in its chemopreventive effects. MCF-7 cells were treated for 48 hours with either PEITC (3 μM or the vehicle. Total RNA was extracted from cell membrane preparations, and labeled cDNA's representing the mRNA pool were reverse-transcribed directly from total RNA isolated for use in the microarray hybridizations. Two specific human GE Array Kits (Superarray Inc. that both contain 23 marker genes, related to signal transduction pathways or cancer/tumor suppression, plus 2 housekeeping genes (β-actin and GAPDH, were utilized. Arrays from treated and control cells (n=4 per group were evaluated using a Student's t-test. Gene expression was significantly induced for tumor protein p53 (p53, cyclin-dependent kinase inhibitor 1C (p57 Kip2, breast cancer Type 2 early onset (BRCA2, cAMP responsive element binding protein 2 (ATF-2, interleukin 2 (IL-2, heat shock 27 KD protein (hsp27, and CYP19 (aromatase. Induction of p57 Kip2, p53, BRCA2, IL-2, and ATF-2 would be expected to decrease cellular proliferation and increase tumor suppression and/or apoptosis. PEITC treatment produced significant alterations in some genes involved in tumor suppression and cellular proliferation/apoptosis that may be important in explaining the chemopreventive effects of PEITC.

  3. Caffeic acid phenethyl ester (CAPE): scavenger of peroxynitrite in vitro and in sepsis models.

    Science.gov (United States)

    Kassim, Mustafa; Mansor, Marzida; Kamalden, Tengku Ain; Shariffuddin, Ina Ismiarti; Hasan, Mohd Shahnaz; Ong, Gracie; Sekaran, Shamala Devi; Suhaimi, Anwar; Al-Abd, Nazeh; Yusoff, Kamaruddin Mohd

    2014-08-01

    Excessive free radical production by immune cells has been linked to cell death and tissue injury during sepsis. Peroxynitrite is a short-lived oxidant and a potent inducer of cell death that has been identified in several pathological conditions. Caffeic acid phenethyl ester (CAPE) is an active component of honeybee products and exhibits antioxidant, anti-inflammatory, and immunomodulatory activities. The present study examined the ability of CAPE to scavenge peroxynitrite in RAW 264.7 murine macrophages stimulated with lipopolysaccharide/interferon-γ that was used as an in vitro model. Conversion of 123-dihydrorhodamine to its oxidation product 123-rhodamine was used to measure peroxynitrite production. Two mouse models of sepsis (endotoxemia and cecal ligation and puncture) were used as in vivo models. The level of serum 3-nitrotyrosine was used as an in vivo marker of peroxynitrite. The results demonstrated that CAPE significantly improved the viability of lipopolysaccharide/interferon-γ-treated RAW 264.7 cells and significantly inhibited nitric oxide production, with effects similar to those observed with an inhibitor of inducible nitric oxide synthase (1400W). In addition, CAPE exclusively inhibited the synthesis of peroxynitrite from the artificial substrate SIN-1 and directly prevented the peroxynitrite-mediated conversion of dihydrorhodamine-123 to its fluorescent oxidation product rhodamine-123. In both sepsis models, CAPE inhibited cellular peroxynitrite synthesis, as evidenced by the absence of serum 3-nitrotyrosine, an in vivo marker of peroxynitrite. Thus, CAPE attenuates the inflammatory responses that lead to cell damage and, potentially, cell death through suppression of the production of cytotoxic molecules such as nitric oxide and peroxynitrite. These observations provide evidence of the therapeutic potential of CAPE treatment for a wide range of inflammatory disorders.

  4. Metformin and phenethyl isothiocyanate combined treatment in vitro is cytotoxic to ovarian cancer cultures

    Directory of Open Access Journals (Sweden)

    Chan Daniel K

    2012-07-01

    Full Text Available Abstract Background High mortality rates in ovarian cancer are largely a result of resistance to currently used chemotherapies. Expanding therapies with a variety of drugs has the potential to reduce this high mortality rate. Metformin and phenethyl isothiocyanate (PEITC are both potentially useful in ovarian cancer, and they are particularly attractive because of their safety. Methods Cell proliferation of each drug and drug combination was evaluated by hemacytometry with Trypan blue exclusion or Sytox green staining for cell death. Levels of total and cleaved PARP were measured by Western blot. General cellular and mitochondrial reactive oxygen species were measured by flow cytometry and live cell confocal microscopy with the fluorescent dyes dihydroethidine and MitoSOX. Results Individually, metformin and PEITC each show inhibition of cell growth in multiple ovarian cancer cell lines. Alone, PEITC was also able to induce apoptosis, whereas metformin was primarily growth inhibitory. Both total cellular and mitochondrial reactive oxygen species were increased when treated with either metformin or PEITC. The growth inhibitory effects of metformin were reversed by methyl succinate supplementation, suggesting complex I plays a role in metformin's anti-cancer mechanism. PEITC's anti-cancer effect was reversed by N-acetyl-cysteine supplementation, suggesting PEITC relies on reactive oxygen species generation to induce apoptosis. Metformin and PEITC together showed a synergistic effect on ovarian cancer cell lines, including the cisplatin resistant A2780cis. Conclusions Here we show that when used in combination, these drugs are effective in both slowing cancer cell growth and killing ovarian cancer cells in vitro. Furthermore, the combination of these drugs remains effective in cisplatin resistant cell lines. Novel combinations such as metformin and PEITC show promise in expanding ovarian cancer therapies and overcoming the high incidence of

  5. A multi-defense strategy: Enhancing bactericidal activity of a medical grade polymer with a nitric oxide donor and surface-immobilized quaternary ammonium compound.

    Science.gov (United States)

    Pant, Jitendra; Gao, Jing; Goudie, Marcus J; Hopkins, Sean P; Locklin, Jason; Handa, Hitesh

    2017-08-01

    Although the use of biomedical devices in hospital-based care is inevitable, unfortunately, it is also one of the leading causes of the nosocomial infections, and thus demands development of novel antimicrobial materials for medical device fabrication. In the current study, a multi-defense mechanism against Gram-positive and Gram-negative bacteria is demonstrated by combining a nitric oxide (NO) releasing agent with a quaternary ammonium antimicrobial that can be covalently grafted to medical devices. Antibacterial polymeric composites were fabricated by incorporating an NO donor, S-nitroso-N-acetyl-penicillamine (SNAP) in CarboSil® polymer and top coated with surface immobilized benzophenone based quaternary ammonium antimicrobial (BPAM) small molecule. The results suggest that SNAP and BPAM individually have a different degree of toxicity towards Gram-positive and Gram-negative bacteria, while the SNAP-BPAM combination is effective in reducing both types of adhered viable bacteria equally well. SNAP-BPAM combinations reduced the adhered viable Pseudomonas aeruginosa by 99.0% and Staphylococcus aureus by 99.98% as compared to the control CarboSil films. Agar diffusion tests demonstrate that the diffusive nature of NO kills bacteria beyond the direct point of contact which the non-leaching BPAM cannot achieve alone. This is important for potential application in biofilm eradication. The live-dead bacteria staining shows that the SNAP-BPAM combination has more attached dead bacteria (than live) as compared to the controls. The SNAP-BPAM films have increased hydrophilicity and higher NO flux as compared to the SNAP films useful for preventing blood protein and bacterial adhesion. Overall the combination of SNAP and BPAM imparts different attributes to the polymeric composite that can be used in the fabrication of antimicrobial surfaces for various medical device applications. A significant increase in the biomedical device related infections (BDRIs), inability of

  6. chromic transitions in phenyl-substituted polythiophenes

    African Journals Online (AJOL)

    The solvatochromic and thermochromic behaviours of phenyl-substituted polythiophenes were studied. The pristine polymers, upon dissolution in chloroform, exhibited blue-shifted absorption. The solid films of the polymers showed significant blue-shifted as well as red-shifted absorptions when heated. While the addition of ...

  7. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject to...

  8. Tetra-butyl-ammonium hydrogen phenyl-arsonate-phenyl-arsonic acid (1/1).

    Science.gov (United States)

    Reck, Lukas; Schmitt, Wolfgang

    2012-09-01

    The structure of the title salt adduct, (C(4)H(9))(4)N(+)·C(6)H(5)AsO(3)H(-)·C(6)H(5)AsO(3)H(2), features chains along the a axis comprising alternating hydrogen phenyl-arsonate anions and phenyl-arsonic acid mol-ecules linked by O-H⋯O hydrogen bonds.

  9. Protective Effect of Caffeic Acid Phenethyl Ester in Rat Cerebral Ischemia/Reperfusion Damage

    Directory of Open Access Journals (Sweden)

    Ertuğrul Uzar

    2011-09-01

    Full Text Available OBJECTIVE: Because oxidative stress is related to cerebral ischemia/reperfusion (I/R injury, modulation of oxygen free radical production may represent a new approach to the management of cerebral I/R. Caffeic acid phenethyl ester (CAPE has been determined to have neuroprotective, antioxidant, anti-inflammatory, and anti-apoptotic activities. The aim of this study was to investigate whether CAPE has a protective effect on cerebral I/R damage, and to determine the possible effects of CAPE on total antioxidant/oxidant status. METHODS: A total of 30 rats were randomly divided into three groups as control group, I/R group, and I/R + CAPE. Total oxidant status (TOS, total antioxidant status (TAS and oxidative stress index (OSI levels and histopathological cellular structures were evaluated in cerebral tissues obtained after the experiment procedure in all groups. RESULTS: In the brain tissue, TOS and OSI levels were found to be significantly increased in the I/R group compared to the controls (p= 0.023, p= 0.001, respectively. Significantly decreased TAS levels were found in the I/R group compared to the controls (p= 0.001. CAPE treatment prevented the increase in TOS and OSI that is produced by cerebral I/R (p= 0.041, p= 0.001, respectively. TAS was found to be increased in the CAPE + I/R group compared with the I/R group (p= 0.002. In the I/R group, the brain sections showed findings of cerebral I/R damage including inflammation, vascular congestion and necrosis (for both variables, p= 0.001. These histopathological cerebral damage findings were found to be significantly reduced in the CAPE + I/R group compared to the I/R group (for both parameters, p< 0.05. CONCLUSION: In this study, it was found that oxidative stress had an important role in the pathogenesis of cerebral I/R damage, and histopathological and biochemical evaluations showed significantly decreased I/R damage following CAPE treatment in rats.

  10. Probing the orientation of surface-immobilized protein G B1 using ToF-SIMS, sum frequency generation, and NEXAFS spectroscopy.

    Science.gov (United States)

    Baugh, Loren; Weidner, Tobias; Baio, J E; Nguyen, Phuong-Cac T; Gamble, Lara J; Stayton, Patrick S; Castner, David G

    2010-11-02

    The ability to orient active proteins on surfaces is a critical aspect of many medical technologies. An important related challenge is characterizing protein orientation in these surface films. This study uses a combination of time-of-flight secondary ion mass spectrometry (ToF-SIMS), sum frequency generation (SFG) vibrational spectroscopy, and near-edge X-ray absorption fine structure (NEXAFS) spectroscopy to characterize the orientation of surface-immobilized Protein G B1, a rigid 6 kDa domain that binds the Fc fragment of IgG. Two Protein G B1 variants with a single cysteine introduced at either end were immobilized via the cysteine thiol onto maleimide-oligo(ethylene glycol)-functionalized gold and bare gold substrates. X-ray photoelectron spectroscopy was used to measure the amount of immobilized protein, and ToF-SIMS was used to measure the amino acid composition of the exposed surface of the protein films and to confirm covalent attachment of protein thiol to the substrate maleimide groups. SFG and NEXAFS were used to characterize the ordering and orientation of peptide or side chain bonds. On both substrates and for both cysteine positions, ToF-SIMS data showed enrichment of mass peaks from amino acids located at the end of the protein opposite to the cysteine surface position as compared with nonspecifically immobilized protein, indicating end-on protein orientations. Orientation on the maleimide substrate was enhanced by increasing pH (7.0-9.5) and salt concentration (0-1.5 M NaCl). SFG spectral peaks characteristic of ordered α-helix and β-sheet elements were observed for both variants but not for cysteine-free wild type protein on the maleimide surface. The phase of the α-helix and β-sheet peaks indicated a predominantly upright orientation for both variants, consistent with an end-on protein binding configuration. Polarization dependence of the NEXAFS signal from the N 1s to π* transition of β-sheet peptide bonds also indicated protein ordering

  11. Probing the Orientation of Surface Immobilized Protein G B1 using ToF SIMS, Sum Frequency Generation, and NEXAFS Spectroscopy

    Science.gov (United States)

    Baugh, Loren; Weidner, Tobias; Baio, J.E.; Nguyen, Phuong Cac; Gamble, Lara J.; Stayton, Patrick S.; Castner, David G.

    2010-01-01

    The ability to orient active proteins on surfaces is a critical aspect of many medical technologies. An important related challenge is characterizing protein orientation in these surface films. This study uses a combination of time-of-flight secondary ion mass spectrometry (ToF-SIMS), sum frequency generation (SFG) vibrational spectroscopy, and near edge x-ray absorption fine structure (NEXAFS) spectroscopy to characterize the orientation of surface-immobilized Protein G B1, a rigid 6 kDa domain that binds the Fc fragment of IgG. Two Protein G B1 variants with a single cysteine introduced at either end were immobilized via the cysteine thiol onto maleimide-oligo(ethylene glycol)-functionalized gold and bare gold substrates. X-ray photoelectron spectroscopy was used to measure the amount of immobilized protein and ToF-SIMS was used to measure the amino acid composition of the exposed surface of the protein films and to confirm covalent attachment of protein thiol to the substrate maleimide groups. SFG and NEXAFS were used to characterize the ordering and orientation of peptide or side chain bonds. On both substrates and for both cysteine positions, ToF-SIMS data showed enrichment of mass peaks from amino acids located at the end of the protein opposite the cysteine surface position compared with nonspecifically immobilized protein, indicating end-on protein orientations. Orientation on the maleimide substrate was enhanced by increasing pH (7.0 to 9.5) and salt concentration (0 to 1.5 M NaCl). SFG spectral peaks characteristic of ordered α-helix and β-sheet elements were observed for both variants but not for cysteine-free wild type protein on the maleimide surface. The phase of the α-helix and β-sheet peaks indicated a predominantly upright orientation for both variants, consistent with an end-on protein binding configuration. Polarization dependence of the NEXAFS signal from the N 1s toπ* transition of β-sheet peptide bonds also indicated protein ordering

  12. Effects of propolis, caffeic acid phenethyl ester, and pollen on renal injury in hypertensive rat: An experimental and theoretical approach.

    Science.gov (United States)

    Salmas, Ramin Ekhteiari; Gulhan, Mehmet Fuat; Durdagi, Serdar; Sahna, Engin; Abdullah, Huda I; Selamoglu, Zeliha

    2017-08-01

    The objective of this study was to evaluate the antioxidant effects of propolis, caffeic acid phenethyl ester (CAPE; active compound in propolis), and pollen on biochemical oxidative stress biomarkers in rat kidney tissue inhibited by N ω -nitro-L-arginine methyl ester (L-NAME). The biomarkers evaluated were paraoxonase (PON1), oxidative stress index (OSI), total antioxidant status (TAS), total oxidant status (TOS), asymmetric dimethylarginine (ADMA), and nuclear factor kappa B (NF-κB). TAS levels and PON1 activity were significantly decreased in kidney tissue samples in the L-NAME-treated group (P propolis, CAPE, and pollen groups compared with the L-NAME-treated group. TOS, ADMA, and NF-κB levels were significantly increased in the kidney tissue samples of the L-NAME-treated group (P propolis, CAPE, and pollen groups (P propolis, CAPE administration. Copyright © 2017 John Wiley & Sons, Ltd.

  13. Enantioseparation of linear and cyclic chiral bis(phenethyl)amines by means of cyclodextrin-modified capillary electrophoresis.

    Science.gov (United States)

    Wedig, M; Thunhorst, M; Laug, S; Decker, M; Lehmann, J; Holzgrabe, U

    2001-09-01

    For two years drugs introduced to the market have had- to be enantiomerically pure. Rapid and cheap methods of high reproducibility must, therefore, be available for evaluation of enantiomeric purity. Within the framework of a larger project dealing with chiral recognition of phenethylamines by means of native and derivatized cyclodextrins it was intended to find capillary electrophoresis methods suitable for separation of the enantiomers of chiral bis(phenethyl)amines and their corresponding cyclic analogues, within 10 min, using small amounts of a chiral selector, to save time and money. Heptakis(2,3-O-diacetyl-6-sulfato)beta-CD was found to be the most promising candidate most often fulfilling these requirements.

  14. Caffeic Acid Phenethyl Ester as a Protective Agent against Nephrotoxicity and/or Oxidative Kidney Damage: A Detailed Systematic Review

    Directory of Open Access Journals (Sweden)

    Sumeyya Akyol

    2014-01-01

    Full Text Available Caffeic acid phenethyl ester (CAPE, an active component of propolis, has been attracting the attention of different medical and pharmaceutical disciplines in recent years because of its antioxidant, anti-inflammatory, antiproliferative, cytotoxic, antiviral, antifungal, and antineoplastic properties. One of the most studied organs for the effects of CAPE is the kidney, particularly in the capacity of this ester to decrease the nephrotoxicity induced by several drugs and the oxidative injury after ischemia/reperfusion (I/R. In this review, we summarized and critically evaluated the current knowledge regarding the protective effect of CAPE in nephrotoxicity induced by several special medicines such as cisplatin, doxorubicin, cyclosporine, gentamycin, methotrexate, and other causes leading to oxidative renal injury, namely, I/R models and senility.

  15. Structure-Activity Relationships in the Cytoprotective Effect of Caffeic Acid Phenethyl Ester (CAPE) and Fluorinated Derivatives: Effects on Heme Oxygenase-1 Induction and Antioxidant Activities

    Science.gov (United States)

    2010-03-09

    derivatives than their direct antioxidant activity. © 2010 Published by Elsevier B.V. 1. Introduction Caffeic acid phenethyl ester (CAPE), a polyphenolic ...al., 2006). Fluorine substitution in the design and synthesis of small molecules for potential therapeutic use has become very common (Kirk, 2006...has been suggested that the methylation of polyphenolic compounds may result in the loss of their free radical scavenging ability (Deng et al., 2006

  16. Chemistry of polycyclic aromatic hydrocarbons formation from phenyl radical pyrolysis and reaction of phenyl and acetylene.

    Science.gov (United States)

    Comandini, A; Malewicki, T; Brezinsky, K

    2012-03-15

    An experimental investigation of phenyl radical pyrolysis and the phenyl radical + acetylene reaction has been performed to clarify the role of different reaction mechanisms involved in the formation and growth of polycyclic aromatic hydrocarbons (PAHs) serving as precursors for soot formation. Experiments were conducted using GC/GC-MS diagnostics coupled to the high-pressure single-pulse shock tube present at the University of Illinois at Chicago. For the first time, comprehensive speciation of the major stable products, including small hydrocarbons and large PAH intermediates, was obtained over a wide range of pressures (25-60 atm) and temperatures (900-1800 K) which encompass the typical conditions in modern combustion devices. The experimental results were used to validate a comprehensive chemical kinetic model which provides relevant information on the chemistry associated with the formation of PAH compounds. In particular, the modeling results indicate that the o-benzyne chemistry is a key factor in the formation of multi-ring intermediates in phenyl radical pyrolysis. On the other hand, the PAHs from the phenyl + acetylene reaction are formed mainly through recombination between single-ring aromatics and through the hydrogen abstraction/acetylene addition mechanism. Polymerization is the common dominant process at high temperature conditions.

  17. The lowest excited singlet state of isolated 1-phenyl-butadiene and 1-phenyl-hexatriene

    NARCIS (Netherlands)

    Kohler, B.E.; Shaler, T.A.; Buma, W.J.; Song, K.; Nuss, J.M.

    1992-01-01

    We report vibrationally resolved S0S1 excitation spectra and vibronic level decay times for the phenyl-substituted polyenes 1-phenylbutadiene and 1-phenylhexatriene seeded in supersonic He expansions. This information was obtained using one- and two-color resonance-enhanced multiphoton ionization

  18. A new class of efficient 4-[(nitro substituted-phenyl ...

    Indian Academy of Sciences (India)

    A new class of efficient colorimetric chemosensors derived from 4-[(nitro substituted-phenyl)-hydrazonomethyl]-1-phenyl-1H-pyrazole-3-carboxylate have been synthesized and characterized. The synthesized receptors exhibit instant color change from yellow to dark purple along with significant bathochromicshifts when ...

  19. N-Phenethyl caffeamide and photodamage: protecting skin by inhibiting type I procollagen degradation and stimulating collagen synthesis.

    Science.gov (United States)

    Chiang, Hsiu-Mei; Chen, Chien-Wen; Lin, Tzu-Yu; Kuo, Yueh-Hsiung

    2014-10-01

    Skin is mainly damaged by genetic and environmental factors such as ultraviolet (UV) light and pollutants. UV light is a well-known factor that causes various types of skin damage and premature aging. Reactive oxygen species (ROS) are commonly involved in the pathogenesis of skin damage by activating the metalloproteinases that break down type I collagen. This study investigated the antioxidant and antiphotodamage activity and mechanisms of N-phenethyl caffeamide (K36) in human skin fibroblasts. The results indicated that K36 demonstrated strong 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging activity, which dose-dependently reduced the production of UVB-induced intracellular ROS in human dermal fibroblasts. K36 prevented UVB-irradiation-induced type I collagen degradation by inhibiting the expression of matrix metalloproteins-1, -3, and -9 and the phosphorylation of mitogen-activated protein (MAP) kinases. Furthermore, K36 elevated collagen synthesis in skin fibroblasts by inhibiting UVB-induced Smad7 overexpression. K36 downregulated the expression of the transcription factor, activator protein-1 (AP-1). Our results indicated that K36 exhibited antioxidant properties and prevented skin collagen degradation caused by UV exposure and the stimulation of collagen synthesis, which suggests the potential use of K36 in preventing photodamage. Copyright © 2014 Elsevier Ltd. All rights reserved.

  20. Effect of Caffeic Acid Phenethyl Ester on Vascular Damage Caused by Consumption of High Fructose Corn Syrup in Rats

    Directory of Open Access Journals (Sweden)

    Aburrahman Gun

    2016-01-01

    Full Text Available Fructose corn syrup is cheap sweetener and prolongs the shelf life of products, but fructose intake causes hyperinsulinemia, hypertriglyceridemia, and hypertension. All of them are referred to as metabolic syndrome and they are risk factors for cardiovascular diseases. Hence, the harmful effects of increased fructose intake on health and their prevention should take greater consideration. Caffeic Acid Phenethyl Ester (CAPE has beneficial effects on metabolic syndrome and vascular function which is important in the prevention of cardiovascular disease. However, there are no known studies about the effect of CAPE on fructose-induced vascular dysfunction. In this study, we examined the effect of CAPE on vascular dysfunction due to high fructose corn syrup (HFCS. HFCS (6 weeks, 30% fed with drinking water caused vascular dysfunction, but treatment with CAPE (50 micromol/kg i.p. for the last two weeks effectively restored this problem. Additionally, hypertension in HFCS-fed rats was also decreased in CAPE supplemented rats. CAPE supplements lowered HFCS consumption-induced raise in blood glucose, homocysteine, and cholesterol levels. The aorta tissue endothelial nitric oxide synthase (eNOS production was decreased in rats given HFCS and in contrast CAPE supplementation efficiently increased its production. The presented results showed that HFCS-induced cardiovascular abnormalities could be prevented by CAPE treatment.

  1. Effect of Caffeic Acid Phenethyl Ester on Vascular Damage Caused by Consumption of High Fructose Corn Syrup in Rats.

    Science.gov (United States)

    Gun, Aburrahman; Ozer, Mehmet Kaya; Bilgic, Sedat; Kocaman, Nevin; Ozan, Gonca

    2016-01-01

    Fructose corn syrup is cheap sweetener and prolongs the shelf life of products, but fructose intake causes hyperinsulinemia, hypertriglyceridemia, and hypertension. All of them are referred to as metabolic syndrome and they are risk factors for cardiovascular diseases. Hence, the harmful effects of increased fructose intake on health and their prevention should take greater consideration. Caffeic Acid Phenethyl Ester (CAPE) has beneficial effects on metabolic syndrome and vascular function which is important in the prevention of cardiovascular disease. However, there are no known studies about the effect of CAPE on fructose-induced vascular dysfunction. In this study, we examined the effect of CAPE on vascular dysfunction due to high fructose corn syrup (HFCS). HFCS (6 weeks, 30% fed with drinking water) caused vascular dysfunction, but treatment with CAPE (50 micromol/kg i.p. for the last two weeks) effectively restored this problem. Additionally, hypertension in HFCS-fed rats was also decreased in CAPE supplemented rats. CAPE supplements lowered HFCS consumption-induced raise in blood glucose, homocysteine, and cholesterol levels. The aorta tissue endothelial nitric oxide synthase (eNOS) production was decreased in rats given HFCS and in contrast CAPE supplementation efficiently increased its production. The presented results showed that HFCS-induced cardiovascular abnormalities could be prevented by CAPE treatment.

  2. The Effect of Caffeic Acid Phenethyl Ester (CAPE) Fortification on the Liver Element Distribution that Occurs After Exercise.

    Science.gov (United States)

    Akil, Mustafa; Coban, Funda Karabag; Yalcinkaya, Ozcan

    2016-08-01

    The purpose of this study is to examine the effect of the caffeic acid phenethyl ester (CAPE) fortification applied to the rats, which were made to exercise, on the liver elements. The study was conducted on 32 Sprague-Dawley male rats. The experimental animals were divided into 4 groups in equal numbers. Group 1 is the group which was applied 10 μmol/kg/day CAPE as intraperitoneal (IP) for 4 weeks, and they were not made to exercise at the end of the application. Group 2 is the group which was applied 10 μmol/kg/day CAPE as IP for 4 weeks, and they were made to exercise at the end of the 4th week. Group 3 is the general control group. Group 4 is the swimming control group. A 10 mmol/kg CAPE application dissolved in ethyl alcohol of 10 % was applied to the CAPE group. Sodium (Na), zinc (Zn), calcium (Ca), iron (Fe), chrome (Cr), magnesium (Mg), potassium (K), copper (Cu) and cadmium (Cd) levels were identified in the liver samples at the end of the application. The results of the study suggest that exercise and CAPE fortification in rats cause changes in the Na, Zn, Ca, Fe and Cr parameters in liver tissues, and it does not affect Cd, Cu, Mg and K element distribution. It is thought that CAPE fortification would be helpful for preserving those parameters whose levels are known to be changing with exercise.

  3. Caffeic acid phenethyl ester downregulates phospholipase D1 via direct binding and inhibition of NFκB transactivation

    Energy Technology Data Exchange (ETDEWEB)

    Park, Mi Hee; Kang, Dong Woo [Department of Molecular Biology, Pusan National University, Busan 609-735 (Korea, Republic of); Jung, Yunjin [College of Pharmacy, Pusan National University, Busan 609-735 (Korea, Republic of); Choi, Kang-Yell [Translational Research Center for Protein Function Control, Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, Seoul (Korea, Republic of); Min, Do Sik, E-mail: minds@pusan.ac.kr [Department of Molecular Biology, Pusan National University, Busan 609-735 (Korea, Republic of)

    2013-12-06

    Highlights: •We found CAFÉ, a natural product that suppresses expression and activity of PLD1. •CAPE decreased PLD1 expression by inhibiting NFκB transactivation. •CAPE rapidly inhibited PLD activity via its binding to a Cys837 of PLD1. •PLD1 downregulation by CAPE inhibited invasion and proliferation of glioma cells. -- Abstract: Upregulation of phospholipase D (PLD) is functionally linked with oncogenic signals and tumorigenesis. Caffeic acid phenethyl ester (CAPE) is an active compound of propolis extract that exhibits anti-proliferative, anti-inflammatory, anti-oxidant, and antineoplastic properties. In this study, we demonstrated that CAPE suppressed the expression of PLD1 at the transcriptional level via inhibition of binding of NFκB to PLD1 promoter. Moreover, CAPE, but not its analogs, bound to a Cys837 residue of PLD1 and inhibited enzymatic activity of PLD. CAPE also decreased activation of matrix metalloproteinases-2 induced by phosphatidic acid, a product of PLD activity. Ultimately, CAPE-induced downregulation of PLD1 suppressed invasion and proliferation of glioma cells. Taken together, the results of this study indicate that CAPE might contribute to anti-neoplastic effect by targeting PLD1.

  4. Differential effects of procaine and phenethyl alcohol on excision repair of DNA in u.v.-irradiated Escherichia coli

    International Nuclear Information System (INIS)

    Tomiyama, H.; Tachibana, A.; Yonei, S.

    1986-01-01

    Experiments were performed to investigate the involvement of the cell membrane in the excision DNA repair process in Escherichia coli. Two membrane-binding drugs, procaine and phenethyl alcohol (PEA), inhibited liquid-holding recovery (LBR) in u.v.-irradiated E. coli wild-type and recA strains. In uvrB and polA strains where, after u.v.-irradiation, LHR was absent the two drugs had no effect. Both drugs markedly reduced the removal of u.v.-induced thymine dimers in the DNA of wild-type cells (H/r30). Analysis by alkaline sucrose gradients revealed that PEA inhibited the incision step in excision repair. In contrast, procaine had no effect on incision but apparently inhibited the late steps in excision repair. PEA dissociated DNA from the cell membrane, whereas procaine did not. The results suggest that the two drugs PEA and procaine inhibit LHR and the excision repair process operating on u.v.-induced damage in E. coli by at least two different mechanisms each of which may involve the cell membrane. (author)

  5. Fibrinolytic Activity and Dose-Dependent Effect of Incubating Human Blood Clots in Caffeic Acid Phenethyl Ester: In Vitro Assays

    Directory of Open Access Journals (Sweden)

    Abuzar Elnager

    2015-01-01

    Full Text Available Background. Caffeic acid phenethyl ester (CAPE has been reported to possess time-dependent fibrinolytic activity by in vitro assay. This study is aimed at investigating fibrinolytic dose-dependent activity of CAPE using in vitro assays. Methods. Standardized human whole blood (WB clots were incubated in either blank controls or different concentrations of CAPE (3.75, 7.50, 15.00, 22.50, and 30.00 mM. After 3 hours, D-dimer (DD levels and WB clot weights were measured for each concentration. Thromboelastography (TEG parameters were recorded following CAPE incubation, and fibrin morphology was examined under a confocal microscope. Results. Overall, mean DD (μg/mL levels were significantly different across samples incubated with different CAPE concentrations, and the median pre- and postincubation WB clot weights (grams were significantly decreased for each CAPE concentration. Fibrin removal was observed microscopically and indicated dose-dependent effects. Based on the TEG test, the Ly30 fibrinolytic parameter was significantly different between samples incubated with two different CAPE concentrations (15.0 and 22.50 mM. The 50% effective dose (ED50 of CAPE (based on DD was 1.99 mg/mL. Conclusions. This study suggests that CAPE possesses fibrinolytic activity following in vitro incubation and that it has dose-dependent activities. Therefore, further investigation into CAPE as a potential alternative thrombolytic agent should be conducted.

  6. Novel Antidepressant-Like Activity of Caffeic Acid Phenethyl Ester Is Mediated by Enhanced Glucocorticoid Receptor Function in the Hippocampus

    Directory of Open Access Journals (Sweden)

    Mi-Sook Lee

    2014-01-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is an active component of propolis that has a variety of potential pharmacological effects. Although we previously demonstrated that propolis has antidepressant-like activity, the effect of CAPE on this activity remains unknown. The present study assessed whether treatment with CAPE (5, 10, and 20 µmol/kg for 21 days has an antidepressant-like effect in mice subjected to chronic unpredictable stress via tail suspension (TST and forced swim (FST tests. CAPE administration induced behaviors consistent with an antidepressant effect, evidenced by decreased immobility in the TST and FST independent of any effect on serum corticosterone secretion. Western blots, conducted subsequent to behavioral assessment, revealed that CAPE significantly decreased glucocorticoid receptor phosphorylation at S234 (pGR(S234, resulting in an increased pGR(S220/S234 ratio. We also observed negative correlations between pGR(S220/(S234 and p38 mitogen-activated protein kinase (p38MAPK phosphorylation, which was decreased by CAPE treatment. These findings suggest that CAPE treatment exerts an antidepressant-like effect via downregulation of p38MAPK phosphorylation, thereby contributing to enhanced GR function.

  7. The zeolite mediated isomerization of allyl phenyl ether

    Science.gov (United States)

    Pebriana, R.; Mujahidin, D.; Syah, Y. M.

    2017-04-01

    Allyl phenyl ether is an important starting material in organic synthesis that has several applications in agrochemical industry. The green transformation of allyl phenyl ether assisted by heterogeneous catalyst is an attractive topic for an industrial process. In this report, we investigated the isomerization of allyl phenyl ether by heating it in zeolite H-ZSM-5 and Na-ZSM-5. The conversion of allyl phenyl ether (neat) in H-ZSM-5 was 67% which produced 40% of 2-allylphenol, 17% of 2-methyldihydrobenzofuran, and other product (4:1.7:1), while in Na-ZSM-5 produced exclusively 2-allylphenol with 52% conversion. These results showed that zeolite properties can be tuned to give a selective transformation by substitution of metal ion into the zeolite interior.

  8. Budesonide and phenethyl isothiocyanate attenuate DNA damage in bronchoalveolar lavage cells of mice exposed to environmental cigarette smoke.

    Science.gov (United States)

    Micale, Rosanna T; D'Agostini, Francesco; Steele, Vernon E; La Maestra, Sebastiano; De Flora, Silvio

    2008-12-01

    Chemoprevention by dietary and pharmacological means provides a strategy for attenuating the health risks resulting from cigarette smoking and in particular from passive exposure to environmental cigarette smoke (ECS). We evaluated the ability of the glucocorticoid budesonide and of the natural agent phenethyl isothiocyanate (PEITC) to affect DNA damage in bronchoalveolar lavage (BAL) cells of CD-1 mice exposed to ECS, starting within 12 h after birth and continuing until the end of the experiment. After weanling, based on a preliminary subchronic toxicity study, groups of mice received daily either budesonide (24 mg/kg diet) or PEITC (1,000 mg/kg diet). After 2 weeks of treatment, all mice were sacrificed and subjected to BAL, mainly recovering pulmonary alveolar macrophages. Evaluation of single-cell DNA strand breaks was made by using the alkaline-halo test, a modification of the comet assay. The analysis of 481 BAL cells yielded the following results (expressed as nuclear spread factor): (a) Sham-exposed mice: mean 0.84 (lower-upper 95% confidence intervals 0.74-0.94); (b) ECS-exposed mice: 2.77 (2.46-3.09); (c) ECS-exposed mice treated with PEITC: 1.15 (1.05-1.26); (d) ECS-exposed mice treated with budesonide: 1.37 (1.25-1.49). Thus, exposure to ECS resulted in a significant increase of DNA damage as compared with sham, and both PEITC and budesonide significantly attenuated this damage. In conclusion, the analysis of sentinel cells collected by BAL, a semi-invasive technique that is commonly used in humans for diagnostic purposes, showed that the investigated chemopreventive agents are able to revert the DNA damage produced by passive exposure to cigarette smoke.

  9. Caffeic acid phenethyl ester preferentially sensitizes CT26 colorectal adenocarcinoma to ionizing radiation without affecting bone marrow radioresponse

    International Nuclear Information System (INIS)

    Chen, Y.-J.; Liao, H.-F.; Tsai, T.-H.; Wang, S.-Y.; Shiao, M.-S.

    2005-01-01

    Purpose: Caffeic acid phenethyl ester (CAPE), a component of propolis, was reported capable of depleting glutathione (GSH). We subsequently examined the radiosensitizing effect of CAPE and its toxicity. Methods and Materials: The effects of CAPE on GSH level, GSH metabolism enzyme activities, NF-κB activity, and radiosensitivity in mouse CT26 colorectal adenocarcinoma cells were determined. BALB/c mouse with CT26 cells implantation was used as a syngeneic in vivo model for evaluation of treatment and toxicity end points. Results: CAPE entered CT26 cells rapidly and depleted intracellular GSH in CT26 cells, but not in bone marrow cells. Pretreatment with nontoxic doses of CAPE significantly enhanced cell killing by ionizing radiation (IR) with sensitizer enhancement ratios up to 2.2. Pretreatment of CT26 cells with N-acetyl-L-cysteine reversed the GSH depletion activity and partially blocked the radiosensitizing effect of CAPE. CAPE treatment in CT26 cells increased glutathione peroxidase, decreased glutathione reductase, and did not affect glutathione S-transferase or γ-glutamyl transpeptidase activity. Radiation activated NF-κB was reversed by CAPE pretreatment. In vivo study revealed that pretreatment with CAPE before IR resulted in greater inhibition of tumor growth and prolongation of survival in comparison with IR alone. Pretreatment with CAPE neither affected body weights nor produced hepatic, renal, or hematopoietic toxicity. Conclusions: CAPE sensitizes CT26 colorectal adenocarcinoma to IR, which may be via depleting GSH and inhibiting NF-κB activity, without toxicity to bone marrow, liver, and kidney

  10. The Protective Effects of Caffeic Acid Phenethyl Ester on Acetylsalicylic Acid-induced Lung Injury in Rats.

    Science.gov (United States)

    Taylan, Mahşuk; Kaya, Halide; Demir, Melike; Evliyaoğlu, Osman; Sen, Hadice Selimoglu; Fırat, Ugur; Keles, Aysenur; Yilmaz, Sureyya; Sezgi, Cengizhan

    2016-12-01

    We aimed to investigate the protective effect of caffeic acid phenethyl ester (CAPE) on acetylsalicylic acid (ASA)-induced lung damage in rats in the present study. A total of 40 rats were randomly divided into five groups, with eight rats in each group-group 1: control, not receiving any medication; group 2: ASA (50 mg/kg/day); group 3: ASA (50 mg/kg/day) plus CAPE (20 μg/kg/day); group 4: ASA (100 mg/kg/day); and group 5: ASA (100 mg/kg/day) plus CAPE (20 μg/kg/day). ASA and CAPE were given via orogastric gavage for 5 days. The total oxidant status (TOS), total antioxidant capacity (TAC), oxidant stress index (OSI), and paraoxonase-1 (PON-1) activity of the blood samples and lung tissues were determined. Histopathological examinations of the lung tissues were performed by using light microscopic methods. CAPE treatment significantly increased antioxidant PON-1 level both in the lung tissue and plasma (p < .05). Plasma antioxidant marker (TAC, PON-1) levels significantly increased and oxidant marker (TOS, OSI) levels significantly decreased in CAPE-treated rats (groups 3,5) compared to ASA given no-CAPE groups (group 2,4) (p < .05). Treatment with CAPE improved pulmonary interstitial inflammation and eosinophil accumulation due to ASA histopathologically. Eosinophil-rich inflammation and oxidative stress play important roles in ASA-induced lung toxicity, and CAPE may protect against ASA-induced lung toxicity by reduction of oxidative damage and inflammation in rats.

  11. Syntheses and Antibacterial Studies of Some 1-Phenyl-3-(4-(2-ethanoloxy phenyl-5-aryl-1H-pyrazoles

    Directory of Open Access Journals (Sweden)

    Anju Goyal

    2013-01-01

    Full Text Available A series of 1-phenyl-3-(4-(2-ethanoloxy phenyl-5-aryl-1H-pyrazoles were synthesized from chalcones, that is, 3-aryl-1-(4-hydroxyphenyl prop-2-en-1-ones and studied for their in vitro antibacterial activity. Chalcones 1 on reaction with phenyl hydrazine in the presence of acetic acid and few drops of hydrochloric acid yielded the corresponding 1-phenyl-3-(4-hydroxyphenyl-5-aryl-1H-pyrazoles 2 which on further reaction with 2-chloroethanol furnished the title compounds 3. These compounds were characterized by CHN analyses, IR, mass and 1H NMR spectral data. All the compounds were evaluated for their in vitro antibacterial activity against two Gram positive strains (Bacillus subtilis and Staphylococcus aureus and two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa, and their minimum inhibitory concentration (MIC was determined.

  12. Tetra­butyl­ammonium hydrogen phenyl­arsonate–phenyl­arsonic acid (1/1)

    Science.gov (United States)

    Reck, Lukas; Schmitt, Wolfgang

    2012-01-01

    The structure of the title salt adduct, (C4H9)4N+·C6H5AsO3H−·C6H5AsO3H2, features chains along the a axis comprising alternating hydrogen phenyl­arsonate anions and phenyl­arsonic acid mol­ecules linked by O—H⋯O hydrogen bonds. PMID:22969495

  13. Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C-H Bond Activation.

    Science.gov (United States)

    Hu, Jundie; Guan, Mingyu; Han, Jian; Huang, Zhi-Bin; Shi, Da-Qing; Zhao, Yingsheng

    2015-08-21

    A highly regioselective palladium-catalyzed ester-directed ortho-olefination of phenyl acetic and propionic esters with olefins via C-H bond activation has been developed. A wide variety of phenyl acetic and propionic esters were tolerated in this transformation, affording the corresponding olefinated aromatic compounds. The ortho-olefination of heterocyclic acetic and propionic esters also took place smoothly giving the products in good yields, thus proving the potential utility of this protocol in synthetic chemistry.

  14. Design and Synthesis of 4-Alkylidene-β-lactams: Benzyl- and Phenethyl-carbamates as Key Fragments to Switch on Antibacterial Activity.

    Science.gov (United States)

    Giacomini, Daria; Martelli, Giulia; Piccichè, Miriam; Calaresu, Enrico; Cocuzza, Clementina Elvezia; Musumeci, Rosario

    2017-09-21

    The emergence of multidrug-resistant bacterial strains is particularly important in chronic pathologies such as cystic fibrosis (CF), in which persistent colonization and selection of resistant strains is favored by the frequent and repeated use of antibacterial agents. Staphylococcus aureus is a common pathogen in CF patients that has an associated increased multidrug resistance. In previous studies we demonstrated that the presence of a 4-alkylidene side chain directly linked to a β-lactam appeared to strengthen the potency against S. aureus, especially against methicillin-resistant S. aureus (MRSA) strains. In the present study, 21 new 4-alkylidene-β-lactams were synthesized and evaluated for antibacterial activity. We designed the new compounds to have aryl, benzyl, or phenethyl-carbamate groups on the C3 hydroxyethyl side chain. We found a correlation between biological activity and the nitrogen substituent of the carbamate group, and two phenethyl-carbamate β-lactams were shown to be valuable antibacterial agents against selected linezolid-resistant strains, with a minimum inhibitory concentrations of 2-4 mg L -1 . © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. Effect of caffeic acid phenethyl ester on Prevotella intermedia lipopolysaccharide-induced production of proinflammatory mediators in murine macrophages.

    Science.gov (United States)

    Choi, E-Y; Choe, S-H; Hyeon, J-Y; Choi, J-I; Choi, I S; Kim, S-J

    2015-12-01

    Caffeic acid phenethyl ester (CAPE) has numerous potentially beneficial properties, including antioxidant, immunomodulatory and anti-inflammatory activities. However, the effect of CAPE on periodontal disease has not been studied before. This study was designed to investigate the efficacy of CAPE in ameliorating the production of proinflammatory mediators in macrophages activated by lipopolysaccharide (LPS) from Prevotella intermedia, a pathogen implicated in periodontal disease. LPS from P. intermedia ATCC 25611 was isolated by using the standard hot phenol-water method. Culture supernatants were assayed for nitric oxide (NO), interleukin (IL)-1β and IL-6. We used real-time polymerase chain reaction to quantify inducible NO synthase, IL-1β, IL-6, heme oxygenase (HO)-1 and suppressors of cytokine signaling (SOCS) 1 mRNA expression. HO-1 protein expression and levels of signaling proteins were assessed by immunoblot analysis. DNA-binding activities of NF-κB subunits were analyzed by using the enzyme-linked immunosorbent assay-based kits. CAPE exerted significant inhibitory effects on P. intermedia LPS-induced production of NO, IL-1β and IL-6 as well as their mRNA expression in RAW264.7 cells. CAPE-induced HO-1 expression in cells activated with P. intermedia LPS, and selective inhibition of HO-1 activity by tin protoporphyrin IX attenuated the inhibitory effect of CAPE on LPS-induced NO production. CAPE did not interfere with IκB-α degradation induced by P. intermedia LPS. Instead, CAPE decreased nuclear translocation of NF-κB p65 and p50 subunits induced with LPS, and lessened LPS-induced p50 binding activity. Further, CAPE showed strong inhibitory effects on LPS-induced signal transducer and activator of transcription 1 and 3 phosphorylation. Besides, CAPE significantly elevated SOCS1 mRNA expression in P. intermedia LPS-stimulated cells. Modulation of host response by CAPE may represent an attractive strategy towards the treatment of periodontal disease

  16. 3-Phenyl-1-(pyrrol-2-ylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Zhen-Qi Gong

    2008-01-01

    Full Text Available The title molecule, C13H11NO, is almost flat, the angle between the pyrrole and the phenyl rings being 10.9 (1°. The atoms of the central C3O unit are coplanar, with a mean deviation from the plane of 0.001 (1 Å. The angles between this plane and the pyrrole and phenyl rings are 3.3 (1 and 8.0 (1°, respectively. The molecules form centrosymmetric dimers through a pair of N—H...O hydrogen bonds with an R22(10 motif.

  17. 2-Methyl-4-phenyl-3,4-dihydroquinazoline

    Directory of Open Access Journals (Sweden)

    Arto Valkonen

    2011-04-01

    Full Text Available The title compound, C15H14N2, was formed during the lithiation of 2-methylquinazoline with phenyllithium followed by hydrolysis of the intermediate lithium 2-methyl-4-phenyl-4H-quinazolin-3-ide. NMR spectra as well as single-crystal X-ray structural data indicate that the reaction product to have the same structure in chloroform solution as in the crystalline state. The phenyl substituent is twisted out of the plane of the 3,4-dihydroquinazoline ring system by 86.47 (7°. In the crystal, intermolecular N—H...N interactions connect the molecules into infinite chains.

  18. Identification of a new psychoactive substance in seized material: the synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (Acrylfentanyl)

    DEFF Research Database (Denmark)

    Breindahl, Torben; Kimergård, Andreas; Andreasen, Mette Findal

    2017-01-01

    -Orbitrap-MS), nuclear magnetic resonance spectroscopy (NMR), and infra-red spectroscopy (IR) confirmed the presence of acrylfentanyl (also known as acryloylfentanyl). Quantitative analysis with liquid chromatography and triple quadrupole mass spectrometry (LC-MS/MS) determined the content of acrylfentanyl in the powder...... of the electron impact mass spectrum of the main, unknown chromatographic peak (GC) tentatively identified an acryloyl analogue of fentanyl. Further analyses by quadrupole time-of-flight high resolution mass spectrometry (QTOF-MS), matrix-assisted laser ionization Orbitrap mass spectrometry (MALDI...

  19. 4-Methyl-N-(4-methyl­phenyl­sulfon­yl)-N-phenyl­benzene­sulfonamide

    Science.gov (United States)

    Eren, Bilge; Demir, Selçuk; Dal, Hakan; Hökelek, Tuncer

    2014-01-01

    The whole mol­ecule of the title compound, C20H19NO4S2, is generated by twofold rotational symmetry. The N atom is located on the twofold rotation axis and has a trigonal-planar geometry. It is bonded by two S atoms of two symmetry-related 4-methyl­phenyl­sulfonyl groups and by the C atom of the phenyl ring, which is bis­ected by the twofold rotation axis. The benzene and phenyl rings are oriented at a dihedral angle of 51.48 (5)° while the pendant benzene rings are inclined to one another by 87.76 (9)°. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network. PMID:24764960

  20. Synthesis of 1-(4-methylsulfone-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3- triazole and 1-(4-sulfonamide-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3- triazole as novel carbon-14 anticonvulsant

    International Nuclear Information System (INIS)

    Saemian, N.; Shirvani, G.; Matloubi, H.

    2006-01-01

    Two 1,2,3-triazole anticonvulsants, 1-(4-methylsulfone-phenyl)-5-(4-fluoro-phenyl)-5-[ 14 C]-1,2,3-triazole and 1-(4-sulfonamide-phenyl)-5-(4- fluoro-phenyl)-5-[ 14 C]-1,2,3-triazole, both labeled with carbon-14 in the 5-position were prepared from para-fluoro-benzonitrile-[cyano- 14 C]. (author)

  1. Caffeic acid phenethyl ester causes p21 induction, Akt signaling reduction, and growth inhibition in PC-3 human prostate cancer cells.

    Directory of Open Access Journals (Sweden)

    Hui-Ping Lin

    Full Text Available Caffeic acid phenethyl ester (CAPE treatment suppressed proliferation, colony formation, and cell cycle progression in PC-3 human prostate cancer cells. CAPE decreased protein expression of cyclin D1, cyclin E, SKP2, c-Myc, Akt1, Akt2, Akt3, total Akt, mTOR, Bcl-2, Rb, as well as phosphorylation of Rb, ERK1/2, Akt, mTOR, GSK3α, GSK3β, PDK1; but increased protein expression of KLF6 and p21(Cip1. Microarray analysis indicated that pathways involved in cellular movement, cell death, proliferation, and cell cycle were affected by CAPE. Co-treatment of CAPE with chemotherapeutic drugs vinblastine, paclitaxol, and estramustine indicated synergistic suppression effect. CAPE administration may serve as a potential adjuvant therapy for prostate cancer.

  2. Caffeic acid phenethyl ester, a promising component of propolis with a plethora of biological activities: a review on its anti-inflammatory, neuroprotective, hepatoprotective, and cardioprotective effects.

    Science.gov (United States)

    Tolba, Mai F; Azab, Samar S; Khalifa, Amani E; Abdel-Rahman, Sherif Z; Abdel-Naim, Ashraf B

    2013-08-01

    Caffeic acid phenethyl ester (CAPE) is an important active component of honey bee propolis that possesses a plethora of biological activities. Propolis is used safely in traditional medicine as a dietary supplement for its therapeutic benefits. This review highlights the recently published data about CAPE bioavailability, anti-inflammatory, neuroprotective; hepatoprotective and cardioprotective activities. CAPE showed promising efficacy both in vitro and in vivo studies in animal models with minimum adverse effects. Its effectiveness was demonstrated in multiple target organs. Despite this fact, it has not been yet investigated as a protective agent or a potential therapy in humans. Investigation of CAPE efficacy in clinical trials is strongly encouraged to elucidate its therapeutic benefit for different human diseases after performing full preclinical toxicological studies and gaining more insights into its pharmacokinetics. © 2013 International Union of Biochemistry and Molecular Biology.

  3. 4-Bromo-3-methoxy-1-phenyl-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Algirdas Šačkus

    2009-11-01

    Full Text Available The title compound was prepared by treatment of 4-bromo-1-phenyl-1H-pyrazol-3-ol with sodium hydride/methyl iodide in good yield. Detailed spectroscopic data (1H NMR, 13C NMR, 15N NMR, IR, MS are presented.

  4. Chemistry of the pyrazolidines. 26. Alkylation of 4-benzyliden-1-phenyl-3,5-dioxopyrazolidines

    International Nuclear Information System (INIS)

    Moldarev, B.L.; Aronzon, M.E.; Adanin, V.M.; Zyakun, A.M.

    1986-01-01

    The reaction of 4-benzyliden-1-phenyl-3,5-dioxopyrazolidines with alkyl halides in the presence of sodium alkoxide gave 1-phenyl-2-alkyl-4-benzyliden- and 1-phenyl-2,4-dialkyl-4-(α-alkoxybenzyl)-3,4-dioxopyrazolines. The structures of these compounds were confirmed by UV, IR, and PMR spectroscopy, and by mass-spectrometry

  5. Epigenetic reactivation of RASSF1A by phenethyl isothiocyanate (PEITC) and promotion of apoptosis in LNCaP cells.

    Science.gov (United States)

    Boyanapalli, Sarandeep S S; Li, Wenji; Fuentes, Francisco; Guo, Yue; Ramirez, Christina N; Gonzalez, Ximena-Parades; Pung, Douglas; Kong, Ah-Ng Tony

    2016-12-01

    Epigenetic silencing of tumor suppressor genes is a phenomenon frequently observed in multiple cancers. Ras-association domain family 1 isoform A (RASSF1A) is a well-characterized tumor suppressor that belongs to the Ras-association domain family. Several studies have demonstrated that hypermethylation of the RASSF1A promoter is frequently observed in lung, prostate, and breast cancers. Phenethyl isothiocyanate (PEITC), a phytochemical abundant in cruciferous vegetables, possesses chemopreventive activities; however, its potential involvement in epigenetic mechanisms remains elusive. The present study aimed to examine the role of PEITC in the epigenetic reactivation of RASSF1A and the induction of apoptosis in LNCaP cells. LNCaP cells were treated for 5days with 0.01% DMSO, 2.5 or 5μM PETIC or 2.5μM azadeoxycytidine (5-Aza) with 0.5μM trichostatin A (TSA). We evaluated the effects of these treatments on CpG demethylation using methylation-specific polymerase chain reaction (MSP) and bisulfite genomic sequencing (BGS). CpG demethylation was significantly enhanced in cells treated with 5μM PEITC and 5-Aza+TSA; therefore, the latter treatment was used as a positive control in subsequent experiments. The decrease in RASSF1A promoter methylation correlated with an increase in expression of the RASSF1A gene in a dose-dependent manner. To confirm that promoter demethylation was mediated by DNA methyltransferases (DNMTs), we analyzed the expression levels of DNMTs and histone deacetylases (HDACs) at the gene and protein levels. PEITC reduced DNMT1, 3A and 3B protein levels in a dose-dependent manner, and 5μM PEITC significantly reduced DNMT3A and 3B protein levels. HDAC1, 2, 4 and 6 protein expression was also inhibited by 5μM PEITC. The combination of 5-Aza and TSA, a DNMT inhibitor and a HDAC inhibitor, respectively, was used as a positive control as this treatment significantly inhibited both HDACs and DNMTs. The function of RASSF1A reactivation in promoting

  6. Surface-immobilized DNAzyme-type biocatalysis

    Science.gov (United States)

    Stefan, Loic; Lavergne, Thomas; Spinelli, Nicolas; Defrancq, Eric; Monchaud, David

    2014-02-01

    The structure of the double helix of deoxyribonucleic acid (DNA, also called duplex-DNA) was elucidated sixty years ago by Watson, Crick, Wilkins and Franklin. Since then, DNA has continued to hold a fascination for researchers in diverse fields including medicine and nanobiotechnology. Nature has indeed excelled in diversifying the use of DNA: beyond its canonical role of repository of genetic information, DNA could also act as a nanofactory able to perform some complex catalytic tasks in an enzyme-mimicking manner. The catalytic capability of DNA was termed DNAzyme; in this context, a peculiar DNA structure, a quadruple helix also named quadruplex-DNA, has recently garnered considerable interest since its autonomous catalytic proficiency relies on its higher-order folding that makes it suitable to interact efficiently with hemin, a natural cofactor of many enzymes. Quadruplexes have thus been widely studied for their hemoprotein-like properties, chiefly peroxidase-like activity, i.e., their ability to perform hemin-mediated catalytic oxidation reactions. Recent literature is replete with applications of quadruplex-based peroxidase-mimicking DNAzyme systems. Herein, we take a further leap along the road to biochemical applications, assessing the actual efficiency of catalytic quadruplexes for the detection of picomolar levels of surface-bound analytes in an enzyme-linked immunosorbent (ELISA)-type assay. To this end, we exploit an innovative strategy based on the functionalization of DNA by a multitasking platform named RAFT (for regioselectivity addressable functionalized template), whose versatility enables the grafting of DNA whatever its nature (duplex-DNA, quadruplex-DNA, etc.). We demonstrate that the resulting biotinylated RAFT/quadruplex systems indeed acquire catalytic properties that allow for efficient luminescent detection of picomoles of surface-bound streptavidin. We also highlight some of the pitfalls that have to be faced during optimization, notably demonstrating that highly optimized experimental conditions can make DNA pre-catalysts catalytically competent whatever their secondary structures.

  7. Electrochemical characterization of azo dye (E)-1-(4-((4-(phenylamino)phenyl)diazenyl)phenyl)ethanone (DPA)

    International Nuclear Information System (INIS)

    Surucu, Ozge; Abaci, Serdar; Seferoğlu, Zeynel

    2016-01-01

    Highlights: • Electrochemical characterization of azo dye DPA was performed. • Pencil graphite electrode was used as working electrode. • Cyclic voltammetry was used to determine the effect of scan rate and pH. • Chronoamperometry was used to determine diffusion constant. • Square wave voltammetry verified the results of cyclic voltammetry. - Abstract: An enormous range of possible dyes are available, especially as the starting molecules are readily available and cheap. As other dye classes become less viable from either an environmental or economic reasons, azo dyes come to the forefront. Therefore, electrochemical characterization of a novel synthesized azo dye (E)-1-(4-((4-(phenylamino) phenyl)diazenyl)phenyl)ethanone was achieved for the first time. Cyclic voltammetry, chronoamperometry and square wave voltammetry techniques were used to investigate the electrochemical behavior and electrocatalytic effect of azo dye (E)-1-(4-((4-(phenylamino) phenyl)diazenyl)phenyl)ethanone at pencil graphite electrode. Cyclic voltammograms were utilized to determine the effect of scan rate and pH on the peak current and peak potential. Chronoamperometry technique was used to determine diffusion constant, D and the type of adsorption isotherms. The kinetics parameters which were the apparent electron transfer rate constant, k s and charge transfer coefficient, α were calculated. Square wave voltammetry was used to verify responses of cyclic voltammetry technique.

  8. Sulfonation of alkyl phenyl ether self-assembled monolayers.

    Science.gov (United States)

    Katash, Irit; Luo, Xianglin; Sukenik, Chaim N

    2010-02-02

    The sulfonation of phenyl ether decorated self-assembled monolayers (SAMs) was studied with an eye toward creating surfaces with a particularly high negative charge density based on a close-packed array of phenyl rings with more than one sulfonic acid group per molecule. The product distribution and kinetics of this process were studied by ultraviolet, infrared, and photoelectron spectroscopies and by monitoring changes in the thickness and wetting properties of the SAM. The sulfonation chemistry could be effected without undermining monolayer integrity and the isomer distribution of ortho- and para-monosulfonated material, along with the percentages of mono- and disulfonated molecules could be established throughout the process. As doubly sulfonated molecules appeared, the reaction slowed drastically. Ultimately, sulfonation stops completely with approximately 60% of the molecules disulfonated and 20% each of the two monosulfonated isomers. This striking constraint on monolayer reactivity and the relationship between the surface chemistry and variations in SAM structure are discussed.

  9. Synthesis of (1,213C)-2-chloroethyl phenyl sulfide

    International Nuclear Information System (INIS)

    Taber, D.F.; Yanong Wang

    1995-01-01

    Incorporation of a double 13 C label into the mustard 2-chloroethyl phenyl sulfide is straightforward, but analysis is complicated by 13 C- 13 C coupling. An alternative is reported, in which the ease of scrambling of sulfur mustards is used to advantage to prepare precisely 50% (1, 2- 13 C) enriched with each carbon of the ethyl chain labelled to provide optimal signal to noise in the 13 C spectrum. (author)

  10. The mechanochemical production of phenyl cations through heterolytic bond scission.

    Science.gov (United States)

    Shiraki, Tomohiro; Diesendruck, Charles E; Moore, Jeffrey S

    2014-01-01

    High mechanical forces applied to polymeric materials typically induce unselective chain scission. For the last decade, mechanoresponsive molecules, mechanophores, have been designed to harness the mechanical energy applied to polymers and provide a productive chemical response. The selective homolysis of chemical bonds was achieved by incorporating peroxide and azo mechanophores into polymer backbones. However, selective heterolysis in polymer mechanochemistry is still mostly unachieved. We hypothesized that highly polarized bonds in ionic species are likely to undergo heterolytic bond scission. To test this, we examined a triarylsulfonium salt (TAS) as a mechanophore. Poly(methyl acrylate) possessing TAS at the center of the chain (PMA-TAS) is synthesized by a single electron transfer living radical polymerization (SET-LRP) method. Computational and experimental studies in solution reveal the mechanochemical production of phenyl cations from PMA-TAS. Interestingly, the generated phenyl cation reacts with its counter-anion (trifluoromethanesulfonate) to produce a terminal trifluoromethyl benzene structure that, to the best of our knowledge, is not observed in the photolysis of TAS. Moreover, the phenyl cation can be trapped by the addition of a nucleophile. These findings emphasize the interesting reaction pathways that become available by mechanical activation.

  11. Fragrance material review on 4-phenyl-3-buten-2-ol.

    Science.gov (United States)

    Scognamiglio, J; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 4-phenyl-3-buten-2-ol when used as a fragrance ingredient is presented. 4-Phenyl-3-buten-2-ol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a secondary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 4-phenyl-3-buten-2-ol were evaluated then summarized and includes physical properties, and genotoxicity data. A safety assessment of the entire Aryl Alkyl Alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Aryl Alkyl Alcohols in fragrances. Copyright © 2011 Elsevier Ltd. All rights reserved.

  12. Fragrance material review on 2-methyl-4-phenyl-2-butanol.

    Science.gov (United States)

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butanol when used as a fragrance ingredient is presented. 2-methyl-4-phenyl-2-butanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a tertiary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-4-phenyl-2-butanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, and skin sensitization data. A safety assessment of the entire Aryl Alkyl Alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Aryl Alkyl Alcohols in fragrances. assessment of aryl alkyl alcohols when used as fragrance ingredients. Copyright © 2011 Elsevier Ltd. All rights reserved.

  13. Synthesis and Characterization of 9-Phenyl-9H-purin-6-amines from 5-Amino-1-phenyl-1H-imidazole-4-carbonitriles

    Directory of Open Access Journals (Sweden)

    Asieh Yahyazadeh

    2007-01-01

    Full Text Available 9-Phenyl-9H-purin-6-amine derivatives have been synthesized in high yields by reaction between 5-amino-1-phenyl-1H-imidazole-4-carbonitrile with HC(OEt3 and Ac2O followed by reaction with ammonia.

  14. Caffeic acid phenethyl ester inhibits 3-MC-induced CYP1A1 expression through induction of hypoxia-inducible factor-1α

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Hyung Gyun [Department of Toxicology, College of Pharmacy, Chungnam National University, Daejeon (Korea, Republic of); Han, Eun Hee [Division of Life Science, Korea Basic Science Institute, Daejeon (Korea, Republic of); Im, Ji Hye; Lee, Eun Ji; Jin, Sun Woo [Department of Toxicology, College of Pharmacy, Chungnam National University, Daejeon (Korea, Republic of); Jeong, Hye Gwang, E-mail: hgjeong@cnu.ac.kr [Department of Toxicology, College of Pharmacy, Chungnam National University, Daejeon (Korea, Republic of)

    2015-09-25

    Caffeic acid phenethyl ester (CAPE), a natural component of propolis, is reported to have anticarcinogenic properties, although its precise chemopreventive mechanism remains unclear. In this study, we examined the effects of CAPE on 3-methylcholanthrene (3-MC)-induced CYP1A1 expression and activities. CAPE reduced the formation of the benzo[a]pyrene-DNA adduct. Moreover, CAPE inhibited 3-MC-induced CYP1A1 activity, mRNA expression, protein level, and promoter activity. CAPE treatment also decreased 3-MC-inducible xenobiotic-response element (XRE)-linked luciferase, aryl hydrocarbons receptor (AhR) transactivation and nuclear localization. CAPE induced hypoxia inducible factor-1α (HIF-1α) protein level and HIF-1α responsible element (HRE) transcriptional activity. CAPE-mediated HIF-1α reduced 3-MC-inducible CYP1A1 protein expression. Taken together, CAPE decreases 3-MC-mediated CYP1A1 expression, and this inhibitory response is associated with inhibition of AhR and HIF-1α induction. - Highlights: • CAPE reduced the formation of the benzo[a]pyrene-DNA adduct. • CAPE inhibited 3-MC-induced CYP1A1 expression. • CAPE induced HIF-1α induction. • CAPE-mediated HIF-1α reduced 3-MC-inducible CYP1A1 expression.

  15. Caffeic Acid Phenethyl Ester and Ethanol Extract of Propolis Induce the Complementary Cytotoxic Effect on Triple-Negative Breast Cancer Cell Lines

    Directory of Open Access Journals (Sweden)

    Anna Rzepecka-Stojko

    2015-05-01

    Full Text Available Chemotherapy of breast cancer could be improved by bioactive natural substances, which may potentially sensitize the carcinoma cells’ susceptibility to drugs. Numerous phytochemicals, including propolis, have been reported to interfere with the viability of carcinoma cells. We evaluated the in vitro cytotoxic activity of ethanol extract of propolis (EEP and its derivative caffeic acid phenethyl ester (CAPE towards two triple-negative breast cancer (TNBC cell lines, MDA-MB-231 and Hs578T, by implementation of the MTT and lactate dehydrogenase (LDH assays. The morphological changes of breast carcinoma cells were observed following exposure to EEP and CAPE. The IC50 of EEP was 48.35 µg∙mL−1 for MDA-MB-23 cells and 33.68 µg∙mL−1 for Hs578T cells, whereas the CAPE IC50 was 14.08 µM and 8.01 µM for the MDA-MB-231 and Hs578T cell line, respectively. Here, we report that propolis and CAPE inhibited the growth of the MDA-MB-231 and Hs578T lines in a dose-dependent and exposure time-dependent manner. EEP showed less cytotoxic activity against both types of TNBC cells. EEP and, particularly, CAPE may markedly affect the viability of breast cancer cells, suggesting the potential role of bioactive compounds in chemoprevention/chemotherapy by potentiating the action of standard anti-cancer drugs.

  16. Caffeic Acid Phenethyl Ester Inhibits Oral Cancer Cell Metastasis by Regulating Matrix Metalloproteinase-2 and the Mitogen-Activated Protein Kinase Pathway

    Directory of Open Access Journals (Sweden)

    Chih-Yu Peng

    2012-01-01

    Full Text Available Caffeic acid phenethyl ester (CAPE, an active component extracted from honeybee hives, exhibits anti-inflammatory and anticancer activities. However, the molecular mechanism by which CAPE affects oral cancer cell metastasis has yet to be elucidated. In this study, we investigated the potential mechanisms underlying the effects of CAPE on the invasive ability of SCC-9 oral cancer cells. Results showed that CAPE attenuated SCC-9 cell migration and invasion at noncytotoxic concentrations (0 μM to 40 μM. Western blot and gelatin zymography analysis findings further indicated that CAPE downregulated matrix metalloproteinase-2 (MMP-2 protein expression and inhibited its enzymatic activity. CAPE exerted its inhibitory effects on MMP-2 expression and activity by upregulating tissue inhibitor of metalloproteinase-2 (TIMP-2 and potently decreased migration by reducing focal adhesion kinase (FAK phosphorylation and the activation of its downstream signaling molecules p38/MAPK and JNK. These data indicate that CAPE could potentially be used as a chemoagent to prevent oral cancer metastasis.

  17. Physicochemical studies of a newly synthesized molecule, 6-methyl-3-phenethyl-3,4-dihydro-1H-quinazoline-2-thione (JSH18) for topical formulations.

    Science.gov (United States)

    Kim, Sujin; Jung, Sang-Hun; Cho, Cheong-Weon

    2008-10-01

    A new molecule having the structure of 6-methyl-3-phenethyl-3,4-dihydro-1H-quinazoline-2-thione (JSH18) was synthesized and possibly presupposed to show depigmentation through the inhibition of tyrosinase which is involved in formation of melanin. Therefore, we are going to develop JSH18 as an inhibitor of melanin synthesis with topical formulations to show its optimal efficiency for skin whitening based on preformulation studies. The preformulation to figure out the physicochemical properties was done by solubility measurements, differential scanning calorimetry study, scanning electron microscopy as well as cell viability assay and skin retention study. Through solubility test, glycofurol, N-methyl pyrrolidones, and isopropanol showed best solubilizing effects. JSH18 showed a strong single endothermic peak at 180.6 degrees C and its millimeter-sized particles could be reduced by grinding suggesting the improvement of solubility. Interestingly, the cytotoxicity of JSH18 was different according to the cell origin type. JSH 18 showed the cell viability at the concentration of 4 uM in human keratinocyte HacaT cells but that was suddenly dropped at the concentration of 400 uM in murine keratinocyte PAM212 cells. Based on above preformulation results, formulation studies of JSH18 will be performed for the development of topical formulations in future.

  18. Cooperative Reinforcement of Ionic Liquid and Reactive Solvent on Enzymatic Synthesis of Caffeic Acid Phenethyl Ester as an In Vitro Inhibitor of Plant Pathogenic Bacteria.

    Science.gov (United States)

    Xu, Yan; Sheng, Sheng; Liu, Xi; Wang, Chao; Xiao, Wei; Wang, Jun; Wu, Fu-An

    2017-01-02

    It is widely believed that lipases in ionic liquids (ILs) possess higher enzyme activity, stability and selectivity; however, reaction equilibrium is always limited by product inhibition, and the product is difficult to separate from non-volatile ILs using distillation. To solve this problem, using trialkylphosphine oxide (TOPO) as a complexing agent, a novel biphase of reactive solvent and IL was firstly reported for caffeic acid phenethyl ester (CAPE) production from methyl caffeate (MC) and 2-phenylethanol (PE) catalyzed by lipase via transesterification. The effects of the reaction parameters and their action mechanism were investigated, and the inhibition of CAPE against bacterial wilt pathogen Ralstonia solanacearum was firstly measured. The MC conversion of 98.83% ± 0.76% and CAPE yield of 96.29% ± 0.07% were obtained by response surface methodology in the 25 g/L TOPO-cyclohexane/[Bmim][Tf₂N] (1:1, v / v ); the complex stoichiometry calculation and FTIR spectrum confirmed that the reversible hydrogen-bond complexation between TOPO and caffeates significantly enhances the cooperative effect of two phases on the lipase-catalyzed reaction. The temperature was reduced by 14 °C; the MC concentration increased by 3.33-fold; the ratio of catalyst to donor decreased by 4.5-fold; and K m decreased 1.08-fold. The EC 50 of CAPE against R. solanacearum was 0.17-0.75 mg/mL, suggesting that CAPE is a potential in vitro inhibitor of plant pathogenic bacteria.

  19. Rapid Analysis Procedures for Triglycerides and Fatty Acids as Pentyl and Phenethyl Esters for the Detection of Butter Adulteration Using Chromatographic Techniques

    Directory of Open Access Journals (Sweden)

    Daniele Naviglio

    2017-01-01

    Full Text Available This paper presents the development of three methods for quality control, fraud detection, and authentication of butter fat and other oils/fats using chromatographic techniques, with one method for triglycerides and two methods for fatty acids (FAs. The procedure for the analysis of triglycerides requires only dissolution of the sample in n-hexane and gas chromatography (GC analysis using a capillary column. The second method is based on the transesterification of triglycerides as pentyl esters in a single-step reaction using sodium pentanoate in pentanol. The reaction proceeds at room temperature and is similar to the potassium hydroxide-catalysed transesterification of triglycerides with methanol and even more similar to the sodium methoxide method and sodium butanoate method. The advantage of using pentyl esters includes reducing the volatility of short-chain FAs, and substantial recoveries were obtained compared with methyl ester analysis. The third method involves the transesterification of triglycerides in fat through reaction with 2-phenylethanol in a single step; 2-phenylethanol possesses a chromophore, and the phenethyl esters formed are analysed by high-performance liquid chromatography (HPLC with UV detection.

  20. Effect of caffeic acid phenethyl ester on oxidant and anti-oxidant status of liver and serum in a rat model with acute methanol intoxication.

    Science.gov (United States)

    Yazgan, Ü C; Elbey, B; Kuş, S; Baykal, B; Keskin, I; Yılmaz, A; Şahin, A

    2017-05-01

    Methanol toxicity is one of the major public health problems because it can cause severe morbidity and mortality. Methanol intoxication causes changes in the balance between the production of free radicals and antioxidant capacity. We aimed to investigate the effects of caffeic acid phenethyl ester (CAPE) on the total oxidant status, total antioxidant status (TAS), and oxidative stress index (OSI) parameters of the liver and the serum in a rat model of acute methanol intoxication. Rats were treated with intraperitoneal (i.p.) Methotrexate (MTX) for 7 days. On the 8th day, i.p. Methanol was administered in the methanol, ethanol and CAPE groups. Four hours after methanol treatment, ethanol was injected i.p. in the ethanol group; CAPE (i.p.) in the CAPE group; serum physiologic i.p. in other groups. After 8 hours, rats were killed and the serum and the liver samples were obtained for biochemical analyses. The OSI value was significantly higher in the methanol group compared to the ethanol and CAPE groups. Serum TAS levels of the methanol group were significantly different compared to the control group, but not compared to the MTX group. The amelioration of oxidative stress was greater in the CAPE group compared to the ethanol group but was not statistically significant. This study demonstrates that CAPE treatment ameliorates oxidative stress in the serum and liver in a rat model of acute methanol intoxication.

  1. Phenethyl isothiocyanate inhibits proliferation and induces apoptosis in pancreatic cancer cells in vitro and in a MIAPaca2 xenograft animal model.

    Science.gov (United States)

    Stan, Silvia D; Singh, Shivendra V; Whitcomb, David C; Brand, Randall E

    2014-01-01

    Pancreatic cancer is often diagnosed at an advanced stage and it has a poor prognosis that points to an increased need to develop effective chemoprevention strategies for this disease. We examined the ability of phenethyl isothiocyanate (PEITC), a naturally occurring isothiocyanate found in cruciferous vegetables, to inhibit the growth of pancreatic cancer cells in vitro and in a MIAPaca2 xenograft animal model. Exposure to PEITC inhibited pancreatic cancer cell growth in a dose-dependent manner, with an IC50 of approximately 7 μmol/L. PEITC treatment induced G2/M phase cell cycle arrest, downregulated the antiapoptotic proteins Bcl-2 and Bcl-XL, upregulated the proapoptotic protein Bak, and suppressed Notch 1 and 2 levels. In addition, treatment with PEITC induced cleavage of poly-(ADP-ribose) polymerase and led to increased cytoplasmic histone-associated DNA fragmentation and subdiploid (apoptotic) fraction in pancreatic cancer cells. Oral administration of PEITC suppressed the growth of pancreatic cancer cells in a MIAPaca2 xenograft animal model. Our data show that PEITC exerts its inhibitory effect on pancreatic cancer cells through several mechanisms, including G2/M phase cell cycle arrest and induction of apoptosis, and supports further investigation of PEITC as a chemopreventive agent for pancreatic cancer.

  2. 1-Acetyl-5-ferrocenyl-3-phenyl-2-pyrazoline

    Directory of Open Access Journals (Sweden)

    Orhan Büyükgüngör

    2009-02-01

    Full Text Available In the title compound, [Fe(C5H5(C16H15N2O], the pyrazoline ring and the phenyl ring are nearly coplanar, making a dihedral angle of 6.54 (2°, while the substituted cyclopentadienyl ring is twisted out of the pyrazoline ring plane by 81.32 (1°. The molecules in the crystal structure are held together by weak C—H...O intermolecular hydrogen bonds and two C—H...π interactions.

  3. N-{2-[N-(4-Methylphenyloxamoyl]phenyl}propanamide

    Directory of Open Access Journals (Sweden)

    Humayun Pervez

    2010-07-01

    Full Text Available The title compound, C18H18N2O3, is the product of the heterocyclic ring cleavage at position 2 of 1-propionylisatin. Two centrosymmetric cyclic motifs, viz. R22(14 and R22(18, are formed by N—H...O hydrogen bonds with the propanamide and aminophenyl units, respectively, as the N—H donors. These motifs combine into two C22(8 chain motifs parallel to the b axis. The chain structure is stabilized by C—H...π interactions between the benzene rings, where C—H is from the phenyl ring of the cleaved part of 1-propionylisatin.

  4. Polymerization of N-(fluoro phenyl) maleimides. [. gamma. radiation

    Energy Technology Data Exchange (ETDEWEB)

    Barrales-Rienda, J.M.; Ramos, J.G.; Chaves, M.S.

    1979-01-01

    Poly(N-aryl maleimide)s of characteristic structures have been synthesized and some of their physical properties studied. The polymerization of N-(fluoro phenyl) maleimides by free-radical initiation in bulk or in solution and by anionic catalyst have been studied to compare the characteristics of polymerization by ..gamma..-ray irradiation with that by free-radical initiation. The polymers were characterized by elemental analysis, intrinsic viscosity, spectroscopy (IR and NMR), programmed thermogravimetric analysis, and x-ray diffraction. Spectra of polymers prepared by radiation and anionic polymerization were nearly identical with those of polymers prepared by free-radical polymerization initiated by azobisisobutyronitrile in bulk or in solution and by the self-initiated thermal polymerization. A variety of reaction conditions were tried, but all attempts to change the molecular structure of the polymers were unsuccessful. Rates of thermal degradation for poly(N-(fluoro phenyl) maleimide)s have been analyzed by using a multiple-heating-rate procedure. Overall activation energy, order of reaction, and frequency factor have been evaluated. 6 figures, 8 tables.

  5. Red Emitting Phenyl-Polysiloxane Based Scintillators for Neutron Detection

    International Nuclear Information System (INIS)

    Dalla Palma, Matteo; Quaranta, Alberto; Marchi, Tommaso; Gramegna, Fabiana; Cinausero, Marco; Carturan, Sara; Collazuol, Gianmaria

    2013-06-01

    In this work, the performances of new red emitting phenyl- substituted polysiloxane based scintillators are described. Three dyes were dispersed in a phenyl-polysiloxane matrix in order to shift the scintillation wavelength towards the red part of the visible spectrum. PPO, Lumogen Violet (BASF) and Lumogen Red (BASF) were mixed to the starting resins with different wt. % and the analysis of the different samples was performed by means of fluorescence measurements. The scintillation yield to alpha particles at the different dye ratios was monitored by detecting either the full spectrum or the red part of the emitted light. Finally, thin red scintillators with selected compositions were coupled to Avalanche Photodiode sensors, which are usually characterized by higher efficiency in the red part of the spectrum. An increased light output of about 17% has been obtained comparing the red scintillators to standard blue emitting systems. Preliminary results on the detection of fast neutrons with the APD-red scintillator system are also presented. (authors)

  6. Ideal gas thermodynamic properties for the phenyl, phenoxy, and o-biphenyl radicals

    Science.gov (United States)

    Burcat, A.; Zeleznik, F. J.; Mcbride, B. J.

    1985-01-01

    Ideal gas thermodynamic properties of the phenyl and o-biphenyl radicals, their deuterated analogs and the phenoxy radical were calculated to 5000 K using estimated vibrational frequencies and structures. The ideal gas thermodynamic properties of benzene, biphenyl, their deuterated analogs and phenyl were also calculated.

  7. 2-(4-Methylpiperazin-1-yl-4-phenyl-6-(thiophen-2-yl-pyridine-3-carbonitrile

    Directory of Open Access Journals (Sweden)

    Nawal Mishriky

    2013-02-01

    Full Text Available 2-(4-Methylpiperazin-1-yl-4-phenyl-6-(thiophen-2-yl-pyridine-3-carbonitrile (4 was synthesized via nucleophilic substitution reaction of 1-methylpiperazine with 2-bromo analogue 3. The latter was obtained through bromination (Br2/AcOH of 2-[3-oxo-1-phenyl-3-(thiophen-2-ylpropyl]malononitrile (2.

  8. Phenyl-β-D-glucopyranoside and Phenyl-β-D-galactopyranoside Dimers: Small Structural Differences but Very Different Interactions

    Directory of Open Access Journals (Sweden)

    Imanol Usabiaga

    2018-02-01

    Full Text Available We report a combination of laser spectroscopy in molecular jets and quantum mechanical calculations to characterize the aggregation preferences of phenyl-β-D-glucopyranoside (β-PhGlc and phenyl-β-D-galactopyranoside (β-PhGal homodimers. At least two structures of β-PhGlc dimer were found maintaining the same intramolecular interactions of the monomers, but with additional intermolecular interactions between the hydroxyl groups. Several isomers were also found for the dimer of β-PhGal forming extensive hydrogen bond networks between the interacting molecules, of very different shape. All the species found present several CH•••π and OH•••π interactions that add stability to the aggregates. The results show how even the smallest change in a substituent, from axial to equatorial position, plays a decisive role in the formation of the dimers. These conclusions reinforce the idea that the small structural changes between sugar units are amplified by formation of intra and intermolecular hydrogen bond networks, helping other molecules (proteins, receptors to easily read the sugar code of glycans.

  9. Cooperative Reinforcement of Ionic Liquid and Reactive Solvent on Enzymatic Synthesis of Caffeic Acid Phenethyl Ester as an In Vitro Inhibitor of Plant Pathogenic Bacteria

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    Yan Xu

    2017-01-01

    Full Text Available It is widely believed that lipases in ionic liquids (ILs possess higher enzyme activity, stability and selectivity; however, reaction equilibrium is always limited by product inhibition, and the product is difficult to separate from non-volatile ILs using distillation. To solve this problem, using trialkylphosphine oxide (TOPO as a complexing agent, a novel biphase of reactive solvent and IL was firstly reported for caffeic acid phenethyl ester (CAPE production from methyl caffeate (MC and 2-phenylethanol (PE catalyzed by lipase via transesterification. The effects of the reaction parameters and their action mechanism were investigated, and the inhibition of CAPE against bacterial wilt pathogen Ralstonia solanacearum was firstly measured. The MC conversion of 98.83% ± 0.76% and CAPE yield of 96.29% ± 0.07% were obtained by response surface methodology in the 25 g/L TOPO-cyclohexane/[Bmim][Tf2N] (1:1, v/v; the complex stoichiometry calculation and FTIR spectrum confirmed that the reversible hydrogen-bond complexation between TOPO and caffeates significantly enhances the cooperative effect of two phases on the lipase-catalyzed reaction. The temperature was reduced by 14 °C; the MC concentration increased by 3.33-fold; the ratio of catalyst to donor decreased by 4.5-fold; and Km decreased 1.08-fold. The EC50 of CAPE against R. solanacearum was 0.17–0.75 mg/mL, suggesting that CAPE is a potential in vitro inhibitor of plant pathogenic bacteria.

  10. Phenethyl Isothiocyanate Induces Apoptotic Cell Death Through the Mitochondria-dependent Pathway in Gefitinib-resistant NCI-H460 Human Lung Cancer Cells In Vitro.

    Science.gov (United States)

    Hsia, Te-Chun; Huang, Yi-Ping; Jiang, Yi-Wen; Chen, Hsin-Yu; Cheng, Zheng-Yu; Hsiao, Yung-Ting; Chen, Cheng-Yen; Peng, Shu-Fen; Chueh, Fu-Shin; Chou, Yu-Cheng; Chung, Jing-Gung

    2018-04-01

    Some lung cancer patients treated with gefitinib develop resistance to this drug resulting in unsatisfactory treatment outcomes. Phenethyl isothiocyanate (PEITC), present in our common cruciferous vegetables, exhibits anticancer activities in many human cancer cell lines. Currently, there is no available information on the possible modification of gefitinib resistance of lung cancer in vitro by PEITC. Thus, the effects of PEITC on gefitinib resistant lung cancer NCI-H460 cells were investigated in vitro. The total cell viability, apoptotic cell death, production of reactive oxygen species (ROS) and Ca 2+ , levels of mitochondria membrane potential (ΔΨ m ) and caspase-3, -8 and -9 activities were measured by flow cytometry assay. PEITC induced chromatin condensation was examined by DAPI staining. PEITC-induced cell morphological changes, decreased total viable cell number and induced apoptotic cell death in NCI-H460 and NCI-H460/G cells. PEITC decreased ROS production in NCI-H460 cells, but increased production in NCI-H460/G cells. PEITC increased Ca 2+ production, decreased the levels of ΔΨ m and increased caspase-3, -8 and -9 activities in both NCI-H460 and NCI-H460/G cells. Western blotting was used to examine the effect of apoptotic cell death associated protein expression in NCI-H460 NCI-H460/G cells after exposure to PEITC. Results showed that PEITC increased expression of cleaved caspase-3, PARP, GADD153, Endo G and pro-apoptotic protein Bax in NCI-H460/G cells. Based on these results, we suggest that PEITC induces apoptotic cell death via the caspase- and mitochondria-dependent pathway in NCI-H460/G cells. Copyright© 2018, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.

  11. Biophysical properties of phenyl succinic acid derivatised hyaluronic acid

    DEFF Research Database (Denmark)

    Neves-Petersen, Maria Teresa; Klitgaard, Søren; Skovsen, Esben

    2010-01-01

    Modification of hyaluronic acid (HA) with aryl succinic anhydrides results in new biomedical properties of HA as compared to non-modified HA, such as more efficient skin penetration, stronger binding to the skin, and the ability to blend with hydrophobic materials. In the present study, hyaluronic...... acid has been derivatised with the anhydride form of phenyl succinic acid (PheSA). The fluorescence of PheSA was efficiently quenched by the HA matrix. HA also acted as a singlet oxygen scavenger. Fluorescence lifetime(s) of PheSA in solution and when attached to the HA matrix has been monitored...... with ps resolved streak camera technology. Structural and fluorescence properties changes induced on HA-PheSA due to the presence of singlet oxygen were monitored using static light scattering (SLS), steady state fluorescence and ps time resolved fluorescence studies. SLS studies provided insight...

  12. SYNTHESIS OF ALLYL PHENYL ETHER AND CLAISEN REARRANGEMENT

    Directory of Open Access Journals (Sweden)

    Gagik Torosyan

    2011-12-01

    Full Text Available It has been established the possibility for phenol allylation on natural zeolites and them analogs. Here is demonstrated the synthesis of allyl phenol, which has wide industrial applications. The offered method in comparison with the traditional methods has more advantages – higher selectivity, smaller material and power resources consumption. It has been obtained the mixture of allylating phenols (30% in general with allyl phenyl ether (1 with 80% yields. At 600 K is obtained allylphenyl ether, at 700 K beginning the formation of allyl phenols, which is the result of direct C-allylation of the aromatic ring. It has been investigated the possibility of Claisen rearrangement in the same conditions. All of that are established by gas-liquid chromatography and liquid chromatography data.

  13. The Exotic Excited State Behavior of 3-PHENYL-2-PROPYNENITRILE

    Science.gov (United States)

    Jawad, Khadija M.; Viquez Rojas, Claudia I.; Slipchenko, Lyudmila V.; Zwier, Timothy S.

    2017-06-01

    3-phenyl-2-propynenitrile (Ph-C≡C-C≡N) is of interest to the study of Titan's atmosphere as it is a likely product of the photochemical reaction between two known species in that environment: benzene and cyanoacetylene. The gas phase jet-cooled resonant two-photon ionization, laser induced fluorescence, and preliminary dispersed fluorescence spectra were previously reported without firm assignments due to the scarcity of totally symmetric vibrations and the prevalence of strong bands of b2 and b1 symmetry vibrations. These had called into question the identity and geometry of the excited state(s) involved in the transitions. We will here present the completed set of dispersed fluorescence data along with an analysis of the potential energy surfaces and vibronic coupling characteristic of the close-lying excited states in this intriguing molecule.

  14. Enhanced biological activity of carotenoids stabilized by phenyl groups.

    Science.gov (United States)

    You, Ji Suk; Jeon, Sunhwa; Byun, Youn Jung; Koo, Sangho; Choi, Shin Sik

    2015-06-15

    Carotenoids are lipid soluble food ingredients with multifunction including antioxidant and anticancer activities. However, carotenoids are destructively oxidized upon reaction with radicals resulting in toxic effects on biological systems. Two synthetic carotenoids (BAS and BTS) containing the aromatic phenyl groups with a para-substituent (OMe and Me, respectively) at C-13 and C-13' position were prepared in order to overcome a structural instability of carotenoid. Both BAS and BTS exerted stronger radical scavenging activity than β-carotene in DPPH and ABTS assays. In particular, BTS significantly reduced in vivo ROS (reactive oxygen species) levels and improved body growth and reproduction of Caenorhabditiselegans. BTS has a great potential for the advanced and modified carotenoid material with stability leading to enhanced bioavailability. Copyright © 2015 Elsevier Ltd. All rights reserved.

  15. 1-Methyl-5-nitro-3-phenyl-1H-indazole

    Directory of Open Access Journals (Sweden)

    Mohammed Naas

    2016-06-01

    Full Text Available The title compound, C14H11N3O2, crystallizes with two molecules in the asymmetric unit. The indazole ring system and the nitro group are nearly coplanar, with the largest deviations from the mean plane being 0.070 (4 Å in one molecule and 0.022 (3 Å in the second. The dihedral angle between the mean plane through the phenyl ring and the mean plane of the indazole ring system is of 23.24 (18° in the first molecule and 26.87 (18° in the second. In the crystal, molecules are linked by two C—H...O hydrogen bonds, forming linear zigzag tapes running along the c-axis direction, and by π–π stacking of molecules along the b axis, generating a three-dimensional structure.

  16. Crystal structures and quantum chemical calculations of dichloro[4-(dimethylamino)phenyl]arsine and tris[4-(dimethylamino)phenyl]arsine

    Science.gov (United States)

    Bani-Fwaz, Mutasem Z.; Fazary, Ahmed E.; Becker, Gerd

    2017-12-01

    Dichloro[4-(dimethylamino)phenyl]arsine (1) and tris[4-(dimethylamino)phenyl]arsine (2) were synthesized and characterized using single crystal X-ray diffraction studies, NMR spectroscopy, IR spectroscopy and elemental analyses techniques. The X-ray structure analysis of 1 (P1bar , triclinic, Z = 4; R1 = 0.0478) revealed two crystallographically independent molecules in the asymmetric part of the unit cell. The average Assbnd Cl bond (220.6 p.m.) is found to be slightly longer than that of arsenic(III) chloride (216.1 or 216.2 p.m.), but to be rather similar to that in the orthorhombic modification of chlorobis[2,4,6-tris(trifluoromethyl)phenyl]arsine (219.2 p.m.). Mean As-Caryl (191.7 p.m.) and Caryl-N bond lengths (135.9 p.m.) suggest extended electronic interactions between the dichloroarsanyl group, the π-electron system of the arene ring and the nitrogen lone pair. In both molecules the nitrogen atoms are found in a planar coordination sphere; the sums of bond angles vary only slightly between 359.1° for 1a and 359.9° for 1b. In contrast to these observations, sums of bond angles of 292.7° for 1a and 293.98° for 1b indicate a pyramidal coordination sphere at arsenic. As well, the X-ray structure analysis of 2 (P1bar , triclinic, Z = 2; R1 = 0.0347) reveals bond lengths and angles at arsenic (Assbnd C 194.9 p.m., Csbnd Assbnd C 99.3°, Assbnd Csbnd C 121.3°) as to be expected and obtained for similar compounds such as triphenyl arsine or triphenyl arsine derivatives. The sums of angles at two of the nitrogen atoms amount to values of 353.6° and 356.1° and deviate significantly from the value of the third (348.1°). Hence, two of three dimethylamino groups are found to be almost planar, whereas the third group shows a coordination sphere which has to be classified as an intermediate between trigonal planar and trigonal pyramidal. The molecule shows a high degree of C3 pseudosymmetry; the sum of angles at arsenic amounts to 298.0°. The average Caryl

  17. Crystal structure of fac-[2-(4-methyl-5-phenyl-pyridin-2-yl)phenyl-κ2C1,N]bis-[2-(pyridin-2-yl)phenyl-κ2C1,N]iridium(III).

    Science.gov (United States)

    Lee, Chi-Heon; Moon, Suk-Hee; Park, Ki-Min; Kang, Youngjin

    2016-12-01

    In the title compound, [Ir(C 11 H 8 N) 2 (C 18 H 14 N)], the Ir III ion adopts a distorted octa-hedral coordination environment defined by three C , N -chelating ligands, one stemming from a 2-(4-phenyl-5-methyl-pyridin-2-yl)phenyl ligand and two from 2-(pyridin-2-yl)phenyl ligands, arranged in a facial manner. The Ir III ion lies almost in the equatorial plane [deviation = 0.0069 (15) Å]. In the crystal, inter-molecular π-π stacking inter-actions, as well as inter-molecular C-H⋯π inter-actions, are present, leading to a three-dimensional network.

  18. Phenyl galactopyranosides – {sup 13}C CPMAS NMR and conformational analysis using genetic algorithm

    Energy Technology Data Exchange (ETDEWEB)

    Wałejko, Piotr, E-mail: pwalejko@uwb.edu.pl [University of Bialystok, Institute of Chemistry, Pilsudskiego 11/4, 15-443 Bialystok (Poland); Paradowska, Katarzyna, E-mail: katarzyna.paradowska@wum.edu.pl [Medical University of Warsaw, Faculty of Pharmacy, Department of Physical Chemistry, Banacha 1, 02-097 Warsaw (Poland); Bukowicki, Jarosław [Medical University of Warsaw, Faculty of Pharmacy, Department of Physical Chemistry, Banacha 1, 02-097 Warsaw (Poland); Witkowski, Stanisław [University of Bialystok, Institute of Chemistry, Pilsudskiego 11/4, 15-443 Bialystok (Poland); Wawer, Iwona [Medical University of Warsaw, Faculty of Pharmacy, Department of Physical Chemistry, Banacha 1, 02-097 Warsaw (Poland)

    2015-08-18

    Highlights: • The structures of phenyl galactosides were studied by {sup 13}C CPMAS NMR. • The GAAGS method was used in conformational analysis of phenyl galactosides. • The rotation of the aglycone was investigated. • {sup 13}C CPMAS NMR supported by GIAO DFT calculations was used as a verification method. - Abstract: Structural analyses of four compounds (phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (1), phenyl β-D-galactopyranoside (2), phenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (3) and phenyl α-D-galactopyranoside (4)) have been performed using solid-state {sup 13}C MAS NMR spectroscopy and theoretical methods. Conformational analysis involved grid search and genetic algorithm (GAAGS). Low-energy conformers found by GAAGS were further optimized by DFT and chemical shifts were calculated using GIAO/DFT approach. {sup 13}C CPMAS NMR chemical shift of carbon C2 is indicative of the glycoside torsional angle. Separated or merged resonances of C2 and C6 suggest free rotation of phenyl ring in the solid phase.

  19. 3,5-Bis(4-methoxyphenyl-1-phenyl-4,5-dihydro-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Zeliha Baktır

    2011-02-01

    Full Text Available In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å and it makes a dihedral angle of 18.5 (2° with the phenyl ring. The dihedral angles between the phenyl and the two methoxy-substituted phenyl rings are 26.2 (2 and 80.6 (2°. The crystal structure is stabilized by C—H...π stacking interactions and weak π–π interactions [centriod–centroid distance = 3.891 (2 Å].

  20. Ameliorating Role of Caffeic Acid Phenethyl Ester (CAPE Against Methotrexate-Induced Oxidative Stress in the Sciatic Nerve, Spinal Cord and Brain Stem Tissues of Rats

    Directory of Open Access Journals (Sweden)

    Ertuğrul Uzar

    2010-03-01

    Full Text Available OBJECTIVE: Methotrexate (MTX-associated neurotoxicity is an important clinical problem in cancer patients, but the mechanisms of MTX-induced neurotoxicity are not yet known exactly. The aims of this study were (1 to investigate the possible role of malondialdehyde (MDA, superoxide dismutase (SOD enzyme, glutathione peroxidase (GSH-Px and catalase (CAT in the pathogenesis of MTX-induced neurotoxicity and (2 to determine whether there is a putative protective effect of caffeic acid phenethyl ester (CAPE on MTX-induced neurotoxicity in the spinal cord, brainstem and sciatic nerve of rats. METHODS: A total of 19 adult Wistar male rats were divided into three experimental groups. Group I, control group; Group II, MTX-treated group; and Group III, MTX + CAPE-treated group. MTX was administered to the MTX and MTX + CAPE groups intraperitoneally (IP with a single dose of 20 mg/kg on the second day of the experiment. CAPE was administered to the MTX + CAPE group IP with a dose of 10 μmol/kg for 7 days. RESULTS: In the sciatic nerve and spinal cord tissue, CAT and GSH-Px activities were increased in the MTX group in comparison with the control group. CAPE treatment with MTX significantly decreased CAT and GSH-Px activities in the neuronal tissues of rats in comparison with the MTX group. In the spinal cord and brainstem tissues, SOD activity in the MTX group was decreased in comparison with the control group, but in the sciatic nerve, there was no significant difference. In the spinal cord and brainstem of rats, SOD activity was increased in the CAPE + MTX group when compared with the MTX group. The level of MDA was higher in the MTX group than in the control group. CAPE administration with MTX injection caused a significant decrease in MDA level when compared with the MTX group. CONCLUSION: These results reveal that MTX increases oxidative stress in the sciatic nerve, spinal cord and brainstem of rats and that CAPE has a preventive effect on the

  1. Protective Effect of Combined Caffeic Acid Phenethyl Ester and Bevacizumab Against Hydrogen Peroxide-Induced Oxidative Stress in Human RPE Cells.

    Science.gov (United States)

    Dinc, Erdem; Ayaz, Lokman; Kurt, Akif Hakan

    2017-12-01

    This study aimed to evaluate the protective effects of caffeic acid phenethyl ester (CAPE) and combined CAPE-bevacizumab against oxidative stress induced by hydrogen peroxide (H 2 O 2 ) in human retinal pigment epithelium. ARPE-19 cells were pretreated with 5, 10, and 30 μM CAPE alone and in combination with bevacizumab for 3 h, then exposed to H 2 O 2 for 16 h. Cell viability was evaluated with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Vascular endothelial growth factor (VEGF) protein levels in the medium were measured using a human VEGF ELISA kit. Total antioxidant status (TAS) and total oxidant status (TOS) were measured in ARPE-19 cells using the test kit from Rel Assay. Expression levels of VEGF, Bax, Bcl-2, cytochrome c, apoptotic protease activating factor-1 (apaf-1), and caspase-3 were determined using reverse transcription polymerase chain reaction. Pretreatment of ARPE-19 cells with 30 μM CAPE and combined CAPE-bevacizumab reduced H 2 O 2 mediated cell death. H 2 O 2 -induced oxidative stress increased TOS and VEGF production, which was significantly inhibited by CAPE and the CAPE-bevacizumab combination. VEGF, Bax, cytochrome c, apaf-1, and caspase-3 gene expressions were significantly decreased in cells pretreated with 5, 10, and 30 μM CAPE and combined CAPE-bevacizumab compared to the H 2 O 2 group. In addition, Bcl-2 expression was significantly increased in both the CAPE and CAPE-bevacizumab combination groups compared to the H 2 O 2 group. CAPE has a protective effect on ARPE-19 cells against oxidative stress, and VEGF protein level and expression can be decreased by incubation with different concentrations of CAPE. These results demonstrate that CAPE suppresses the mitochondria-mediated apoptosis in ARPE-19 cells under oxidative stress. In addition, the use of CAPE in combination with bevacizumab has an additive effect.

  2. Caffeic acid phenethyl ester promotes anti-inflammatory effects by inhibiting MAPK and NF-κB signaling in activated HMC-1 human mast cells.

    Science.gov (United States)

    Cho, Mi Suk; Park, Won Sun; Jung, Won-Kyo; Qian, Zhong-Ji; Lee, Dae-Sung; Choi, Jung-Sik; Lee, Da-Young; Park, Sae-Gwang; Seo, Su-Kil; Kim, Hak-Ju; Won, Jun Yeon; Yu, Byeng Chul; Choi, Il-Whan

    2014-07-01

    Caffeic acid phenethyl ester (CAPE), an active component of honeybee propolis, is known to have antioxidant, anti-inflammatory, and other beneficial medicinal properties. However, the molecular mechanisms underlying its anti-allergic effects in mast cells are unknown. The purpose of the present study was to examine whether CAPE modulates the immunoglobulin E (IgE)-mediated local allergic reaction in animals, as well as to elucidate the effects of CAPE on mast cells in vitro. To investigate the bioactive potential of CAPE (10 or 20 µM), HMC-1 cells were stimulated with phorbol 12-myristate 13-acetate plus calcium ionophore A23187 (PMACI) for 24 h in the presence or absence of CAPE. To study the pharmacological effects of CAPE, enzyme-linked immunosorbent assays (ELISAs), RT-PCR, Western blot analysis, electrophoretic mobility shift assays (EMSAs), and fluorescence assays were used. CAPE (10 mg/kg) inhibited local IgE-mediated allergic reactions (0.164 versus 0.065 O.D.) in a mouse model. Additionally, CAPE (20 µM) attenuated PMACI-stimulated histamine release (3146.42 versus 2564.83 pg/ml) and the production of inflammatory cytokines, such as interleukin (IL)-1β (4.775 versus 0.713 pg/ml, IC50 = 6.67 µM), IL-6 (4771.5 versus 449.1 pg/ml, IC50 = 5.25 µM), and IL-8 (5991.7 versus 2213.1 pg/ml, IC50 = 9.95 µM) in HMC-1 cells. In activated HMC-1 cells, pretreatment with CAPE decreased the phosphorylation of c-Jun N-terminal kinase. In addition, CAPE inhibited PMACI-induced nuclear factor (NF)-κB activation by suppressing IκBα phosphorylation and its degradation. Our results indicated that CAPE can modulate mast cell-mediated allergic disease.

  3. Induction of lung lesions in Wistar rats by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and its inhibition by aspirin and phenethyl isothiocyanate

    International Nuclear Information System (INIS)

    Ye, Bo; Zhang, Yu-Xia; Yang, Fei; Chen, Hong-Lei; Xia, Dong; Liu, Ming-Qiu; Lai, Bai-Tang

    2007-01-01

    The development of effective chemopreventive agents against cigarette smoke-induced lung cancer could be greatly facilitated by suitable laboratory animal models, such as animals treated with the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). In the current study, we established a novel lung cancer model in Wistar rats treated with NNK. Using this model, we assessed the effects of two chemopreventive agents, aspirin and phenethyl isothiocyanate (PEITC), on tumor progression. First, rats were treated with a single-dose of NNK by intratracheal instillation; control rats received iodized oil. The animals were then sacrificed on the indicated day after drug administration and examined for tumors in the target organs. PCNA, p63 and COX-2 expression were analyzed in the preneoplastic lung lesions. Second, rats were treated with a single-dose of NNK (25 mg/kg body weight) in the absence or presence of aspirin and/or PEITC in the daily diet. The control group received only the vehicle in the regular diet. The animals were sacrificed on day 91 after bronchial instillation of NNK. Lungs were collected and processed for histopathological and immunohistochemical assays. NNK induced preneoplastic lesions in lungs, including 33.3% alveolar hyperplasia and 55.6% alveolar atypical dysplasia. COX-2 expression increased similarly in alveolar hyperplasia and alveolar atypical dysplasia, while PCNA expression increased more significantly in the latter than the former. No p63 expression was detected in the preneoplastic lesions. In the second study, the incidences of alveolar atypical dysplasia were reduced to 10%, 10% and 0%, respectively, in the aspirin, PEITC and aspirin and PEITC groups, compared with 62.5% in the carcinogen-treated control group. COX-2 expression decreased after dietary aspirin or aspirin and PEITC treatment. PCNA expression was significantly reduced in the aspirin and PEITC group. (1) A single dose of 25 mg/kg body weight

  4. Theoretical investigation of tautomeric equilibrium in ortho-hydroxy phenyl Schiff bases

    Science.gov (United States)

    Kluba, M.; Lipkowski, P.; Filarowski, A.

    2008-10-01

    This Letter presents a study of the tautomeric equilibrium in ortho-hydroxy phenyl Schiff bases. The influence of substitution and solvent (simulated by the self-consistent reaction field model, SCRF) on the energy barrier of the transition state and on proton transfer is investigated. Dependencies of the HOMA and HOSE aromaticity indices on the molecular, transition state, and proton transfer forms were obtained. The state of chelate chain and phenyl ring aromaticity depending on the tautomeric equilibrium is studied.

  5. The fluorescence and electronic structure of phenyl-substituted tetraazachlorin molecules

    Science.gov (United States)

    Pershukevich, P. P.; Volkovich, D. I.; Gladkov, L. L.; Dudkin, S. V.; Stupak, A. P.; Kuzmitsky, V. A.; Makarova, E. A.; Solovyov, K. N.

    2014-11-01

    The effect of the addition of phenyl groups to pyrrole rings of tetraazachlorins, a new class of tetrapyrroles, on the photophysical properties and electronic structure of the molecules has been investigated by a complex of experimental and theoretical methods. Characteristics of fluorescence at 293 and 77 K have been determined for phenyl-substituted tetraazachlorins. The objects of this study include unsubstituted tetraazaporphine. The introduction of phenyl groups affords a marked increase in the fluorescence quantum yield. For tetraazaporphine and phenyl-substituted tetraazachlorins, fluorescence buildup occurs as the temperature is decreased from 293 to 77 K, but to a lesser extent than for tetraazachlorins having no phenyl groups, which were earlier studied by the authors. The fluorescence buildup mechanism is discussed. The singlet oxygen generation quantum yield has been determined for the tetrapyrroles examined. This characteristic increases upon tetrapyrrole is phenylation. The electronic structure and absorption spectra of unsubstituted porphine and chlorin, tetraazaporphine, tetraazachlorin, octaphenyltetraazaporphine, and tetramethylhexaphenyltetraazachlorin have been calculated by the INDO/Sm method (original modification of the INDO/S method) with molecular geometry optimization using DFT. The results of the quantum-chemical calculation of the absorption spectra are in good agreement with experimental data for transitions to the lowest excited electronic states Q x( S 1) and Q y( S 2).

  6. An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones from 2-Halobenzoic Acids

    International Nuclear Information System (INIS)

    Song, Yoon Ju; Choi, Jin Sun; Lee, Jae In

    2013-01-01

    The present method offers an efficient synthesis of 1-alkyl-2-phenyl-4-quinolones from 2-haloben-zoic acids. It has the advantages with respect to (i) synthesis of 2 equiv of alkynones 5 from 1 equiv of 4,6-pyrimidyl di(2-halobenzoates) 3, (ii) synthesis of versatile 1-alkyl-2-phenyl-4-quinolones in high overall yields, and (iii) use of readily available and cheap starting materials. Therefore, this method could be utilized as a practical synthesis of 1-alkyl-2-phenyl-4-quinolones. Several methods have been developed to synthesize 1-alkyl-2-phenyl-4-quinolones from 2'-substituted acetophenones, anilines, and 2-halobenzoyl chlorides as starting materials. The reaction of N-methylisatoic anhydride with the lithium enolate of an 4'-methoxyacetophenone afforded the 1-methyl-2-phenyl-4-quinolone in a short sequence, but the yield was low. N-(2-Acetylphenyl)benzamides, prepared by Friedel-Crafts acylation of N-phenyl benzamides with acetyl chloride or benzoylation of 2'-aminoacetophenones with benzoyl chlorides,8 were cyclized with potassium t-butoxide to yield 2-aryl-4-quinolones, which were further alkylated with alkyl iodides to give 1-alkyl-2-aryl-4-quinolones

  7. Synthesis and characterization of MnO2/NiO nanocomposites for photocatalysis of tetracycline antibiotic and modification with guanidine for carriers of Caffeic acid phenethyl ester-an anticancer drug.

    Science.gov (United States)

    Gupta, Vinod Kumar; Fakhri, Ali; Agarwal, Shilpi; Ahmadi, Elham; Nejad, Pedram Afshar

    2017-09-01

    In the present studies, modified NiO nanoparticles and MnO 2 /NiO nanocomposites with guanidine were synthesized by anchoring method for carriers of anticancer drug "Caffeic acid phenethyl ester". The prepared nanocomposites were characterized by using Scanning Electron Microscopy, Raman and Fourier transform infrared spectroscopy, X-ray diffraction, Vibrating sample magnetometer. The results from XRD indicated that the crystalline size of NiO nanoparticles and MnO 2 /NiO nanocomposites are 12 and 15nm, respectively. Saturation magnetization (Ms) for NiO NPs and MnO 2 /NiO nanocomposites was to be 0.60, and 0.68emu/g indicating that these are superparamagnetic and ferromagnetic properties in nature. The prepared nanocomposites were evaluated as catalyst for degradation of antibiotics in photocatalysis process. Particularly, the MnO 2 /NiO composite demonstrated the higher degradation rate (89.55%) of tetracycline antibiotic under UV light irradiation than the NiO (67.80%). Drug load on and release from nanopowders was investigated by using UV-Vis spectroscopy method. Time of drug loading was 100min and the drug release in 1-10h with 20-80% drug release were found, and then, it's applicable to in-vivo drug delivery. Therefore, the NiO nanoparticles and MnO 2 /NiO nanocomposites are promising for targeted Caffeic acid phenethyl ester anticancer drug delivery applications. The anticancer drug loaded on guanidine-NiO and guanidine-MnO 2 /NiO in high concentration has an antioxidant property. Copyright © 2017 Elsevier B.V. All rights reserved.

  8. Phenyl-doped graphitic carbon nitride: photoluminescence mechanism and latent fingerprint imaging.

    Science.gov (United States)

    Song, Zhiping; Li, Zhihong; Lin, Lihua; Zhang, Yongfan; Lin, Tianran; Chen, Ling; Cai, Zhuang; Lin, Sen; Guo, Liangqia; Fu, Fengfu; Wang, Xinchen

    2017-11-23

    The photoluminescence (PL) emission mechanism of graphitic carbon nitride (g-C 3 N 4 ) is still ambiguous and the application of PL g-C 3 N 4 powder as a solid sensing platform has not been explored. Herein we highlight a strategy to prepare g-C 3 N 4 powder with strong green PL by doping phenyl groups in a carbon nitride network. Compared with pristine g-C 3 N 4 , doping of phenyl groups greatly enhances the PL efficiency and Stokes shift. Theoretical calculations based on density function theory indicate that phenyl groups change the electronic structure of the carbon nitride network and have an obvious contribution to the LUMO of phenyl-doped g-C 3 N 4 , which may be the main reason for the enhancement of the PL efficiency and Stokes shift. Taking advantage of the high PL efficiency, large Stokes shift and high photo-stability, phenyl-doped g-C 3 N 4 powder shows promising application for the imaging of latent fingerprints.

  9. Synthesis and structure-activity relationship exploration of some potent anti-cancer phenyl amidrazone derivatives.

    Science.gov (United States)

    Habashneh, Almeqdad Y; El-Abadelah, Mustafa M; Bardaweel, Sanaa K; Taha, Mutasem O

    2017-12-04

    Amidrazones have been reported to have significant anti-tumor properties against several cancer cell lines. The current project aims to profile the structure-anticancer activity relationship of phenyl-amidrazons. Fifteen phenyl-amidrazone-piperazine derivatives were prepared and tested against four cancer cell lines (leukemia, prostate, breast and colon cancers). Six compounds illustrated low micromolar anticancer IC50 values, while the remaining compounds were either inactive or of moderate potencies. All compounds were virtually nontoxic against normal fibroblast cells. Docking into the oncogenic kinase bcr/abl illustrated the critical importance of (i) p-halogen substituent on the ligand's phenyl ring and (ii) the presence of positive ionizable moiety at the ligand's piperazine fragment for anticancer activity. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  10. Esterification of phenyl acetic acid withp-cresol using metal cation exchanged montmorillonite nanoclay catalysts.

    Science.gov (United States)

    Bhaskar, M; Surekha, M; Suma, N

    2018-02-01

    The liquid phase esterification of phenyl acetic acid with p -cresol over different metal cation exchanged montmorillonite nanoclays yields p -cresyl phenyl acetate. Different metal cation exchanged montmorillonite nanoclays (M n +  = Al 3+ , Zn 2+ , Mn 2+ , Fe 3+ , Cu 2+ ) were prepared and the catalytic activity was studied. The esterification reaction was conducted by varying molar ratio of the reactants, reaction time and catalyst amount on the yield of the ester. Among the different metal cation exchanged catalysts used, Al 3+ -montmorillonite nanoclay was found to be more active. The characterization of the material used was studied under different techniques, namely X-ray diffraction, scanning electron microscopy and thermogravimetric analysis. The product obtained, p -cresyl phenyl acetate, was identified by thin-layer chromotography and confirmed by Fourier transform infrared, 1 H NMR and 13 C NMR. The regeneration activity of used catalyst was also investigated up to fourth generation.

  11. Production of allyl phenyl carbinol (APC by biotrans-formation using Rhizopus arrhizus

    Directory of Open Access Journals (Sweden)

    Vilas B. Shukla

    2000-01-01

    Full Text Available The objective of the present work was to study the stereoselective synthesis of homo-allylic alcohol using stereoselective hydrolysis by Rhizopus arrhizus and also to study the stereoselective synthesis of allyl phenyl carbinol (APC or 1-Phenyl-3-butene-1-o by combination of chemical synthesis and biotransformation from cheap raw materials such as benzaldehyde and allyl bromide. Stereospecific synthesis of allyl phenyl carbinol (APC was achieved by acetate hydrolysis by R. arrhizus giving R (+ enantiomer. Maximum enantiomeric excess of APC was obtained at 16 h where as maximum yield of it was obtained at 48 h of biotransformation.O objetivo deste trabalho foi estudar a síntese estereo-seletiva do álcool homo-allylico usando hidrólise estereo-seletiva pelo Rhizopus arrhizus e também estudar a síntese estereo-seletiva do allyl phenyl carbinol (APC ou 1-Phenyl-3-butene- 1-o pela combinação da síntese química e biotransformação dos materiais brutos e baratos, tais como; benzaldehyde and allyl bromide. A síntese Stereospecifica do allyl phenyl carbinol (APC foi conseguida pela hidrólise de acetato pelo R. arrhizus fornecendo enantiomero R (+. O excesso máximo do enantiomérico do APC foi obtido em 16 h sendo que seu rendimento máximo foi obtido após 48 h de biotransformação.

  12. Synthesis of 3-{4-[4-(Benzylideneaminobenzenesulfonyl]- phenyl}-2-phenylquinazolin-4(3H-one

    Directory of Open Access Journals (Sweden)

    Sunil Manohar Babu

    2009-01-01

    Full Text Available The present work describes the synthesis of a Schiff base, 3-{4-[4-(benzylideneamino benzenesulfonyl]phenyl}-2-phenylquinazolin-4(3H-one from a novel quinazolinone, 3-[4-(4 aminobenzenesulfonylphenyl]-2-phenylquinazolin-4(3H-one. The quinazolinone was prepared by reacting 2-phenyl-4H-3,1 benzoxazin-4-one with dapsone. The structure of the synthesized Schiff base is confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis.-

  13. 5-(2,4-Dichlorophenoxy-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

    Directory of Open Access Journals (Sweden)

    S. Madan Kumar

    2016-07-01

    Full Text Available In the crystal structure of the title compound, C17H12Cl2N2O2, the pyrazole ring makes dihedral angles of 65.0 (2 and 43.9 (2° with the dichlorophenyl and phenyl rings, respectively. The dihedral angle between the chlorophenyl and phenyl rings is 59.1 (2°. In the crystal, the molecules are linked by C—H...O hydrogen bonds and weak C—Cl...π and C—H...π interactions, generating a three-dimensional network.

  14. 1-[3-(2-Nitrophenyl-5-phenyl-2-pyrazolin-1-yl]ethanone

    Directory of Open Access Journals (Sweden)

    Huan-Mei Guo

    2010-07-01

    Full Text Available The title compound, C17H15N3O3, was prepared from 1-(2-nitrophenyl-3-phenylprop-2-en-1-one and hydrazine. The dihedral angle between the benzene and phenyl rings is 74.55 (2°. The pyrazoline ring is in a slight envelope conformation with the C atom bonded to the phenyl ring forming the flap. In the crystal structure, weak intermolecular C—H...O hydrogen bonds connect molecules into chains along [100].

  15. Controlled switching of single-molecule junctions by mechanical motion of a phenyl ring

    Directory of Open Access Journals (Sweden)

    Yuya Kitaguchi

    2015-10-01

    Full Text Available Mechanical methods for single-molecule control have potential for wide application in nanodevices and machines. Here we demonstrate the operation of a single-molecule switch made functional by the motion of a phenyl ring, analogous to the lever in a conventional toggle switch. The switch can be actuated by dual triggers, either by a voltage pulse or by displacement of the electrode, and electronic manipulation of the ring by chemical substitution enables rational control of the on-state conductance. Owing to its simple mechanics, structural robustness, and chemical accessibility, we propose that phenyl rings are promising components in mechanical molecular devices.

  16. UV-visible spectrum of the phenyl radical and kinetics of its reaction with NO in the gas phase

    DEFF Research Database (Denmark)

    Wallington, T.J.; Egsgaard, H.; Nielsen, O.J.

    1998-01-01

    Pulse radiolysis transient UV-visible absorption spectroscopy was used to study the UV-visible absorption spectrum (225-575 nm) of the phenyl radical, C6H5(.), and kinetics of its reaction with NO. Phenyl radicals have a strong broad featureless absorption in the region of 225-340 nm...

  17. Preconcentration of Zn(II from Sample Water by Phenyl-iminodiacetic Acid Grafted Multiwalled Carbon Nanotubes

    Directory of Open Access Journals (Sweden)

    A. Moghimi

    2012-11-01

    Full Text Available : phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes were prepared by grafted phenyl-iminodiacetic acid groups onto multi-walled carbon nanotubes via a diazotation reaction. The stability of chemically phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes in concentrated hydrochloric acid which was then used as a recycling and pre-concentration reagent for further uses of phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes. The application of this  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes for sorption of a series of metal ions was performed by using different controlling factors such as the pH of metal ion solution and the equilibration shaking time by the static technique. Zn(II was found to exhibit the highest affinity towards extraction by these  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes phases. The pronounced selectivity was also confirmed from the determined distribution coefficient (Kd of all the metal ions, showing the highest value reported for Zn(II to occur by  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes. The potential applications of  phenyl-iminodiacetic acid grafted multiwalled carbon nanotubes for selective extraction of Zn(II to occur from aqueous solution were successfully accomplished as well as pre- concentration of low concentration of Zn(II (60 pg ml-1 from natural tap water with a pre-concentration factor of 100 for Zn(II off-line analysis by flame atomic absorption analysis. 

  18. Synthesis and Characterization of Ti-Phenyl at SiO2 Core-Shell Nanoparticles Catalyst

    International Nuclear Information System (INIS)

    Syamsi Aini; Jon Efendi; Syamsi Aini; Jon Efendi

    2012-01-01

    This study highlights the potential use of Ti-Phenyl at SiO 2 core-shell nanoparticles as heterogeneous catalysis in oxidation reaction. The Ti-Phenyl at SiO 2 was synthesized by reduction of TiCl 4 and diazonium salt with sodium borohydride to produce phenyl titanium nanoparticles (Ti-Phenyl), followed by the silica shell coating using tetraethyl orthosilicate (TEOS). The Ti-Phenyl at SiO 2 nanoparticles were characterized by Fourier transform infrared (FTIR) spectrometer, diffuse reflectance (DR) UV-visible spectrometer, thermogravimetric analyzer (TGA), X-ray diffraction (XRD) spectrometer, field emission scanning electron microscope (FESEM) and transmission electron microscope (TEM). The core-shell size of Ti-Phenyl at SiO 2 was in the range of 40 to 100 nm with its core composed with an agglomeration of Ti-Phenyl. The Ti-Phenyl at SiO 2 was active as a catalyst in the liquid phase epoxidation of 1-octene with aqueous hydrogen peroxide as an oxidant. (author)

  19. [2-(2,4-dimethylphenylthio)phenyl] aniline and its amide derivatives ...

    Indian Academy of Sciences (India)

    YOGESH PATIL

    2018-02-15

    Feb 15, 2018 ... These derivatives could be considered as a precursor structure for further design of antituberculosis agent. Keywords. [2-(2,4-dimethylphenylthio)phenyl] aniline; antituberculosis activity; cytotoxicity. 1. Introduction. Tuberculosis (TB) is a contagious disease caused by the. Mycobacterium tuberculosis (MTB).

  20. (2E-3-(3-Methoxy-1-phenyl-1H-pyrazol-4-yl-2-propenal

    Directory of Open Access Journals (Sweden)

    Algirdas Šačkus

    2009-12-01

    Full Text Available The palladium-catalyzed reaction of 4-bromo-3-methoxy-1-phenyl-1H-pyrazole with acrolein diethyl acetal gives the title compound in good yield. Detailed spectroscopic data (1H NMR, 13C NMR, 15N NMR, IR, MS are presented.

  1. Complexometric determination of lanthanides with 3-hydroxy-3-phenyl-1-p-sulfonato phenyltriazenes

    International Nuclear Information System (INIS)

    Purohit, D.N.; Cahuhan, R.S.

    1985-01-01

    The use of 3-hydroxy-3-phenyl-1-p-sulphonato phenyltriazene as metallocromic indicator for complexometric determination of fourteen lanthanides is reported. The preparation of this indicator is described as well as the effects of pH and temperature on quantitative titrations. (C.L.B.) [pt

  2. Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions

    CSIR Research Space (South Africa)

    Madala, NE

    2012-07-01

    Full Text Available Biotechnology Letters July 2012/ Vol. 34 No.7, pp 1351-1356 Biotransformation of isonitrosoacetophenone (2-keto-2- phenyl-acetaldoxime) in tobacco cell suspensions Ntakadzeni E. Madala 1 , P. A. Steenkamp 2 , L. A. Piater 1 and I. A. Dubery 1 1...

  3. Behaviour of phenyl-urea type herbicides and related chemical residues in soil-plant systems

    International Nuclear Information System (INIS)

    Suess, A.; Eben, C.

    1975-01-01

    Uniformly 14 C-labelled aniline derivatives were used to indicate the degradation of phenyl-urea type herbicides. The results suggested cleavage of the benzene ring when present as a soil residue, cleavage apparently being reduced by increased chlorination of the ring. (author)

  4. Bis[(5-phenyl-1,3,4-thiadiazol-2-ylsulfanyl]methane

    Directory of Open Access Journals (Sweden)

    He-wen Wang

    2010-12-01

    Full Text Available The asymmetric unit of the title compound, C17H12N4S4, contains one half-molecule situated on a twofold rotational axis. In the molecule, the thiadiazole and attached phenyl rings are twisted by 5.8 (3°.

  5. Triplet state spectroscopy of .sigma.-conjugated poly[methyl(phenyl)silylene

    Czech Academy of Sciences Publication Activity Database

    Skryshevski, Y.; Piryatinski, Y.; Vakhnin, A.; Blonsky, I.; Kadashchuk, A.; Nešpůrek, Stanislav

    2007-01-01

    Roč. 30, č. 3 (2007), s. 384-392 ISSN 0925-3467 R&D Projects: GA AV ČR IAA100100622; GA AV ČR KAN401770651 Institutional research plan: CEZ:AV0Z40500505 Keywords : poly[methyl(phenyl)silylene] * polysilane * photoluminescence Subject RIV: BM - Solid Matter Physics ; Magnetism Impact factor: 1.519, year: 2007

  6. Pharmacological Studies of p, N-(3, 4-Methylenedioxy phenyl Benzoic Acid (RRL-1364 - Part-I

    Directory of Open Access Journals (Sweden)

    Dahanukar Sharadini

    1978-01-01

    Full Text Available Detailed pharmacological investigations of p-N-(3, 4-methylene dioxy phenyl benzoic acid revealed marked hypotensive action which was dose dependent and most marked in cats; it was absent in rats. Atropine could block this hypotensive action, thus suggest-ing cholinomimetic mechanism. Further studies indicated that the hypotension produced was central and possibly medullary in origin.

  7. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives

    International Nuclear Information System (INIS)

    Elhadi, S. A.

    2004-09-01

    Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, 1 H-and 13 C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl -6-sulphanilamide-quinolin-4-carboxylic acid showed the highest activity against the four standard tested organisms.(Author)

  8. 3,5-Bis(4-meth-oxy-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

    Science.gov (United States)

    Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S; Narayana, B; Yathirajan, H S

    2011-01-12

    In the title compound, C(23)H(22)N(2)O(2), the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two meth-oxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C-H⋯π stacking inter-actions and weak π-π inter-actions [centriod-centroid distance = 3.891 (2) Å].

  9. GYF-21, an Epoxide 2-(2-Phenethyl-Chromone Derivative, Suppresses Innate and Adaptive Immunity via Inhibiting STAT1/3 and NF-κB Signaling Pathways

    Directory of Open Access Journals (Sweden)

    Ran Guo

    2017-05-01

    Full Text Available Multiple sclerosis is a chronic inflammatory autoimmune disease of the central nervous system characterized by demyelinating plaques and axonal loss. Inhibition on over activation of innate and adaptive immunity provides a rationale strategy for treatment of multiple sclerosis. In the present study, we investigated the inhibitory effects of GYF-21, an epoxide 2-(2-phenethyl-chromone derivative isolated from Chinese agarwood, on innate and adaptive immunity for revealing its potential to treat multiple sclerosis. The results showed that GYF-21 markedly inhibited the activation of microglia, and dendritic cells as well as neutrophils, all of which play important roles in innate immunity. Furthermore, GYF-21 significantly suppressed adaptive immunity via inhibiting the differentiation of naive CD4+ T cells into T helper 1 (Th1 and T helper 17 (Th17 cells, and suppressing the activation, proliferation, and IFN-γ secretion of CD8+ T cells. The mechanism study showed that GYF-21 evidently inhibited the activation of STAT1/3 and NF-κB signaling pathways in microglia. In conclusion, we demonstrated that GYF-21 can significantly inhibit innate and adaptive immunity via suppressing STAT1/3 and NF-κB signaling pathways, and has potential to be developed into therapeutic drug for multiple sclerosis.

  10. Caffeic Acid Phenethyl Ester (Propolis Extract) Ameliorates Insulin Resistance by Inhibiting JNK and NF-κB Inflammatory Pathways in Diabetic Mice and HepG2 Cell Models.

    Science.gov (United States)

    Nie, Jiarui; Chang, Yaning; Li, Yujia; Zhou, Yingjun; Qin, Jiawen; Sun, Zhen; Li, Haibin

    2017-10-18

    Caffeic acid phenethyl ester (CAPE), extracted from propolis, was evaluated for the ameliorative effects on insulin resistance and the mechanisms were identified, using non-insulin-dependent diabetes mellitus (NIDDM) model mice and insulin resistance (IR) model cells. After 5 weeks of CAPE supplementation, insulin sensitivity, hyperlipidemia, and peroxisome proliferator-activated receptor-α (PPAR-α) levels were improved in mice. Proinflammatory cytokines in serum and the expressions of tumor necrosis factor-alpha (TNF-α) mRNA in tissues were markedly downregulated from CAPE-treated mice. In vitro, CAPE supplement significantly improved glucose consumption, glucose uptake, glycogen content, and oxidative stress and decreased expression of glucose-6-phosphatase (G6Pase) mRNA in cells. Both in vivo and in vitro, CAPE enhanced p-Akt (Ser473) and p-insulin receptor substrate (IRS)-1 (Tyr612), but inhibited p-JNK (Thr183/Tyr185), p-NF-κB p65 (Ser536), and nuclear translocation of p-NF-κB p65 (Ser536). In summary, CAPE can ameliorate insulin resistance through modulation of JNK and NF-κB signaling pathway in mice and HepG2 cells.

  11. Crystal structures of (E-3-(furan-2-yl-2-phenyl-N-tosylacrylamide and (E-3-phenyl-2-(m-tolyl-N-tosylacrylamide

    Directory of Open Access Journals (Sweden)

    Dong Cheng

    2016-06-01

    Full Text Available In the title N-tosylacrylamide compounds, C20H17NO4S, (I, and C23H21NO3S, (II, the conformation about the C=C bond is E. The acrylamide groups, [–NH—C(=O—C=C–], are almost planar, with the N—C—C=C torsion angle being −170.18 (14° in (I and −168.01 (17° in (II. In (I, the furan, phenyl and 4-methylbenzene rings are inclined to the acrylamide mean plane by 26.47 (11, 69.01 (8 and 82.49 (9°, respectively. In (II, the phenyl, 3-methylbenzene and 4-methylbenzene rings are inclined to the acrylamide mean plane by 11.61 (10, 78.44 (10 and 78.24 (10°, respectively. There is an intramolecular C—H...π interaction present in compound (II. In the crystals of both compounds, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(8 ring motif. In (I, the dimers are reinforced by C—H...O hydrogen bonds and linked by C—H...π interactions, forming chains along [011]. In the crystal of (II, the dimers are linked via C—H...O hydrogen bonds, forming chains along [100]. The chains are further linked by C—H...π interactions, forming layers parallel to (010.

  12. First principle evaluation of the chiroptical activity of the di-phenyl-diazene derivatives

    Science.gov (United States)

    Benassi, Enrico; Corni, Stefano

    2012-09-01

    Azobenzene (di-phenyl-diazene) is well-known as a photoisomerisable molecule and has been widely studied as a molecular photoswitcher. Molecular rods, where di-phenyl arms are bound to the diazene moiety, have been also synthesized. In this article we explore by first principle density functional theory calculations the chiroptical properties (electronic circular dichroism spectra, ECD) of azobenzene and its homologues with polyphenyl arms. In particular, we demonstrate that for molecules in the cis configuration the intrinsic chirality of the distorted cis diazene group dominates the ECD response, while for trans species the non-planarity of the polyphenyl arms induces peaks in the ECD spectrum. Finally, the possibility of obtaining a light-controlled chiral switch by proper functionalization is also speculated.

  13. Liquid Crystals Derived from 2-phenyl-isoindoles: Synthesis and Characterization

    Science.gov (United States)

    Jow, Kenny G.; Dingemans, Theo J.; Bushnell, Dennis M. (Technical Monitor)

    2001-01-01

    2-Phenyl-isoindole was investigated as the rigid core unit in a series of asymmetric mesogenic molecules. When the 2-phenyl-isoindole core was terminated with a hexyl tail, no mesophase formation could be observed. When 4-n-(tridecafluorohexyl) was used, however, we observed both monotropic and enantiotropic phase behavior. We found that most functionalities at the anhydride 5-position results in the formation of smectic A (SmA) phases in the temperature range of 70-180 C. Functionalities at the anhydride 4-position suppress mesophase formation. Large substituents (-Br, -NO2) and symmetric substitution patterns (5,6-dichloro, 4,7-dichloro and 4,5,6,7-tetrachloro) on the anhydride moiety increase the melting point and destabilize the mesophase. Temperature dependent X-ray diffraction experiments suggest an interdigitated SmA packing for this family of compounds.

  14. Synthesis and antifungal activities of N-aryl-4-phenyl-3-(4-phenoxyphenyl)butanamides.

    Science.gov (United States)

    Lee, S H; Kim, I O; Cheong, C S; Chung, B Y

    1999-10-01

    Various N-aryl-4-phenyl-3-(4-phenoxyphenyl)butanamides (2 and 3) were tested for fungicidal activities against Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea, Phytophthora infestans, Puccinia recondita, and Erysiphe graminis in vivo. Butanamides (2 and 3a) that have an electron withdrawing group (Cl, F) attached to the meta position of the phenyl ring showed good to excellent activities against Pyricularia oryzae, Puccinia recondita, and Erysiphe graminis in high concentration while those that have a strong electron withdrawing group (CN, NO2) or electron donating group (OCH3, CH3) attached to the meta position did not show good activities against all test fungi at 250 mg L-1. The antifungal activities of the compounds synthesized were compared with reference compounds such as Tricyclazole, Moncozeb, and Benomyl.

  15. (4E-1-Phenyl-4-{[(pyridin-2-ylamino]methylidene}pyrazolidine-3,5-dione

    Directory of Open Access Journals (Sweden)

    Shaaban K. Mohamed

    2016-06-01

    Full Text Available The title compound, C15H12N4O2, contains two independent molecules in the asymmetric unit. These differ in terms of dihedral angles that the phenyl and 2-pyridyl rings subtend with the central five-membered ring; 15.2 (2 and 2.9 (2°, respectively, in one molecule, 8.9 (2 and 5.1 (2°for the second. In the crystal, the independent molecules each self-associate to form layers through N—H...O and C—H...O hydrogen bonding. The layers associate through π–π interactions between the phenyl rings and isolated carbon–carbon double bonds [shortest midpoint–centroid distance = 3.347 (4 Å]. The crystal studied was refined as a two-component twin.

  16. Duplex and Triplex Formation of Mixed Pyrimidine Oligonucleotides with Stacking of Phenyl-triazole Moieties in the Major Groove

    DEFF Research Database (Denmark)

    Andersen, Nicolai Krog; Døssing, Holger; Jensen, Frank

    2011-01-01

    5-(1-Phenyl-1,2,3-triazol-4-yl)-2'-deoxycytidine was synthesized from a modified CuAAC protocol and incorporated into mixed pyrimidine oligonucleotide sequences together with the corresponding 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine. With consecutive incorporations of the two modified...... nucleosides, improved duplex formation with a complementary RNA and improved triplex formation with a complementary DNA duplex were observed. The improvement is due to π-π stacking of the phenyl-triazole moieties in the major groove. The strongest stacking and most pronounced positive influence on thermal...... stability was found in between the uridine analogues or with the cytidine analogue placed in the 3' direction to the uridine analogue. Modeling indicated a different orientation of the phenyl-triazole moieties in the major groove to account for the difference between the two nucleotides. The modified...

  17. Photooxidation of poly[methyl(phenyl)silylene] and effect of photostabilizers

    Czech Academy of Sciences Publication Activity Database

    Meszároš, Oto; Schmidt, Pavel; Pospíšil, Jan; Nešpůrek, Stanislav

    2006-01-01

    Roč. 91, č. 3 (2006), s. 573-578 ISSN 0141-3910. [International Conference on Modification, Degradation , Stabilization Conference /3./. Lyon, 29.08.2004-02.09.2004] R&D Projects: GA MŠk ME 700; GA MŠk OC D14.30 Institutional research plan: CEZ:AV0Z40500505 Keywords : polysilane degradation * poly[methyl(phenyl)silylene] * photooxidation Subject RIV: CD - Macromolecular Chemistry Impact factor: 2.174, year: 2006

  18. Synthesis and properties of complexes of 1-phenyl-2,3-dimetylpyrazolone-5-thione with metals

    International Nuclear Information System (INIS)

    Bikkulova, A.T.; Kapina, A.P.; Medvedeva, E.A.

    1985-01-01

    Cadmium complexes with thiopyrine (1-phenyl-2.3-dimethylpyrazolone-5-thione) (R) of the composition CdR 2 X 2 are obtained by precipitation from hydrochloric acid solutions at pH=1 and at chloride and bromide (X) excess. The formation of coordination bond of a metal through the sulphur atom is established by the IR- and NMR-spectroscopy methods. Fungicidal activity of the compositions obtained is detected

  19. Dynamic changes of paraoxonase 1 activity towards paroxon and phenyl acetate during coronary artery surgery.

    Science.gov (United States)

    Wysocka, Anna; Cybulski, Marek; Berbeć, Henryk; Wysokiński, Andrzej; Stążka, Janusz; Daniluk, Jadwiga; Zapolski, Tomasz

    2017-04-04

    Serum paraoxonase 1 (PON1), an enzyme associated with high - density lipoproteins (HDL) particles, inhibits the oxidation of serum lipoproteins and cell membranes. PON1 activity is lower in patients with atherosclerosis and in inflammatory diseases. The systemic inflammatory response provoked during cardiopulmonary bypass grafting may contribute to the development of postoperative complications. The aim of the present study was to estimate the dynamic changes in paraoxonase 1 (PON1) activity towards paraoxon and phenyl acetate during and after coronary artery surgery. Twenty six patients with coronary heart disease undergoing coronary artery bypass grafting (CABG) were enrolled into the study. Venous blood samples were obtained preoperatively, after aortic clumping, after the end of operation, at 6, 18, 30 and 48 h after operation. Paraoxonase activity was measured spectrophotometrically in 50 mM glycine/NaOH buffer (pH 10.5) containing 1.0 mM paraoxon, and 1.0 mM CaCl 2 . Arylesterase activity was measured in 20 mM TrisCl buffer (pH 8.0) containing 1 mM phenyl acetate and 1 mM CaCl 2 . PON1 activity toward paraoxon and phenyl acetate significantly decreased after aorta cross clumping and increased directly after operation. PON1 activity towards paraoxon in preoperative period and PON1 activity towards phenyl acetate in seventh stage of experiment tended to inversely correlate with the occurrence of postoperative complications. The paraoxonase 1 plasma activity is markedly reduced during CABG surgery.

  20. Synthesis, Characterization and Chelating Properties of 4-Butyrylsemicarbazone-1-phenyl-3-methyl-2-pyrazolin-5-one

    Directory of Open Access Journals (Sweden)

    J. D. Patel

    2010-01-01

    Full Text Available 4-Butyrylsemicarbazone-1-phenyl-3-methyl-2-pyrazolin-5-one (BUMP-SC was prepared and its metal chelates of Cu2+, Ni2+, Co2+, Mn2+, Fe2+, Fe3+, Cr3+, UO2 and OV were prepared. The ligands and its chelates were characterized by elemental analysis, metal:ligand (M:L stoichiometry, IR-electronic spectral studies and magnetic properties. The compounds also were screened for their antimicrobial activity.

  1. Synthesis and Application of Phenyl Nitrone Derivatives as Acidic and Microbial Corrosion Inhibitors

    OpenAIRE

    Chen, Shijun; Zhao, Kang; Chen, Gang

    2015-01-01

    Nitrone has drawn great attention due to its wide applications as a 1,3-dipole in heterocyclic compounds synthesis and the bioactivities. With the special structure, nitrone can also be used as ligand in inorganic chemistry. Based on the current research, the nitrones are anticipated to be effective inhibitors against acidic and microbial corrosion. The aim of this work is to investigate the inhibitory action of nitrones. In this work, a series of phenyl nitrone derivatives (PN) was synthesiz...

  2. {2,6-Bis[(di-tert-butyl-phosphino)-methyl]-phenyl}chloridonickel(II).

    Science.gov (United States)

    Boro, Brian J; Dickie, Diane A; Goldberg, Karen I; Kemp, Richard A

    2008-09-20

    In the title compound, [Ni(C(24)H(43)P(2))Cl], the Ni atom adopts a distorted square-planar geometry, with the P atoms of the 2,6-bis-[(di-tert-butyl-phosphino)meth-yl]phenyl ligand trans to one another. The P-Ni-P plane is twisted out of the plane of the aromatic ring by 21.97 (6)°.

  3. Corrosion inhibition of alpha brass by 1-phenyl-3-methyl-pyrazol-5 ...

    African Journals Online (AJOL)

    Corrosion inhibition of alpha brass by 1-phenyl-3-methyl-pyrazol-5-one in acidic media at different temperatures. ... Global Journal of Engineering Research ... The corrosion inhibition efficiency (C.I.E.) of the alpha brass was 99.83%, using the condition of 3.0M HNO3 for the uninhibited experiment and 0.03M HPMP for the ...

  4. New phenyl-ethanediols from the culture broth of Boletus edulis.

    Science.gov (United States)

    Yang, Wan-Qiu; Qin, Xiang-Dong; Shao, Hong-Jun; Fang, Li-Zhen; Wang, Fei; Ding, Zhi-Hui; Dong, Ze-Jun; Liu, Ji-Kai

    2007-04-01

    A new phenyl-ethanediol, (1S)-(4-acetylphenyl)-1, 2-ethanediol (1), and a new natural product, (1S)-(3-ethenylphenyl)-1, 2-ethanediol (2), were isolated from the culture broth of the basidiomycete Boletus edulis together with three related known compounds, 1-(4-ethylphenyl)-1, 2-ethanediol (3), 1-(3-ethylphenyl)-1, 2-ethanediol (4) and 1-(3-formylphenyl)-ethanone (5). Their structures were elucidated by spectroscopic methods including extensive 2D-NMR techniques.

  5. Synthesis and anti-HIV activity of novel phenyl branched cyclopropyl nucleosides.

    Science.gov (United States)

    Wu, Ying; Hong, Joon Hee

    2005-09-01

    Novel phenyl branched cyclopropyl nucleoside analogues were designed and synthesized as potential antiviral agents. Cyclopropanation was performed via classical Simmons-Smith reaction using Zn(Et)2 and CH2I2. Coupling of the mesylates 11 and 12 with natural bases (A,C,T,U) and desilylation afforded a series of novel cyclopropyl nucleosides 21-28. The synthesized compounds were evaluated for their antiviral and antitumor activity against various viruses such as HIV, HSV-1, HSV-2 and HCMV.

  6. Photoinduced metastability and degradation of poly[methyl(phenyl)silylene] as seen by thermoluminescence

    Czech Academy of Sciences Publication Activity Database

    Kadashchuk, A.; Nešpůrek, Stanislav; Ostapenko, N.; Skryshevskii, Yu.; Zaika, V.

    2001-01-01

    Roč. 35, special issue (2001), s. 413-428 ISSN 1058-725X R&D Projects: GA AV ČR IAA1050901; GA MŠk OC 518.10; GA AV ČR KSK4050111 Institutional research plan: CEZ:AV0Z4050913 Keywords : metastability * degradation * poly[methyl(phenyl)silylene] Subject RIV: BG - Nuclear, Atomic and Molecular Physics, Colliders Impact factor: 0.457, year: 2001

  7. Studies on thermal degradation kinetics of thermal and UV cured N-(4-hydroxy phenyl) maleimide derivatives

    International Nuclear Information System (INIS)

    Pitchaimari, G.; Vijayakumar, C.T.

    2014-01-01

    Graphical abstract: - Highlights: • UV cure materials are more thermally stable than the thermally cured materials. • Cyanate ester functionalization offers better thermal stability. • The Ea values for Poly NVPs are low compared to other materials investigated. • The UV cured materials showed higher Ea values than the thermally cured materials. - Abstract: The results of the studies concerning the thermal and photo initiated copolymerization of N-(4-acryloyloxy phenyl) maleimide (AX), N-(4-methacryloyloxy phenyl) maleimide (MAX) and N-(4-cyanato phenyl) maleimide (CNX) with N-vinyl-2-pyrrolidone (NVP) were presented. The structures of all the copolymers prepared were confirmed by FTIR studies. The thermogravimetric studies of both the thermal and UV cured materials indicated that the UV cured materials were comparatively thermally more stable than the thermally polymerized materials during thermal degradation. Of all the materials investigated, liquid composition having NVP and CNX cured by UV irradiation showed better thermal stability. The degradation kinetic studies using Flynn–Wall–Ozawa, Vyazovkin and Friedman methods showed that the activation energies (Ea) for the thermal degradation of polymeric materials cured by UV irradiation were slightly higher than the Ea values calculated for the thermally polymerized materials

  8. ED50 AP block predictions for phenyl substituted and unsubstituted n-alkanols.

    Science.gov (United States)

    Hahin, R; Kondratiev, A

    2001-03-15

    A series of n-alkanols and phenyl-substituted n-alkanols (phi-alkanols) of increasing chain length and phenol were characterized for their ability to block action potentials (APs) in frog sciatic nerves. APs were recorded using the single sucrose-gap method. The degree of AP attenuation when the nerve was exposed to different concentrations of an alcohol was used to construct dose-response curves. The reciprocals of the half-blocking doses (ED50s) were used to obtain a measure of the potency of the alcohols. For n-alkanols and phi-alkanols, increasing the chain length by the addition of a methylene group increased the potency on average by 3.1 for both groups of alkanols. The addition of a phenyl group caused a potency increase that ranged between the values of 77 and 122. The ED50 for both groups of alkanols could not be solely predicted by the log octanol-water partition coefficient (Kow). Using linear solvation energy relations (LSER), the log ED50 could be described as a linear combination of the intrinsic (van der Waals) molar volume (VI), polarity (P), and hydrogen bond acceptor basicity (beta) and donor acidity (alpha). Size alone could not predict the ED50 for both n-alkanols and phi-alkanols. The results are consistent with the hypothesis that alkanols bind to and interact with Na channels to cause AP block. Phenyl group addition to an alkanol markedly increases the molecule's potency.

  9. Optimization of lipase-catalyzed enantioselective production of 1-phenyl 1-propanol using response surface methodology.

    Science.gov (United States)

    Soyer, Asli; Bayraktar, Emine; Mehmetoglu, Ulku

    2010-01-01

    Optically active 1-phenyl 1-propanol is used as a chiral building block and synthetic intermediate in the pharmaceutical industries. In this study, the enantioselective production of 1-phenyl 1-propanol was investigated systematically using response surface methodology (RSM). Before RSM was applied, the effects of the enzyme source, the type of acyl donor, and the type of solvent on the kinetic resolution of 1-phenyl 1-propanol were studied. The best results were obtained with Candida antartica lipase (commercially available as Novozym 435), vinyl laurate as the acyl donor, and isooctane as the solvent. In the RSM, substrate concentration, molar ratio of acyl donor to the substrate, amount of enzyme, temperature, and stirring rate were chosen as independent variables. The predicted optimum conditions for a higher enantiomeric excess (ee) were as follows: substrate concentration, 233 mM; molar ratio of acyl donor to substrate, 1.5; enzyme amount, 116 mg; temperature, 47 °C; and stirring rate, 161 rpm. A verification experiment conducted at these optimized conditions for maximum ee yielded 91% for 3 hr, which is higher than the predicted value of 83%. The effect of microwave on the ee was also investigated and ee reached 87% at only 5 min.

  10. On the molecular conformation of bisaromatic systems the case of 2-phenyl-2H-benzotriazoles

    International Nuclear Information System (INIS)

    Catalan, Javier; Perez, Pilar; Claramunt, Rosa Maria; Maria, Dolores Santa; Bobosik, Vladimir

    2007-01-01

    2-Phenyl-2H-benzotriazole exhibits a planar molecular conformation both in its ground electronic state (S 0 ) and its first excited singlet (S 1 ) and triplet state (T 1 ). However, introducing one or two methyl groups in the ortho positions of the phenyl ring causes the aromatic systems in the compound to lose their coplanarity in both S 0 and T 1 electronic states. On the other hand, 2-(2-methylphenyl)-2H-benzotriazole regains such coplanarity in its first excited singlet state S 1 , giving rise to population inversion that could be used to generate stimulated radiation around 350 nm. As shown in this work, the effectiveness of the ISC process in these compounds is markedly dependent on the twisting angle, θ, of the structure; accordingly, ISC occurs to a negligible extent in a planar compound such as 2-phenyl-2H-benzotriazole, where θ = 0 o . This evidence supports the assumption that planar molecular forms of the TIN-P photoprotectors are more photostable than non-planar ones due to the non effective generation via ISC of their triplet states

  11. Novel organic dyes based on phenyl-substituted benzimidazole for dye sensitized solar cells

    Energy Technology Data Exchange (ETDEWEB)

    Saltan, Gözde Murat [Department of Chemistry, Faculty of Arts and Science, Celal Bayar University, Yunus Emre, 45140 Manisa (Turkey); Dinçalp, Haluk, E-mail: haluk.dincalp@cbu.edu.tr [Department of Chemistry, Faculty of Arts and Science, Celal Bayar University, Yunus Emre, 45140 Manisa (Turkey); Kıran, Merve; Zafer, Ceylan [Solar Energy Institute, Ege University, Bornova, 35100 Izmir (Turkey); Erbaş, Seçil Çelik [Celal Bayar University, Materials Engineering Department, Faculty of Engineering, Yunus Emre, 45140 Manisa (Turkey)

    2015-08-01

    Two new sensitizers derived from benzimidazole core for dye-sensitized solar cell (DSSC) applications were designed and synthesized as D–π–A structures, in which two phenyl-substituted benzimidazole group, a phenyl ring and a cyanoacrylic acid were used as the electron donor, π-conjugated linkage and the electron acceptor, respectively. Effect of methoxy- and N,N-dimetylamino- moieties attached to the phenyl groups of benzimidazole were investigated by means of optical and photovoltaic measurements. The compounds exhibit broad absorption maximum at 387 nm with the tail extending up to 500 nm on TiO{sub 2}-coated thin film. The longer wavelength absorption band around 360 nm and the much longer decay components could be attributed to the existence of charge transfer state of the dyes in solutions. DSSC device fabricated by using methoxy substituted dye (BI5a) as a sensitizer shows much better incident photon-to-current conversion efficiency (IPCE) of 64% giving cell efficiency of 2.68%. - Graphical abstract: Display Omitted - Highlights: • Long decay times suggest the delayed fluorescence caused by the existence of ICT. • The best solar energy conversion efficiency was obtained for BI5a dye (2.68%). • More fluorescent BI5a dye gives higher photocurrent generation.

  12. Click functionalization of phenyl-capped bithiophene on azide-terminated self-assembled monolayers

    International Nuclear Information System (INIS)

    Zheng, Yijun; Cui, Jiaxi; Ikeda, Taichi

    2015-01-01

    Graphical abstract: - Highlights: • Electrochemically-active self-assembled monolayers with phenyl-capped bithiophene were prepared. • Post-functionalization method based on click chemistry solved the solubility issue of phenyl-capped thiophene alkanethiol. • The capture and release of the counter anions during the redox reaction were detectable by E-QCM. - Abstract: We immobilized tetra(ethylene glycol)-substituted phenyl-capped bithiophene with alkyne terminals (Ph2TPh-alkyne) on azide-terminated self-assembled monolayers (N 3 -SAMs) by Cu-catalyzed azide-alkyne cycloaddition reaction. Ph2TPh-functionalized SAMs on a gold substrate showed reversible electrochemical response. The surface densities of the azide groups in N 3 -SAMs and Ph2TPh units in Ph2TPh-functionalized SAMs were estimated to be 7.3 ± 0.3 × 10 −10 mol cm −2 and 4.6 ± 0.3 × 10 −10 mol cm −2 , respectively, by quartz crystal microbalance (QCM). Most of Ph2TPh-alkynes are considered to be anchored on N 3 -SAMs via both terminal groups. Ph2TPh-functionalized SAMs exhibited reversible redox peaks in cyclic voltammetry (CV). In redox reaction, reversible capture and release of the counter anion could be monitored by electrochemical QCM (E-QCM).

  13. Click functionalization of phenyl-capped bithiophene on azide-terminated self-assembled monolayers

    Energy Technology Data Exchange (ETDEWEB)

    Zheng, Yijun; Cui, Jiaxi [Max Planck Institute for Polymer Research (MPIP), Ackermannweg 10, Mainz 55128 (Germany); Ikeda, Taichi, E-mail: IKEDA.Taichi@nims.go.jp [Max Planck Institute for Polymer Research (MPIP), Ackermannweg 10, Mainz 55128 (Germany); Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 305-0044 (Japan)

    2015-11-15

    Graphical abstract: - Highlights: • Electrochemically-active self-assembled monolayers with phenyl-capped bithiophene were prepared. • Post-functionalization method based on click chemistry solved the solubility issue of phenyl-capped thiophene alkanethiol. • The capture and release of the counter anions during the redox reaction were detectable by E-QCM. - Abstract: We immobilized tetra(ethylene glycol)-substituted phenyl-capped bithiophene with alkyne terminals (Ph2TPh-alkyne) on azide-terminated self-assembled monolayers (N{sub 3}-SAMs) by Cu-catalyzed azide-alkyne cycloaddition reaction. Ph2TPh-functionalized SAMs on a gold substrate showed reversible electrochemical response. The surface densities of the azide groups in N{sub 3}-SAMs and Ph2TPh units in Ph2TPh-functionalized SAMs were estimated to be 7.3 ± 0.3 × 10{sup −10} mol cm{sup −2} and 4.6 ± 0.3 × 10{sup −10} mol cm{sup −2}, respectively, by quartz crystal microbalance (QCM). Most of Ph2TPh-alkynes are considered to be anchored on N{sub 3}-SAMs via both terminal groups. Ph2TPh-functionalized SAMs exhibited reversible redox peaks in cyclic voltammetry (CV). In redox reaction, reversible capture and release of the counter anion could be monitored by electrochemical QCM (E-QCM).

  14. Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ- butyro lactones: Key intermediates in the synthesis of β-phenyl-Gaba and baclofene

    International Nuclear Information System (INIS)

    Gomez G, J.; Melendez R, M.; Suarez C, O. R.; Castelan D, L. E.; Fragoso V, M. J.; Lopez V, E.; Sanchez Z, M.

    2014-01-01

    the preparation of β-phenyl- and β-(4-chlorophenyl)-γ-butyro lactones (±)-4 and their resolution to the corresponding (+)-(S)-3, (-)-(R)-3 and (+)-(S)-4, (-)-(R)-4 through formation, flash column chromatography separation and subsequent hydrolysis of dia stereoisomeric 4-hydroxybutyramide s (2'R,3S)-5, (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6. (Author)

  15. Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ- butyro lactones: Key intermediates in the synthesis of β-phenyl-Gaba and baclofene

    Energy Technology Data Exchange (ETDEWEB)

    Gomez G, J.; Melendez R, M.; Suarez C, O. R.; Castelan D, L. E.; Fragoso V, M. J.; Lopez V, E.; Sanchez Z, M., E-mail: melendez@uaeh.edu.mx [Universidad Autonoma del Estado de Hidalgo, Area Academica de Quimica, Carretera Pachuca-Tulancingo Km. 4.5, Mineral de la Reforma 42184, Hidalgo (Mexico)

    2014-07-01

    the preparation of β-phenyl- and β-(4-chlorophenyl)-γ-butyro lactones (±)-4 and their resolution to the corresponding (+)-(S)-3, (-)-(R)-3 and (+)-(S)-4, (-)-(R)-4 through formation, flash column chromatography separation and subsequent hydrolysis of dia stereoisomeric 4-hydroxybutyramide s (2'R,3S)-5, (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6. (Author)

  16. Caffeic acid phenethyl ester induces adrenoleukodystrophy (Abcd2) gene in human X-ALD fibroblasts and inhibits the proinflammatory response in Abcd1/2 silenced mouse primary astrocytes.

    Science.gov (United States)

    Singh, Jaspreet; Khan, Mushfiquddin; Singh, Inderjit

    2013-04-01

    X-linked adrenoleukodystrophy (X-ALD) is a peroxisomal disorder caused by mutations in the ABCD1 gene. Accumulation of very long chain fatty acids (VLCFA) that have been attributed to reduced peroxisomal VLCFA β-oxidation activity are the hallmark of the disease. Overexpression of ABCD2 gene, the closest homolog of ABCD1, has been shown to compensate for ABCD1, thus correcting the VLCFA derangement. The accumulation of VLCFA leads to a neuroinflammatory disease process associated with demyelination of the cerebral white matter. The present study underlines the importance of caffeic acid phenethyl ester (CAPE) in inducing the expression of ABCD2 (ALDRP), and normalizing the peroxisomal β-oxidation as well as the levels of saturated and monounsaturated VLCFAs in cultured human skin fibroblasts of X-ALD patients. The expression of ELOVL1, the single elongase catalyzing the synthesis of both saturated VLCFA (C26:0) and mono-unsaturated VLCFA (C26:1), was also reduced by CAPE treatment. Importantly, CAPE upregulated Abcd2 expression and peroxisomal β-oxidation and lowered the VLCFA levels in Abcd1-deficient U87 astrocytes and B12 oligodendrocytes. In addition, using Abcd1/Abcd2-silenced mouse primary astrocytes we examined the effects of CAPE in VLCFA-induced inflammatory response. CAPE treatment decreased the inflammatory response as the expression of inducible nitric oxide synthase, inflammatory cytokine, and activation of NF-κB in Abcd1/Abcd2-silenced mouse primary astrocytes was reduced. The observations indicate that CAPE corrects both the metabolic disease of VLCFA as well as secondary inflammatory disease; therefore, it may be a potential drug candidate to be tested for X-ALD therapy in humans. Copyright © 2013 Elsevier B.V. All rights reserved.

  17. Caffeic Acid Phenethyl Ester Induces Adrenoleukodystrophy (Abcd2) Gene in Human X-ALD Fibroblasts and Inhibits the Proinflammatory Response in Abcd1/2 Silenced Mouse Primary Astrocytes

    Science.gov (United States)

    Singh, Jaspreet; Khan, Mushfiquddin; Singh, Inderjit

    2013-01-01

    X-linked adrenoleukodystrophy (X-ALD) is a peroxisomal disorder caused by mutations in the ABCD1 gene. Accumulation of very long chain fatty acids (VLCFA) that have been attributed to reduced peroxisomal VLCFA β-oxidation activity are the hallmark of the disease. Overexpression of ABCD2 gene, the closest homolog of ABCD1, has been shown to compensate for ABCD1, thus correcting the VLCFA derrangement. The accumulation of VLCFA leads to a neuroinflammatory disease process associated with demyelination of the cerebral white matter. The present study underlines the importance of caffeic acid phenethyl ester (CAPE) in inducing the expression of ABCD2 (ALDRP), and normalizing the peroxisomal β-oxidation as well as the levels of saturated and monounsaturated VLCFAs in cultured human skin fibroblasts of X-ALD patients. The expression of ELOVL1, the single elongase catalyzing the synthesis of both saturated VLCFA (C26:0) and mono-unsaturated VLCFA (C26:1), was also reduced by CAPE treatment. Importantly, CAPE upregulated Abcd2 expression and peroxisomal β-oxidation and lowered the VLCFA levels in Abcd1-deficient U87 astrocytes and B12 oligodendrocytes. In addition, using Abcd1/Abcd2-silenced mouse primary astrocytes we examined the effects of CAPE in VLCFA-induced inflammatory response. CAPE treatment decreased the inflammatory response as the expression of inducible nitric oxide synthase, inflammatory cytokine, and activation of NF-κB in Abcd1/Abcd2-silenced mouse primary astrocytes was reduced. The observations indicate that CAPE corrects both the metabolic disease of VLCFA as well as secondary inflammatory disease; therefore, it may be a potential drug candidate to be tested for X-ALD therapy in humans. PMID:23318275

  18. Selected alkyl(phenyl)-N,N-dialkylcarbamoylmethylphosphine oxides as extractants for Am(III) from nitric acid media

    International Nuclear Information System (INIS)

    Horwitz, E.P.; Kalina, D.G.; Kaplan, L.; Mason, G.W.; Diamond, H.

    1982-01-01

    A new series of neutral bifunctional extractants, alkyl(phenyl)-N,N-dialkyl-carbamoylmethylphosphine oxides, has been prepared and studied as extractants for Am(III) from nitric acid media. Two types of alkyl(phenyl)-N,N-dialkyl CMPO compounds were prepared, one containing N,N-diethyl groups and the other containing N,N-diisobutyl groups. The N,N-diethyl series contained hexyl(phenyl) and 6-methylheptyl(phenyl) derivatives, abbreviated H phi DECMPO and 6-MH phi DECMPO, respectively. The N,N-diisobutyl series contained the n-octyl(phenyl), 6-methylheptyl(phenyl), and the 2-ethylhexyl(phenyl) derivatives, abbreviated O phi D[IB]CMPO, 6-MH phi D[IB]CMPO, and 2-EH phi D[IB]CMPO, respectively. Third power extractant dependencies for the extraction of Am(III) from 0.5 and 3 M HNO 3 were obtained at low ( 3 . The H phi DECMPO, 6-MH phi DECMPO, 6-MH phi D[IB]CMPO, and O phi D[IB]CMPO [all 0.5 M in diethylbenzene (DEB)] are significantly better extractants than DHDECMPO for Am(III) from 1 to 6 M HNO 3 . These same extractants have lower D/sub Am/ values than DHDECMPO at low acidities. H phi DECMPO and O phi D[IB]CMPO also have better selectivity for Am(III) over Fe(III) than DHDECMPO. H phi DECMPO in DEB has a strong tendency toward the formation of a second liquid organic phase on extracting macroconcentrations of Nd(III) and U(VI) from 3 M HNO 3 ; however, this behavior is substantially diminished with the O phi D[IB]CMPO and 6-MH phi D[IB]CMPO compounds

  19. Toward the Oxidation of the Phenyl Radical and Prevention of PAH Formation in Combustion Systems.

    Science.gov (United States)

    Parker, Dorian S N; Kaiser, Ralf I; Troy, Tyler P; Kostko, Oleg; Ahmed, Musahid; Mebel, Alexander M

    2015-07-16

    The reaction of the phenyl radical (C6H5) with molecular oxygen (O2) plays a central role in the degradation of poly- and monocyclic aromatic radicals in combustion systems which would otherwise react with fuel components to form polycyclic aromatic hydrocarbons (PAHs) and eventually soot. Despite intense theoretical and experimental scrutiny over half a century, the overall reaction channels have not all been experimentally identified. Tunable vacuum ultraviolet photoionization in conjunction with a combustion simulating chemical reactor uniquely provides the complete isomer specific product spectrum and branching ratios of this prototype reaction. In the reaction of phenyl radicals and molecular oxygen at 873 K and 1003 K, ortho-benzoquinone (o-C6H4O2), the phenoxy radical (C6H5O), and cyclopentadienyl radical (C5H5) were identified as primary products formed through emission of atomic hydrogen, atomic oxygen and carbon dioxide. Furan (C4H4O), acrolein (C3H4O), and ketene (C2H2O) were also identified as primary products formed through ring opening and fragmentation of the 7-membered ring 2-oxepinoxy radical. Secondary reaction products para-benzoquinone (p-C6H4O2), phenol (C6H5OH), cyclopentadiene (C5H6), 2,4-cyclopentadienone (C5H4O), vinylacetylene (C4H4), and acetylene (C2H2) were also identified. The pyranyl radical (C5H5O) was not detected; however, electronic structure calculations show that it is formed and isomerizes to 2,4-cyclopentadienone through atomic hydrogen emission. In combustion systems, barrierless phenyl-type radical oxidation reactions could even degrade more complex aromatic radicals. An understanding of these elementary processes is expected to lead to a better understanding toward the elimination of carcinogenic, mutagenic, and environmentally hazardous byproducts of combustion systems such as PAHs.

  20. Synthesis and fuel cell characterization of blend membranes from phenyl phosphine oxide containing flourinated novel polymers

    Science.gov (United States)

    Gürtekin Seden, Merve; Baştürk, Emre; Inan, Tülay Y.; Kayaman Apohan, Nilhan; Güngör, Atilla

    2014-12-01

    Novel fluorinated poly(arylene ether)'s are synthesized from polycondensation of bis (p-hydroxy-tetrafluoro) phenyl) phenyl phosphine oxide (PFPPO-OH) with 4,4‧-dichlorodiphenyl sulfone (DCDPS) and 2,2-bis(4-hydroxyphenyl)propane (Bisfenol A) (Copolymer 1a) or 2,2-bis(4-hydroxyphenyl) hexafluoropropane (Bisphenol AF) (Copolymer 1b). The fluorinated copolymers have been blended with sulphonated poly(ether ether ketone)-SPEEK by solvent casting method. The water uptake and proton conductivity of the blend membranes decreases with the increase of copolymer content as expected, but proton conductivity values are still comparable to that of Nafion117® membrane. Addition of hydrophobic copolymer 1b to the SPEEK caused increase in water vapor transmission. Methanol permeability of the membranes is decreased to 8.2 × 10-8 cm2 s-1 and 1.3 × 10-9 cm2 s-1 by addition of Copolymer 1a and 1b, respectively and they are much lower than that of Nafion® 117 (1.21E-06 (cm2 s-1). The blend membranes endure up to 6.5 h before it starts to dissolve. Hydrogen and oxygen permeability of the blend membranes is one-hundredth of the Nafion®. Fluorinated polymer improved chemical, mechanical, and hydrolytic stability and also phenyl phosphine oxide structure in the ionomer increased the thermal stability, gas and methanol permeability and overcomed the drawbacks of the Nafion® type membranes.

  1. Diazido{(S-1-phenyl-N,N-bis[(2-pyridylmethyl]ethanamine}copper(II

    Directory of Open Access Journals (Sweden)

    Sankara Rao Rowthu

    2011-07-01

    Full Text Available In the title compound, [Cu(N32(C20H21N3], the CuII ion is coordinated by the three N atoms of the (S-1-phenyl-N,N-bis[(2-pyridylmethyl]ethanamine ligand and two N atoms from two azide anions, resulting in a distorted square-pyramidal environment. A weak intermolecular C—H...N hydrogen-bonding interaction between one pyridine group of the ligand and an azide N atom of an adjacent complex unit gives a one-dimensional chain structure parallel to the c axis.

  2. Conducting polymers of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester

    International Nuclear Information System (INIS)

    Cirpan, A.; Guner, Y.; Toppare, L.

    2004-01-01

    A dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and decanedioyl dichloride. The electrochemical behavior of this monomer was studied. Polymerization of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester (DAPE) was achieved by chemical and constant current electrolyses methods. Copolymerization of DAPE with thiophene was performed by constant potential electrolysis in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB), dichloromethane-TBAFB, solvent-electrolyte couples. The chemical structures and properties were investigated by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, differential scanning calorimetry and thermal gravimetry analysis. The conductivities of the samples were measured by a four-probe technique

  3. Conducting polymers of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester

    Energy Technology Data Exchange (ETDEWEB)

    Cirpan, A.; Guner, Y.; Toppare, L

    2004-05-15

    A dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and decanedioyl dichloride. The electrochemical behavior of this monomer was studied. Polymerization of decanedioic acid bis-(4-pyrrol-1-yl-phenyl) ester (DAPE) was achieved by chemical and constant current electrolyses methods. Copolymerization of DAPE with thiophene was performed by constant potential electrolysis in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB), dichloromethane-TBAFB, solvent-electrolyte couples. The chemical structures and properties were investigated by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, differential scanning calorimetry and thermal gravimetry analysis. The conductivities of the samples were measured by a four-probe technique.

  4. 3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile

    Directory of Open Access Journals (Sweden)

    Sabry H. H. Younes

    2013-03-01

    Full Text Available In the title compound, C20H14N2O, the phenyl ring is almost normal to the naphthalene ring system with a dihedral angle of 86.72 (9°. The 4H-pyran ring fused with the naphthalene ring system has a boat conformation. In the crystal, molecules are linked into a helical supramolecular chain along the b axis via N—H...N hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H...π interactions.

  5. Derivatives of phenyl tribromomethyl sulfone as novel compounds with potential pesticidal activity

    Directory of Open Access Journals (Sweden)

    Krzysztof M. Borys

    2012-02-01

    Full Text Available A halogenmethylsulfonyl moiety is incorporated in numerous active herbicides and fungicides. The synthesis of tribromomethyl phenyl sulfone derivatives as novel potential pesticides is reported. The title sulfone was obtained by following three different synthetic routes, starting from 4-chlorothiophenol or 4-halogenphenyl methyl sulfone. Products of its subsequent nitration were subjected to the SNAr reactions with ammonia, amines, hydrazines and phenolates to give 2-nitroaniline, 2-nitrophenylhydrazine and diphenyl ether derivatives. Reduction of the nitro group of 4-tribromomethylsulfonyl-2-nitroaniline yielded the corresponding o-phenylenediamine substrate for preparation of structurally varied benzimidazoles.

  6. Crystal structure of a diaryl carbonate: 1,3-phenylene bis(phenyl carbonate

    Directory of Open Access Journals (Sweden)

    Marina A. Solomos

    2017-12-01

    Full Text Available The whole molecule of the title compound, C20H14O6, is generated by mirror symmetry, the mirror bisecting the central benzene ring. The carbonate groups adopt an s-cis-s-cis conformation, with torsion angles of 58.7 (2 and 116.32 (15°. The crystal structure of 1,3-phenylene bis(phenyl carbonate contains no strong hydrogen bonds, though weak C—H...O and offset π–π interactions are observed, forming layers parallel to the ac plane.

  7. Tris(phenyl 2-pyridyl ketone oxime-κ2N,N′cadmium(II dinitrate

    Directory of Open Access Journals (Sweden)

    Juan Yan

    2009-06-01

    Full Text Available The Cd atom in the title compound, [Cd(C12H10N2O3](NO32, adopts a distorted octahedral geometry, being ligated by six N atoms from three different phenyl-2-pyridyl ketone oxime ligands. In the crystal structure, intermolecular O—H...O and C—H...O hydrogen bonds link the molecules into a chain structure propagating along [100]. The chains are further linked into a three-dimensional supramolecular structure via van der Waals forces.

  8. Dichloridobis(phenyl 2-pyridyl ketone oximenickel(II acetone solvate

    Directory of Open Access Journals (Sweden)

    Guang-Xiang Liu

    2009-02-01

    Full Text Available The Ni atom in the title compound, [NiCl2(C12H10N2O2]·C3H6O, adopts a distorted octahedral geometry, being ligated by four N atoms from two different phenyl 2-pyridyl ketone oxime ligands and two Cl atoms. In the crystal structure, intermolecular O—H...Cl hydrogen bonds link the molecules into a chain structure along [010]. There is a π–π contact between the pyridine rings [centroid–centroid distance = 3.824 (5 Å].

  9. Study of methyl- and phenyl-substituted thermostable polysiloxane-silarylene motionless phases for capillary gas chromatography

    Science.gov (United States)

    Komarova, A. O.; Shashkov, M. V.; Sidel'nikov, V. N.

    2017-11-01

    Capillary columns based on a number of thermostable polysiloxane-silarylene motionless phases are prepared and their properties are studied. Three polymers with different contents of methyl and phenyl groups are synthesized: dimethylsiloxanesilarylene (DMS), methylphenylsiloxanesilarylene (MPhS), and diphenylsiloxanesilarylene (DPhS). Studies of their thermostability show that the level of the background current of these columns upon heating to 350°C is several times lower than that of a column based on polydimethylsiloxane. Based on McReynolds' studies of polarity and Abraham's studies of the selectivity of prepared columns according to the parameters of intermolecular interactions, it is found that silarylene MLPs are more affected by the contributions from specific interactions (especially for dipole-dipole, π-π-, and n-π-interactions) than MLPs with no phenylene inserts. The effect on the selectivity of a phenyl group inside a chain differs from the one produced by the phenyl groups in side MLP chains. The effect on the selectivity of a phenyl group inside a chain differs from the one produced by the phenyl groups in side MLP chains. Examples of the separation of test mixtures of aromatic and oxygen-containing compounds are obtained, along with an extract of thistle oil containing tocopherols and phytosterols at a final temperature of analysis of 350°C.

  10. Design, synthesis and inhibitory activities of 8-(substituted styrol-formamido)phenyl-xanthine derivatives on monoamine oxidase B.

    Science.gov (United States)

    Hu, Suwen; Nian, Siyun; Qin, Kuiyou; Xiao, Tong; Li, Lingna; Qi, Xiaolu; Ye, Faqing; Liang, Guang; Hu, Guoxin; He, Jincai; Yu, Yinfei; Song, Bo

    2012-01-01

    The design and synthesis of two series of 8-(substituted styrol-formamido)phenyl-xanthine derivatives are described. Their in vitro monoamine oxidase B (MAO-B) inhibition were tested and the effect of substituents on the N-7, phenyl and the substituted positions are discussed. It was observed that compound 9b displayed significant MAO-B inhibition activity and selectivity, fluorine substitution plays a key role in the selectivity of MAO-B inhibition, and the styrol-formamido group at position-3' may enhance the activity and selectivity of 8-phenyl-xanthine analogues. These results suggest that such compounds may be utilized for the development of new candidate MAO-B inhibitors for treatment of Parkinson's disease.

  11. 4-Phenyl quinoline derivatives as potential serotonin receptor ligands with antiproliferative activity.

    Science.gov (United States)

    Joshi, Pranaya V; Sayed, Alim A; RaviKumar, Ameeta; Puranik, Vedavati G; Zinjarde, Smita S

    2017-08-18

    Antagonists of signaling receptors are often effective non-toxic therapeutic agents. Over the years, there have been evidences describing the role of serotonin or 5-hydroxytryptamine (5-HT) in development of cancer. Although there are reports on the antiproliferative effects of some serotonin receptor antagonists, there are very few investigations related to understanding their structure-activity relationships. In this study, we report the screening of a library of 4-phenyl quinoline derivatives for their antiproliferative activities. Preliminary docking studies indicated that these ligands had the ability to bind to two of the serotonin receptors, 5-HT 1B and 5-HT 2B . The results of the in silico experiments were validated by performing in vitro studies on MCF-7 breast cancer cell line. The ethylpiperazine derivatives showed maximum toxicity against this cancer cell line. The compounds inhibited Calcium ion efflux (induced by serotonin) and ERK activation. One of the most active 4-phenyl quinoline derivatives (H3a) also induced apoptosis, thereby, suggesting the use of this scaffold as a potential anticancer drug. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  12. Photochemical oxidation processes for the elimination of phenyl-urea herbicides in waters

    Energy Technology Data Exchange (ETDEWEB)

    Benitez, F. Javier [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain)]. E-mail: javben@unex.es; Real, Francisco J. [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain); Acero, Juan L. [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain); Garcia, Carolina [Departamento de Ingenieria Quimica y Energetica, Universidad de Extremadura, 06071 Badajoz (Spain)

    2006-11-16

    Four phenyl-urea herbicides (linuron, chlorotoluron, diuron, and isoproturon) were individually photooxidized by monochromatic UV radiation in ultra-pure aqueous solutions. The influence of pH and temperature on the photodegradation process was established, and the first-order rate constants and quantum yields were evaluated. The sequence of photodecomposition rates was: linuron > chlorotoluron > diuron > isoproturon. The simultaneous photooxidation of mixtures of the selected herbicides in several types of waters was then performed by means of UV radiation alone, and by UV radiation combined with hydrogen peroxide. The types of waters used were: ultra-pure water, a commercial mineral water, a groundwater, and a lake water. The influence of the independent variables in these processes - the presence or absence of tert-butyl alcohol, types of herbicide and waters, and concentration of hydrogen peroxide - were established and discussed. A kinetic study was performed using a competitive kinetic model that allowed various rate constants to be evaluated for each herbicide. This kinetic model allows one to predict the elimination of these phenyl-urea herbicides in contaminated waters by the oxidation systems used (UV alone and combined UV/H{sub 2}O{sub 2}). The herbicide concentrations predicted by this model agree well with the experimental results that were obtained.

  13. Photochemical oxidation processes for the elimination of phenyl-urea herbicides in waters

    International Nuclear Information System (INIS)

    Benitez, F. Javier; Real, Francisco J.; Acero, Juan L.; Garcia, Carolina

    2006-01-01

    Four phenyl-urea herbicides (linuron, chlorotoluron, diuron, and isoproturon) were individually photooxidized by monochromatic UV radiation in ultra-pure aqueous solutions. The influence of pH and temperature on the photodegradation process was established, and the first-order rate constants and quantum yields were evaluated. The sequence of photodecomposition rates was: linuron > chlorotoluron > diuron > isoproturon. The simultaneous photooxidation of mixtures of the selected herbicides in several types of waters was then performed by means of UV radiation alone, and by UV radiation combined with hydrogen peroxide. The types of waters used were: ultra-pure water, a commercial mineral water, a groundwater, and a lake water. The influence of the independent variables in these processes - the presence or absence of tert-butyl alcohol, types of herbicide and waters, and concentration of hydrogen peroxide - were established and discussed. A kinetic study was performed using a competitive kinetic model that allowed various rate constants to be evaluated for each herbicide. This kinetic model allows one to predict the elimination of these phenyl-urea herbicides in contaminated waters by the oxidation systems used (UV alone and combined UV/H 2 O 2 ). The herbicide concentrations predicted by this model agree well with the experimental results that were obtained

  14. Microwave Assisted Enzymatic Kinetic Resolution of (±-1-Phenyl-2-propyn-1-ol in Nonaqueous Media

    Directory of Open Access Journals (Sweden)

    Saravanan Devendran

    2014-01-01

    Full Text Available Kinetic resolution of 1-phenyl-2-propyn-1-ol, an important chiral synthon, was studied through trans-esterification with acyl acetate to investigate synergism between microwave irradiation and enzyme catalysis. Lipases from different microbial origins were employed for the kinetic resolution of (R/S-1-phenyl-2-propyn-1-ol, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435, was found to be the best catalyst in n-hexane as solvent. Vinyl acetate was the most effective among different acyl esters studied. The effect of various parameters was studied in a systematic manner. Definite synergism between microwave and enzyme was observed. The initial rate was improved around 1.28 times under microwave irradiation than conventional heating. Under optimum conditions, maximum conversion (48.78% and high enantiomeric excess (93.25% were obtained in 2 h. From modeling studies, it is concluded that the reaction follows the Ping-Pong bi-bi mechanism with dead end alcohol inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is green, clean, and easily scalable as compared to the chemical process.

  15. Self-assembly of aromatic-derivatized amphiphiles: Phenyl, biphenyl, and terphenyl fatty acids and phospholipids

    Energy Technology Data Exchange (ETDEWEB)

    Geiger, H.C.; Perlstein, J.; Lachicotte, R.J.; Wyrozebski, K.; Whitten, D.G. [Univ. of Rochester, NY (United States)]|[Los Alamos National Lab., NM (United States). Chemical Science and Technology Div.

    1999-08-17

    This paper reports the synthesis of a series of amphiphiles (fatty acids and phosphatidylcholine derivatives) containing phenyl, biphenyl, and terphenyl chromophores inserted in the hydrocarbon chain and a study of their self-assembly in Langmuir-Blodgett films and aqueous dispersions. As observed and reported earlier for amphiphiles containing trans-stilbene, styrylthiophene, or azobenzene chromophores, several of the biphenyl and terphenyl derivatives show strong evidence of ground state association to form H aggregates characterized by a blue shift in absorption and a structured, red-shifted fluorescence. The phenyl amphiphiles show different behavior, suggesting that, even for pure films or bilayers, there is very little or no ground state association. For the biphenyl and terphenyl phospholipids, aqueous suspensions obtained by sonication are closed bilayer vesicles similar in size to those formed from the corresponding saturated phospholipids. The overall results of the present study indicate that biphenyl and terphenyl amphiphiles undergo aggregation processes to form compact arrays formally similar to those observed with stilbenen tolan, azobenzene, and squaraine derivatives but that the aromatic-aromatic interactions are considerably weaker than those for the more extended aromatics and lead to less distortion of the assembly structure.

  16. Kinetic α secondary deuterium isotope effects for O-ethyl S-phenyl benzaldehyde acetal hydrolysis

    International Nuclear Information System (INIS)

    Ferraz, J.P.; Cordes, E.H.

    1979-01-01

    The rate of hydrolysis of O-ethyl S-phenyl benzaldehyde acetal at 25 0 C in 20% dioxane--80% water is independent of pH over the range pH6-12; k/sub obsd/ = 1.9 x 10 -7 s -1 . Under more acidic conditions, the rate increases linearly with the activity of the hydrated proton; k 2 = 2.95 x 10 -2 M -1 s -1 . The kinetic α secondary deuterium isotope effect for acid-catalyzed hydrolysis of O-ethyl S-phenyl benzaldehyde acetal, measured at 25 0 C in 20% aqueous dioxane containing 0.05 M HCl, is k/sub H//k/sub D/ = 1.038 +- 0.008, a value consistent with a transition state in which the C--S bond is stretched rather little. In contrast, the corresponding isotope effect for the pH-independent hydrolysis of this substrate, measured at 42.5 0 C in 20% dioxane, is 1.13 +- 0.02, a value consistent with complete C--S bond cleavage in the transition state and rate-determining diffusion apart of the ion-pair formed as the initial intermediate, in accord with the suggestion of Jensen and Jencks. 1 figure, 4 tables

  17. 4-Methyl-5-phenyl-1H-pyrazol-3(2H-one

    Directory of Open Access Journals (Sweden)

    V. Vijayakumar

    2011-01-01

    Full Text Available The asymmetric unit of the title compound, C10H10N2O, contains two crystallographically independent molecules with similar geometries, which exist in the keto form. The C=O bond lengths are 1.2878 (12 Å in molecule A and 1.2890 (12 Å in molecule B, indicating that the compound undergoes enol-to-keto tautomerism during the crystallization process. In molecule A, the pyrazole ring is approximately planar [maximum deviation = 0.007 (1 Å] and forms a dihedral angle of 36.67 (6° with the attached phenyl ring. In molecule B, the dihedral angle formed between the pyrazole ring [maximum deviation = 0.017 (1 Å] and the phenyl ring is 41.19 (6°. In the crystal, intermolecular N—H...O hydrogen bonds link neighbouring molecules into dimers generating R22(8 ring motifs. These dimers are linked into ribbons along [101] via intermolecular N—H...O hydrogen bonds, forming R42(10 ring motifs.

  18. Enhanced dispersion of multiwall carbon nanotubes in natural rubber latex nanocomposites by surfactants bearing phenyl groups.

    Science.gov (United States)

    Mohamed, Azmi; Anas, Argo Khoirul; Bakar, Suriani Abu; Ardyani, Tretya; Zin, Wan Manshol W; Ibrahim, Sofian; Sagisaka, Masanobu; Brown, Paul; Eastoe, Julian

    2015-10-01

    Here is presented a systematic study of the dispersibility of multiwall carbon nanotubes (MWCNTs) in natural rubber latex (NR-latex) assisted by a series of single-, double-, and triple-sulfosuccinate anionic surfactants containing phenyl ring moieties. Optical polarising microscopy, field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), and Raman spectroscopy have been performed to obtain the dispersion-level profiles of the MWCNTs in the nanocomposites. Interestingly, a triple-chain, phenyl-containing surfactant, namely sodium 1,5-dioxo-1,5-bis(3-phenylpropoxy)-3-((3-phenylpropoxy)carbonyl) pentane-2-sulfonate (TCPh), has a greater capacity the stabilisation of MWCNTs than a commercially available single-chain sodium dodecylbenzenesulfonate (SDBS) surfactant. TCPh provides significant enhancements in the electrical conductivity of nanocomposites, up to ∼10(-2) S cm(-1), as measured by a four-point probe instrument. These results have allowed compilation of a road map for the design of surfactant architectures capable of providing the homogeneous dispersion of MWCNTs required for the next generation of polymer-carbon-nanotube materials, specifically those used in aerospace technology. Copyright © 2015 Elsevier Inc. All rights reserved.

  19. Preparation of nanosheet by exfoliation of layered iron phenyl phosphate under ultrasonic irradiation

    International Nuclear Information System (INIS)

    Tanaka, Hidekazu; Okumiya, Takeshi; Ueda, Shun-kichi; Taketani, Yukihiko; Murakami, Masahiko

    2009-01-01

    Synthetic layered iron phenyl phosphate (Fe(OH)(C 6 H 5 PO 4 H) 1.6 (H 2 PO 4 ) 0.4 .5.1H 2 O: FePP), which is composed of a multilayer alternating bilayer of phenyl groups of the phosphates and amorphous iron phosphate phase, was exfoliated in ethanol under ultrasonic irradiation. The exfoliation of FePP was recognized at 10-10,000 ppm of FePP concentration. No reaggregation and reprecipitation of the nanosheets took place for at least 6 months of standing at room temperature. The UV-vis measurements indicated that the nanosheet dispersing solution possessed a UV absorption property which would be due to the charge transfer transition of Fe-O. The FePP nanosheet-doped silica gel with UV absorption property could be prepared by sol-gel process. The Beer's plot and EDX elemental mapping analysis for Fe and P revealed that the nanosheets are homogeneously dispersed in the silica gels

  20. The Influence of Alkoxy Substitutions on the Properties of Diketopyrrolopyrrole-Phenyl Copolymers for Solar Cells

    Directory of Open Access Journals (Sweden)

    Paul Heremans

    2013-07-01

    Full Text Available A previously reported diketopyrrolopyrrole (DPP-phenyl copolymer is modified by adding methoxy or octyloxy side chains on the phenyl spacer. The influence of these alkoxy substitutions on the physical, opto-electronic properties, and photovoltaic performance were investigated. It was found that the altered physical properties correlated with an increase in chain flexibility. Well-defined oligomers were synthesized to verify the observed structure-property relationship. Surprisingly, methoxy substitution on the benzene spacer resulted in higher melting and crystallization temperatures in the synthesized oligomers. This trend is not observed in the polymers, where the improved interactions are most likely counteracted by the larger conformational possibilities in the polymer chain upon alkoxy substitution. The best photovoltaic performance was obtained for the parent polymer: fullerene blends whereas the modifications on the other two polymers result in reduced open-circuit voltage and varying current densities under similar processing conditions. The current densities could be related to different polymer: fullerene blend morphologies. These results show that supposed small structural alterations such as methoxy substitution already significantly altered the physical properties of the parent polymer and also that oligomers and polymers respond divergent to structural alterations made on a parent structure.

  1. Hydrolytic metabolism of phenyl and benzyl salicylates, fragrances and flavoring agents in foods, by microsomes of rat and human tissues.

    Science.gov (United States)

    Ozaki, Hitomi; Sugihara, Kazumi; Tamura, Yuki; Fujino, Chieri; Watanabe, Yoko; Uramaru, Naoto; Sone, Tomomichi; Ohta, Shigeru; Kitamura, Shigeyuki

    2015-12-01

    Salicylates are used as fragrance and flavor ingredients for foods, as UV absorbers and as medicines. Here, we examined the hydrolytic metabolism of phenyl and benzyl salicylates by various tissue microsomes and plasma of rats, and by human liver and small-intestinal microsomes. Both salicylates were readily hydrolyzed by tissue microsomes, predominantly in small intestine, followed by liver, although phenyl salicylate was much more rapidly hydrolyzed than benzyl salicylate. The liver and small-intestinal microsomal hydrolase activities were completely inhibited by bis(4-nitrophenyl)phosphate, and could be extracted with Triton X-100. Phenyl salicylate-hydrolyzing activity was co-eluted with carboxylesterase activity by anion exchange column chromatography of the Triton X-100 extracts of liver and small-intestinal microsomes. Expression of rat liver and small-intestinal isoforms of carboxylesterase, Ces1e and Ces2c (AB010632), in COS cells resulted in significant phenyl salicylate-hydrolyzing activities with the same specific activities as those of liver and small-intestinal microsomes, respectively. Human small-intestinal microsomes also exhibited higher hydrolyzing activity than liver microsomes towards these salicylates. Human CES1 and CES2 isozymes expressed in COS cells both readily hydrolyzed phenyl salicylate, but the activity of CES2 was higher than that of CES1. These results indicate that significant amounts of salicylic acid might be formed by microsomal hydrolysis of phenyl and benzyl salicylates in vivo. The possible pharmacological and toxicological effects of salicylic acid released from salicylates present in commercial products should be considered. Copyright © 2015. Published by Elsevier Ltd.

  2. Synthesis, Characterization, and Biological Activity of 5-Phenyl-1,3,4-thiadiazole-2-amine Incorporated Azo Dye Derivatives

    OpenAIRE

    Chinnagiri T. Keerthi Kumar; Jathi Keshavayya; Tantry N. Rajesh; Sanehalli K. Peethambar; Angadi R. Shoukat Ali

    2013-01-01

    5-Phenyl-1,3,4-thiadiazole-2-amine has been synthesized by single step reaction. A series of heterocyclic azodyes were synthesized by diazotisation of 5-phenyl-1,3,4-thiadiazole-2-amine by nitrosyl sulphuric acid followed by coupling with different coupling compounds such as 8-hydroxyquinoline, 2,6-diaminopyridine, 2-naphthol, N,N-dimethyl aniline, resorcinol, and 4,6-dihydroxypyrimidine. The dyes were characterized by UV-Vis, IR, 1H-NMR, 13C NMR, and elemental analysis. The synthesized compo...

  3. Substituted piperazines as nootropic agents: 2- or 3-phenyl derivatives structurally related to the cognition-enhancer DM235.

    Science.gov (United States)

    Guandalini, Luca; Martino, Maria Vittoria; Di Cesare Mannelli, Lorenzo; Bartolucci, Gianluca; Melani, Fabrizio; Malik, Ruchi; Dei, Silvia; Floriddia, Elisa; Manetti, Dina; Orlandi, Francesca; Teodori, Elisabetta; Ghelardini, Carla; Romanelli, Maria Novella

    2015-04-15

    A series of 2-phenyl- or 3-phenyl piperazines, structurally related to DM235 and DM232, two potent nootropic agents, have been prepared and tested in the mouse passive-avoidance test, to assess their ability to revert scopolamine-induced amnesia. Although the newly synthesized molecules were less potent than the parent compounds, some useful information has been obtained from structure-activity relationships. A small but significant enantioselectivity has been found for the most potent compound 5a. Copyright © 2015 Elsevier Ltd. All rights reserved.

  4. Synthesis, Characterization, and Biological Activity of 5-Phenyl-1,3,4-thiadiazole-2-amine Incorporated Azo Dye Derivatives

    Directory of Open Access Journals (Sweden)

    Chinnagiri T. Keerthi Kumar

    2013-01-01

    Full Text Available 5-Phenyl-1,3,4-thiadiazole-2-amine has been synthesized by single step reaction. A series of heterocyclic azodyes were synthesized by diazotisation of 5-phenyl-1,3,4-thiadiazole-2-amine by nitrosyl sulphuric acid followed by coupling with different coupling compounds such as 8-hydroxyquinoline, 2,6-diaminopyridine, 2-naphthol, N,N-dimethyl aniline, resorcinol, and 4,6-dihydroxypyrimidine. The dyes were characterized by UV-Vis, IR, 1H-NMR, 13C NMR, and elemental analysis. The synthesized compounds were also screened for biological activity.

  5. 4-[(Z-(n-Butylamino(phenylmethylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H-one

    Directory of Open Access Journals (Sweden)

    Hai-Wen Wang

    2012-04-01

    Full Text Available The title compound, C21H23N3O, exists in an enamine–keto form with the amino group involved in an intramolecular N—H...O hydrogen bond. The dihedral angle between the phenyl rings is 73.59 (6°. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7 Å, and makes dihedral angles of 4.81 (6 and 69.81 (5° wth the phenyl rings. In the crystal, pairs of weak C—H...O interactions link the molecules into centrosymmetric dimers.

  6. Crystal structure of 3-({[(morpholin-4-yl)carbono-thio-yl]sulfan-yl}acet-yl)phenyl benzoate.

    Science.gov (United States)

    Ambekar, Sachin P; Mahesh Kumar, K; Shirahatti, Arun Kumar M; Kotresh, O; Anil Kumar, G N

    2014-11-01

    In the title compound, C20H19NO4S2, the morpholine ring adopts the expected chair conformation. The central phenyl ring makes dihedral angles of 67.97 (4) and 7.74 (3)°, respectively, with the benzoate phenyl ring and the morpholine mean plane. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions link centrosymmetrically related mol-ecules, reinforcing the three-dimensional structure.

  7. Magnetic isotopic effect and mechanisms of chemical reactions. Photolysis of dimethylphenylsilyl phenyl ketone and of its carbon analog in micelles

    International Nuclear Information System (INIS)

    Step, E.N.; Tarasov, V.F.; Buchachenko, A.L.

    1986-01-01

    In the photolysis of cumyl phenyl ketone in micelles, for which photodecomposition occurs with the formation of a triplet geminal radical pair (Norrish type-I breakdown), with high efficiency the separation of carbon isotopes, induced by the magnetic isotopic effect, occurs for the original ketone. The isotopic composition of dimethylphenylsilyl phenyl ketone, either with respect to carbon or with respect to silicon, does not change in photolysis, i.e., in the primary act of the photolysis the separation of isotopes does not occur. It follows that the primary act of the photolysis of the ketone is not the formation of a radical pair, but is probably isomerization into a carbene

  8. Ethanol extract of propolis and its constituent caffeic acid phenethyl ester inhibit breast cancer cells proliferation in inflammatory microenvironment by inhibiting TLR4 signal pathway and inducing apoptosis and autophagy.

    Science.gov (United States)

    Chang, Huasong; Wang, Yuehua; Yin, Xusheng; Liu, Xinying; Xuan, Hongzhuan

    2017-09-26

    Propolis and its major constituent - caffeic acid phenethyl ester (CAPE) have good abilities on antitumor and anti-inflammation. However, little is known about the actions of propolis and CAPE on tumor in inflammatory microenvironment, and inflammatory responses play decisive roles at different stages of tumor development. To understand the effects and mechanisms of ethanol-extracted Chinese propolis (EECP) and its major constituent - CAPE in inflammation-stimulated tumor, we investigated their effects on Toll-like receptor 4 (TLR4) signaling pathway which plays a crucial role in breast cancer MDA-MB-231 cell line. 80% confluent breast cancer MDA-MB-231 cells were stimulated with 1 μg/mL lipopolysaccaride (LPS). Then the cells were divided for treatment by CAPE (25 μg/mL) and EECP (25, 50 and 100 μg/mL), respectively. Cell viability, nitric oxide (NO) production and cell migration were measured by sulforhodamine B assay, chemical method and scratch assay. The levels of TLR4, MyD88, IRAK4, TRIF, caspase 3, PARP, LC3B and p62 were investigated through western blotting. The expression of TLR4, LC3B and nuclear factor-κB p65 (NF-κB p65) were tested by immunofluorescence microscopy assay. Treatment of different concentrations of EECP (25, 50 and 100 μg/mL) and CAPE (25 μg/mL) significantly inhibited LPS-stimulated MDA-MB-231 cell line proliferation, migration and NO production. Furthermore, EECP and CAPE activated caspase3 and PARP to induce cell apoptosis, and also upregulated LC3-II and decreased p62 level to induce autophagy during the process. TLR4 signaling pathway molecules such as TLR4, MyD88, IRAK4, TRIF and NF-κB p65 were all down-regulated after EECP and CAPE treatment in LPS-stimulated MDA-MB-231 cells. These findings indicated that EECP and its major constituent - CAPE inhibited breast cancer MDA-MB-231 cells proliferation in inflammatory microenvironment through activating apoptosis, autophagy and inhibiting TLR4 signaling pathway. EECP and

  9. Thermal Decomposition Reaction of cis-6-Phenyl-5,6-(2-phenylpropilydene-3,3-tetramethylene-1,2,4-trioxacyclohexane in Different Solvents

    Directory of Open Access Journals (Sweden)

    L. F. R. Cafferata

    2000-03-01

    Full Text Available The kinetics of the thermal decomposition reaction of cis-6-phenyl-5,6-(2-phenyl-propilydene-3,3-tetramethylene-1,2,4-trioxacyclohexane (I was investigated in the temperature range of 100-130°C in selected solvents of different physicochemical properties to evaluate a solvent effect on the reaction.

  10. Techniques in gas-phase thermolyses - Part 7. Direct surface participation in gas-phase Curie-point pyrolysis: The pyrolysis of phenyl azide

    DEFF Research Database (Denmark)

    Egsgaard, Helge; Carlsen, Lars

    1986-01-01

    The possible direct participation of the hot reactor surface in the formation of pyrolysis products was elucidated through the pyrolytic decomposition of phenyl azide. It is demonstrated that the intermediate phenyl nitrene generated reacts with elemental carbon at the filament surface, leading...

  11. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Science.gov (United States)

    2010-07-01

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721...]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. (a) Chemical substance and significant new uses... alpha-[2,4,6-tris(1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate (PMN P-98-185...

  12. Synthesis of 2,3-epoxy-1-phenyl-3-aryl-1-propanone by combination of phase transfer catalyst and ultrasound irradiation

    Directory of Open Access Journals (Sweden)

    Ji-Tai Li

    2009-03-01

    Full Text Available Seven 2,3-epoxy-1-phenyl-3-aryl-1-propanones were synthesized via epoxidation of thecorresponding 1-phenyl-3-aryl-2-propen-1-ones with 30% aqueous hydrogen peroxide in 74-99% yields usingbenzyldimethyltetradecylammonium chloride as phase transfer catalyst under ultrasound irradiation.

  13. Preparation of lanthanide arylphosphonates and crystal structures of lanthanum phenyl- and benzylphosphonates

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Ren-Chang; Zhang, Y.; Hu, Hengliang; Frausto, R.R.; Clearfield, A. (Texas A M Univ., College Station, TX (United States))

    A series of phenyl- and benzylphosphonates of the lanthanide elements has been prepared. In the lanthanum system single crystals have been obtained and the crystal structures determined. Lanthanum phenylphosphate, La(O[sub 3]PC[sub 6]H[sub 5])(HO[sub 3]PC[sub 6]H[sub 5]), triclinic, space group. The structure is a layered one in which the lanthanum atoms are eight-coordinate. Both phosphonate groups chelate the metal atom. One oxygen of each chelate ring then bridges to an adjacent La atom, while the third oxygen bridges to lanthanum at right angles to the bridging of the chelating oxygens. The phenyl rings protrude into the interlamellar space but are disordered. This disorder arises because the true unit cell has a doubled c axis. Thus, the phenyl rings in any one row are parallel to each other in the a-axis direction but are inclined to each other in adjacent rows in the c-axis direction at angle of 58[degrees]. A short hydrogen bond (2.41 [angstrom] O-O distance) is present within the layers. La(O[sub 3]PCH[sub 2]C[sub 6]H[sub 5])(HO[sub 3]PCH[sub 2]C[sub 6]HJ[sub 5])[center dot]2H[sub 2]O is orthorhombic, space group Pbcn. This structure is also a layered one with 8-fold coordination about the lanthanum atom. There are six phosphonate and two water oxygens in the La coordination sphere in a distorted dodecahedral arrangement. One phosphonate group chelates the lanthanum, while the remaining oxygen bridges to an adjacent La atom. One of the chelating oxygens also bonds to an adjacent lanthanum atom. The second phosphonate group bridges across two La atoms with two of its oxygens, while the third bonds to hydrogen. This acid proton and the water molecules form an extensive system of intralayer hydrogen bonds. A second type of rare-earth phosphonate of composition Ln[sub 2](O[sub 3]PC[sub 6]H[sub 5])[sub 3] was prepared in slightly alkaline media. 35 refs., 6 figs., 8 tabs.

  14. 4-{[(1-Phenyl-1H-pyrazol-3-yloxy]methyl}-1,3-dioxolan-2-one

    Directory of Open Access Journals (Sweden)

    Algirdas Šačkus

    2012-11-01

    Full Text Available The title compound was obtained by the reaction of tosylated glycerol carbonate with 1-phenyl-1H-pyrazol-3-ol in a good 71% yield. Detailed spectroscopic data (1H-NMR, 13C-NMR, 15N-NMR, IR, MS are presented.

  15. Methyl 6-Methyl-1-(4-methylphenyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Haiping Wang

    2012-04-01

    Full Text Available Methyl 6-methyl-1-(4-methylphenyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate has been synthesized via the modified Biginelli reaction from benzaldehyde, p-tolylurea, and methyl acetoacetate, promoted with microwave irradiation and catalyzed by TsOH under solvent-free conditions in high yield.

  16. 4-(3,5-Dibromo-4-hydroxyphenyl-3-butoxycarbonyl-5-ethoxycarbonyl-2-methyl-6-phenyl-1,4-dihydropyridine

    Directory of Open Access Journals (Sweden)

    Zhen Wang

    2011-04-01

    Full Text Available One-pot two-step Hantzsch synthesis of 4-(3,5-dibromo-4-hydroxyphenyl-3- butoxycarbonyl-5-ethoxycarbonyl-2-methyl-6-phenyl-1,4-dihydropyridine under solvent- and catalyst-free conditions promoted with microwave irradiation is presented.

  17. Annulation Reactions of Donor-Acceptor Cyclopropanes with (1-Azidovinyl)benzene and 3-Phenyl-2H-azirine.

    Science.gov (United States)

    Curiel Tejeda, Joanne E; Irwin, Lauren C; Kerr, Michael A

    2016-09-16

    Under the influence of heat and Lewis acid, donor/acceptor cyclopropanes underwent annulation reactions with (1-azidovinyl)benzene and 3-phenyl-2H-azirine to form an unusual azabicyclic scaffold with an imbedded aziridine. The mechanism of reaction is believed to proceed via a vinyl nitrene intermediate.

  18. Bis{2-[(dimethylamino)methyl]phenyl}silverlithium. A tetranuclear organometallic compound with bridging aryl groups between silver and lithium

    NARCIS (Netherlands)

    Koten, G. van; Leusink, A.J.; Marsman, J.W.; Noltes, J.G.

    1973-01-01

    Bis{2-[(dimethylamino)methyl]phenyl}silverlithium has been prepared and characterized. Molecular weight determinations, and }1{}3{C NMR and }1{H NMR spectra reveal that the compound exists (in benzene) as a tetranuclear mixed metal cluster containing aryl groups bridging the silver and lithium

  19. Synthesis and 99Tcm labelling of three kinds of derivatives of β-methyl-15-phenyl pentadecanoic acid

    International Nuclear Information System (INIS)

    Lu Chunxiong; Ji Shuren; Wu Chunying; Fang Ping

    2002-01-01

    Three kinds of derivatives of β-methyl-15-phenyl pentadecanoic acid (BMPPA) are synthesized. These derivatives are characterized by IR, MS and elementary analysis. These derivatives are labelled with 99 Tc m , the labelling yields are higher than 70% confirmed by TLC and HPLC and the radiochemical purity are more than 95% after extraction

  20. Separation of hexabromocyclododecane diastereomers: Application of C18 and phenyl-hexyl ultra-performance liquid chromatography columns.

    Science.gov (United States)

    Baek, Song-Yee; Lee, Sunyoung; Kim, Byungjoo

    2017-03-10

    This study was performed to establish the proper liquid chromatographic conditions for the separation of hexabromocyclododecane (HBCD) diastereomers. Column selectivity towards HBCD diastereomers was evaluated for C18 and phenyl-hexyl stationary phases. First, the baseline separation of the primary HBCDs (α-, β-, and γ-HBCD) was obtained using the ultra-performance liquid chromatography (UPLC) column with C18 stationary phase chosen in most previous studies for HBCD analysis; however, co-elution of δ- and ε-HBCD with the primary HBCD diastereomers was observed. To prevent the interference from δ- and ε-HBCD, we adopted a phenyl-hexyl UPLC column to resolve the HBCD diastereomers. The phenyl-hexyl UPLC column showed significantly different selectivity for the HBCD diastereomers compared with the C18 column, which allowed the clear isolation of δ-HBCD and ε-HBCD from the primary HBCD diastereomers. In addition, by checking the retention times of all HBCD diastereomers using both C18 and phenyl-hexyl columns, we confirmed the presence of δ-, ε-, η-, and θ-HBCDs in two technical HBCD mixtures. Copyright © 2017 Elsevier B.V. All rights reserved.

  1. Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea

    KAUST Repository

    Wang, Chao-Yi

    2016-10-26

    Marine organism-derived secondary metabolites are promising potential sources for discovering environmentally safe antifouling agents. In present study, 55 marine secondary metabolites and their synthesized derivatives were tested and evaluated for their antifouling activities and security. These compounds include 44 natural products isolated from marine invertebrates and their symbiotic microorganisms collected from the South China Sea and 11 structural modified products derived from the isolated compounds. The natural secondary metabolites, covering phenyl ether derivatives, terpenoids, 9, 11-secosteroids, anthraquinones, alkaloids, nucleoside derivatives and peptides, were isolated from two corals, one sponge and five symbiotic fungi. All of the isolated and synthesized compounds were tested for their antifouling activities against the cyprids of barnacle Balanus (Amphibalanus) amphitrite Darwin. Noticeably, five phenyl ether derivatives (9, 11, 13–15) exhibited potent anti-larval settlement activity with the EC50 values lower than 3.05 μM and the LC50/EC50 ratios higher than 15. The study of structure–activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities. This is the first report on the SAR of phenyl ether derivatives on antifouling activity against barnacle B. amphitrite. The polybrominated diphenyl ether derivative, 2, 4, 6, 2′, 4′, 6′-hexabromo-diorcinol (13), which displayed excellent antifouling activity, was considered as a promising candidate of environmentally friendly antifouling agents.

  2. New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius.

    Science.gov (United States)

    Bai, Zhi-Qiang; Lin, Xiuping; Wang, Yizhu; Wang, Junfeng; Zhou, Xuefeng; Yang, Bin; Liu, Juan; Yang, Xianwen; Wang, Yi; Liu, Yonghong

    2014-06-01

    Two new aromatic butyrolactones, flavipesins A (1) and B (2), two new natural products (3 and 4), and a known phenyl dioxolanone (5) were isolated from marine-derived endophytic fungus Aspergillus flavipes. The structures of compounds 1-5 were elucidated by 1D- and 2D-NMR and MS analysis, the absolute configurations were assigned by optical rotation and CD data, and the stereochemistry of 1 was determined by X-ray crystallography analysis. 1 demonstrated lower MIC values against Staphylococcus aureus (8.0 μg/mL) and Bacillus subtillis (0.25 μg/mL). 1 also showed the unique antibiofilm activity of penetration through the biofilm matrix and kills live bacteria inside mature S. aureus biofilm. Copyright © 2014 Elsevier B.V. All rights reserved.

  3. Block-Localized Wavefunction (BLW) Based Two-State Approach for Charge Transfers between Phenyl Rings.

    Science.gov (United States)

    Mo, Yirong; Song, Lingchun; Lin, Yuchun; Liu, Minghong; Cao, Zexing; Wu, Wei

    2012-03-13

    The block-localized wave function (BLW) method is the simplest and most efficient variant of ab initio valence bond (VB) theory which defines electron-localized resonance states following the conventional VB concepts. Here, a BLW-based two-state approach is proposed to probe the charge/hole transfer reactions within the Marcus-Hush model. With this approach, both the electronic coupling and reorganization energies can be derived at the ab initio level. Pilot applications to the electron/hole transfers between two phenyl rings are presented. Good exponential correlation between the electronic coupling energy and the donor-acceptor distance is shown, whereas the inner-sphere reorganization shows little geometric dependency. Computations also support the assumption in Marcus theory that the thermal electron transfer barrier (ΔG*), which is a sum of the reaction barrier (ΔEa) for electron/hole transfer and the coupling energy (VAB), is a quarter of the reorganization energy (λ).

  4. Photovoltaic Properties of Solar Cells Based on Poly(methyl phenyl silane) and C60

    Science.gov (United States)

    Mizuno, Toya; Akasaka, Yumeno; Tachibana, Hiroaki

    2012-10-01

    Photovoltaic (PV) devices using blend films of poly(methyl phenyl silane) (PMPS) and fullerene (C60) are fabricated, and the effects of various technical parameters during device fabrication on the PV characteristics under AM 1.5G simulated solar light illumination of 100 mW/cm2 intensity are investigated. The PV performance of the devices depends on the mixing ratio of PMPS:C60, the kind of buffer layer, the thickness of the buffer layer, and the thermal annealing temperature of the devices. The devices optimized for the mixing ratio, kind of buffer layer, and thermal annealing temperature exhibit a short-circuit current density (JSC) of 2.26 mA/cm2, an open circuit voltage (VOC) of 0.71 V, a fill factor (FF) of 0.35, and a power conversion efficiency (PCE) of 0.57%.

  5. 3-Benzyl-3-hydroxy-2-phenyl-3H-indole 1-oxide

    Directory of Open Access Journals (Sweden)

    Corrado Rizzoli

    2010-08-01

    Full Text Available The asymmetric unit of the title compound, C21H17NO2, contains two crystallographically independent molecules of similar geometry. The indole ring systems form dihedral angles of 8.30 (5 and 9.58 (5° with the attached phenyl rings, and 56.96 (5 and 57.68 (5° with the aromatic rings of the respective benzyl groups. The molecular conformations are stabilized by intramolecular C—H...O hydrogen bonds. In the crystal structure, centrosymmetrically related pairs of molecules are linked into dimers through pairs of intermolecular O—H...O hydrogen bonds, generating 12-membered rings with R22(12 motifs. The dimers are further linked into a three-dimensional network by C—H...O interactions.

  6. Kinetics and Mechanism of Nanoparticles-Catalyzed Piperidinolysis of Anionic Phenyl Salicylate

    Directory of Open Access Journals (Sweden)

    Norazizah Abd. Razak

    2014-01-01

    Full Text Available The values of the relative counterion (X binding constant RXBr (=KX/KBr, where KX and KBr represent cetyltrimethylammonium bromide, CTABr, micellar binding constants of Xv- (in non-spherical micelles, v=1,2, and Br− (in spherical micelles are 58, 68, 127, and 125 for Xv−=1−, 12−, 2−, and 22-, respectively. The values of 15 mM CTABr/[NavX] nanoparticles-catalyzed apparent second-order rate constants for piperidinolysis of ionized phenyl salicylate at 35°C are 0.417, 0.488, 0.926, and 0.891 M−1 s−1 for NavX = Na1, Na21, Na2, and Na22, respectively. Almost entire catalytic effect of nanoparticles catalyst is due to the ability of nonreactive counterions, Xv-, to expel reactive counterions, 3−, from nanoparticles to the bulk water phase.

  7. Nucleophilic reactions of hydrazido(2-) complexes of molybdenum and tungsten with succinyl dichloride and phenyl isocyanate

    International Nuclear Information System (INIS)

    Iwanami, Kiyotaka; Mizobe, Yasushi; Takahashi, Tamotsu; Kodama, Teruyuki; Uchida, Yasuzo

    1981-01-01

    Nucleophilic attack of the WNNH 2 group in the hydrazido(2-) complex [WF(NNH 2 )(dpe) 2 ][BF 4 ] (dpe = Ph 2 PCH 2 CH 2 PPh 2 ) on succinyl dichloride gives a novel ethanedioylhydrazido(2-) complex, [WF(NNCOCH 2 CH 2 CO)(dpe) 2 ][BF 4 ]. X-Ray structural analysis shows that the carbon, nitrogen, and oxygen atoms of the ethanedioylhydrazido(2-) ligand lie nearly in the same plane, indicating sp 2 character of the nitrogen atom bearing the two carbonyl groups. Phenyl isocyanate also undergoes nucleophilic attack by the hydrazido(2-) complex [MBr(NNH 2 )(dpe) 2 ]Br (M = Mo or W) to yield the phenylsemicarbazido(2-) type complex, [MBr(NNHCONHPh)(dpe) 2 ]Br. Treatment of the semicarbazido(2-) complex with triethylamine gives a new diazenido complex [MBr(NNCONHPh)(dpe) 2 ]. (author)

  8. Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors.

    Science.gov (United States)

    Paul, R; Hallett, W A; Hanifin, J W; Reich, M F; Johnson, B D; Lenhard, R H; Dusza, J P; Kerwar, S S; Lin, Y; Pickett, W C

    1993-09-17

    The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2- pyrimidinamine (1-27) was chosen for toxicological evaluation.

  9. Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response.

    Science.gov (United States)

    Barbosa, Maria Letícia de Castro; Ramos, Thiago José Figueira; de Arantes, Ana Carolina Santos; Martins, Marco Aurélio; Silva, Patrícia Machado Rodrigues E; Barreiro, Eliezer J; Lima, Lídia Moreira

    2012-12-10

    In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 planned by structural modification on the anti-inflammatory prototype LASSBio-468 (1). Among the synthesized analogues, the tetrafluorophthalimide LASSBio-1439 (2e) stands out showing an in vitro anti-TNF-α effect similar to the standard thalidomide. The relevance of tetrafluorination of the phthalimide nucleus was also confirmed by the anti-inflammatory profile of 2e, through oral administration, in a murine model of pulmonary inflammation. The corresponding tetrafluorocarboxyamide metabolite LASSBio-1454 (15), generated from partial hydrolysis of the derivative 2e, presented a significant in vitro effect and a pronounced anti-inflammatory activity in vivo.

  10. Donor-substituted phenyl-pi-chromones: electrochemiluminescence and intriguing electronic properties.

    Science.gov (United States)

    Yang, Shu-Wen; Elangovan, Arumugasamy; Ho, Tong-Ing

    2005-04-01

    Phenylethynylchromones bearing different donor groups at the phenyl moiety have been prepared and their photophysical and electrogenerated chemiluminescence (ECL) properties have been studied with respect to their structural features. Intriguingly, the presence and variation of donor groups do not much influence the absorption spectra, which can be compared with the spectrum of unsubstituted chromone, whereas the photoluminescence (PL) spectra show pronounced changes. Density functional theory (DFT) calculations indicate enhancement of HOMO energy levels upon increasing the donor strength. The photophysical properties have also been studied in various solvents, and the PL spectra in particular show the anticipated trend. The introduction of pi-extension imparts ECL to the new molecules and the electronic coupling between the donor and the acceptor moieties through C-C triple bond influences ECL emission maxima. Weaker donors impart excimer ECL while stronger donors impart monomeric intramolecular charge transfer (ICT) ECL.

  11. Hybrid Detectors for Neutrons Combining Phenyl- Polysiloxanes with 3D Silicon Detectors

    International Nuclear Information System (INIS)

    Dalla Palma, Matteo; Quaranta, Alberto; Collazuol, Gianmaria; Carturan, Sara; Cinausero, Marco; Gramegna, Fabiana; Marchi, Tommaso; Dalla Betta, Gian-Franco; Mendicino, Roberto; Povoli, Marco; Boscardin, Maurizio; Giacomini, Gabriele; Ronchin, Sabina; Zorzi, Nicola

    2013-06-01

    We report on the initial results of a research project aimed at the development hybrid detectors for fast neutrons by combining a phenyl-polysiloxane-based converter with a 3D silicon detector. To this purpose, new 3D sensor structures have been designed, fabricated and electrically tested, showing low depletion voltage and good leakage current. Moreover, the radiation detection capability of 3D sensors was tested by measuring the signals recorded from alpha particles, gamma rays, and pulsed lasers. The converter has been poured into the 3D cavities with excellent coupling, as confirmed by cross-section SEM analyses. Preliminary tests with neutrons have been carried out on the first hybrid detector prototypes at the CN accelerator of INFN LNL. The device design and technology are discussed, along with the first results from the electrical and functional characterization. (authors)

  12. 1-Phenyl-5-{[2-(trimethylsilylethyl]sulfonyl}-1H-tetrazole

    Directory of Open Access Journals (Sweden)

    David Tymann

    2011-09-01

    Full Text Available The title compound, C12H18N4O2SSi, was synthesized to be employed in a Julia–Kocieński olefination. In the molecule, the dihedral angle between the phenyl ring and the tetrazole ring is 41.50 (5°. The significantly longer Si—C(methylene bond [1.8786 (13 Å] and the shortened adjacent C—C bond [1.5172 (18 Å], as well as the significant deviation of the corresponding Si—C—C angle [114.16 (9°] from the ideal tetrahedral angle, can be attributed to the β-effect of silicon. In the crystal, molecules are held together by van der Waals interactions.

  13. Synergistic extraction of trivalent lanthanoids with 3-phenyl-4-benzoyl-5-isoxazolone and various sulphoxides

    International Nuclear Information System (INIS)

    Sahu, S.K.; Chakravortty, V.; Reddy, M.L.P.; Ramamohan, T.R.

    1999-01-01

    Synergistic extraction of trivalent lanthanoids Nd, Tb and Tm with mixtures of 3-phenyl-4-benzoyl-5-isoxazolone (HPBI) and dioctyl sulphoxide (DOSO), bis-2-ethylhexyl sulphoxide (B2EHSO) or diphenyl sulphoxide (DPhSO) in xylene from perchlorate solution was investigated. Lanthanoids were found to be extracted as Ln(PBI) 3 with HPBI alone. In the presence of sulphoxides, Nd(III) was found to be extracted as Nd(PBI) 3 . S and Nd(PBI) 3 . 2 S (where S = sulphoxide). On the other hand, Tb(III) and Tm(III) were extracted as Tb(PBI) 3 . S and Tm(PBI) 3 . S respectively. The equilibrium constants of the synergistic species were found to increase monotonically with decreasing ionic radii of these metal ions. The addition of a sulphoxide to the metal chelate system not only enhances the extraction efficiency but also improves the selectivities among these trivalent lanthanoids. (orig.)

  14. [Removal of oral Prevotella intermedia Endotoxin by octyl phenyl polyoxyethylene ether extraction method].

    Science.gov (United States)

    Wang, Ai-wu; Liu, Yan; Hu, Kong-xin; Cheng, Qian

    2012-12-01

    To investigate an effective purification method for removing endotoxin from Prevotella intermedia. The main protein ingredients of bacteria prepared from ammonium sulfate precipitation were further treated with octyl phenyl polyoxyethylene ether (Triton X-114), and then processed at 4°C, 37°C and 25°C. The obtained aqueous phase after at least two more cycle repeated operations was assayed for endotoxin by Western blotting, LAL-clotting method, in vitro cell stimulation and in vivo animal experiments. Western blotting and LAL-clotting method demonstrated that the reduction in endotoxin level was greater than 99.99% and recovery of the proteins after endotoxin removal was greater than 90% with Triton X-114 treatment for 3 cycles. The cytokines expression level was lower in both in vitro cell stimulation and in vivo animal experiments than in untreated group (P Prevotella intermedia.

  15. Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine.

    Science.gov (United States)

    Papadopoulou, Christina; Geronikaki, Athina; Hadjipavlou-Litina, Dimitra

    2005-01-01

    A series of thiazolyl-N-phenyl piperazines has been synthesised and tested for anti-inflammatory activity. Their R(M) values were determined as an expression of their lipophilicity. Theoretical calculation of their lipophilicity, as clog P and logPsk also performed. The effect of the synthesised compounds on inflammation, using the carrageenin induced mouse paw oedema model was studied. In general, the studied compounds were found to be potent anti-inflammatory agents (44-74.1%). Anti-inflammatory activity was influenced by some structural characteristics of the synthesised compounds. An attempt was made to correlate their biological activity with some physicochemical parameters using a quantitative structure-activity relationship approach (QSAR).

  16. 5-(4-Methoxyphenyl-4-methyl-1-phenyl-3-p-tolyl-1H-pyrazole

    Directory of Open Access Journals (Sweden)

    Yahya Ben Soumane

    2017-11-01

    Full Text Available The title compound, C24H22N2O, crystallizes with two independent molecules (A and B in the asymmetric unit. The phenyl, p-tolyl and p-methoxyphenyl rings are inclined to the pyrazole ring by 42.5 (2, 17.68 (19 and 52.20 (19°, respectively, in molecule A, and by 39.5 (2, 40.77 (19 and 59.76 (18°, respectively, in molecule B. In the asymmetric unit, the pyrarole ring of molecule A makes a dihedral angle of 3.7 (2° with that of molecule B. In the crystal, the two independent molecules are linked to each other by a C—H...O hydrogen bond.

  17. 3-Phenyl-6-(2-pyridyl-1,2,4,5-tetrazine

    Directory of Open Access Journals (Sweden)

    Daniel Chartrand

    2008-01-01

    Full Text Available The title compound, C13H9N5, is the first asymmetric diaryl-1,2,4,5-tetrazine to be crystallographically characterized. We have been interested in this motif for incorporation into supramolecular assemblies based on coordination chemistry. The solid state structure shows a centrosymmetric molecule, forcing a positional disorder of the terminal phenyl and pyridyl rings. The molecule is completely planar, unusual for aromatic rings with N atoms in adjacent ortho positions. The stacking observed is very common in diaryltetrazines and is dominated by π stacking [centroid-to-centroid distance between the tetrazine ring and the aromatic ring of an adjacent molecule is 3.6 Å, perpendicular (centroid-to-plane distance of about 3.3 Å].

  18. Novel Scintillating Materials Based on Phenyl-Polysiloxane for Neutron Detection and Monitoring

    Science.gov (United States)

    Degerlier, M.; Carturan, S.; Gramegna, F.; Marchi, T.; Palma, M. Dalla; Cinausero, M.; Maggioni, G.; Quaranta, A.; Collazuol, G.; Bermudez, J.

    Neutron detectors are extensively used at many nuclear research facilities across Europe. Their application range covers many topics in basic and applied nuclear research: in nuclear structure and reaction dynamics (reaction reconstruction and decay studies); in nuclear astrophysics (neutron emission probabilities); in nuclear technology (nuclear data measurements and in-core/off-core monitors); in nuclear medicine (radiation monitors, dosimeters); in materials science (neutron imaging techniques); in homeland security applications (fissile materials investigation and cargo inspection). Liquid scintillators, widely used at present, have however some drawbacks given by toxicity, flammability, volatility and sensitivity to oxygen that limit their duration and quality. Even plastic scintillators are not satisfactory because they have low radiation hardness and low thermal stability. Moreover organic solvents may affect their optical properties due to crazing. In order to overcome these problems, phenyl-polysiloxane based scintillators have been recently developed at Legnaro National Laboratory. This new solution showed very good chemical and thermal stability and high radiation hardness. The results on the different samples performance will be presented, paying special attention to a characterization comparison between synthesized phenyl containing polysiloxane resins where a Pt catalyst has been used and a scintillating material obtained by condensation reaction, where tin based compounds are used as catalysts. Different structural arrangements as a result of different substituents on the main chain have been investigated by High Resolution X-Ray Diffraction, while the effect of improved optical transmittance on the scintillation yield has been elucidated by a combination of excitation/fluorescence measurements and scintillation yield under exposure to alpha and γ-rays.

  19. Combination Phenyl Propionate/Pheromone Traps for Monitoring Navel Orangeworm (Lepidoptera: Pyralidae) in Almonds in the Vicinity of Mating Disruption.

    Science.gov (United States)

    Burks, Charles S

    2017-04-01

    Aerosol mating disruption is used for management of navel orangeworm, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), in an increasing portion of California almonds and pistachios. This formulation suppresses pheromone monitoring traps far beyond the treatment block, potentially complicating monitoring and management of this key pest. Phenyl propionate is an attractant used to capture adults in the presence of mating disruption, completely suppressing pheromone traps, and lures combining phenyl propionate with a pheromone lure (PPO-combo lure) synergize trap capture in the presence of mating disruption. In this study, laboratory and field trials of different phenyl propionate dispensers indicate a useful life of six weeks. Controlled experiments found similar numbers of adults captured in phenyl propionate and PPO-combo lures in the presence of varying levels of mating disruption intensity. A subsequent trial compared monitoring of field plots at various distances from fields under commercial mating disruption for much of the growing season with pheromone and PPO-combo lures. Although there was some evidence of partial suppression of capture in PPO-combo traps closer to mating disruption compared with lures farther away, there was no failure of detection as occurred with pheromone lures. The ratio of adults in pheromone and PPO-combo traps varied with proximity from treated fields. These results indicate that, in addition to monitoring in mating disruption plots, phenyl propionate lures can be useful for insuring against failure of detection of navel orangeworm pressure in areas where mating disruption is widely used. Published by Oxford University Press on behalf of Entomological Society of America 2017. This work is written by a US Government employee and is in the public domain in the US.

  20. 3,5-Bis(4-meth­oxy­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

    OpenAIRE

    Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S.; Narayana, B.; Yathirajan, H. S.

    2011-01-01

    In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two methoxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C—H...π stacking interactions and weak π–π interactions [cen...

  1. A VUV photoionization study of the multichannel reaction of phenyl radicals with 1,3-butadiene under combustion relevant conditions.

    Science.gov (United States)

    Golan, Amir; Ahmed, Musahid; Mebel, Alexander M; Kaiser, Ralf I

    2013-01-07

    We studied the reaction of phenyl radicals (C(6)H(5)) with 1,3-butadiene (H(2)CCHCHCH(2)) exploiting a high temperature chemical reactor under combustion-like conditions (300 Torr, 873 K). The reaction products were probed in a supersonic beam by utilizing VUV radiation from the Advanced Light Source and by recording the experimental PIE curves at mass-to-charge ratios of m/z = 130 (C(10)H(10)(+)), 116 (C(9)H(8)(+)), and 104 (C(8)H(8)(+)). Our data suggest that the atomic hydrogen (H), methyl (CH(3)), and vinyl (C(2)H(3)) losses are open with estimated branching ratios of about 86 ± 4%, 8 ± 2%, and 6 ± 2%, respectively. The isomer distributions were probed further by fitting the experimentally recorded PIE curves with a linear combination of the PIE curves of individual C(10)H(10), C(9)H(8), and C(8)H(8) isomers. These fits indicate the formation of three C(10)H(10) isomers (trans-1,3-butadienylbenzene, 1,4-dihydronaphthalene, 1-methylindene), three C(9)H(8) isomers (indene, phenylallene, 1-phenyl-1-methylacetylene), and a C(8)H(8) isomer (styrene). A comparison with results from recent crossed molecular beam studies of the 1,3-butadiene-phenyl radical reaction and electronic structure calculations suggests that trans-1,3-butadienylbenzene (130 amu), 1,4-dihydronaphthalene (130 amu), and styrene (104 amu) are reaction products formed as a consequence of a bimolecular reaction between the phenyl radical and 1,3-butadiene. 1-Methylindene (130 amu), indene (116 amu), phenylallene (116 amu), and 1-phenyl-1-methylacetylene (116 amu) are synthesized upon reaction of the phenyl radical with three C(4)H(6) isomers: 1,2-butadiene (H(2)CCCH(CH(3))), 1-butyne (HCCC(2)H(5)), and 2-butyne (CH(3)CCCH(3)); these C(4)H(6) isomers can be formed from 1,3-butadiene via hydrogen atom assisted isomerization reactions or via thermal rearrangements of 1,3-butadiene involving hydrogen shifts in the high temperature chemical reactor.

  2. Synthesis and electropolymerization properties of [(4-{3-[3-(dimethylamino)phenoxy]propoxy}phenyl)metoxy] and [(4-{3-[3-(diethylamino)phenoxy]propoxy}phenyl)metoxy] substituted silicon naphthalocyanines

    Science.gov (United States)

    Biyiklioglu, Zekeriya; Sofuoğlu, Ayşenur

    2017-11-01

    In this study, the first synthesis of axially disubstituted silicon naphthalocyanines bearing electropolymerizable bis[(4-{3-[3-(dimethylamino)phenoxy]propoxy}phenyl)metoxy], bis[(4-{3-[3-(diethylamino)phenoxy]propoxy}phenyl)metoxy] units has been reported. Aggregation behavior of silicon naphthalocyanines were examined in different solvents and concentrations. In all studied solvents and concentrations, silicon naphthalocyanines were non-aggregated. Electrochemical and electropolymerization properties of the silicon naphthalocyanines were studied by cyclic and square wave voltammetry. Electrochemical studies reveal that axially disubstituted silicon naphthalocyanines gave only naphthalocyanine based reduction process during the cathodic potential scans, but they were electropolymerized on the working electrode during the anodic potential scan because of the oxidative electropolymerization of dimethylamino and diethylamino groups on the substituents of the complexes. Therefore, this study is the first example of electropolymerization of axially disubstituted silicon naphthalocyanines.

  3. Synthesis of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives and evaluation of their anticancer activity

    Directory of Open Access Journals (Sweden)

    Nitin Kumar

    2017-05-01

    Full Text Available A novel series of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives were synthesized. In the first step salicylaldehyde was reacted with ethylacetoacetate at room temperature by stirring which gives compound (I. Compound (I when refluxed with substituted benzaldehyde and diethylamine in the presence of n-butanol for 4–5 h gives substituted derivatives (IIa–d. Compounds synthesized in step 2 when refluxed with phenyl hydrazine in the presence of pyridine for 6–7 h gives the title compounds (IIIa–d. All the synthesized compounds were sent to NCI for anticancer activity. Synthesized compounds were tested for anticancer activity against 60 different cell lines. From the data thus obtained it was observed that simple coumarin ring derivatives were more effective in inhibiting the growth of cancerous cell lines, than coumarin-pyrazoline derivatives. Among all the synthesized compounds, irrespective of compounds having simple coumarin ring and coumarin-pyrazoline combination, compounds IIa–c, IIIb and IIId were potent anticancer agents. Compounds were active for the single dose therapeutic program at the dose of 1.00E-5 molar concentration. The main anti cancer activity is assumed to be due to the presence of the lactone structure in coumarin moiety.

  4. Spectral Properties of Novel 1,3-oxazol-5(4H)-ones With Substituted Benzylidene and Phenyl Rings

    DEFF Research Database (Denmark)

    Palcut, Marián

    2009-01-01

    In the present work, five novel (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) were investigated by the infra-red (IR) and nuclear magnetic resonance spectroscopy (NMR) of the 1H and 13C nuclei. The spectral properties of the oxazolone ring were monitored with respect to the subst......In the present work, five novel (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) were investigated by the infra-red (IR) and nuclear magnetic resonance spectroscopy (NMR) of the 1H and 13C nuclei. The spectral properties of the oxazolone ring were monitored with respect...

  5. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine inhibits proton motive force in energized liver mitochondria

    International Nuclear Information System (INIS)

    Singh, Y.; Bhatnagar, R.; Sidhu, G.S.; Batra, J.K.; Krishna, G.

    1989-01-01

    It is known that 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), which induces Parkinson's-like disease in primates and humans, depletes hepatocytes of ATP and subsequently causes cell death. Incubation of rat liver mitochondria with MPTP and 1-methyl-4-phenyl pyridinium ion (MPP+) significantly inhibited incorporation of 32 Pi into ATP. MPTP and MPP+ inhibited the development of membrane potential and pH gradient in energized rat liver mitochondria, suggesting that reduction of the proton motive force may have reduced ATP synthesis. Since deprenyl, an inhibitor of monoamine oxidase, prevented the formation of MPP+ and inhibited the decrease in membrane potential caused by MPTP, but not that caused by MPP+, these effects of MPTP, as well as cell death, probably were mediated by MPP+. This mechanism may play a role in the specific loss of dopaminergic neurons resulting in MPTP-induced Parkinson's disease

  6. 2-(2,4-Dichlorophenyl-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline

    Directory of Open Access Journals (Sweden)

    K. Balamurugan

    2009-08-01

    Full Text Available In the title compound, C23H15Cl2NS, the quinoline system is almost planar [r.m.s. deviation = 0.013 (2 Å]. The phenyl group is disordered over two positions with site occupancies of 0.55 and 0.45, and is oriented in a nearly perpendicular configuration to the quinoline ring [the dihedral angles between the quinoline ring and the major and minor disordered components of the phenyl ring are 81.8 (2 and 71.6 (2°, respectively]. The dihydrothiene ring adopts an envelope conformation. The dihedral angle between the chlorophenyl ring and the quinoline system is 79.32 (1°. In the crystal weak C—H...π interactions occur.

  7. Purification of di-nonyl phenyl phosphoric acid (DNPPA) for synergistic extraction of uranium from strong phosphoric acid

    International Nuclear Information System (INIS)

    Singh, D.K.; Vijayalakshmi, R.; Singh, H.; Sharma, J.N.; Ruhela, R.

    2009-01-01

    Di-nonyl phenyl phosphoric acid (DNPPA) obtained from various synthesis methods is always associated with impurities such as mono-nonyl phenyl phosphoric acid and nonyl phenol which need to be separated for its effective use in the extraction of uranium from strong phosphoric acid. Two methods of purification namely liquid-solid separation method using neodymium salt and liquid-liquid separation method using methylene glycol have been described. In the liquid solid separation method the purity of DNPPA obtained was about 95% with less than 1.0% monoester, however it heavily suffers in the recovery aspect which is of the order of 50-60%. The methylene glycol treatment method, results in high purity and recovery of the product. Purity obtained was about 95.0% diester and less than 0.5% monoester and recovery was more than 90%. Analysis of DNPPA was done by potentiometric titration method using autotitrator. (author)

  8. Crystal structures and hydrogen bonding in the isotypic series of hydrated alkali metal (K, Rb and Cs) complexes with 4-amino?phenyl?arsonic acid

    OpenAIRE

    Smith, Graham; Wermuth, Urs D.

    2017-01-01

    The structures of the alkali metal (K, Rb and Cs) complex salts with 4-amino?phenyl?arsonic acid (p-arsanilic acid) manifest an isotypic series with the general formula [M 2(C6H7AsNO3)2(H2O)3], with M = K {poly[di-?3-4-amino?phenyl?arsonato-tri-?2-aqua-dipotassium], [K2(C6H7AsNO3)2(H2O)3], (I)}, Rb {poly[di-?3-4-amino?phenyl?arsonato-tri-?2-aqua-dirubidium], [Rb2(C6H7AsNO3)2(H2O)3], (II)}, and Cs {poly[di-?3-4-amino?phenyl?arsonato-tri-?2-aqua-dirubidium], [Cs2(C6H7AsNO3)2(H2O)3], (III)}, in ...

  9. Synthesis of poly[methyl(phenyl)silanediyl] containing 1,3,4-oxadiazole electron-transporting moieties

    Czech Academy of Sciences Publication Activity Database

    Kotva, Rudolf; Cimrová, Věra; Výprachtický, Drahomír

    2003-01-01

    Roč. 50, č. 4 (2003), s. 227-234 ISSN 0170-0839 R&D Projects: GA ČR GA102/98/0696; GA ČR GA203/01/0512 Institutional research plan: CEZ:AV0Z4050913 Keywords : oxadiazole derivative * poly[methyl(phenyl)silanediyl] * modified polysilanes Subject RIV: CD - Macromolecular Chemistry Impact factor: 0.795, year: 2003

  10. IR Laser Ablative and Conventional Decomposition of Poly(vinyl phenyl ketone) : Different Processes and Different Products.

    Czech Academy of Sciences Publication Activity Database

    Pokorná, Dana; Šubrt, Jan; Galíková, Anna; Pola, Josef

    2007-01-01

    Roč. 92, 3 (2007) , s. 352-358 ISSN 0141-3910 R&D Projects: GA ČR(CZ) GA104/04/2028 Institutional research plan: CEZ:AV0Z40720504; CEZ:AV0Z40320502 Keywords : laser ablation * poly(vinyl phenyl ketone ) * laser degradation Subject RIV: CC - Organic Chemistry Impact factor: 2.073, year: 2007

  11. 3-Phenyl-6-(2-pyrid­yl)-1,2,4,5-tetra­zine

    OpenAIRE

    Chartrand, Daniel; Laverdière, François; Hanan, Garry

    2007-01-01

    The title compound, C13H9N5, is the first asymmetric diaryl-1,2,4,5-tetrazine to be crystallographically characterized. We have been interested in this motif for incorporation into supramolecular assemblies based on coordination chemistry. The solid state structure shows a centrosymmetric molecule, forcing a positional disorder of the terminal phenyl and pyridyl rings. The molecule is completely planar, unusual for aromatic rings with N atoms in adjacent ortho positions. The stacking observed...

  12. Design, synthesis, docking and biological evaluation of 4-phenyl-thiazole derivatives as autotaxin (ATX) inhibitors.

    Science.gov (United States)

    Balupuri, Anand; Lee, Dae-Yon; Lee, Myeong Hwi; Chae, Sangeun; Jung, Eunmi; Kim, Yunki; Ryu, Jeonghee; Kang, Nam Sook

    2017-09-01

    The autotaxin-lysophophatidic acid (ATX-LPA) signaling pathway is involved in several human diseases such as cancer, autoimmune diseases, inflammatory diseases neurodegenerative diseases and fibrotic diseases. Herein, a series of 4-phenyl-thiazole based compounds was designed and synthesized. Compounds were evaluated for their ATX inhibitory activity using FS-3 and human plasma assays. In the FS-3 assay, compounds 20 and 21 significantly inhibited the ATX at low nanomolar level (IC 50 =2.99 and 2.19nM, respectively). Inhibitory activity of 21 was found to be slightly better than PF-8380 (IC 50 =2.80nM), which is one of the most potent ATX inhibitors reported till date. Furthermore, 21 displayed higher potency (IC 50 =14.99nM) than the first clinical ATX inhibitor, GLPG1690 (IC 50 =242.00nM) in the human plasma assay. Molecular docking studies were carried out to explore the binding pattern of newly synthesized compounds within active site of ATX. Docking studies suggested the putative binding mode of the novel compounds. Good ATX inhibitory activity of 21 was attributed to the hydrogen bonding interactions with Asn230, Trp275 and active site water molecules; electrostatic interaction with catalytic zinc ion and hydrophobic interactions with amino acids of the hydrophobic pocket. Copyright © 2017 Elsevier Ltd. All rights reserved.

  13. Potential Activity of 3-(2-Chlorophenyl)-1-phenyl-propenonein Accelerating Wound Healing in Rats

    Science.gov (United States)

    Dhiyaaldeen, Summaya M.; Alshawsh, Mohammed A.; Salama, Suzy M.; Alwajeeh, Nahla S. I.

    2014-01-01

    Wound healing involves inflammation followed by granular tissue development and scar formation. In this study, synthetic chalcone 3-(2-Chlorophenyl)-1-phenyl-propenone (CPPP) was investigated for a potential role in enhancing wound healing and closure. Twenty-four male rats were divided randomly into 4 groups: carboxymethyl cellulose (CMC) (0.2 mL), Intrasite gel, and CPPP (25 or 50 mg/mL). Gross morphology, wounds treatment with the CPPP, and Intrasite gel accelerate the rate of wound healing compared to CMC group. Ten days after surgery, the animals were sacrificed. Histological assessment revealed that the wounds treated with CPPP showed that wound closure site contained little amount of scar and the granulation tissue contained more collagen and less inflammatory cells than wound treated with CMC. This finding was confirmed with Masson's trichrome staining. The antioxidant defence enzymes catalase (CAT) and superoxide dismutase (SOD) were significantly increased in the wound homogenates treated with CPPP (P healing. PMID:24587992

  14. Negative polarity of phenyl-C61 butyric acid methyl ester adjacent to donor macromolecule domains

    International Nuclear Information System (INIS)

    Alley, Olivia J.; Dawidczyk, Thomas J.; Hardigree, Josué F. Martínez; Katz, Howard E.; Wu, Meng-Yin; Johns, Gary L.; Markovic, Nina; Arnold, Michael S.

    2015-01-01

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (V oc ) can also be dependent on the interfacial fields, in the event that they modulate the energy gap between donor HOMO and acceptor LUMO. A rise in the vacuum level of the acceptor will increase the gap and the V oc , which can be beneficial for device efficiency. Here, we measure the interfacial potential differences at donor-acceptor junctions using Scanning Kelvin Probe Microscopy, and quantify how much of the potential difference originates from physical contact between the donor and acceptor. We see a statistically significant and pervasive negative polarity on the phenyl-C 61 butyric acid methyl ester (PCBM) side of PCBM/donor junctions, which should also be present at the complex interfaces in bulk heterojunctions. This potential difference may originate from molecular dipoles, interfacial interactions with donor materials, and/or equilibrium charge transfer due to the higher work function and electron affinity of PCBM. We show that the contact between PCBM and poly(3-hexylthiophene) doubles the interfacial potential difference, a statistically significant difference. Control experiments determined that this potential difference was not due to charges trapped in the underlying substrate. The direction of the observed potential difference would lead to increased V oc , but would also pose a barrier to electrons being injected into the PCBM and make recombination more favorable. Our method may allow unique information to be obtained in new donor-acceptor junctions

  15. Synthesis and Application of Phenyl Nitrone Derivatives as Acidic and Microbial Corrosion Inhibitors

    Directory of Open Access Journals (Sweden)

    Shijun Chen

    2015-01-01

    Full Text Available Nitrone has drawn great attention due to its wide applications as a 1,3-dipole in heterocyclic compounds synthesis and the bioactivities. With the special structure, nitrone can also be used as ligand in inorganic chemistry. Based on the current research, the nitrones are anticipated to be effective inhibitors against acidic and microbial corrosion. The aim of this work is to investigate the inhibitory action of nitrones. In this work, a series of phenyl nitrone derivatives (PN was synthesized and used as acidic and microbial corrosion inhibitors. The results indicate that several compounds show moderate to high inhibition efficiency (IE in 3% HCl. Accompanied with HMTA or BOZ, the IEs greatly increase, and the highest efficiency of 98.5% was obtained by using PN4 + BOZ. Investigation of the antibacterial activity against oilfield microorganism shows that the nitrone derivatives can inhibit SRB, IB, and TGB with moderate to high efficiency under 1,000 mg/L, which makes them potential to be used as bifunctional oilfield chemicals.

  16. Inactivation of acetylcholinesterase by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride.

    Science.gov (United States)

    Zang, Lun-Yi; Misra, Hara P

    2003-12-01

    The neurotoxicant 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) has been shown to reversibly inhibit the activity of acetylcholinesterase. The inactivation of the enzyme was detected by monitoring the accumulation of yellow color produced from the reaction between thiocholine and dithiobisnitrobenzoate ion. The kinetic parameter, Km for the substrate (acetylthiocholine), was found to be 0.216 mM and Ki for MPTP inactivation of acetylcholinesterase was found to be 2.14 mM. The inactivation of enzyme by MPTP was found to be dose-dependent. It was found that MPTP is neither a substrate of AChE nor the time-dependent inactivator. The studies of reaction kinetics indicate the inactivation of AChE to be a linear mixed-type inhibition. The dilution assays indicate that MPTP is a reversible inhibitor for AChE. These data suggest that once MPTP enters the basal ganglia of the brain, it can inactivate the acetylcholinesterase enzyme and thereby increase the acetylcholine level in the basal ganglia of brain, leading to potential cell dysfunction. It appears that the nigrostriatal toxicity by MPTP leading to Parkinson's disease-like syndrome may, in part, be mediated via the acetylcholinesterase inactivation.

  17. Mechanisms of catalytic cleavage of benzyl phenyl ether in aqueous and apolar phases

    Energy Technology Data Exchange (ETDEWEB)

    He, Jiayue; Lu, Lu; Zhao, Chen; Mei, Donghai; Lercher, Johannes A.

    2014-03-01

    Catalytic pathways for the cleavage of ether bonds in benzyl phenyl ether (BPE) in liquid phase using Ni- and zeolite-based catalysts are explored. In the absence of catalysts, the C-O bond is selectively cleaved in water by hydrolysis, forming phenol and benzyl alcohol as intermediates, followed by alkylation. The hydronium ions catalyzing the reactions are provided by the dissociation of water at 523 K. Upon addition of HZSM-5, rates of hydrolysis and alkylation are markedly increased in relation to proton concentrations. In the presence of Ni/SiO2, the selective hydrogenolysis dominates for cleaving the Caliphatic-O bond. Catalyzed by the dual-functional Ni/HZSM-5, hydrogenolysis occurs as the major route rather than hydrolysis (minor route). In apolar undecane, the non-catalytic thermal pyrolysis route dominates. Hydrogenolysis of BPE appears to be the major reaction pathway in undecane in the presence of Ni/SiO2 or Ni/HZSM-5, almost completely suppressing radical reactions. Density functional theory (DFT) calculations strongly support the proposed C-O bond cleavage mechanisms on BPE in aqueous and apolar phases. These calculations show that BPE is initially protonated and subsequently hydrolyzed in the aqueous phase. Finally, DFT calculations suggest that the radical reactions in non-polar solvents lead to primary benzyl and phenoxy radicals in undecane, which leads to heavier condensation products as long as metals are absent for providing dissociated hydrogen.

  18. Observation of the a_1 CH Stretching Modes of Phenyl Radical

    Science.gov (United States)

    Chang, Chih-Hsuan; Buckingham, Grant T.; Nesbitt, David J.

    2013-06-01

    High resolution spectroscopy for infrared rovibrational transitions in the CH stretching manifold of phenyl radical (C_6H_5) has been investigated in the slit-jet supersonic expansion at sub-Doppler resolution (60 MHz). Two new fundamental modes are observed and analyzed in this present study, corresponding to b-type structure originating from excitation of the fundamentals v_1 and v_2 mode. The band origins are determined to be 3073.96850(8) cm^{-1} and 3062.26480(7) cm^{-1}, respectively, which agree well with theoretical anharmonic scaling prediction within 5 cm^{-1} based on the B3LYP/6-311g++(3df,3dp) basis set, but shifted by 11 cm^{-1} from the corresponding experimental Ar-matrix's results of Ellison and coworkers. Intensities for the three bands are also analyzed, with the relative intensities between these three agreeing well with theoretical calculation. The physical interpretation of the inertia defect and perturbations of the band positions to explain the experimental observation and the frequencies shift. Anders. V. Friderichsen, Juliusz G. Radziszewski, Mark R. Nimols, Paul R. Winter, David C. Dayton, Donald E. David, and G. Barney Ellison, J. Am. Chem. Soc. 123, 1977 (2001)

  19. Synthesis and molecular modelling studies of phenyl linked oxadiazole-phenylhydrazone hybrids as potent antileishmanial agents.

    Science.gov (United States)

    Taha, Muhammad; Ismail, Nor Hadiani; Imran, Syahrul; Anouar, El Hassane; Selvaraj, Manikandan; Jamil, Waqas; Ali, Muhammad; Kashif, Syed Muhammad; Rahim, Fazal; Khan, Khalid Mohammed; Adenan, Mohd Ilham

    2017-01-27

    Molecular hybridization yielded phenyl linked oxadiazole-benzohydrazones hybrids 6-35 and were evaluated for their antileishmanial potentials. Compound 10, a 3,4-dihydroxy analog with IC 50 value of 0.95 ± 0.01 μM, was found to be the most potent antileishmanial agent (7 times more active) than the standard drug pentamidine (IC 50  = 7.02 ± 0.09 μM). The current series 6-35 conceded in the identification of thirteen (13) potent antileishmanial compounds with the IC 50 values ranging between 0.95 ± 0.01-78.6 ± 1.78 μM. Molecular docking analysis against pteridine reductase (PTR1) were also performed to probe the mode of action. Selectivity index showed that compounds with higher number of hydroxyl groups have low selectivity index. Theoretical stereochemical assignment was also done for certain derivatives by using density functional calculations. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  20. Methyl 6-methoxycarbonylmethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Lucia Veizerová

    2008-09-01

    Full Text Available The title compound, C15H16N2O5, belongs to the class of monastrol-type anti-cancer agents and was selected for crystal structure determination in order to determine the conformational details needed for subsequent structure–activity relationship studies. The central tetrahydropyrimidine ring has a flat-envelope conformation. The 4-phenyl group occupies a pseudo-axial position and is inclined at an angle of ca 90° to the mean plane of the heterocyclic ring. Of the two methyl ester groups, one (in the 5-position is in a coplanar and the other (in the 6-position in a perpendicular orientation with respect to the heterocyclic plane. The coplanar 5-ester group has its carbonyl bond oriented cis with respect to the pyrimidine C=C double bond. By comparison of the structural results for the present compound with those determined previously for its diethyl analogue, we have identified the molecular factors which control the dual course of the Biginelli reaction with salicylaldehyde. The crystal structure is dominated by two hydrogen bonds which link the molecules into chains of dimers.

  1. Synthesis of Highly Branched Polyolefins Using Phenyl Substituted α-Diimine Ni(II Catalysts

    Directory of Open Access Journals (Sweden)

    Fuzhou Wang

    2016-04-01

    Full Text Available A series of α-diimine Ni(II complexes containing bulky phenyl groups, [ArN = C(NaphthC = NAr]NiBr2 (Naphth: 1,8-naphthdiyl, Ar = 2,6-Me2-4-PhC6H2 (C1; Ar = 2,4-Me2-6-PhC6H2 (C2; Ar = 2-Me-4,6-Ph2C6H2 (C3; Ar = 4-Me-2,6-Ph2C6H2 (C4; Ar = 4-Me-2-PhC6H3 (C5; Ar = 2,4,6-Ph3C6H2 (C6, were synthesized and characterized. Upon activation with either diethylaluminum chloride (Et2AlCl or modified methylaluminoxane (MMAO, all Ni(II complexes showed high activities in ethylene polymerization and produced highly branched amorphous polyethylene (up to 145 branches/1000 carbons. Interestingly, the sec-butyl branches were observed in polyethylene depending on polymerization temperature. Polymerization of 1-alkene (1-hexene, 1-octene, 1-decene and 1-hexadecene with C1-MMAO at room temperature resulted in branched polyolefins with narrow Mw/Mn values (ca. 1.2, which suggested a living polymerization. The polymerization results indicated the possibility of precise microstructure control, depending on the polymerization temperature and types of monomers.

  2. Synthesis and Optical Properties of Near-Infrared meso-Phenyl-Substituted Symmetric Heptamethine Cyanine Dyes

    Directory of Open Access Journals (Sweden)

    Andrew Levitz

    2018-01-01

    Full Text Available Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.

  3. Synthesis, characterization and corrosion inhibition efficiency of N-(4-(Morpholinomethyl Carbamoyl Phenyl Furan-2-Carboxamide

    Directory of Open Access Journals (Sweden)

    N. Zulfareen

    2016-01-01

    Full Text Available A mannich base namely N-(4-(Morpholinomethyl Carbamoyl Phenyl Furan-2-Carboxamide (MFC was synthesized and characterized by FT-IR, 1H NMR, and 13C NMR. The molecular weight of MFC was confirmed by LC-MS. The inhibition effect of MFC on brass in 1 M HCl medium has been investigated by weight loss measurement, potentiodynamic polarization, electrochemical impedance spectroscopy (EIS and cyclic voltametry (CV. Thermodynamic parameters such as free energy, entropy and enthalpy were calculated to describe the mechanism of corrosion inhibitor. The inhibition efficiency of MFC increases with increase in concentration and temperature ranges from 30 °C to 60 °C. Polarization measurements indicated that MFC acts as a mixed type corrosion inhibitor. AC impedance indicates that Rct value increases with increase in the concentration of inhibitor. CV reveals that the oxidation of the copper is controlled by the addition of inhibitor on the brass metal. Surface analysis using scanning electron microscope (SEM shows a significant morphological improvement on the brass surface with the addition of the inhibitor. The adsorption of MFC on brass obeys Langmuir adsorption isotherm. The molecular structure of MFC was distorted to quantum chemical indices using density functional theory (DFT which indicates that the inhibition efficiency of MFC is closely related to quantum parameters.

  4. Mg(II Selective PVC Membrane Electrode Based on Methyl Phenyl Semicarbazone as an Ionophore

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2013-01-01

    Full Text Available A PVC-membrane-based Mg(II selective electrode was constructed using methyl phenyl semicarbazone (MPS as a neutral carrier. The sensor exhibits a Nernstian response for Mg(II ion over a wide concentration range 1.0×10-8  to  1.0×10-1 M with the slope of 28.4 mV/per decade having detection limit 1.7×10-9 M. It was relatively a fast response time (<10 s for concentration ≥1.0×10-3 and <15 s for concentration of ≥1.0×10-6 M and can be used for 8 months without any considerable divergence in potentials. The proposed sensor revealed relatively good selectivity and high sensitivity for Mg(II over a mono-, di-, and trivalent cation and can be used in a pH range of 1.0–9.5. It was also successfully used as an indicator electrode in potentiometer titration and in the analysis of concentration of magnesium in various real samples.

  5. Incorporating Methyl and Phenyl Substituted Stannylene Units into Oligosilanes. The Influence on Optical Absorption Properties.

    Science.gov (United States)

    Stella, Filippo; Marschner, Christoph; Baumgartner, Judith

    2017-12-12

    Molecules containing catenated heavy group 14 atoms are known to exhibit the interesting property of σ-bond electron delocalization. While this is well studied for oligo- and polysilanes the current paper addresses the UV-absorption properties of small tin containing oligosilanes in order to evaluate the effects of Sn-Si and Sn-Sn bonds as well as the results of substituent exchange from methyl to phenyl groups. The new stannasilanes were compared to previously investigated oligosilanes of equal chain lengths and substituent pattern. Replacing the central SiMe₂ group in a pentasilane by a SnMe₂ unit caused a bathochromic shift of the low-energy band (λ max = 260 nm) of 14 nm in the UV spectrum. If, instead of a SnMe 2, a SnPh₂ unit is incorporated, the bathochromic shift of 33 nm is substantially larger. Keeping the SnMe₂ unit and replacing the two central silicon with tin atoms causes shift of the respective band (λ = 286 nm) some 26 nm to the red. A similar approach for hexasilanes where the model oligosilane [(Me₃Si)₃Si]₂(SiMe₂)₂ (λ max = 253 nm) was modified in a way that the central tetramethyldisilanylene unit was exchanged for a tetraphenyldistannanylene caused a 50 nm bathochromic shift to a low-energy band with λ max = 303 nm.

  6. In vitro photosensitization initiated by camphorquinone and phenyl propanedione in dental polymeric materials.

    Science.gov (United States)

    Christensen, Terje; Morisbak, Else; Tønnesen, Hanne Hjorth; Bruzell, Ellen M

    2010-09-02

    Documentation is scarce on the photobiological effects of photoinitiators present in dental light curable materials. The aim of this study was to determine cellular effects of the photoinitiators camphorquinone (CQ) and phenyl propanedione (PPD) and to investigate whether these substances produced reactive oxygen species after low and high doses of optical radiation (between 0 and 17J/cm(2)). Rat salivary gland cells in vitro were exposed to visible blue light and/or UVA. Hematoporphyrin (HP), a photosensitizer used in medicine, and the UVA-filter 2-methoxy-4-hydroxy-benzophenone (B-3) were used as reference substances. It was found that PPD produced hydrogen peroxide, but not singlet oxygen, upon light irradiation. CQ produced neither hydrogen peroxide nor singlet oxygen. Cell death by necrosis and apoptosis was induced by irradiation in the presence of CQ, PPD and HP. Doses higher than 6J/cm(2) UVA and blue visible light from a source similar to clinically applied sources, induced apoptosis even in the absence of photosensitizers added. A reciprocity relationship was found between radiant exposure (at constant irradiance) and concentration of photoinitiators. In conclusion, the oral cells under investigation were light sensitive, and the sensitivity increased in presence of photoinitiators. PPD acted by mechanisms that included reactive oxygen species and CQ probably by formation of free radicals. Copyright (c) 2010 Elsevier B.V. All rights reserved.

  7. 2-Acetylpyridine N4-Phenyl- Thiosemicarbazone as a new tool for tumour diagnosis

    International Nuclear Information System (INIS)

    Soares, Marcella Araugio; Pesquero, Jorge Luiz

    2009-01-01

    The aim of this work was to determine in vivo biodistribution of radiolabelled 2-acetylpyridine N4 phenyl thiosemicarbazone (Ph) and to evaluate its applicability for tumour diagnosis. Ph was labelled with 125 I using lactoperoxidase method and radiochemical analysis was performed by chromatography. 125 I-Ph production was successful with 86 ± 9.2% of radiochemical purity and high specific activity (17.6 TBq /mmol). 125 I-Ph was used for biodistribution and pharmacokinetics studies on Swiss mice bearing Ehrlich solid tumour. 125 I-Ph presented a rapid blood clearance (T 1/2 = 97.2 min.) and the kidneys were the main excretion pathway (CL0.01 mL/min). 125 I-Ph uptake was significant in tumour (2.5%ID/g) and tumour-to-normal tissue uptake was more than 20-fold higher depending on the organ. The uptake by the organs like heart, lungs, stomach and liver followed the blood perfusion. Our results suggest that 125 I-Ph possess indispensable characteristics for an efficient radiopharmaceutical for tumour diagnosis. The next step will be to evaluate the quality of tumour SPECT images provided by 131 I-Ph. (author)

  8. Efficient kinetic resolution of phenyl glycidyl ether by a novel epoxide hydrolase from Tsukamurella paurometabola.

    Science.gov (United States)

    Wu, Kai; Wang, Hualei; Sun, Huihui; Wei, Dongzhi

    2015-11-01

    Enantioselective hydrolysis of racemic epoxides mediated by epoxide hydrolases (EHs) is one of the most promising approaches to obtain enantiopure epoxides. In this study, we identified and characterized a novel EH (TpEH1) from Tsukamurella paurometabola by analyzing the conserved catalytic residues of EH. TpEH1 was overexpressed and purified, and its catalytic properties were studied using racemic phenyl glycidyl ether (PGE) and its derivatives as substrates. TpEH1 showed excellent enantioselectivity to the substrates PGE, 3-methylPGE, and 3-nitroPGE. The highest enantioselectivity (E > 100) was achieved when 3-nitroPGE was used as the substrate. The recombinant Escherichia coli TpEH1 demonstrated high substrate tolerance toward PGE and could hydrolyze PGE at concentrations of up to 400 mM (60 g/L) with high enantioselectivity (E = 65), giving (R)-PGE with enantiomeric excess of more than 99 % ee and 45 % yield within 1 h. This concentration of PGE is the highest reported concentration catalyzed by native EHs to date. Thus, the easily available and highly active E. coli TpEH1 showed great potential for the practical preparation of optically pure (R)-PGE.

  9. Bioimaging of peroxynitrite in MCF-7 cells by a new fluorescent probe rhodamine B phenyl hydrazide.

    Science.gov (United States)

    Ambikapathi, Gopi; Kempahanumakkagari, Suresh Kumar; Ramappa Lamani, Babu; Kuramkote Shivanna, Devaraju; Bodagur Maregowda, Harish; Gupta, Anushree; Malingappa, Pandurangappa

    2013-07-01

    Peroxynitrite is a potent oxidizing and nitrating agent which has detrimental effects on cells by altering the structure and function of biomolecules present within. A fluorescent probe rhodamine B phenyl hydrazide (RBPH) has been proposed for peroxynitrite (ONOO(-)) imaging in MCF-7 cells based on its oxidation property, which converts RBPH to pink colored and highly fluorescent rhodamine B. The fluorescence emission intensity of the rhodamine B produced in the above process is linearly related to the concentration of peroxynitrite. The method obeys Beer's law in the concentration range 2-20 nM and the detection limit has been found to be 1.4 nM. The possible reaction mechanism of peroxynitrite with RBPH to produce rhodamine B has been discussed with spectroscopic evidence. The Probe is selective to the peroxynitrite in the pH range 6-8 which is near physiological pH. Fluorescence microscopic studies suggest that the probe is cell permeable and hence peroxynitrite was imaged in MCF-7 cells.

  10. Electronic Structures and Optical Properties of Phenyl C71 Butyric Acid Methyl Esters

    Directory of Open Access Journals (Sweden)

    Cai-Rong Zhang

    2013-01-01

    Full Text Available Phenyl C71 butyric acid methyl ester (PC71BM has been adopted as electron acceptor materials in bulk heterojunction solar cells with relatively higher power conversion efficiency. The understanding of the mechanism and performance for the devices based upon PC71BM requires the information of conformations, electronic structures, optical properties, and so forth. Here, the geometries, IR and Raman, electronic structures, polarizabilities, and hyperpolarizabilities of PC71BM isomers are studied by using density functional theory (DFT; the absorption and excitation properties are investigated via time-dependent DFT with B3LYP, PBE0, and CAM-B3LYP functionals. The calculated results show that [6,6]PC71BM is more stable than [5,6]PC71BM due to the lower total energy. The vibrational modes of the isomers at IR and Raman peaks are quite similar. As to absorption properties, CAM-B3LYP functional is the suitable functional for describing the excitations of PC71BM because the calculated results with CAM-B3LYP functional agree well with that of the experiment. The analysis of transition configurations and molecular orbitals demonstrated that the transitions at the absorption maxima in UV/Vis region are localized π-π* transitions in fullerenes cages. Furthermore, the larger isotropic polarizability of PC71BM indicates that the response of PC71BM to applied external electric field is stronger than that of PC61BM, and therefore resulting into better nonlinear optical properties.

  11. Design, Synthesis and Fungicidal Activity of 2-Substituted Phenyl-2-oxo-, 2-Hydroxy- and 2-Acyloxyethylsulfonamides

    Directory of Open Access Journals (Sweden)

    Minlong Wang

    2017-05-01

    Full Text Available Sulfonyl-containing compounds, which exhibit a broad spectrum of biological activities, comprise a substantial proportion of and play a vital role, not only in medicines but also in agrochemicals. As a result increasing attention has been paid to the research and development of sulfonyl derivatives. A series of thirty-eight 2-substituted phenyl-2-oxo- III, 2-hydroxy- IV and 2-acyloxyethylsulfonamides V were obtained and their structures confirmed by IR, 1H-NMR, and elemental analysis. The in vitro and in vivo bioactivities against two Botrytis cinerea strains, DL-11 and HLD-15, which differ in their sensitivity to procymidone, were evaluated. The in vitro activity results showed that the EC50 values of compounds V-1 and V-9 were 0.10, 0.01 mg L−1 against the sensitive strain DL-11 and 3.32, 7.72 mg L−1 against the resistant strain HLD-15, respectively. For in vivo activity against B. cinerea, compound V-13 and V-14 showed better control effect than the commercial fungicides procymidone and pyrimethanil. The further in vitro bioassay showed that compounds III, IV and V had broad fungicidal spectra against different phytopathogenic fungi. Most of the title compounds showed high fungicidal activities, which could be used as lead compounds for further developing novel fungicidal compounds against Botrytis cinerea.

  12. Photochemistry of phenyl alkyl ketones. The lifetime of the intermediate biradicals

    International Nuclear Information System (INIS)

    Small, R.D. Jr.; Scalano, J.C.

    1977-01-01

    The lifetimes of a number of biradicals produced in the photochemical Norrish type II reaction of phenyl alkyl ketones have been measured. The decay of the biradicals was followed by monitoring the competition with electron transfer to paraquat dications using nanosecond laser techniques. The lifetimes are rather insensitive to changes in temperature, substitution, and solvent, and are typically in the neighborhood of 100 ns. It is concluded that intersystem crossing is the main factor determining the biradical lifetimes. The rate constant for electron transfer to paraquat dications is 3.7 x 10 9 M -1 s -1 in methanol at room temperature for 1,4-ketyl--alkyl biradicals, and considerably higher for diketyl biradicals, apparently reflecting a change in path degeneracy. Oxygen behaves as a biradical scavenger with a rate constant of 6.2 x 10 9 M -1 s -1 in methanol. The lifetimes of the excited ketone triplets have also been determined at room temperature under the experimental conditions employed; this is an important parameter in determining the viability of the measurements of biradical lifetimes by this technique

  13. Entry of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine into the rat brain

    International Nuclear Information System (INIS)

    Riachi, N.J.; LaManna, J.C.; Harik, S.I.

    1989-01-01

    We studied blood-to-brain entry of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 1-methyl-4-phenylpyridinium (MPP+) and butanol in anesthetized rats using the indicator-fractionation method with right atrial bolus injection. Minimal amounts of MPP+, which has low octanol/water partition coefficient, crossed the blood-brain barrier. MPTP and butanol, both of which have high octanol/water partition coefficients, were almost completely extracted by all regions of the brain on the first pass. The main difference between the MPTP and butanol tracers is that butanol rapidly left the brain with an exponential rate constant of 1.24 min-1, whereas MPTP was avidly retained by the brain with a washout rate constant of 0.10 min-1 (mean values for the four brain regions that we studied). Early retention of MPTP by the brain was not due to its rapid metabolism by monoamine oxidase because pargyline pretreatment did not affect this rate constant. However, 30 min after [ 3 H]MPTP injection, brain retention of the 3H tracer was reduced significantly by pargyline treatment, and the ratio of brain MPTP/MPP+ was increased markedly

  14. Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform.

    Science.gov (United States)

    Kudryavtsev, Konstantin V; Bentley, Matthew L; McCafferty, Dewey G

    2009-04-01

    cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.

  15. Synthesis of 2-iodo- and 2-phenyl-[11C]melatonin: potential PET tracers for melatonin binding sites

    International Nuclear Information System (INIS)

    Chen Jiajun; Fiehn-Schulze, Brita; Firnau, Guenter; Brough, Paul A.; Snieckus, Victor

    1998-01-01

    Two 11 C-labelled melatonin derivatives, 2-iodo-[ 11 C]melatonin (2-iodo-5-methoxy-N[ 11 C-acetyl]-tryptamine, an agonist) and 2-phenyl-[ 11 C]melatonin (2-phenyl-5-methoxy-N[ 11 C-acetyl]tryptamine, a putative antagonist) were synthesized from [ 11 C]carbon dioxide. The reaction sequence was common to both compounds and consisted of three steps: (i) carbonylation of methyl magnesium bromide with [ 11 C]carbon dioxide, (ii) conversion of the adduct to [ 11 C]acetyl chloride, (iii) acetylation of the amine precursors (2-iodo-5-methoxy-tryptamine or 2-phenyl-5-methoxy-tryptamine) with [ 11 C]acetyl chloride. The precursors were especially prepared. The radiochemical yield was 19% for 2-iodomelatonin and 32% for 2-phenymelatonin, based on [ 11 C]carbon dioxide; the specific activity ranged from 300 to 600 mCi/μmol. Both labelled 2-substituted-melatonins are intended to be used as radiotracers to study melatonin binding sites in man with positron emission tomography

  16. Isothermal (vapour + liquid) equilibrium (VLE) for binary mixtures containing diethyl carbonate, phenyl acetate, diphenyl carbonate, or ethyl acetate

    International Nuclear Information System (INIS)

    Ho, Hsiao-Yun; Shu, So-Siou; Wang, San-Jang; Lee, Ming-Jer

    2015-01-01

    Highlights: • Isothermal (vapour + liquid) equilibrium (VLE) data were measured. • Binary mixtures contain ethyl acetate, diethyl carbonate, phenyl acetate, diphenyl carbonate. • No azeotrope formed in the systems investigated. • The VLE data were correlated well with Wilson-HOC, NRTL-HOC, UNIQUAC-HOC models. - Abstract: The isothermal (vapour + liquid) equilibrium (VLE) (P–T–x i –y i ) was determined the binary systems of (ethyl acetate + diethyl carbonate) from T = (373.2 to 453.2) K, (ethyl acetate + phenyl acetate) at T = 373.2 K, and (diethyl carbonate + phenyl acetate) at T = 373.2 K, while the VLE (P–T–x i ) of three diphenyl carbonate-containing binary systems was also determined experimentally at temperatures from (373.2 to 453.2) K. The experimental results show no azeotrope formation and near ideal solution behaviour for each binary system. These new VLE (P–T–x i –y i ) data have been passed by the point, area, and infinite dilution thermodynamic consistency tests. The Wilson-HOC, the NRTL-HOC, and the UNIQUAC-HOC models were applied to correlate the VLE results and the optimal values of the model parameters have been determined through data reduction. Comparable results were obtained from these three models.

  17. Separation of flavonoids on different phenyl-bonded stationary phases-the influence of polar groups in stationary phase structure.

    Science.gov (United States)

    Janas, Petr; Bocian, Szymon; Jandera, Pavel; Kowalkowski, Tomasz; Buszewski, Bogusław

    2016-01-15

    Four phenyl-bonded stationary phases, differing in polar embedded group between spacer and phenyl ring, were used for the separation of flavonoids in reversed-phase conditions. In addition, the work was focused on the comparison of these stationary phases in terms of retention and nature of interactions between flavonoid solutes and both, mobile and stationary phases. The differences and similarities between the columns and between individual flavonoids were evaluated by a statistical analysis. The retention over the wider range of mobile phase composition was described using well known model suggested for partition chromatographic systems. Due to differences in polarity of flavonoids, gradient elution had to be applied to achieve appropriate conditions for the successful separation. A chromatographic optimization software was employed for establish the appropriate profiles of gradient separations using UV detection at 275 nm. The most appropriate conditions for the separation of flavonoids were apparent on the phenyl and phenoxy columns. Copyright © 2015 Elsevier B.V. All rights reserved.

  18. Synthesis and Antiplasmodial Activity of 2-(4-Methoxyphenyl-4-Phenyl-1,10-Phenanthroline Derivative Compounds

    Directory of Open Access Journals (Sweden)

    Nazudin

    2012-08-01

    Full Text Available A unique of synthetic methods was employed to prepare 2-(4-methoxyphenyl-4-phenyl-1,10-phenanthroline (5 derivatives from 4-methoxy-benzaldehyde (1, acetophenone (2, and 8-aminoquinoline (4 with aldol condensation and cyclization reactions. The derivatives were tested through antiplasmodial test. The synthesis of derivatives compound 5 was conducted in three steps. The 3-(4-methoxyphenyl-1-phenylpropenone 3 was synthesized through aldol condensation of 1 and 2 which has a yield of 96.42%. The compound 5 was synthesized through cyclization of compound 4 and 3 with 84.55% yield. The derivative of compound 5 was synthesized from compound 5 using DMS and DES reagents which refluxed for 21 and 22 h, to produce (1-N-methyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (6 and (1-N-ethyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (7 with 91.42 and 86.36% yields, respectively. Results of in vitro testing of antiplasmodial activity of compound 5 derivatives (i.e., compound 6 and 7 against chloroquine-resistant P. falciparum FCR3 strain showed that compound 7 had higher antimalarial activity than compounds 5 and 6. Whereas, results of in vitro testing against chloroquine-sensitive P. falciparum D10 strain showed that compound 6 has higher antimalarial activity than compounds 5 and 7.

  19. Synthesis, studies and in-vitro antibacterial activity of N-substituted 5-(furan-2-yl-phenyl pyrazolines

    Directory of Open Access Journals (Sweden)

    Mamta Rani

    2015-03-01

    Full Text Available Novel compounds with antibacterial properties: pyrazoline derivatives were synthesized by the cyclization of various -1-[2-(alkoxyphenyl]-3-(furan-2-yl prop-2-en-1-one 1a–1d with N-substituted phenyl hydrazine in the presence of CH3COOH in ethanol. The structures of these compounds were elucidated by, IR, 1H NMR, 13C NMR, ESI-MS spectral data and their purities were confirmed by elemental analyses. The in vitro antibacterial activity of these compounds was evaluated against two Gram-positive and two Gram-negative bacteria Aeromonas hydrophila, Yersinia enterocolitica, Listeria monocytogenes, and Staphylococcus aureus by microdilution method and then the minimum inhibitory concentration (MIC of compounds were determined. The results showed that compounds (5R-5-(furan-2-yl-1-phenyl-3-[2-(benzyloxyphenyl]-4, 5-dihydro-1H-pyrazole (2b and (5R-5-(furan-2-yl-1-phenyl-3-[2-(naphthalen-2-ylmethoxy prop-2-en-1-yloxyphenyl]-4,5-dihydro-1H-pyrazole (2d showing most promising antibacterial activities as compared to Gentamicin and Tetracycline are given.

  20. Electrochemical and Spin-Trapping Properties of para-substituted α-Phenyl-N-tert-butyl Nitrones

    International Nuclear Information System (INIS)

    Rosselin, Marie; Tuccio, Béatrice; Pério, Pierre; Villamena, Frederick A.; Fabre, Paul-Louis; Durand, Grégory

    2016-01-01

    Nitrones are known both as therapeutic antioxidants and efficient spin-traps. In this work, the redox behavior of various para-substituted α-phenyl-N-tert-butyl nitrones (PBN) was studied by cyclic voltammetry. The polar effect of the substituents was found to correlate with the electrochemical properties of the nitronyl function. Compounds bearing an electron-withdrawing group were more easily reduced than those having an electron-donating group and an opposite trend was observed for the oxidation. Ease of oxidation was also computationally rationalized using DFT approach showing increased ease of oxidation with electron donating functionalities. Since electrochemical properties of nitrones are known to correlate with biological properties, this work provides insights in the design of potent nitrone antioxidants. Using cyclic voltammetry the relative rate of superoxide trapping by nitrones was investigated and compared to the classical antioxidant BHT. The determination of the relative rate of phenyl radical trapping was also carried out but showed no clear correlation with the nature of the substituents. This indicates the absence of a polar effect in agreement with previous data and further supports the intermediate nature, that is, non- or weakly nucleophile, of phenyl radical. On the contrary kinetics of hydroxymethyl radical trapping was found to correlate with the nature of the substituents, demonstrating the nucleophilic nature of its addition onto nitrones.

  1. SYNTHESIS OF 1,4-BIS [(1-HYDROXY-4-T-BUTYL-PHENYL METHYL]PIPERAZINE AS ANTIOXIDANTS

    Directory of Open Access Journals (Sweden)

    Susy Yunita Prabawati

    2016-11-01

    Full Text Available A study has been conducted to synthesize 1,4-bis [(1-hydroxy-4-t-butyl-phenyl-methyl]piperazin using phenol derivate and investigate the capability of that compound, as an antioxidant. The synthesis was carried out through Mannich reaction using p-t-butylphenol, paraformaldehyde, and piperazine. The product was characterized by IR and 1H NMR spectroscopic. Testing of antioxidant activity was done with the immersion of DPPH (1,1-diphenyl-2 picrylhydrazyl free radical method. The product was obtained as a white solid, with a point of 252,7-254,7 ºC and a yield of 65.76%. The test of antioxidant activity with DPPH method showed that 1,4-bis [(1-hydroxy-4-t-butyl-phenyl-methyl]piperazin had the IC50 values was 0.84 nM. It means that the 1,4- bis[(1-hydroxy-4-t-butyl-phenyl methyl]piperazine has potential as antioxidants.

  2. Drug-induced protein free radical formation is attenuated by unsaturated fatty acids by scavenging drug-derived phenyl radical metabolites.

    Science.gov (United States)

    Narwaley, Malyaj; Michail, Karim; Arvadia, Pratik; Siraki, Arno G

    2011-07-18

    Aromatic amine drugs like aminoglutethimide (AG) and related congeners have been shown to produce phenyl radicals through metabolism by myeloperoxidase (MPO)/H(2)O(2), which has been proposed to play a role in drug-induced agranulocytosis. AG has also been shown to induce MPO protein radical formation, but the ultimate fate of these metabolically generated phenyl radicals is still unknown. We tested the reactivity of linoleic acid (LA) and GSH with aniline-based compounds in the presence of horseradish peroxidase (HRP)/H(2)O(2) by measuring oxygen consumption. We found a qualitative correlation between drugs or xenobiotics that formed phenyl radical metabolites with the cooxidation of LA. Most compounds that reacted with LA did not react with GSH. Furthermore, an AG-derived phenyl radical was detected by EPR spin-trapping with MNP (2-methyl-2-nitrosopropane), in a reaction containing AG and HRP/H(2)O(2); these spectra were attenuated in the presence of LA and docosahexaenoic acid (DHA) indicating that phenyl radical scavenging occurred. Since it has been proposed that the phenyl radical metabolite leads to protein radical formation on MPO, we investigated the effect of LA and DHA in immuno-spin trapping experiments with MPO-containing HL-60 cell lysate. Using anti-DMPO, a protein radical was detected on a putative MPO fragment from the reaction of DMPO, AG, and glucose/glucose oxidase. When LA or DHA was included in this reaction, protein radical formation was significantly inhibited. Our results show that certain polyunsaturated fatty acids (PUFAs) act as scavengers of aromatic amine drug-derived phenyl radicals which in turn prevent protein radical formation. However, the interaction of phenyl radical drug metabolites with PUFAs will be dictated by their relative concentrations compared to those of other targets. Most importantly, it is possible to differentiate peroxidase substrates that generate phenyl radical metabolites from N-centered radicals on the basis

  3. Dimethyl phenyl piperazine iodide (DMPP) induces glioma regression by inhibiting angiogenesis

    Energy Technology Data Exchange (ETDEWEB)

    He, Yan-qing; Li, Yan; Wang, Xiao-yu [Key Laboratory for Regenerative Medicine of the Ministry of Education, Division of Histology and Embryology, Medical College, Jinan University, Guangzhou 510632 (China); He, Xiao-dong [Institute of Vascular Biological Sciences, Guangdong Pharmaceutical University, Guangzhou 510006 (China); Jun, Li [Guangdong Provincial Key Laboratory of Bioengineering Medicine, National Engineering Research Centre of Genetic Medicine, College of Life Science and Technology, Jinan University, Guangzhou 510632 (China); Chuai, Manli [Division of Cell and Developmental Biology, University of Dundee, Dundee, DD1 5EH (United Kingdom); Lee, Kenneth Ka Ho [Key Laboratory for Regenerative Medicine of the Ministry of Education, School of Biomedical Sciences, Chinese University of Hong Kong, Shatin (Hong Kong); Wang, Ju [Guangdong Provincial Key Laboratory of Bioengineering Medicine, National Engineering Research Centre of Genetic Medicine, College of Life Science and Technology, Jinan University, Guangzhou 510632 (China); Wang, Li-jing, E-mail: wanglijing62@163.com [Institute of Vascular Biological Sciences, Guangdong Pharmaceutical University, Guangzhou 510006 (China); Yang, Xuesong, E-mail: yang_xuesong@126.com [Key Laboratory for Regenerative Medicine of the Ministry of Education, Division of Histology and Embryology, Medical College, Jinan University, Guangzhou 510632 (China)

    2014-01-15

    1,1-Dimethyl-4-phenyl piperazine iodide (DMPP) is a synthetic nicotinic acetylcholine receptor (nAChR) agonist that could reduce airway inflammation. In this study, we demonstrated that DMPP could dramatically inhibit glioma size maintained on the chick embryonic chorioallantoic membrane (CAM). We first performed MTT and BrdU incorporation experiments on U87 glioma cells in vitro to understand the mechanism involved. We established that DMPP did not significantly affect U87 cell proliferation and survival. We speculated that DMPP directly caused the tumor to regress by affecting the vasculature in and around the implanted tumor on our chick CAM model. Hence, we conducted detailed analysis of DMPP's inhibitory effects on angiogenesis. Three vasculogenesis and angiogenesis in vivo models were used in the study which included (1) early chick blood islands formation, (2) chick yolk-sac membrane (YSW) and (3) CAM models. The results revealed that DMPP directly suppressed all developmental stages involved in vasculogenesis and angiogenesis – possibly by acting through Ang-1 and HIF-2α signaling. In sum, our results show that DMPP could induce glioma regression grown on CAM by inhibiting vasculogenesis and angiogenesis. - Highlights: ●We demonstrated that DMPP inhibited the growth of glioma cells on chick CAM. ●DMPP did not significantly affect the proliferation and survival of U87 cells. ●We revealed that DMPP suppressed vasculogenesis and angiogenesis in chick embryo. ●Angiogenesis in chick CAM was inhibited by DMPP via most probably Ang-1 and HIF-2α. ●DMPP could be potentially developed as an anti-tumor drug in the future.

  4. 2-((2-((dimethylamino)methyl)phenyl)thio)-5-iodophenylamine (ADAM): an improved serotonin transporter ligand

    Energy Technology Data Exchange (ETDEWEB)

    Oya, Shunichi; Choi, S.-R.; Hou, Catherine; Mu Mu; Kung, M.-P.; Acton, Paul D.; Siciliano, Michael; Kung, Hank F. E-mail: kunghf@sunmac.spect.upenn.edu

    2000-04-01

    Serotonin transporters (SERT) are target-sites for commonly used antidepressants, such as fluoxetine, paroxetine, sertraline, and so on. Imaging of these sites in the living human brain may provide an important tool to evaluate the mechanisms of action as well as to monitor the treatment of depressed patients. Synthesis and characterization of an improved SERT imaging agent, ADAM (2-((2-((dimethylamino)methyl)phenyl)thio)-5-iodophenylamine)(7) was achieved. The new compound, ADAM(7), displayed an extremely potent binding affinity toward SERT (K{sub i}=0.013 nM, in membrane preparations of LLC-PK{sub 1}-cloned cell lines expressing the specific monoamine transporter). ADAM(7) also showed more than 1,000-fold selectivity for SERT over norepinephrine transporter (NET) and dopamine transporter (DAT) (K{sub i}=699 and 840 nM, for NET and DAT, respectively). The radiolabeled compound [{sup 125}I]ADAM(7) showed an excellent brain uptake in rats (1.41% dose at 2 min post intravenous [IV] injection), and consistently displayed the highest uptake (between 60-240 min post IV injection) in hypothalamus, a region with the highest density of SERT. The specific uptake of [{sup 125}I]ADAM(7) in the hypothalamus exhibited the highest target-to-nontarget ratio ([hypothalamus - cerebellum]/cerebellum was 3.97 at 120 min post IV injection). The preliminary imaging study of [{sup 123}I]ADAM in the brain of a baboon by single photon emission computed tomography (SPECT) at 180-240 min post IV injection indicated a specific uptake in midbrain region rich in SERT. These data suggest that the new ligand [{sup 123}I]ADAM(7) may be useful for SPECT imaging of SERT binding sites in the human brain.

  5. Studies on the Synthesis, Photophysical and Biological Evaluation of Some Unsymmetrical Meso-Tetrasubstituted Phenyl Porphyrins

    Directory of Open Access Journals (Sweden)

    Rica Boscencu

    2017-10-01

    Full Text Available Abstract: We designed three unsymmetrical meso-tetrasubstituted phenyl porphyrins for further development as theranostic agents for cancer photodynamic therapy (PDT: 5-(4-hydroxy-3-methoxyphenyl-10,15,20-tris-(4-acetoxy-3-methoxyphenylporphyrin (P2.2, Zn(II-5-(4-hydroxy-3-methoxyphenyl-10,15,20-tris-(4-acetoxy-3-methoxyphenylporphyrin (Zn(II2.2 and Cu(II-5-(4-hydroxy-3-methoxyphenyl-10,15,20-tris-(4-acetoxy-3-methoxyphenylporphyrin (Cu(II2.2. The porphyrinic compounds were synthesized and their structures were confirmed by elemental analysis, FT-IR, UV-Vis, EPR and NMR. The compounds had a good solubility in polar/nonpolar media. P2.2 and, to a lesser extent, Zn(II2.2 were fluorescent, albeit with low fluoresence quantum yields. P2.2 and Zn(II2.2 exhibited PDT-acceptable values of singlet oxygen generation. A “dark” cytotoxicity study was performed using cells that are relevant for the tumor niche (HT-29 colon carcinoma cells and L929 fibroblasts and for blood (peripheral mononuclear cells. Cellular uptake of fluorescent compounds, cell viability/proliferation and death were evaluated. P2.2 was highlighted as a promising theranostic agent for PDT in solid tumors considering that P2.2 generated PDT-acceptable singlet oxygen yields, accumulated into tumor cells and less in blood cells, exhibited good fluorescence within cells for imagistic detection, and had no significant cytotoxicity in vitro against tumor and normal cells. Complexing of P2.2 with Zn(II or Cu(II altered several of its PDT-relevant properties. These are consistent arguments for further developing P2.2 in animal models of solid tumors for in vivo PDT.

  6. Controllable sulfonation of aromatic poly(arylene ether ketone)s containing different pendant phenyl rings

    Energy Technology Data Exchange (ETDEWEB)

    Li, Zhiliang; Liu, Xincai; Chao, Danming; Zhang, Wanjin [Alan G. MacDiarmid Institute, Jilin University, Qianjin Street 2699, Changchun 130012 (China)

    2009-09-05

    The sulfonation selectivity of various pendant phenyl groups in poly(arylene ether ketone) (Ph-3F-PAEK) is invested via the postsulfonation approach. The sulfonated Ph-3F-PAEKs with different degrees of sulfonation (DS) are quantitatively synthesized by controlling the length of the segments that cannot be sulfonated. In this study, {sup 1}H NMR and FT-IR are used to confirmed the structures of the polymers and the experimentally DS values were calculated by {sup 1}H NMR. The experimentally observed DSs are corresponding to the theoretical values expected from the monomer ratios. All the sulfonated membranes have excellent mechanical properties (with a Young's modulus >1.3 GPa, a tensile strength >55 MPa and the elongation >10%). Thermogravimetric analysis (TGA) is used to characterized the thermal stability of these polymers, and all the polymers show excellent thermal properties at high temperatures. The methanol permeability values of Ph-3F-SPAEKs in the range of 0.37 x 10{sup -7} cm{sup 2} s{sup -1} to 4.12 x 10{sup -7} cm{sup 2} s{sup -1} are much lower than that of Nafion {sup registered} 117 (1.55 x 10{sup -6} cm{sup 2} s{sup -1}). It should be noted that the polymer with highest DS, Ph-3F-SPAEK-100 with an ion exchange capacity of 2.16 mequiv. g{sup -1}, exhibits high proton conductivity of 0.187 S cm{sup -1} at 80 C, which is also higher than that of Nafion {sup registered} 117. (author)

  7. Phenyl vs Alkyl Polythiophene: A Solar Cell Comparison Using a Vinazene Derivative as Acceptor

    KAUST Repository

    Woo, Claire H.

    2010-03-09

    The solar cell performance of poly[3-(4-n-octyl)-phenylthiophene] (POPT) and poly(3hexylthiophene) (P3HT) are compared in devices using 4,7-bis(2-(l-(2-ethylhexyl)-4,5-dicyanoimidazol-2-yl)vinyi)benzo[c][l,2,5] -thiadiazole (EV-BT) as the electron acceptor. Despite their reduced light absorption, POPT:EV-BT devices generate higher photocurrents in both bilayer and bulk heterojunction (BHJ) architectures than analogous P3HT:EV-BT devices. Optimized POPT:EV-BT BHJ devices achieve 1.4% average efficiency, whereas the analogous P3HT devices only reach 1.1%. Morphology does not account for the large difference in performance as AFM studies of the active layer suggest, comparable levels of phase separation in the two systems. Reverse bias analysis demonstrates that P3HT devices have a higher maximum potential than POPT devices, but P3HT devices appear to be more severely limited by recombination losses under standard operating conditions. A possible explanation for the superior performance in POPT devices is that the pendant phenyl ring in POPT can twist out-of-plane and increase the separation distance with the acceptor molecule. A larger donor/acceptor separation distance can destabilize the geminate pair and lead to more efficient charge separation in POPT:EV-BT devices. Our results emphasize the importance of donor/acceptor pair interactions and its effect on charge separation, processes in polymer solar cells. © 2010 American Chemical Society.

  8. Comparative effects of 4-phenyl-3-butenoic acid and vorinostat on cell growth and signaling.

    Science.gov (United States)

    Burns, Timothy J; Ali, Amna; Matesic, Diane F

    2015-02-01

    4-phenyl-3-butenoic acid (PBA) is a small-molecule anti-inflammatory agent, which has been shown to inhibit growth, increase gap junction intercellular communication and modulate activation of p38 mitogen-activated protein kinase (p38 MAPK) and c-jun n-terminal kinase (JNK) in tumorigenic cells at concentrations that do not similarly affect non-tumorigenic cells. Vorinostat is an anticancer agent structurally similar to PBA. The purpose of this study was to compare the effects of these two agents on JNK and p38 activation, cell growth and gap junction intercellular communication (GJIC). Cell growth, GJIC and western blot analyses were performed utilizing tumorigenic WBras1 and H2009 human carcinoma cells, and non-tumorigenic WBneo3 and human bronchial epithelial (HBE) cells. Both compounds significantly inhibited WBras1 and H2009 tumorigenic cell growth and increased GJIC in WBras1 cells, as previously reported for PBA. Under similar conditions, both compounds increased phosphorylation of p38 MAPK in tumorigenic but not in non-tumorigenic cells and decreased phosphorylation of JNK in tumorigenic cells. However, a decrease in phosphorylation of JNK occurred in non-tumorigenic WBras1 cells following vorinostat treatment but not PBA treatment. Both compounds showed a selective growth inhibition of H2009 human carcinoma over normal HBE lung cells but, unlike PBA, vorinostat significantly decreased cell growth in WBneo3 cells. Overall, PBA exhibited similar effects to vorinostat in tumorigenic cells, while also showing reduced effects on JNK phosphorylation and growth in non-tumorigenic cells compared to ras-transformed cells. Copyright© 2015 International Institute of Anticancer Research (Dr. John G. Delinassios), All rights reserved.

  9. PAH formation under single collision conditions: reaction of phenyl radical and 1,3-butadiene to form 1,4-dihydronaphthalene.

    Science.gov (United States)

    Kaiser, R I; Parker, D S N; Zhang, F; Landera, A; Kislov, V V; Mebel, A M

    2012-05-03

    The crossed beam reactions of the phenyl radical (C(6)H(5), X(2)A(1)) with 1,3-butadiene (C(4)H(6), X(1)A(g)) and D6-1,3-butadiene (C(4)D(6), X(1)A(g)) as well as of the D5-phenyl radical (C(6)D(5), X(2)A(1)) with 2,3-D2-1,3-butadiene and 1,1,4,4-D4-1,3-butadiene were carried out under single collision conditions at collision energies of about 55 kJ mol(-1). Experimentally, the bicyclic 1,4-dihydronaphthalene molecule was identified as a major product of this reaction (58 ± 15%) with the 1-phenyl-1,3-butadiene contributing 34 ± 10%. The reaction is initiated by a barrierless addition of the phenyl radical to the terminal carbon atom of the 1,3-butadiene (C1/C4) to form a bound intermediate; the latter underwent hydrogen elimination from the terminal CH(2) group of the 1,3-butadiene molecule leading to 1-phenyl-trans-1,3-butadiene through a submerged barrier. The dominant product, 1,4-dihydronaphthalene, is formed via an isomerization of the adduct by ring closure and emission of the hydrogen atom from the phenyl moiety at the bridging carbon atom through a tight exit transition state located about 31 kJ mol(-1) above the separated products. The hydrogen atom was found to leave the decomposing complex almost parallel to the total angular momentum vector and perpendicularly to the rotation plane of the decomposing intermediate. The defacto barrierless formation of the 1,4-dihydronaphthalene molecule involving a single collision between a phenyl radical and 1,3-butadiene represents an important step in the formation of polycyclic aromatic hydrocarbons (PAHs) and their partially hydrogenated counterparts in combustion and interstellar chemistry.

  10. 1H and 13C NMR spectra, structure and physicochemical features of phenyl acridine-9-carboxylates and 10-methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulphonates--alkyl substituted in the phenyl fragment.

    Science.gov (United States)

    Krzymiński, K; Malecha, P; Zadykowicz, B; Wróblewska, A; Błażejowski, J

    2011-01-01

    The 1H and 13C NMR spectra of twelve phenyl acridine-9-carboxylates--alkyl-substituted in the phenyl fragment--and their 10-methyl-9-(phenoxycarbonyl)acridinium salts dissolved in CD3CN, CD3OD, CDCl3 and DMSO-d6 were recorded in order to examine the influence of the structure of these compounds and the properties of the solvents on chemical shifts and 1H-(1)H coupling constants. Experimental data were compared with 1H and 13C chemical shifts predicted at the GIAO/DFT level of theory for DFT(B3LYP)/6-31G** optimised geometries of molecules, as well as with values of 1H chemical shifts and 1H-(1)H coupling constants, estimated using ACD/HNMR database software to ensure that the assignment was correct. To investigate the relations between chemical shifts and selected structural or physicochemical characteristics of the target compounds, the values of several of these parameters were determined at the DFT or HF levels of theory. The HOMO and LUMO energies obtained at the HF level yielded the ionisation potentials and electron affinities of molecules. The DFT method provided atomic partial charges, dipole moments, LCAO coefficients of pz LUMO of selected C atoms, and angles reflecting characteristic structural features of the compounds. It was found that the experimentally determined 1H and 13C chemical shifts of certain atoms relate to the predicted dipole moments, the angles between the acridine and phenyl moieties, and the LCAO coefficients of the pz LUMO of the C atoms believed to participate in the initial step of the oxidation of the target compounds. The spectral and physicochemical characteristics of the target compounds were investigated in the context of their chemiluminogenic ability. Copyright © 2010 Elsevier B.V. All rights reserved.

  11. Synthesis and evaluation of fluorine-substituted phenyl acetate derivatives as ultra-short recovery sedative/hypnotic agents.

    Science.gov (United States)

    Zhang, Heng; Xu, Xiangqing; Chen, Yin; Qiu, Yinli; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen

    2014-01-01

    Soft drugs are molecules that are purposefully designed to be rapidly metabolized (metabolically labile). In anesthesia, the soft drug is useful because it enables precise titration to effect and rapid recovery, which might allow swift and clear-headed recovery of consciousness and early home readiness. Propofol may cause delayed awakening after prolonged infusion. Propanidid and AZD3043 have a different metabolic pathway compared to propofol, resulting in a short-acting clinical profile. Fluorine imparts a variety of properties to certain medicines, including an enhanced absorption rate and improved drug transport across the blood-brain barrier. We hypothesized that the introduction of fluorine to the frame structure of propanidid and AZD3043 would further accelerate the swift and clear-headed recovery of consciousness. To test this hypothesis, we developed a series of fluorine-containing phenyl acetate derivatives. Fluorine-containing phenyl acetate derivatives were synthesized, and their hypnotic potencies and durations of LORR following bolus or infusion administration were determined in mice, rats and rabbits. The metabolic half-lives in the blood of various species were determined chromatographically. In vitro radioligand binding and γ-aminobutyric acidA (GABAA) receptor electrophysiology studies were performed. Among the 12 synthesized fluorine-containing phenyl acetate derivatives, compound 5j induced comparable duration of LORR with AZD3043, but more rapid recovery than AZD3043, propanidid and propofol. The time of compound 5j to return to walk and behavioral recovery are approximately reduced by more than 50% compared to AZD3043 in mice and rats and rabbits. The HD50 of compound 5j decreased with increasing animal size. The rapid recovery might make compound 5j suitable for precise titration and allow swift and clear-headed recovery of consciousness and early home readiness.

  12. Synthesis and evaluation of fluorine-substituted phenyl acetate derivatives as ultra-short recovery sedative/hypnotic agents.

    Directory of Open Access Journals (Sweden)

    Heng Zhang

    Full Text Available BACKGROUND: Soft drugs are molecules that are purposefully designed to be rapidly metabolized (metabolically labile. In anesthesia, the soft drug is useful because it enables precise titration to effect and rapid recovery, which might allow swift and clear-headed recovery of consciousness and early home readiness. Propofol may cause delayed awakening after prolonged infusion. Propanidid and AZD3043 have a different metabolic pathway compared to propofol, resulting in a short-acting clinical profile. Fluorine imparts a variety of properties to certain medicines, including an enhanced absorption rate and improved drug transport across the blood-brain barrier. We hypothesized that the introduction of fluorine to the frame structure of propanidid and AZD3043 would further accelerate the swift and clear-headed recovery of consciousness. To test this hypothesis, we developed a series of fluorine-containing phenyl acetate derivatives. METHODOLOGY/PRINCIPAL FINDINGS: Fluorine-containing phenyl acetate derivatives were synthesized, and their hypnotic potencies and durations of LORR following bolus or infusion administration were determined in mice, rats and rabbits. The metabolic half-lives in the blood of various species were determined chromatographically. In vitro radioligand binding and γ-aminobutyric acidA (GABAA receptor electrophysiology studies were performed. Among the 12 synthesized fluorine-containing phenyl acetate derivatives, compound 5j induced comparable duration of LORR with AZD3043, but more rapid recovery than AZD3043, propanidid and propofol. The time of compound 5j to return to walk and behavioral recovery are approximately reduced by more than 50% compared to AZD3043 in mice and rats and rabbits. The HD50 of compound 5j decreased with increasing animal size. CONCLUSIONS/SIGNIFICANCE: The rapid recovery might make compound 5j suitable for precise titration and allow swift and clear-headed recovery of consciousness and early home

  13. Photophysical properties of 4-methyl 3-phenyl coumarin organized in Langmuir-Blodgett films: Formation of aggregates

    Energy Technology Data Exchange (ETDEWEB)

    Acharya, Somobrata [Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105 (Israel)], E-mail: acharya@bgumail.bgu.ac.il; Kamilya, Tapanendu [Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700032 (India); Sarkar, Jyotirmoy [Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700032 (India); Parichha, Tapan Kr. [Department of Chemistry, Suri Vidyasagar College, Suri, Birbhum (India); Pal, Prabir [Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700032 (India); Talapatra, G.B. [Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700032 (India)], E-mail: spgbt@iacs.res.in

    2007-07-15

    Langmuir-Blodgett (LB) films of 4-methyl 3-phenyl coumarin (MPC), a non-amphiphilic derivative of coumarin mixed with stearic acid (SA) are studied. The surface pressure-area ({pi}-A) isotherm study at air-water interface reveals a repulsive type of interaction between the MPC and SA molecules resulting in the formation of aggregates of MPC molecules. Absorption, fluorescence and phosphorescence studies indicate the formation of J-type aggregate in LB film. Low temperature (77 K) phosphorescence lifetime is found to be decreased due to aggregate formation. Micro structured aggregates are observed after examining the surface morphology of LB film by scanning electron microscopy (SEM)

  14. 1-[(6-Chloro-3-pyridylmethyl]-N-(4-ethoxyphenyl-3-phenyl-1H-pyrazole-5-carboxamide

    Directory of Open Access Journals (Sweden)

    Zheng Tang

    2009-04-01

    Full Text Available In the title compound, C24H21ClN4O2, the pyrazole ring makes dihedral angles of 7.70 (11, 89.17 (11 and 40.68 (11° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H...O and C—H...π bonds giving rigidity to the molecule, while weak intermolecular N—H...N and C—H...π hydrogen bonds link the molecules into a two-dimensional structure.

  15. Transition-Metal-Catalyzed Cyanation by Using an Electrophilic Cyanating Agent, N-Cyano-N-phenyl-p-toluenesulfonamide (NCTS).

    Science.gov (United States)

    Cui, Jie; Song, Jian; Liu, Qing; Liu, Hui; Dong, Yunhui

    2018-03-02

    The ability to introduce a nitrile group into a biologically active compound is very useful in organic synthesis, owing to the importance of nitrile groups in transformations and tuning molecular properties. To date, nucleophilic cyanation has been the most used strategy for this purpose, whilst electrophilic cyanation reactions are less developed. Recently, the electrophilic cyanation reagent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) has received increasing attention, owing to its superior properties in terms of safety and practicality. This Focus Review summarizes recent progress in transition-metal-catalyzed cyanation reactions that use NCTS. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Contribution to the study of gamma radiolysis of 2-furyl butyl or substituted phenyl ketones in isopropanol

    International Nuclear Information System (INIS)

    El Dessouky Aly, M.M.

    1982-03-01

    The following ketones: 2-furyl butyl ketone (I), 2 furyl phenyl ketone (II), 2-furyl p-methylphenyl ketone (III) and 2-furyl p-methoxyphenyl ketone (IV) were synthesised and characterised. The yields of hydrogen and methane obtained during radiolysis of the mixtures ketones (I to IV)-2-propanol were determined. These yields are always lower than with pure 2-propanol. Radiolysis products for ketones (I) and (II) are studied. Analysis of radiolitical products were conducted by gas chromatography. Effect of radiation dose and ketone concentration is determined. Reaction mechanisms are studied [fr

  17. Effects of methylglyoxal bis(guanylhydrazone) and two phenylated analogues on S-adenosylmethionine decarboxylase activity from Eimeria stiedai (Apicomplexa).

    Science.gov (United States)

    San-Martín Núñez, B; Alunda, J M; Balaña-Fouce, R; Ordóñez Escudero, D

    1987-01-01

    1. Activity of S-adenosylmethionine decarboxylase, one of the rate-limiting enzymes of polyamine biosynthesis, was determined in oocysts of Eimeria stiedai, a coccidian parasite of the rabbit. 2. Several properties of the enzyme were compared to the mammalian enzyme. It showed considerably less substrate affinity than the analog enzyme from the rabbit. 3. The E. stiedai enzyme showed a low sensitivity to methylglyoxal bis(guanylhydrazone), a frequently used inhibitor of the enzyme in mammals, and two phenylated derivatives. 4. Results with the inhibitors are discussed in view of their potential use in chemotherapy.

  18. Effects of phenylated compounds of methylglyoxal bis(guanylhydrazone) on diamine oxidase activity from rat small intestine.

    Science.gov (United States)

    Balaña-Fouce, R; Pulido, T G; Escudero, D O; Sanz-Sanchez, F

    1986-01-01

    Two phenylated compounds of methylglyoxal bis(guanylhydrazone), potentially inhibitors of diamine oxidase activity, have been synthesized: phenylglyoxal bis(guanylhydrazone) and diphenylglyoxal bis(guanylhydrazone). Their inhibitory capacity was tested: while PGBG was able to reduce the enzyme activity by 50% at 1.3 microM, DPGBG was only able to reduce diamine oxidase activity by less than 2% at a concentration 1000-fold higher. The inhibition of PGBG was non-competitive and the Ki calculated by a Dixon plot was estimated as 1.7 microM.

  19. 3-Phenoxymethyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

    Directory of Open Access Journals (Sweden)

    Shaaban K. Mohamed

    2016-04-01

    Full Text Available In the title compound, C16H12N4OS, the bicyclic triazolothiadiazole core is approximately planar, with an r.m.s. deviation of 0.018 Å. The phenyl rings are inclined to its mean plane by 7.66 (7 and 71.79 (7°. In the crystal, molecules are linked via a C—H...π interaction and a π–π interaction [intercentroid distance = 3.2942 (9 Å] involving inversion-related triazole rings. These interactions result in the formation of chains propagating along [10-1].

  20. Synthesis and Activity of a New Series of(Z-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors

    Directory of Open Access Journals (Sweden)

    Shao-Jie Wang

    2007-04-01

    Full Text Available During the course of studies directed towards the discovery of novel aldose reductase inhibitors for the treatment of diabetic complications, we synthesized a series of new (Z-3-phenyl-2-benzoylpropenoic acid derivatives and tested their in vitro inhibitory activities on rat lens aldose reductase. Of these compounds, (Z-3-(3,4-dihydroxyphenyl-2-(4-methylbenzoylpropenoicacid(3k was identified as the most potent inhibitor, with an IC50 of 0.49μM. The theoretical binding mode of 3k was obtained by simulation of its docking into the active site of the human aldose reductase crystal structure.

  1. Radiochemical study of ion-molecular reactions of free phenyl-vinyl cations with some oxygen-containing compounds

    International Nuclear Information System (INIS)

    Nefedov, V.D.; Sinotova, E.N.; Kuzhelev, L.P.; Lebedev, V.P.

    1987-01-01

    Ion-molecular reactions of free phenyl-vinyl cations with water, ethanol and diethyl ether in different aggregate states are studied by radiochemical method. Free cations were produced by nuclear-chemical method (in the result of β-decay of tritium atoms in styrene composition - C 6 H 5 CT=CHT). It is shown that such electrophilic addition products as acetophenone, phenylethenol and isomeric ethoxy styrene appear to be the main. Competing process - cation deprotonation - leads to phenylacetylene formation. Quantum-chemical interpretation of the results obtained is given within the framework of molecular orbital perturbation theory

  2. Phenyl-N,N-dibutylcarbamoylmethyl sulfoxide as a new bifunctional extractant for extraction of uranium(VI) in toluene

    International Nuclear Information System (INIS)

    Han Jing-Tian; Sun Guo-Xin; Shao Hua; Bao Bo-Rong; Chen Shu-Feng

    1999-01-01

    A new bifunctional extractant named phenyl-N,N-dibutylcarbamoylmethyl sulfoxide (PCMSO) is synthesized and characterized in order to investigate its selectivity and capability in the extraction from acidic nitrate media in nuclear reprocessing. The extraction of uranium(VI) with PCMSO in toluene has been studied at various concentrations of nitric acid, extractant and salting-out agent (LiNO 3 ). The mechanism of extraction is discussed in the light of the results obtained. The extracted species has also been investigated using FT-IR spectrometry. The related thermodynamic functions were calculated. The IR spectral study was also made of the extracted species. (author)

  3. Synthesis and Biological Activity of 3-[Phenyl(1,3-thiazol-2-yl-amino]propanoic Acids and Their Derivatives

    Directory of Open Access Journals (Sweden)

    Vytautas Mickevičius

    2013-12-01

    Full Text Available New N,N-disubstituted β-amino acids and their derivatives with thiazole, aromatic, and heterocyclic substituents were synthesized from N-phenyl-N-thiocarbamoyl-β-alanine by the Hantzsch method; derivatives with hydrazone fragments were also obtained. Some of the synthesized compounds exhibited discrete antimicrobial activity, and 3-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl(phenylamino]propanoic acid was found to promote rapeseed growth and to increase seed yield and oil content.

  4. Synthesis and Biological Activity of 3-Chloro-1-(4-perimidine methylcarbonylamino-4-phenyl-azetidin-2-one

    Directory of Open Access Journals (Sweden)

    Dinesh R. Panchasara

    2009-01-01

    Full Text Available Perimidine-1-acetic acid hydrazide (1 undergoes facile condensation with aromatic aldehydes to afford the corresponding azomethine (i.e. Schiff base derivatives (2a-h in good yield. Cyclocondensation of compounds (2a-h with chloro acetyl chloride affords 3-chloro-1-(4-perimidine methylcarbonylamino-4-phenyl-azetidin-2-ones (3a-h. The structures of these compounds were established on the basis of analytical and spectral data. The newly synthesized compounds were evaluated for their antibacterial and antifungal activities.

  5. Ethyl 2,2-dimethyl-4-oxo-6-phenyl-3,4-dihydro-2H-pyran-5-carboxylate

    Directory of Open Access Journals (Sweden)

    N. Sharmila

    2016-12-01

    Full Text Available The title compound, C16H18O4, is a derivative of 3,4-dihydro-2H-pyran-4-one. The plane of the pyranone ring system forms a dihedral angle of 42.76 (10° with that of the phenyl group. The crystal structure is stabilized by C—H...O interactions that enclose an R21(6 ring motif and link the molecules into chains along the c axis. A short intramolecular O...O contact [2.942 (3 Å] gives rise to an S(5 motif.

  6. Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent

    International Nuclear Information System (INIS)

    Gallardo, Hugo; Conte, Gilmar; Bryk, Fernando; Lourenco, Maria Cristina S.; Costa, Marilia S.; Ferreira, Vitor F.

    2007-01-01

    Fourteen small molar mass 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives were prepared using a straightforward and efficient method for the regioselective synthesis of [1,2,3]-triazoles and the compounds were screened for antimycobacterial activity against multiple-drug-resistant strains of Mycobacterium tuberculosis H37Rv. The synthetic methodology consisted of a Cu(I)-catalyzed 1,3-dipolar cycloaddition of aryl azides to terminal arylacetylenes (click-reaction). Six [1,2,3]-triazoles were found to be more active against M. tuberculosis than the positive control ethambutol. (author)

  7. Nitrogen-Doped Carbon Nanotubes Synthesised by Pyrolysis of (4-{[(pyridine-4-yl)methylidene]amino}phenyl)ferrocene

    OpenAIRE

    Keru, Godfrey; Ndungu, Patrick G.; Nyamori, Vincent O.

    2013-01-01

    Nitrogen-doped carbon nanotubes (N-CNTs) were synthesized by pyrolysis of (4-{[(pyridine-4-yl)methylidene]amino}phenyl)ferrocene in a solution of either acetonitrile or toluene as carbon source. This was achieved by testing three different growth temperatures (800, 850, and 900°C), and the 850°C was found to be the most favourable condition for N-CNT growth. At the lower temperature of 800°C, amorphous carbon was mainly formed while at the higher temperature of 900°C, the yield of carbon sphe...

  8. SYNTHESIS OF 1,2 FUSED SYSTEMS BASED ON THE 3-ARYLIDENE-5-PHENYL-1,2-DIHYDRO-3H-1,4- BENZODIAZEPINE-2-ONES

    Directory of Open Access Journals (Sweden)

    V. I. Pavlovsky

    2014-12-01

    Full Text Available By the reaction of 7-bromo-5-aryl-1,2-dihydro-3H-1,4-benzodiazepine-2-ones with Lawesson reagent, 7-bromo-5-aryl-1,2-dihydro-3H-1,4-benzodiazepine-2-tiones were synthesized from which 3-arylidene-7-bromo-2-hydrazino-5-phenyl-3H-1,4-benzodiazepines were obtained by the reaction with hydrazine hydrate. The condensation of 3-arylidene-7-bromo-2-hydrazino-5-phenyl-3H-1,4-benzodiazepines with triethylorthoformate (triethylorthoacetate or formic acid (acetic acid gave 4-arylidene-8-bromo-6-phenyl-4H-[1,2,4]triazolo[4,3-а][1,4]-benzodiazepines. Latter were also synthesized by the reaction of 7-bromo-5-aryl-1,2-dihydro-3H-1,4-benzodiazepine-2-tiones with acetylhydrazine. 4-Arylidene-8-bromo-6-phenyl-4H-[1,2,3,4] tetrazolo[1,5-а][1,4]-benzodiazepines were obtained by the reaction of 3-arylidene-7-bromo-2-hydrazino-5-phenyl-3H-1,4-benzodiazepines with sodium nitrite.

  9. Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea.

    Science.gov (United States)

    Kashaw, Sushil K; Kashaw, Varsha; Mishra, Pradeep; Jain, N K; Stables, J P

    2009-11-01

    Several new 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea were synthesized and screened for anticonvulsant, CNS depressant and sedative-hypnotic activity in the mice. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight synthesized compounds were examined in the maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data and elemental analysis were consistent with the newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. Compounds E1, E6, E9, E12, P3, P4 and P6 were found to be active in the MES screen whereas E1, P4, P6 and P11 were found to be active in the scPTZ screen. All except E6, E11 and P6 showed more than 50% decrease in locomotor activity at 1h of compound administration via actophotometer screen. CNS depressant activity screened with the help of the forced swim method resulted into some potent compounds. All the compounds were found to exhibit potent CNS depressants activity as indicated by increased immobility time. It can be concluded that newly synthesized compounds possessed promising CNS activities.

  10. Synthesis and characterization of 1-phenyl-3-(4-phenyl-[1,2,3]triazol-1-yl)-4-styryl-azetidin-2-one films for light-emitting applications

    International Nuclear Information System (INIS)

    Mahajan, Aman; Bedi, R.K.; Singh, Pardeep; Kumar, Vipan

    2010-01-01

    Triazole derivatives have attracted considerable interest in OLEDs because of their electron transporting as well as hole blocking and/or exciton confining properties. To improve the quantum efficiency and lower the operating voltage of OLEDs, a novel derivative of triazole namely 1-phenyl-3-(4-phenyl-[1,2,3]triazol-1-yl)-4-styryl-azetidin-2-one (TAZ) has been designed as an electron transporting material. Thin films of TAZ have been prepared by the vacuum evaporation technique onto a glass substrate kept at different temperatures under different experimental conditions. These films have been systematically studied for their structural, optical and electrical properties. X-ray diffraction and FESEM studies of the films show an increase in crystallinity with an increase in the substrate temperature. The electrical resistance of these films is found to be 10 7 ohm at room temperature. Analysis of optical absorption measurements on the films indicate that the interband transition energies lie within 3.4-3.6 eV. These wide band gaps show that TAZ layers can work as a hole blocking (HB) material in OLED.

  11. Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

    Science.gov (United States)

    Obasi, L. N.; Kaior, G. U.; Rhyman, L.; Alswaidan, Ibrahim A.; Fun, Hoong-Kun; Ramasami, P.

    2016-09-01

    The Schiff base, 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (TPMC/AAP) was synthesized by the condensation of 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and trans-para-methoxycinnamaldehyde (trans-3,4-methoxyphenyl-2-propenal) in dry methanol at 75 °C. The compound was characterized using elemental microanalysis, IR, NMR, UV spectroscopies and single-crystal X-ray crystallography. The X-ray structure determination shows that the Schiff base, (TPMC/AAP) is orthorhombic with the Pbca space group. The anti-microbial screening of the compound was carried out with Escherichia coli, Bacillus subtillis, Staphylococcus aureus, Pseudemonas aeruginosa, Candida albicans and Aspergillus niger using agar well diffusion method. The Schiff base possesses significant antimicrobial activity. The minimum inhibitory concentration (MIC) of the compound was also determined and the activity was compared with that of conventional drugs ciprofloxacin and ketoconazole. The compound (TPMC/AAP) showed varying activity against the cultured bacteria and fungi used. To complement the experimental data, density functional theory (DFT) was used to have deeper understanding into the molecular parameters and infrared spectra of the compound.

  12. Quantum mechanical and spectroscopic (FT-IR, 13C, 1H NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide.

    Science.gov (United States)

    Vitnik, Vesna D; Vitnik, Željko J; Banjac, Nebojša R; Valentić, Nataša V; Ušćumlić, Gordana S; Juranić, Ivan O

    2014-01-03

    This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wavenumber showed very good agreement with the experimental values. The (1)H and (13)C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the σ(*) and π(*) antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent DFT (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule. Copyright © 2013 Elsevier B.V. All rights reserved.

  13. Design, synthesis, and biological activity of 5'-phenyl-1,2,5,6-tetrahydro-3,3'-bipyridine analogues as potential antagonists of nicotinic acetylcholine receptors.

    Science.gov (United States)

    Jin, Yafei; Huang, Xiaoqin; Papke, Roger L; Jutkiewicz, Emily M; Showalter, Hollis D; Zhan, Chang-Guo

    2017-09-15

    Starting from a known non-specific agonist (1) of nicotinic acetylcholine receptors (nAChRs), rationally guided structural-based design resulted in the discovery of a small series of 5'-phenyl-1,2,5,6-tetrahydro-3,3'-bipyridines (3a-3e) incorporating a phenyl ring off the pyridine core of 1. The compounds were synthesized via successive Suzuki couplings on a suitably functionalized pyridine starting monomer 4 to append phenyl and pyridyl substituents off the 3- and 5-positions, respectively, and then subsequent modifications were made on the flanking pyridyl ring to provide target compounds. Compound 3a is a novel antagonist, which is highly selective for α3β4 nAChR (K i =123nM) over the α4β2 and α7 receptors. Copyright © 2017 Elsevier Ltd. All rights reserved.

  14. 3,5-Bis(4-meth­oxy­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

    Science.gov (United States)

    Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S.; Narayana, B.; Yathirajan, H. S.

    2011-01-01

    In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two meth­oxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C—H⋯π stacking inter­actions and weak π–π inter­actions [centriod–centroid distance = 3.891 (2) Å]. PMID:21523013

  15. [The peculiar features of the distribution of 2-(dimethylamino)ethyl- (1-hydroxycyclopentyl) (phenyl) acetate in the organism of warm-blooded animals after its intravenous administration].

    Science.gov (United States)

    Shormanov, V K; Pravdyuk, M F

    The objective of the present study was to elucidate the dynamics of the distribution of 2-(dimethylamino)ethyl-(1-hydroxycyclopentyl)(phenyl) acetate in the organism of warm-blooded animals (rats) after its intravenous administration to the animals. The identification and the quantitative determination of 2-(dimethylamino)ethyl-(1-hydroxycyclopentyl)(phenyl) acetate present in the organs and blood of the warm-blooded animals were carried out with the use of chromatography in a thin layer of silica gel, chromogenic reaction for the synthesis of the acinitro salt, UV spectrophotometry, and gas chromatography mass-spectrometry (GCh-MS). The quantitation was performed on days 5, 20, 150, and 360 minutes after the intravenous administration of 2-(dimethylamino)ethyl-(1-hydroxycyclopentyl)(phenyl) acetate to the rats. The maximum amounts of cyclopentolate were found in the spleen, brain, lungs, and heart of the experimental animals.

  16. Crystal structure of chlorido(η2-phenyl isothiocyanate-κ2C,S-mer-tris(trimethylphosphane-κPiridium(I

    Directory of Open Access Journals (Sweden)

    Joseph S. Merola

    2014-11-01

    Full Text Available The molecule of the title compound, [IrCl(C7H5NS(C3H9P3], is a distorted octahedral iridium complex with three PMe3 ligands arranged in a meridional geometry, a chloride ion cis to all three PMe3 groups and the phenyl isothiocyanate ligand bonded in an η2-fashion through the C and S atoms. The C atom is trans to the chloride ion and the S atom is responsible for a significant deviation from an ideal octahedral geometry. The geometric parameters for the metal-complexing phenyl isothiocyanate group are compared with other metal-complexed phenyl isothiocyanates, as well as with examples of uncomplexed aryl isothiocyanates.

  17. A effective flame retardant for epoxy resins based on poly(DOPO substituted dihydroxyl phenyl pentaerythritol diphosphonate)

    International Nuclear Information System (INIS)

    Wang Xin; Song Lei; Xing Weiyi; Lu Hongdian; Hu Yuan

    2011-01-01

    Poly(DOPO substituted dihydroxyl phenyl pentaerythritol diphosphonate) (PFR) was synthesized via the reaction between 10-(2,5-dihydroxyl-phenyl)-9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-BQ) and pentaerythritol diphosphonate dichloride (SPDPC). The structures of PFR were characterized by Fourier transformed infrared (FTIR) spectroscopy and 1 H nuclear magnetic resonance ( 1 H NMR). Thermal degradation behaviors and flame retardant properties of the epoxy resin (ER)/PFR systems were investigated from the thermogravimetric analysis (TGA), UL-94 test and the limiting oxygen index (LOI) test. Moreover, the surface morphology of the char residue was studied by scanning electron microscopy (SEM). When the PFR content reached 10 wt%, the epoxy resin system met the UL-94 V0 classification and the LOI value of 30.2. The microscale combustion calorimetry (MCC) was used to evaluate the combustion behaviors of the ER/PFR. It was found that the addition of PFR obviously decreased the value of peak heat release rate and total heat release of the hybrids. The TGA results showed that the epoxy resin with 10 wt% PFR exhibited high char yields. The high char yields and the high limiting oxygen index values were found to certify the excellent flame retardancy of this phosphorus-containing epoxy resin.

  18. Phenyl and ionic liquid based bifunctional periodic mesoporous organosilica supported copper: An efficient nanocatalyst for clean production of polyhydroquinolines.

    Science.gov (United States)

    Elhamifar, Dawood; Ardeshirfard, Hakimeh

    2017-11-01

    A novel phenyl and ionic liquid based bifunctional periodic mesoporous organosilica supported copper (Cu@BPMO-Ph-IL) is prepared, characterized and its catalytic application is developed in the clean production of polyhydroquinolines. The Cu@BPMO-Ph-IL was prepared via chemical grafting of ionic liquid groups onto phenyl-based PMO followed by treatment with copper acetate. This nanocatalyst was characterized with transmission electron microscopy (TEM), scanning electron microscopy (SEM), diffuse reflectance infrared Fourier transform spectroscopy (DRIFTs), thermal gravimetric analysis (TGA), powder X-ray diffraction (PXRD), nitrogen-sorption and energy dispersive X-ray (EDX) analyses. This was successfully applied in the one-pot Hantzsch condensation of aldehydes, ammonium acetate, alkylacetoacetates and dimedone to prepare a set of different derivatives of polyhydroquinolines in high yields and selectivity. The catalyst was effectively recovered and reused several times without important decrease in efficiency. The recovered catalyst was also characterized with TEM analysis to study its stability and durability under applied conditions. Copyright © 2017 Elsevier Inc. All rights reserved.

  19. Synthesis and bioevaluation of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acids as potent xanthine oxidase inhibitors.

    Science.gov (United States)

    Guan, Qi; Cheng, Zengjin; Ma, Xiaoxue; Wang, Lijie; Feng, Dongjie; Cui, Yuanhang; Bao, Kai; Wu, Lan; Zhang, Weige

    2014-10-06

    A series of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acid derivatives (8a-f, 9a-m) were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Structure-activity relationship analyses have also been presented. Most of the target compounds exhibited potency levels in the nanomolar range. Compound 9e emerged as the most potent xanthine oxidase inhibitor (IC50 = 5.5 nM) in comparison to febuxostat (IC50 = 18.6 nM). Steady-state kinetics measurements with the bovine milk enzyme indicated a mixed type inhibition with Ki and Ki' values of 0.9 and 2.3 nM, respectively. A molecular modeling study on compounds 9e was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acid scaffold. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  20. Synthesis, preclinical evaluation and antidepressant activity of 5-substituted phenyl-3-(thiophen-2-yl)-4, 5-dihydro-1H-pyrazole-1-carbothioamides

    OpenAIRE

    Mathew, Bijo; Suresh, Jerad; Anbazhagan, S.

    2014-01-01

    A series of phenyl-3-(thiophen-2-yl)-4, 5-dihydro-1H-pyrazole-1-carbothioamides (TTa-TTg) were synthesized by the ring closure reaction of phenyl-1-(thiophen-2-yl) prop-2-en-1-ones with thiosemicarbazide in alcoholic basic medium. All the final derivatives were evaluated for their antidepressant and neurotoxicity screening. The structures of the compounds were characterized by IR, 1H NMR, 13C NMR, Mass and elemental analyses. Preclinical evaluation of the compounds were ascertained by in sili...

  1. Crystal structure of 3-({[(morpholin-4-yl)carbono­thio­yl]sulfan­yl}acet­yl)phenyl benzoate

    Science.gov (United States)

    Ambekar, Sachin P.; Mahesh Kumar, K.; Shirahatti, Arun Kumar M.; Kotresh, O.; Anil Kumar, G. N.

    2014-01-01

    In the title compound, C20H19NO4S2, the morpholine ring adopts the expected chair conformation. The central phenyl ring makes dihedral angles of 67.97 (4) and 7.74 (3)°, respectively, with the benzoate phenyl ring and the morpholine mean plane. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C—H⋯π inter­actions link centrosymmetrically related mol­ecules, reinforcing the three-dimensional structure. PMID:25484757

  2. Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1H-phenalen-1-one: a functional group exclusion approach.

    Science.gov (United States)

    Duque, Luisa; Zapata, Carolina; Rojano, Benjamín; Schneider, Bernd; Otálvaro, Felipe

    2013-07-19

    2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elata, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore the effect of each functional group. H-Atom transfer from the phenolic hydroxyl, a captodative effect from the hydroxy ketone, and the presumed involvement of the phenyl ring in the termination step of the radical reaction were disclosed as relevant features of this type of antioxidant.

  3. Synthesis and antibacterial activity of some new 4-anilino-5-phenyl-4H-1,2,4-triazole-3-thiol derivatives

    Directory of Open Access Journals (Sweden)

    Abd El-Badih A.G. Ghattas

    2016-11-01

    Full Text Available 4-Anilino-5-phenyl-4H-1,2,4-triazole-3-thiol (1 reacted with formaldehyde and different amines to give Mannich bases 2a–i. Treatment of compound 1 with formaldehyde afforded the corresponding 2-hydroxymethyl derivative 3, which upon its reaction with thionyl chloride yielded the corresponding chloromethyl derivative 4. Treatment of compound 4 with some thiols gave the corresponding sulfides 5a–f. The ring closure reaction of chloromethyl derivative 4 with hydrazine hydrate, phenyl hydrazine, hydroxylamine, urea and thiourea afforded triazolo-, oxadiazolo- and triazinotriazoles 6–10, respectively.

  4. Synthesis of Arylplatinum(II) Complexes with Chiral Monoanionic Aryldiamine ligands. The X-ray Crystal Structure of)[(1R)2,6bis{1(dimethylamino)propyl}phenyl]chloroplatinum,

    NARCIS (Netherlands)

    Koten, G. van; Donkervoort, J.G.; Vicario, J.L.; Jastrzebski, J.T.B.H.; Smeets, W.J.J.; Spek, A.L.

    1998-01-01

    The new chiral arylplatinum(II) compounds [2, 6-bis(1-(dimethylamino)ethyl)phenyl]chloroplatinum(II) (4) and (-)-[(1R,1'R)-bis(1-(dimethylamino)propyl)phenyl]chloroplatinum(II) (5) have been synthesized. The transmetallation of the corresponding aryllithium compounds does not affect either

  5. In vitro activities of 3-(halogenated phenyl)-5-acyloxymethyl-2,5-dihydrofuran-2-ones against common and emerging yeasts and molds

    Czech Academy of Sciences Publication Activity Database

    Buchta, V.; Pour, M.; Kubanová, P.; Silva, L.; Votruba, Ivan; Vopršálková, M.; Schiller, R.; Fáková, H.; Špulák, M.

    2004-01-01

    Roč. 48, č. 3 (2004), s. 873-878 ISSN 0066-4804 Institutional research plan: CEZ:AV0Z4055905 Keywords : 3-(halogenated phenyl)-5-acyloxymethyl-2,5-dihydrofuran-2-ones * yeast * molds Subject RIV: CC - Organic Chemistry Impact factor: 4.216, year: 2004

  6. Crystal structure of (E-13-{4-[(Z-2-cyano-2-(3,4,5-trimethoxyphenylethenyl]phenyl}parthenolide methanol hemisolvate

    Directory of Open Access Journals (Sweden)

    Narsimha Reddy Penthala

    2014-10-01

    Full Text Available The title compound, C33H35NO6 [systematic name: (Z-3-(4-{(E-[(E-1a,5-dimethyl-9-oxo-2,3,7,7a-tetrahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-8(1aH,6H,9H,10aH,10bH-ylidene]methyl}phenyl-2-(3,4,5-trimethoxyphenylacrylonitrile methanol hemisolvate], C33H35NO6·0.5CH3OH, was prepared by the reaction of (Z-3-(4-iodophenyl-2-(3,4,5-trimethoxyphenylacrylonitrile with parthenolide [systematic name: (E-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH-one] under Heck reaction conditions. The molecule is built up from fused ten-, five- (lactone and three-membered (epoxide rings with a {4-[(Z-2-cyano-2-(3,4,5-trimethoxyphenylethenyl]phenyl}methylidene group as a substituent. The 4-[(Z-2-cyano-2-(3,4,5-trimethoxyphenylethenyl]phenyl group on the parthenolide exocyclic double bond is oriented in a trans position to the lactone ring to form the E isomer. The dihedral angle between the benzene ring of the phenyl moiety and the lactone ring mean plane is 21.93 (4°.

  7. Microwave Assisted Synthesis and Antimicrobial Activities of Some 2-Amino-4-aryl-3-cyano-6-(4’-hydroxy phenyl-pyridines

    Directory of Open Access Journals (Sweden)

    Priya Gothwal

    2011-01-01

    Full Text Available 4’-Hydroxy chalcones were treated with malononitrile in the presence of ammonium acetate under solventless microwave assisted condition to get 2-amino-4-aryl-3-cyano-6-(4’-hydroxy phenyl-pyridines. The prepared compounds were screened for their antimicrobial activity; some of them have exhibited promising antimicrobial activity.

  8. Methyl 2-{1-[(Z-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene]ethylamino}-3-phenylpropanoate

    Directory of Open Access Journals (Sweden)

    Hualing Zhu

    2010-06-01

    Full Text Available The molecule of the title compound, C22H23N3O3, exists in the enamine–keto form. A strong intramolecular N—H...O hydrogen bond occurs, generating an S(6 ring. The dihedral angle between the heterocycle and the adjacent phenyl ring is 3.75 (15°.

  9. Reaction of α-bromocyclopropyl phenyl ketones with lithium thiophenolate by a mechanism or latent nucleophilic substitution at the halogen atom

    International Nuclear Information System (INIS)

    Kulinkovich, O.G.; Tishchenko, I.G.; Sviridov, S.V.; Divak, V.A.

    1987-01-01

    The reaction of E-1-benzoyl-1-bromo-2-phenylcyclopropane with lithium thiophenolate in THF leads to the formation of E-1-benzoyl-2-phenyl-1-phenylthiocyclopropane. Phenyl α-phenylthiocyclopropyl ketones are also produced with good yields by the action of sodium thiophenolate on 7-endo-benzoyl-7-exo-bromobicyclo[4.1.0]-heptane, E-1-benzoyl-1-bromo-2-butylcyclopropane, and 1-benzoyl-1-bromocyclopropane, whereas Z-1-benzoyl-1-bromo-2-phenylcyclopropane undergoes reductive dehalogenation under analogous conditions. The stereochemical data and also the data on the composition of the products from the reaction in the presence of methanol indicate that the phenyl α-phenylthiocyclopropyl ketones are formed by a mechanism of latent nucleophilic substitution at the halogen atom in the initial α-bromocyclopropyl phenyl ketones. The PMR spectra of solutions of the substances in carbon tetrachloride or benzene were obtained on a Tesla BS-467A spectrometer at 60 MHz with HMDS as internal standard. The IR spectra of solutions of the substances in carbon tetrachloride were recorded on a Specord IR-75 spectrometer. The reactions were carried out in an atmosphere of dry argon

  10. Synthesis of new derivatives of 1-(3-aminophenyl-4-benzoyl-5-phenyl-1H-pyrazole-3-carboxylic acid

    Directory of Open Access Journals (Sweden)

    RAHMI KASIMOGULLAR

    2010-12-01

    Full Text Available 1-(3-Aminophenyl-4-benzoyl-5-phenyl-1H-pyrazole-3-carboxylic acid (1 was synthesized according to the literature. 2-(3-Aminophenyl-2,6-dihydro-3,4-diphenyl-7H-pyrazolo[3,4-d]pyridazin-7-one (5 was obtained by the cyclocondensation reaction of 1 with hydrazine hydrate. New pyrazole derivatives of compounds 1 and 5 were synthesized by their reaction with β-diketones, β-ketoesters, β-naphthol, phenol and various other reagents. The structures of the synthesized compounds were characterized by 1H-NMR, 13C-NMR, IR and mass spectroscopy, as well as elemental analysis.

  11. A study of the possibility of using 3-(3'-5'Dinitro-4' - Hydroxy phenyl) phthalide as an indicator

    International Nuclear Information System (INIS)

    Khalil, A. R.; Al-Hamdany, R.

    1998-01-01

    This paper describes a ur-visible spectroscopic characterization and acid-base equilibrium studies of 3-(3 ' -5 ' -din tro-4 ' - hydroxy phenyl) phthalide (1) for its possible use as an indicator. The ionization constant (K 2 ) has been evaluated by potentiometric titration indicating that the reagent is a weak acid comparable to acetic acid. The (pK 2 ) has been attributed to deprotonation of the compound to give the corresponding anion, which possesses considerable resonance stabilization. The different colour shown by each species involved in equilibrium allows the use of this reagent as an acid-base indicator, placing the transition interval between ph 2.0 (colourless) and 3.0 (yellow). (authors). 11 refs., 1 fig., 2 tabs

  12. Dextromethorphan prevents the diethyldithiocarbamate enhancement of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine toxicity in mice.

    Science.gov (United States)

    Vaglini, Francesca; Pardini, Carla; Bonuccelli, Ubaldo; Maggio, Roberto; Corsini, Giovanni U

    2003-05-30

    In this report we show that dextromethorphan, a non-opioid cough suppressant, prevents the neurodegeneration of dopaminergic neurons in the substantia nigra of mice treated with diethyldithiocarbamate (DDC) and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). This effect is further substantiated by the assessment of dopamine (DA) content in the striatum of these animals. Dextromethorphan does not attenuate the striatal DA fall induced by MPTP alone but completely prevents DDC-induced enhancement after the combined treatment. Moreover, a study of DA metabolites has confirmed this neuroprotective property. The striatal levels of serotonin, which were studied as a control neuronal marker, did not change with any of the treatments administered. Furthermore, we show that dextromethorphan reduces the toxicity of glutamate against dopamine neurons in mesencephalic cell cultures. In line with previous data suggesting that dextromethorphan can prevent neuronal damage, our observations supply new evidence regarding the possibility of this compound being of therapeutic use in neurodegenerative diseases.

  13. Crystal structure of ethyl (4R-2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Joel T. Mague

    2015-07-01

    Full Text Available In the title compound, C18H17NO4, the dihedral angle between the phenyl ring and the fused six-membered ring is 77.65 (4°. The conformation of the molecule is determined in part by an intramolecular N—H...O hydrogen bond between the amino H atom and the carbonyl O atom, forming an S(6 motif. In the crystal, molecules are linked into N—H...O hydrogen-bonded inversion dimers which are then connected into chains along [001], forming a two-dimensional network parallel to (100 via O—H...O hydrogen bonds. C—H...O interactions further contribute to the crystal stability. The ethyl group is disordered over two sets of sites in a 0.801 (5:0.199 (5 ratio.

  14. Ethyl 2-[1-(3-methylbutyl-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxoacetate

    Directory of Open Access Journals (Sweden)

    Muhammad Hafeez

    2013-12-01

    Full Text Available In the title compound, C17H21N3O3, the non-planar (r.m.s. deviation = 0.212 Å ethyl (oxoacetate group is oriented towards the phenyl substituent. The triazole and benzene rings are twisted with respect to each other, making a dihedral angle of 41.69 (6°. In the crystal, molecules are arranged into centrosymmetric R22(10 dimers via pairs of C—H...O interactions involving the ethyl (oxoacetate groups. In addition, the triazole rings show π–π stacking interactions, with their centroids at a distance of 3.745 (2 Å.

  15. Ethyl 2-(6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridin-1-ylacetate

    Directory of Open Access Journals (Sweden)

    Mohammed Yassin Hjouji

    2016-05-01

    Full Text Available In the title compound, C16H14BrN3O2, the fused-ring system is essentially planar, with the largest deviation from the mean plane being 0.0216 (15 Å for the substituted N atom of the five-membered ring, the plane of which makes dihedral angles of 28.50 (7 and 77.48 (7° with the terminal phenyl ring and the ethoxycarbonylmethyl group mean planes, respectively. In the crystal, C—H...N hydrogen bonds link the molecules into inversion dimers. These combine with weak C—H...N contacts to stack the molecules into columns along the b-axis direction.

  16. Organonickel(II) complexes with anionic tridentate 1, 3-bis(azolylmethyl)phenyl ligands. synthesis, structural characterization and catalytic behavior

    Energy Technology Data Exchange (ETDEWEB)

    Hurtado, John; Rojas, Rene; Valderrama, Mauricio, E-mail: jmvalder@puc.cl [Departamento de Quimica Inorganica, Facultad de Quimica, Pontificia Universidad Catolica de Chile, Santiago (Chile); Ibanez, Andres [Centro para la Investigacion Interdisciplinaria Avanzada en Ciencia de los Materiales (CIMAT), Santiago (Chile); Froehlich, Roland [Organisch Chemisches Institut der Universitaet Muenster, Muenster (Germany)

    2011-09-15

    The reaction of 2-bromo-1,3-bis(bromomethyl)benzene with 3,5-dimethylpyrazole and {sup 1}H-indazole yields the tridentate ligands 2-bromo-1,3-bis(3,5-dimethylpirazol-1-ylmethyl)benzene (1) and 2-bromo-1,3-bis(indazol-2-ylmethyl)benzene (2). These compounds react with [Ni(cod)2] in tetrahydrofuran (thf) to form the oxidative addition complexes [NiBr{l_brace}1,3-bis(azolylmethyl)phenyl-N,C,N{r_brace}], azol 3,5-dimethylpyrazol (3), indazol (4), which were isolated in good yields as stable yellow solids and characterized by elemental analysis, Fourier-transform infrared spectroscopy (FTIR), mass spectroscopy and nuclear magnetic resonance (NMR). In addition, the molecular structures of 2 and 4 were determined by single-crystal X-ray diffraction analysis. Complex 4 was tested as a catalyst in ethylene polymerization reaction. (author)

  17. Preparation and characterization of proton exchange poly (ether sulfone)s membranes grafted propane sulfonic acid on pendant phenyl groups

    International Nuclear Information System (INIS)

    Lim, Youngdon; Seo, Dongwan; Hossain, Md. Awlad; Lee, Soonho; Lim, Jinseong; Jang, Hohyoun; Hong, Taehoon; Kim,; Kim, Whangi

    2014-01-01

    Poly(ether sulfone)s containing hexaphenyl (PHP) was prepared by 1,2-bis(4-hydroxyphenyl)-3,4,5,6-tetraphenylbenzene, 4,4-hydroxyphenylsulfone, and 4,4-fluorophenylsulfone, followed bromination on phenyl groups to produce brominated PHP (Br-PHP). Grafted sulfonated poly(ether sulfone)s containing hexaphenyl (GSPHP) were prepared from Br-PHP and 3-bromopropane sulfonic acid with potassium salt and copper powder. The salt form was converted to free acid using 1 M sulfuric acid solution. All these membranes were cast from dimethylacetamide (DMAc). The structural properties of the synthesized polymers were investigated by 1 H-NMR spectroscopy. The membranes were studied with regard to ion exchange capacity (IEC), water uptake, Fenton test, and proton conductivity. These grafted polymer membranes were compared with normal sulfonated poly(ether sulfone)s and Nafion

  18. Dibromido(4′-phenyl-2,2′:6′,2′′-terpyridylcopper(II hemihydrate

    Directory of Open Access Journals (Sweden)

    Zhen Ma

    2010-04-01

    Full Text Available The title CuII complex, [CuBr2(C21H15N3]·0.5H2O, was obtained by the hydrothermal reaction of copper(II bromide, 4′-phenyl-2,2′:6′,2′′-terpyridyl (4′-Ph-terpy or L and sodium citrate in water in 31% yield. There are two unique complex molecules and a water molecule in the asymmetric unit. The CuII cation is ligated by three N atoms of L and two bromide anions, forming an irregular CuN3Br2 polyhedron with a distorted square-pyramidal coordination geometry. In the crystal structure, O—H...Br hydrogen bonds link the molecules in a three-dimensional network.

  19. Ethyl 5-cyano-4-[2-(2,4-dichlorophenoxyacetamido]-1-phenyl-1H-pyrrole-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Jing Xu

    2009-08-01

    Full Text Available In the title compound, C22H17Cl2N3O4, the pyrrole ring and the 2,4-dichlorophenyl group form a dihedral angle of 8.14 (13°; the phenyl ring is twisted with respect to the pyrrole ring, forming a dihedral angle of 60.77 (14°. The C=O bond length is 1.213 (3 Å, indicating that the molecule is in the keto form, associated with a –CONH– group, and the amide group adopts the usual trans conformation. The molecule is stabilized by an intramolecular N—H...O hydrogen-bonding interaction. In the crystal, the stacked molecules exhibit intermolecular C—H...O and C—H...N hydrogen-bonding interactions.

  20. Synthesis of carbon C-14 labelled 2-phenyl-4-alpha-alkylaminomethyl-quinolinemethanol: a potential anti-leishmaniasis agent

    Energy Technology Data Exchange (ETDEWEB)

    Wang, T.S.T.; Fawwaz, R.A.; Heertum, R.L.van [Columbia Univ., New York, NY (United States). Coll. of Physicians and Surgeons

    1995-07-01

    Using sodium acetate, [1-{sup 14}C] as a starting material, a total of seven steps were required to synthesize the title compound. This involved acylation of ortho-dichlorobenzene to form dichloroacetophenone, [2-{sup 14}C] (I). The 2-phenyl-4-quinoline carboxylic acid, [2-{sup 14}C] (II) was prepared by the Pfitzinger reaction from (1) and dichloroisatin. Compound 11 was converted to the acid chloride (III) by reaction with SOCl{sub 2} in benzene. Grignard condensation reaction of (III) yielded 4-quinolylmethylketone, [2-{sup 14}C] (IV) which was then converted to the bromomethylketone (V). Compound V was reacted with NaBH{sub 4} to form the ethylene oxide (VI). Alkylation of the oxide yielded the title compound (VII). The overall radiochemical yield was 10.1% and the specific activity was 3.0 mCi/mmol, with a radiochemical purity of >99.5%. (author).

  1. Extraction of hafnium by 1-phenyl-3-methyl-4-benzoyl-5-pyralozone from aqueous-alcoholic solutions

    International Nuclear Information System (INIS)

    Hala, J.; Prihoda, J.

    1975-01-01

    Extraction of hafnium by 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (HL) in benzene, toluene, chloroform and tetrachloromethane from aqueous-alcoholic solutions of the formal acidity of 2M-HClO 4 was studied. Methyl, ethyl, n- and isopropyl, tert-butyl and allyl alcohol as well as ethylene glycol monomethyl ether and propylene glycol were used as organic components of the mixed aqueous-organic phase. Their presence in some cases resulted in a synergic increase in the distribution ratio of hafnium. The increase is interpreted using the results of a slope analysis and measurements of the alcohol distribution and the relative permittivity of the organic phase. It is suggested that HfL 4 molecules were solvated by alcohol molecules in the organic phase. At high alcohol concentration synergism changed into antagonism. This was caused by changes in the distribution of HL and its interaction with the alcohol in the organic phase. (author)

  2. Correlations between retention indices and molecular structure of their benzoyl derivatives on phenyl substituted polysiloxane stationary phases

    International Nuclear Information System (INIS)

    Pias, J.B.; Gasco, L.

    1976-01-01

    The retention indices of aliphaticalcohols of carbon number up to Csub(g), and of their benzoyl derivatives up to C 7 , were determined in columns packed with Chromosorb G (AW-DMCS-HP) coated previously with 5% methyl, and methyl phenyl polysiloxanes with increasing polarity (SE-30, OV-3, OV-7; OV-11, OV-17 and OV-25). Correlations between retention indices and chain length for 1-alcohols, 2-alcohols, 3-alcohols, 1, on -3-alcohols, 2-methyl-1-alcohols and for their corresponding benzoyl derivatives were calculated at 100, 120 and 140 0 C. In alcohols, a -CH 2 - group increases I approximately 100 units, and in their benzoyl derivatives from 80 to 100 units. Dispersion indices ΔI, and positional and structural increments of I were evaluated for -OH and benzoyl groups in terms for phase polarity and chain length. Effects of chain length, chain branching and double bond location on retention parameters were also studied. (author)

  3. Spectrophotometric studies of rhenium complexes with 4-amino 5-mercapto 3 phenyl 4:1:2 triazole

    International Nuclear Information System (INIS)

    Bag, S.P.; Chanda, C.R.

    1981-01-01

    The reagent 4-amino-5-mercapto 3 phenyl 4:1:2 triazole forms a stable reddish brown complex with rhenium on reducing it with stannous chloride in 1(M) to 5(M) hydrochloric acid medium and the metal can be estimated by extractive photometry in chloroform medium. The system obeys Beer's Law from 2-38 ppm at 380 nm. The molar absorptivity is 5.21 x 10 3 and the Sandell's sensitivity is 0.0351 μg cm -2 . The metal forms a 1:1 complex (metal to ligand) with the ligand. Stability constant (log K) of the Re-complex has been evaluated by the Leden (4.25), Rossotti and Rossotti (4.34), and Harvey and Manning (4.53) methods. (author)

  4. Morphology characterization of phenyl-C61-butyric acid methyl ester films via an electrohydrodynamic spraying route

    International Nuclear Information System (INIS)

    Park, Sung-Eun; Park, Ji-Woon; Hwang, Jungho

    2014-01-01

    In this study, we fabricated a thin film layer of phenyl-C61-butyric acid methyl ester (PCBM) fine particles using electrohydrodynamic (EHD) spray and evaluated the effects of the process parameters on the film morphology. After the PCBM was dissolved in dichloromethane, the solution was sprayed onto a substrate using the stable cone-jet mode of EHD spraying at various flow rates ranging from 5 to 15 μl/min and electric potentials ranging from 3 to 5 kV. The effects of the liquid flow rate, nozzle-plate distance, solute fraction, and electrical conductivity on the spray characteristics were investigated. The sizes of the PCBM particles deposited on the substrate were calculated using a scaling law and a mass balance equation, the results of which were in agreement with those obtained by scanning electron microscopy. A thin film was obtained with the structure of PCBM particles deposited without any void or agglomeration from the EHD spraying technique. The electrical conductivity of the PCBM solution was the dominant parameter in controlling the size of the PCBM particles. As the conductivity was increased to 2.4 × 10 −3 S/m from 4.3 × 10 −9 S/m, the particle size decreased from 6.7 μm to 320 nm. The size distribution measured using a scanning mobility particle sizer also supported the generation of nano-scale PCBM particles. The decrease of the particle size with increasing electrical conductivity may lead to a better morphology of PCBM films. - Highlights: • The phenyl-C61-butyric acid methyl ester thin film was obtained by electrospray. • The morphology of film consisting of microparticles was investigated. • The particle size was controlled by adjusting experimental parameters. • The nanoparticle was obtained by increasing the solution conductivity. • The particle size distribution was studied using a scanning mobility particle sizer

  5. Fluorescence and FTIR Spectra Analysis of Trans-A2B2-Substituted Di- and Tetra-Phenyl Porphyrins

    Directory of Open Access Journals (Sweden)

    Chantal Andraud

    2010-08-01

    Full Text Available A series of asymmetrically substituted free-base di- and tetra-phenylporphyrins and the associated Zn-phenylporphyrins were synthesized and studied by X-ray diffraction, NMR, infrared, electronic absorption spectra, as well as fluorescence emission spectroscopy, along with theoretical simulations of the electronic and vibration structures. The synthesis selectively afforded trans-A2B2 porphyrins, without scrambling observed, where the AA and BB were taken as donor- and acceptor-substituted phenyl groups. The combined results point to similar properties to symmetrically substituted porphyrins reported in the literature. The differences in FTIR and fluorescence were analyzed by means of detailed density functional theory (DFT calculations. The X-ray diffraction analysis for single crystals of zinc-containing porphyrins revealed small deviations from planarity for the porphyrin core in perfect agreement with the DFT optimized structures. All calculated vibrational modes (2162 modes for all six compounds studied were found and fully characterized and assigned to the observed FTIR spectra. The most intense IR bands are discussed in connection with the generic similarity and differences of calculated normal modes. Absorption spectra of all compounds in the UV and visible regions show the typical ethio type feature of meso-tetraarylporphyrins with a very intense Soret band and weak Q bands of decreasing intensity. In diphenyl derivatives, the presence of only two phenyl rings causes a pronounced hypsochromic shift of all bands in the absorption spectra. Time-dependent DFT calculations revealed some peculiarities in the electronic excited states structure and connected them with vibronic bands in the absorption and fluorescence spectra from associated vibrational sublevels.

  6. Structural and photophysical properties of HPPCO (4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one) derivatives.

    Science.gov (United States)

    Jeong, Yong-Kwang; Kim, Min-Ah; Lee, Hyo-Sung; Kim, Jong-Moon; Lee, Sung Woo; Kang, Jun-Gill

    2015-01-05

    Proton-substitution effects of 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one (HPPCO) on structural and photophysical properties were presented. HPPCO crystallized in the orthorhombic space group Pbca with an intermolecular hydrogen bonding between OH and oxygen atom of the carbonyl. The proton-substituted derivatives, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl acetate (OPPCA) and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl benzoate (OPPCB), crystallized in the monoclinic P2₁/c space group. For OPPCA and OPPCB, a weak interaction between carbonyl oxygen atom in the substituted group and carbon atom in the fused ring was responsible for three-dimensional arrangements. In addition, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl furan-2-carboxylate (OPPCF), and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl naphthoate (OPPCN) were also synthesized. HPPCO and the four derivatives excited by ultraviolet (UV) light produced blue emission. Proton substitution of the OH group significantly increased the radiative transitions and moderately decreased the non-radiative transitions. Consequently the luminescence quantum yields of the derivatives enhanced more than 4.6-fold, no matter what the groups were substituted. Structural and optical properties were further determined using density functional theory (DFT) and ZINDO calculations. The planar structure of the pyridocarbazole-fused ring resulted in π→π(*) electronic transitions within the main frame, with an additional transition from the n(O) of carbonyl to the π(*) of the main frame. The three excited states that arose from these transitions were responsible for the blue luminescence. Copyright © 2014 Elsevier B.V. All rights reserved.

  7. DFT study on the influence of meso-phenyl substitution on the geometric, electronic structure and vibrational spectra of free base porphyrin

    International Nuclear Information System (INIS)

    Zhang Yinghui; Ruan Wenjuan; Li Zhiyun; Wu Yang; Zheng Jianyu

    2005-01-01

    The influence of meso-phenyl substitution on the geometric, electronic structure and vibrational spectra of free base porphyrin were studied by DFT calculation and experimental observation on a series of meso-phenylporphyrins: 5-monophenylporphine (H 2 MPP), 5,15-diphenyporphine (H 2 D O PP), 5,10-diphenyl porphine (H 2 D A PP), 5,10,15-triphenylporphine (H 2 TrPP), and 5,10,15,20-tetraphenylporphine (H 2 TPP). Theoretical calculation indicates that meso-phenyl substitution brings about significant in-plane distortion to porphyrin ring, whereas the resulted out-of-plane distortion is negligible. Thus, the observed redshift of electronic absorption peaks (both B and Q bands) upon increasing meso-phenyl substitution, which is also indicated by theoretical calculation, was attributed to in-plane nuclear reorganization (IPNR) induced by phenyl-substitution rather than nonplanarity mechanism, though the contribution of the latter could not be excluded completely. The vibrational spectra analysis (both Raman and IR spectra) indicates that meso-phenyl substitution results in different evolution for different vibrational modes of porphyrin ring. For example, both experiment and calculation shows the great downshift of ν 10 and ν 28 modes and the upshift of some other structure-sensitive bands (for instance ν 2 , ν 6 , ν 15 , and ν 8 modes) in different extent. This evolution differs from the downshift of structure-sensitive bands (for instance ν 2 and ν 3 mode) caused by nonplanarity mechanism, and was also attributed to IPNR mechanism rather than nonplanarity mechanism. Further comparison indicates that calculation predicted shift of vibrational frequencies are consistent well with experimental observation, which indicates that DFT calculation at B3LYP/6-31G(d) level give convincible prediction on substitution-resulted frequency evolution of porphyrin

  8. Studies on complex π-π and T-stacking features of imidazole and phenyl/p-halophenyl units in series of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides and their carbonitrile derivatives: Role of halogens in tuning of conformation

    Science.gov (United States)

    Das, Aniruddha

    2017-11-01

    5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides (N-phenyl AICA) (2a-e) and 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitriles (N-phenyl AICN) (3a-e) had been synthesized. X-ray crystallographic studies of 2a-e and 3a-e had been performed to identify any distinct change in stacking patterns in their crystal lattice. Single crystal X-ray diffraction studies of 2a-e revealed π-π stack formations with both imidazole and phenyl/p-halophenyl units in anti and syn parallel-displaced (PD)-type dispositions. No π-π stacking of imidazole occurred when the halogen substituent is bromo or iodo; π-π stacking in these cases occurred involving phenyl rings only. The presence of an additional T-stacking had been observed in crystal lattices of 3a-e. Vertical π-π stacking distances in anti-parallel PD-type arrangements as well as T-stacking distances had shown stacking distances short enough to impart stabilization whereas syn-parallel stacking arrangements had got much larger π-π stacking distances to belie any syn-parallel stacking stabilization. DFT studies had been pursued for quantifying the π-π stacking and T-stacking stabilization. The plotted curves for anti-parallel and T-stacked moieties had similarities to the 'Morse potential energy curve for diatomic molecule'. The minima of the curves corresponded to the most stable stacking distances and related energy values indicated stacking stabilization. Similar DFT studies on syn-parallel systems of 2b corresponded to no π-π stacking stabilization at all. Halogen-halogen interactions had also been observed to stabilize the compounds 2d, 2e and 3d. Nano-structural behaviour of the series of compounds 2a-e and 3a-e were thoroughly investigated.

  9. X-ray crystallographic, electrochemical and spectroscopic properties of 2-pyridinio 2-pyridyl ketone phenyl hydrazone chloride hydrate

    Science.gov (United States)

    Bakir, Mohammed; Hassan, Ishmael; Johnson, Toni; Brown, Ordel; Green, Orville; Gyles, Colin; Coley, Michael D.

    2004-01-01

    In contrast to the reaction between di-2-pyridyl ketone with a variety of hydrazines or hydrazides in refluxing acidified alcoholic solution to form unprotonated di-2-pyridyl ketone hydrazones (dpkhydrazones), the reaction between di-2-pyridyl ketone and phenyl hydrazine hydrochloric acid under the same conditions gave unprecedented pyridyl protonated 2-pyridinio 2-pyridyl ketone phenyl hydrazone chloride hydrate, dpkphh·HCl·3H 2O. Crystals of dpkphh·HCl·3H 2O obtained from an ethanolic solution of dpkphh·HCl·3H 2O that contains a few drops of HCl are in the centric triclinic space group P-1. Structure analysis reveals non-coplanar dpkphh·H + along with a chloride anion and three water molecules. The molecules pack show infinite stacks of anti-parallel dpkphh·H + locked to the chloride anion and water molecules via novel fused hydrogen bonded oxygen-chloride four and six-membered cyclic rings propagating between the stacks. Electrochemical measurements on dpkphh·HCl·3H 2O in non-aqueous solvents show solvent dependence, single and multi-electronic transfers in DMF and in CH 3CN single electronic redox transfers. The reversibility of the second electronic reduction following the first irreversible electronic transfer hints to the stability of electrochemically generated intermediate following the sequential electronic transfers. In contrast to the optical behavior of a variety unprotonated and metal coordinated dpkhydrazones, protonation of one pyridine ring in dpkphh·HCl·3H 2O decreases the electron density on the pyridine ring ceases the intraligand charge transfer electronic transition and renders the protonated systems (dpkphh·HCl·3H 2O plus surrounding solvent molecules) insensitivity to their surroundings although the spectra show strong solvent-solute interactions. 1H NMR measurements on dpkphh·HCl·3H 2O in non-aqueous media reveal sensitivity to solvent and temperature variations that point to strong solvent-solute interactions. The amide and

  10. Facile N-oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by the flavin-containing monooxygenase. A convenient synthesis of tritiated [methyl-3H]-4-phenyl-2,3-dihydropyridinium species

    International Nuclear Information System (INIS)

    Cashman, J.R.

    1988-01-01

    A rapid, efficient procedure useful for the radiosynthesis of [Me- 3 H]-MPDP+ ([methyl- 3 H]-4-phenyl-2,3-dihydropyridinium species) is described. Hog liver microsomes or the highly purified flavin-containing monooxygenase from hog liver quantitatively biotransforms [Me- 3 H]-MPTP to its corresponding radiolabeled N-oxide. For the small-scale synthesis required for radiolabeling procedures, this enzymatic process is superior to H 2 O 2 -mediated N-oxygenation of MPTP. In the presence of 0.5 mM NADPH, 4.5 mM n-octylamine, and 2 microCi [Me- 3 H]-MPTP, the only product detected in extracts from incubations performed with hog liver microsomes or purified hog liver flavin-containing monooxygenase is [Me- 3 H]-MPTP N-oxide. [Me- 3 H]-MPTP N-oxide is almost completely converted to [Me- 3 H]-MPDP+ by the action of trifluoroacetic anhydride. This procedure has the advantage of using a commercially available tritiated starting material, efficient transformations, and easily accomplished purification to afford a rapid synthesis of [Me- 3 H]-MPDP+

  11. Reducing Escherichia coli growth on a composite biomaterial by a surface immobilized antimicrobial peptide

    Energy Technology Data Exchange (ETDEWEB)

    Buckholtz, Gavin A.; Reger, Nina A. [Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, PA 15282 (United States); Anderton, William D.; Schimoler, Patrick J. [Orthopaedic Biomechanics Research Laboratory, Allegheny General Hospital, Pittsburgh, PA 15212 (United States); Roudebush, Shana L.; Meng, Wilson S. [Division of Pharmaceutical Sciences, Duquesne University, Pittsburgh, PA 15282 (United States); Miller, Mark C. [Orthopaedic Biomechanics Research Laboratory, Allegheny General Hospital, Pittsburgh, PA 15212 (United States); Gawalt, Ellen S., E-mail: gawalte@duq.edu [Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, PA 15282 (United States); McGowan Institute for Regenerative Medicine, University of Pittsburgh, Pittsburgh, PA 15219 (United States)

    2016-08-01

    A new composite bioceramic consisting of calcium aluminum oxide (CaAlO) and hydroxyapatite (HA) was functionalized with the synthetic antimicrobial peptide Inverso-CysHHC10. CaAlO is a bioceramic that can be mold cast easily and quickly at room temperature. Improved functionality was previously achieved through surface reactions. Here, composites containing 0–5% HA (by mass) were prepared and the elastic modulus and modulus of rupture were mechanically similar to non-load bearing bone. The addition of hydroxyapatite resulted in increased osteoblast attachment (> 180%) and proliferation (> 140%) on all composites compared to 100% CaAlO. Antimicrobial peptide (AMP) immobilization was achieved using an interfacial alkene-thiol click reaction. The linked AMP persisted on the composite (> 99.6% after 24 h) and retained its activity against Escherichia coli based on N-phenylnaphthylamine uptake and bacterial turbidity tests. Overall, this simple scaffold system improves osteoblast activity and reduces bacterial activity. - Highlights: • Calcium aluminum oxide and hydroxyapatite were cast into a composite material. • Osteoblast attachment and proliferation were significantly increased on composites. • An active antimicrobial peptide was linked to and remained stable on the composite. • Bacterial turbidity and NPN uptake tests showed modified composites had an effect equal to a 10 μM Inverso-CysHHC10 solution. • Antimicrobial peptide linkage did not affect the increased osteoblast performance.

  12. Analytical performance of molecular beacons on surface immobilized gold nanoparticles of varying size and density.

    Science.gov (United States)

    Uddayasankar, Uvaraj; Krull, Ulrich J

    2013-11-25

    The high quenching efficiency of metal nanoparticles has facilitated its use as quenchers in molecular beacons. To optimize this system, a good understanding of the many factors that influence molecular beacon performance is required. In this study, molecular beacon performance was evaluated as a function of gold nanoparticle size and its immobilization characteristics. Gold nanoparticles of 4 nm, 15 nm and 87 nm diameter, were immobilized onto glass slides. Each size regime offered distinctive optical properties for fluorescence quenching of molecular dyes that were conjugated to oligonucleotides that were immobilized to the gold nanoparticles. Rigid double stranded DNA was used as a model to place fluorophores at different distances from the gold nanoparticles. The effect of particle size and also the immobilization density of nanoparticles was evaluated. The 4 nm and 87 nm gold nanoparticles offered the highest sensitivity in terms of the change in fluorescence intensity as a function of distance (3-fold improvement for Cy5). The optical properties of the molecular fluorophore was of significance, with Cy5 offering higher contrast ratios than Cy3 due to the red-shifted emission spectrum relative to the plasmon peak. A high density of gold nanoparticles reduced contrast ratios, indicating preference for a monolayer of immobilized nanoparticles when considering analytical performance. Molecular beacon probes were then used in place of the double stranded oligonucleotides. There was a strong dependence of molecular beacon performance on the length of a linker used for attachment to the nanoparticle surface. The optimal optical performance was obtained with 4 nm gold nanoparticles that were immobilized as monolayers of low density (5.7×10(11)particles cm(-2)) on glass surfaces. These nanoparticle surfaces offered a 2-fold improvement in analytical performance of the molecular beacons when compared to other nanoparticle sizes investigated. The principles developed in this study would assist in the design of solid phase molecular beacons using gold nanoparticles. Copyright © 2013 Elsevier B.V. All rights reserved.

  13. Influence of cosolvents on the hydrophobic surface immobilization topography of Candida antarctica lipase B

    Science.gov (United States)

    The presence of cosolvents and co-solutes during the immobilization of lipases on hydrophobic supports may influence the extent of lipase immobilization and the long-term catalytic stability of the biocatalyst. Candida antarctica B lipase immobilization was examined on a hydrophobic surface, i.e., ...

  14. Surface Immobilization of Engineered Nanomaterials for in Situ Study of their Environmental Transformations and Fate

    Science.gov (United States)

    The transformation and environmental fate of engineered nanomaterials (ENMs) is the focus of intense research due to concerns about their potential impacts in the environment as a result of their uniquely engineered properties. Many approaches are being applied to investigate th...

  15. Surface-immobilized hydrogel patterns on length scales from micrometer to nanometer

    Science.gov (United States)

    Zeira, Assaf

    The present work concentrates on the study of pattern generation and transfer processes of monolayer covered surfaces, deriving from the basic working concept of Constructive Lithography. As an advancement of constructive lithography, we developed a direct, one-step printing (contact electrochemical printing, CEP) and replication (contact electrochemical replication, CER) of hydrophilic organic monolayer patterns surrounded by a hydrophobic monolayer background. In addition, we present a process of transfer of metal between two contacting solid surfaces to predefined monolayer template pattern sites (contact electrochemical transfer, CET). This thesis shows that CEP, CER, and CET may be implemented under a variety of different experimental conditions, regardless of whether the initial "master" pattern was created by a parallel (fast) or serial (slow) patterning process. CEP and CER also posses the unique attractive property that each replica may equally function as master stamp in the fabrication of additional replicas. Moreover, due to a mechanism of selfcorrection patterned surfaces produced these process are often free of defects that the initial "master" stamp may had. We finally show that the electrochemical patterning of OTS monolayers on silicon can be further extended to flexible polymeric substrate materials as well as to a variety of chemical manipulations, allowing the fabrication of tridimensional (3D) composite structures made on the basis of readily available OTS compound. The results obtained suggest that such contact electrochemical processes could be used to rapidly generate multiple copies of surface patterns spanning variable length scales, this basic approach being applicable to rigid as well as flexible substrate materials.

  16. 4-[(3-Phenyl-4,5-dihydroisoxazol-5-ylmethyl]-2H-benzo[b][1,4]thiazin-3(4H-one

    Directory of Open Access Journals (Sweden)

    Nada Kheira Sebbar

    2016-06-01

    Full Text Available In the title compound, C18H16N2O2S, the 5-dihydroisoxazol-5-yl ring and its phenyl substituent are nearly coplanar, with the largest deviation from the mean plane being 0.0184 (16 Å. The thiomorpholin-3-one ring adopts a screw-boat conformation and the attached benzene ring makes a dihedral angle of 42.26 (7° with the mean plane through the 3-phenyl-4,5-dihydroisoxazol-5-yl ring system. In the crystal, molecules are linked by pairs of C—H...N hydrogen bonds, forming inversion dimers. These dimers are linked via C—H...O hydrogen bonds, generating a three-dimensional network.

  17. Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-amino­phenyl­arsonate tetra­hydrate

    Science.gov (United States)

    Smith, Graham; Wermuth, Urs D.

    2016-01-01

    In the structure of the brucinium salt of 4-amino­phenyl­arsonic acid (p-arsanilic acid), systematically 2,3-dimeth­oxy-10-oxostrychnidinium 4-amino­phenyl­ar­son­ate tetra­hydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water mol­ecules of solvation are accommodated between the layers and are linked to them through a primary cation N—H⋯O(anion) hydrogen bond, as well as through water O—H⋯O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure. PMID:27308034

  18. Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-amino-phenyl-arsonate tetra-hydrate.

    Science.gov (United States)

    Smith, Graham; Wermuth, Urs D

    2016-05-01

    In the structure of the brucinium salt of 4-amino-phenyl-arsonic acid (p-arsanilic acid), systematically 2,3-dimeth-oxy-10-oxostrychnidinium 4-amino-phenyl-ar-son-ate tetra-hydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water mol-ecules of solvation are accommodated between the layers and are linked to them through a primary cation N-H⋯O(anion) hydrogen bond, as well as through water O-H⋯O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure.

  19. Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy-1-phenyl-1H-pyrazole-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Imtiaz Khan

    2012-07-01

    Full Text Available A facile one-pot synthesis of methyl 5-(4-chlorobenzoyloxy-1-phenyl-1H-pyrazole-3-carboxylate (4 is described. The title compound was efficiently synthesized by the reaction of phenyl hydrazine, dimethyl acetylenedicarboxylate and 4-chlorobenzoyl chloride in dichloromethane under reflux in good yield. The structure of the target compound was deduced by modern spectroscopic and analytical techniques and unequivocally confirmed by a single crystal X-ray diffraction analysis. The crystal of the title compound belongs to orthorhombic system, space group P 21 21 21 with cell parameters a = 6.6491(3 Å, b = 7.9627(6 Å, c = 30.621(5 Å, α = β = γ = 90° and Z = 4. The crystal packing of the compound (4 is stabilized by an offset π-stacking between the planar benzoyl-substituted diazole moieties.

  20. Reaction of bis[(2-chlorocarbonyl)phenyl] Diselenide with Phenols, Aminophenols, and Other Amines towards Diphenyl Diselenides with Antimicrobial and Antiviral Properties.

    Science.gov (United States)

    Giurg, Mirosław; Gołąb, Anna; Suchodolski, Jakub; Kaleta, Rafał; Krasowska, Anna; Piasecki, Egbert; Piętka-Ottlik, Magdalena

    2017-06-12

    A reaction of bis[(2-chlorocarbonyl)phenyl] diselenide with various mono and bisnucleophiles such as aminophenols, phenols, and amines have been studied as a convenient general route to a series of new antimicrobial and antiviral diphenyl diselenides. The compounds, particularly bis[2-(hydroxyphenylcarbamoyl)]phenyl diselenides and reference benzisoselenazol-3(2 H )-ones, exhibited high antimicrobial activity against Gram-positive bacterial species ( Enterococcus spp., Staphylococcus spp.), and some compounds were also active against Gram-negative E. coli and fungi ( Candida spp., A. niger ). The majority of compounds demonstrated high activity against human herpes virus type 1 (HHV-1) and moderate activity against encephalomyocarditis virus (EMCV), while they were generally inactive against vesicular stomatitis virus (VSV).

  1. Potentiometric, spectrometric, thermal and conductimetric studies on some 3-phenyl-4-(arylazo)-5-pyrazolones and their complexes with divalent cobalt metal ion

    Science.gov (United States)

    Hassib, H. B.; Abdel-Latif, S. A.

    2003-09-01

    3-phenyl-4-arylazo-5-pyrazolones (I-IV) have been synthesized and characterized by elemental, infrared (IR), ultraviolet and visible spectra (UV-Vis), proton nuclear magnetic resonance ( 1H NMR) and Mass spectra. It has been proved that these compounds exhibit a keto-enol tautomerism in solution. The donor character of the substituent increases the enol form. The ionization constants of the investigated ligands have been determined potentiometrically and found to decrease in the order OCH 3(IV)>CH 3(III)>H(I)>Cl(II). The Co(II) complexes of the investigated 3-phenyl-4-arylazo-5-pyrazolones (I-IV) have been prepared and characterized by elemental and thermal analyses as well as by IR, UV-Vis, electronic transition, potentiometric, conductimetric and magnetic measurements. The data suggest octahedral geometry for Co(II) (1:1) complexes and tetrahedral for Co(II) (2:3) complexes.

  2. 1-Benzyl-2-phenyl-1H-benzimidazole–4,4′-(cyclohexane-1,1-diyldiphenol (1/1

    Directory of Open Access Journals (Sweden)

    Chunhua Ge

    2011-07-01

    Full Text Available The asymmetric unit of the title co-crystal, C20H16N2·C18H20O2, contains one molecule of 4,4′-(cyclohexane-1,1-diyldiphenol (in which the cyclohexane ring adopts a chair conformation and one molecule of 1-benzyl-2-phenyl-1H-benzimidazole, which are paired through an O—H...N hydrogen bond. These pairs are further linked by intermolecular O—H...O hydrogen bonds into chains along [010]. Weak intermolecular C—H...O and C—H...π interactions further consolidate the crystal packing. The dihedral angles between the pendant phenyl rings and the benzimidazole ring are 86.9 (2 and 43.1 (2°.

  3. 2,3-Di­phenyl­male­imide 1-methyl­pyrrol­idin-2-one monosolvate

    Science.gov (United States)

    Bulatov, Evgeny; Boyarskaya, Dina; Chulkova, Tatiana; Haukka, Matti

    2014-01-01

    In the title compound, C16H11NO2·C5H9NO, the dihedral angles between the male­imide and phenyl rings are 34.7 (2) and 64.8 (2)°. In the crystal, the 2,3-di­phenyl­male­imide and 1-methyl­pyrrolidin-2-one mol­ecules form centrosymmetrical dimers via pairs of strong N—H⋯O hydrogen bonds and π–π stacking inter­actions between the two neighboring male­imide rings [centroid–centroid distance = 3.495 (2) Å]. The dimers are further linked by weak C—H⋯O and C—H⋯π hydrogen bonds into a three-dimensional framework. PMID:24764976

  4. Effect of the number of phenyl groups per molecule on the reactivity of hydroxyl or carboxyl group in hydrogen-isotope exchange reaction

    International Nuclear Information System (INIS)

    Okada, Minoru; Imaizumi, Hiroshi; Oguma, Shuichi

    1989-01-01

    Hydrogen-exchange reactions in solid alcohols (or solid carboxylic acids) which contain phenyl group(s) in each molecule have been observed in a gas-solid system or liquid-solid system at 40 ≅ 80deg C. The data thus obtained have been analyzed by using the A''-McKay plot method, and 'the acidities based on kinetic logic' have been obtained for those compounds. From the acidities the following four characteristics have been determined. (1) The acidity increases with increases of temperature. (2) The reactivities of carboxylic acids are larger than those of alcohols at any temperature. (3) The effect of the number of phenyl groups on the reactivity of the functional group in the molecule in question is fairly large. (4) Acidity based on kinetic logic can be applied not only to gas-solid reactions, but also to liquid-solid reactions. (orig.)

  5. PREPARATION AND PROPERTIES OF THREE NEUTRAL COPPER (I COMPLEXES BASED ON BIS[2-(DIPHENYLPHOSPHINOPHENYL]ETHER PHENYL] ETHER AND SUBSTITUTED IMIDAZOLE-2,9-DIMETHYL-1,10-PHENANTHROLINE

    Directory of Open Access Journals (Sweden)

    Xin Fang Liu

    2017-10-01

    Full Text Available With deprotonated 2-(4-nitro phenyl-, 2-(4-methyl phenyl-, and 2-(4-methoxy phenyl imidazoled-2,9-dimethyl-1,10-phenanthroline (NPIP, MPIP and MoPIP as nitrogen ligands, as well as bis[2-(diphenylphosphino phenyl]ether (DPEphos as phosphorus ligand, three Cu(I neutral complex has been synthesized and characterized by infrared spectroscopy (IR, elemental analysis and 1H NMR methods. TG-DTA shows that the complex begins to decompose when the temperature reached about 220 oC, indicating their high thermo-stability. The emission spectrum shows that the complexes exhibit yellow emission with a peak emission wavelength of 576, 585 and 596 nm under excitation of 287 nm in powder state.

  6. Tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-ylpropan-1-one-κN4]bis(thiocyanato-κNnickel(II

    Directory of Open Access Journals (Sweden)

    Jian-Hua Guo

    2010-12-01

    Full Text Available In the centrosymmetric mononuclear title complex, [Ni(NCS2(C11H11N3O4], the NiII atom, located on an inversion centre, is hexacoordinated in a distorted octahedral geometry comprising four N atoms of four monodentate 1-phenyl-3-(1H-1,2,4-triazol-1-ylpropan-1-one ligands and two N atoms from thiocyanate anions.

  7. N′-[(Z-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylmethylidene]-2-hydroxybenzohydrazide

    Directory of Open Access Journals (Sweden)

    Muhammad Aslam

    2012-02-01

    Full Text Available In the title compound, C19H18N4O3, the pyrazole ring is oriented at dihedral angles of 41.12 (7 and 12.25 (10°, respectively, with respect to the planes of the phenyl and benzene rings. Intramolecular N—H...O and O—H...O hydrogen bonds generate seven- and six-membered S(7 and S(6 ring motifs, respectively.

  8. The thermal stability and pyrolysis mechanism of boron-containing phenolic resins: The effect of phenyl borates on the char formation

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Shujuan; Wang, Yong; Bian, Cheng; Zhong, Yuhu [Department of Applied Chemistry, School of Science, Xi’an Jiaotong University, Xi’an 710049, People’ s Republic of China (China); Jing, Xinli, E-mail: rgfp-jing@mail.xjtu.edu.cn [Department of Applied Chemistry, School of Science, Xi’an Jiaotong University, Xi’an 710049, People’ s Republic of China (China); MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi’an, 710049, People’ s Republic of China (China)

    2015-03-15

    Graphical abstract: - Highlights: • The thermal stability and pyrolysis mechanism of cured BPR are investigated. • The high char yield of BPR results from the formed phenyl borates during curing. • Boron oxide is formed on the surface of carbonized product during pyrolysis. • The formed boron oxide revealed the cleavage of O–C bonds from phenyl borates. • The graphitization degree and graphite crystallites of PR are improved by introducing boron. - Abstract: Boron-containing phenolic resin (BPR) is a kind of the ablative resins with high-performance. Due to the lack of the exact knowledge concerning the pyrolysis mechanism of BPR, its development and application are greatly impeded. In the present paper, the chemical structure of the cured BPR and its structural evolution at high temperatures are investigated to clarify the reason for the high char yield of BPR. The results indicate that the high char yield of BPR is mainly attributed to the phenyl borates formed during curing, which can block parts of phenolic hydroxyl groups, and effectively inhibit their thermal decomposition reaction. Boron oxide is formed on the surface of carbonization products by the cleavage of O–C bonds from phenyl borates via pyrolysis, which avoids the release of volatile carbon dioxide and reduces the development of micro-structural defects of carbonization products. Introducing boron into PR improves the graphitization degree and graphite crystallites of carbonization products, which promotes the formation of a more ordered glassy carbon during pyrolysis. This study provides a new vision for the understanding of the high char yield of BPR, which makes it possible to develop a new ablative resin through molecular design.

  9. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). 721.5375 Section... Substances § 721.5375 Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino...

  10. Crystal structure of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl-1H-pyrazole-4-carbaldehyde

    Directory of Open Access Journals (Sweden)

    Joel T. Mague

    2014-10-01

    Full Text Available In the title compound, C15H13N3O, the pyrrolyl and phenyl rings make dihedral angles of 58.99 (5 and 34.95 (5°, respectively, with the central pyrazole ring. In the crystal, weak, pairwise C—H...O interactions across centers of symmetry form dimers, which are further associated into corrugated sheets running approximately parallel to (100 via weak C—H...N interactions.

  11. 1-[3-(2-Methyl-4-phenylquinolin-3-yl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-propane-1-one

    Directory of Open Access Journals (Sweden)

    Allaoua Kedjadja

    2015-06-01

    Full Text Available A novel compound, 1-[3-(2-methyl-4-phenylquinolin-3-yl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-propane-1-one (3 has been synthesized by cyclocondensation of (E-1-(2-methyl-4-phenylquinolin-3-yl-3-phenylprop-2-en-1-one (2 and hydrazine hydrate in propionic acid. The structure of this compound was established by elemental analysis, IR, 1H-NMR, 13C-NMR and MS data.

  12. Cyclic α-Alkoxyphosphonium Salts from (2-(Diphenylphosphino)phenyl)methanol and Aldehydes and Their Application in Synthesis of Vinyl Ethers and Ketones via Wittig Olefination.

    Science.gov (United States)

    Huang, Wenhua; Rong, Hong-Ying; Xu, Jie

    2015-07-02

    Cyclic α-alkoxyphosphonium salts have been synthesized from (2-(diphenylphosphino)phenyl)methanol and aldehydes in 36-89% yields. These phosphonium salts are bench-stable solids and undergo Wittig olefination with aldehydes under basic conditions (K2CO3 or t-BuOK) to form benzylic vinyl ethers, which are readily hydrolyzed to 1,2-disubstituted ethanones under acidic conditions. The formation mechanism of these phosphonium salts via hemiacetal is also proposed.

  13. Determination of the Thermodynamic Properties of Poly [2-(3-phenyl-3-methylcyclobutyl)-2-hydroxyethyl methacrylate-co-methacrylic acid] at Infinite Dilution by Inverse Gas Chromatography

    OpenAIRE

    KAYA, İsmet

    2014-01-01

    Some thermodynamic quantities were obtained for the interactions of poly [2-(3-phenyl -3- methylcyclobutyl)-2-hydroxyethyl methacrylate-co-methacrylic acid] Poly (PCHEMA-co-MA) with alcohols, ketones, acetates, aromatics and n-alkanes by inverse gas chromatography in the temperature range of 150-180oC. The specific retention volumes, Vgo, weight fraction activity coefficients of solute probes at infinite dilution, W1\\infty and Flory-Huggins thermodynamic interaction parameters, c12...

  14. Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound

    Science.gov (United States)

    El-Gamel, Nadia E. A.; Farghaly, Thoraya A.

    2013-11-01

    Cu(II) (1), Ni(II) (2), Cr(III) (3) and Fe(III) (4) complexes with 3-acetyl-4-benzoyl-1-phenyl-1H-pyrazole (L1) were prepared and structurally characterized. Usual coordination of L1 was achieved through nitrogen of pyrazole moiety and carbonyl acetyl group. Electronic spectra of the complexes indicate that the geometry of the metal center was six coordinate octahedral. In vitro antimicrobial activity of the ligand and complex compounds was screened in terms of antibacterial effect on Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative) and antifungal effect on the fungi Aspergillus flavus and candida albicans using the modified Kirby-Bauer disc diffusion and minimum inhibitory concentrations (MIC) methods. Ni(II) complex (2) exhibited remarkable antifungal inhibition against Candida albicans equal to the standard antifungal agent. To continue our study some structural modifications are formed by adding 4-fluoro-benzoyl moiety to L1 in different forms to produce different ligands, 3-acetyl-4-(4-flourobenzoyl)-1-phenyl-1H-pyrazole (L2) and 3-[(3-acetyl-1-phenyl-1H-4-pyrazolyl)carbonyl]-1-phenyl-4-(4-flourobenzoyl)-1H-pyrazole (L3), Ni complexes (5 and 6) are prepared and comparable in vitro antimicrobial study is evaluated. In vitro cytotoxicity of the Ni(II) complex (2) is studied using MTT assay. The analysis of the cell test showed that (2) displayed quite small cytotoxic response at the higher concentration level which indeed would further enable us for more opportunities in therapeutic and biomedical challenges. Both of the capability as a potent in vitro antifungal agent and the cell test analysis show Ni(II) complex (2) as a promising material in the translation of observed in vitro biological phenomenon into clinical therapies settings.

  15. Photophysical Parameters, Excitation Energy Transfer, and Photoreactivity of 1,4-Bis(5-phenyl-2-oxazolylbenzene (POPOP Laser Dye

    Directory of Open Access Journals (Sweden)

    Samy A. El-Daly

    2012-01-01

    Full Text Available The effect of solvents on the absorption and emission spectra of 1,4-bis(5-phenyl-2-oxazolylbenzene (POPOP laser dye has been studied in various solvents at 298 K. A bathochromic shift was observed in absorption and fluorescence spectra upon increase of solvent polarity, which indicates that this transition is π-∗. The ground and excited state dipole moments were calculated as 2.23 and 6.34 Debye, respectively. The dye solution in MeOH, n-heptane, and methyl isobutyl ketone gives laser emission in the blue region upon excitation by a 337.1 nm nitrogen pulse; the gain coefficient and emission cross section as well as normalized photostability have been determined. Excitation energy transfer from POPOP to rhodamine B and fluorescine was studied to improve the laser emission from these dyes. Such an energy transfer dye laser system (ETDL obeys a long range columbic energy transfer mechanism with a critical transfer distance, R0, of 25 and 33 Å and kq equal to 10.4×1012 and 26.2×1012M−1s−1 for the POPOP/RB and POPOP/fluorescine pair, respectively. The POPOP dye is highly photostable in polar protic and polar aprotic solvents, while it displays photodecomposition in chloromethane solvent via formation of a contact ion pair. The photochemical quantum yield and rate of photodecomposition depend on the electron affinity of solvent.

  16. DPPC/poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) chimeric nanostructures as potential drug nanocarriers

    Energy Technology Data Exchange (ETDEWEB)

    Pippa, Natassa [Faculty of Pharmacy, National and Kapodistrian University of Athens, Department of Pharmaceutical Technology (Greece); Kaditi, Eleni; Pispas, Stergios [Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation (Greece); Demetzos, Costas, E-mail: demetzos@pharm.uoa.gr [Faculty of Pharmacy, National and Kapodistrian University of Athens, Department of Pharmaceutical Technology (Greece)

    2013-06-15

    In this study, we report on the self assembly behavior and on stability studies of mixed (chimeric) nanosystems consisting of dipalmitoylphosphatidylcholine (DPPC) and poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) (MPOx) gradient copolymer in aqueous media and in fetal bovine serum (FBS). A gamut of light scattering techniques and fluorescence spectroscopy were used in order to extract information on the size and morphological characteristics of the nanoassemblies formed, as a function of gradient block copolymer content, as well as temperature. The hydrodynamic radii (R{sub h}) of nanoassemblies decreased in the process of heating up to 50 Degree-Sign C, while the fractal dimension (d{sub f}) values, also increased. Indomethacin was successfully incorporated into these chimeric nanocarriers. Drug release was depended on the components ratio. The present studies show that there are a number of parameters that can be used in order to alter the properties of chimeric nanosystems, and this is advantageous to the development of 'smart' nanocarriers for drug delivery.

  17. Continuous enantioselective esterification of trans-2-phenyl-1-cyclohexanol using a new Candida rugosa lipase in a packed bed bioreactor.

    Science.gov (United States)

    Sánchez, A; del Río, J L; Valero, F; Lafuente, J; Faus, I; Solà, C

    2001-11-17

    Enantioselective resolution of trans-2-phenyl-1-cyclohexanol (TPCH) by a Candida rugosa lipase, obtained by fermentation in the laboratory, and immobilised on EP100 polypropylene powder has been carried out using isooctane as solvent and propionic acid as esterifying agent. The study have included the utilisation of this biocatalyst in a batch process and the optimisation of the esterification conditions by means of a Box-Hunter-based experimental design. The main variables controlling the process, concentration of acid and alcohol, have been numerically optimised using initial esterification rate as objective function. The optimal concentrations for the batch process were 50 mM for the alcohol and 71 mM for the acid. This esterification reaction kinetics corresponded to a reversible Michaelis-Menten kinetic law for the optimal conditions, which has permitted to select a plug-flow packed bed bioreactor as the most appropriate configuration to minimise the residence time and to avoid shear stress effect on the biocatalyst. The behaviour of the continuous packed bed bioreactor at two different residence times (302 and 582 min) was in accordance with predictions from batch experiments, with slightly deviations (less than 10%). Continuous experiments maintained high values of enantioselectivity (enantiomeric factor was practically 1) and conversion near equilibrium value (35%) when long-time operation was carried out. Besides, long-time stability of biocatalyst has permitted to scale-up the production of enantioenriched (1R,2S)-TPCH propionate to yield gram quantities.

  18. Photocatalytic Conversion of CO2 to CO using Rhenium Bipyridine Platforms Containing Ancillary Phenyl or BODIPY Moieties

    Science.gov (United States)

    Andrade, Gabriel A.; Pistner, Allen J.; Yap, Glenn P.A.; Lutterman, Daniel A.; Rosenthal, Joel

    2013-01-01

    Harnessing of solar energy to drive the reduction of carbon dioxide to fuels requires the development of efficient catalysts that absorb sunlight. In this work, we detail the synthesis, electrochemistry and photophysical properties of a set of homologous fac-ReI(CO)3 complexes containing either an ancillary phenyl (8) or BODIPY (12) substituent. These studies demonstrate that both the electronic properties of the rhenium center and BODIPY chromophore are maintained for these complexes. Photolysis studies demonstrate that both assemblies 8 and 12 are competent catalysts for the photochemical reduction of CO2 to CO in DMF using triethanolamine (TEOA) as a sacrificial reductant. Both compounds 8 and 12 display TOFs for photocatalytic CO production upon irradiation with light (λex ≥ 400 nm) of ~5 hr−1 with TON values of approximately 20. Although structural and photophysical measurements demonstrate that electronic coupling between the BODIPY and fac-ReI(CO)3 units is limited for complex 12, this work clearly shows that the photoactive BODIPY moiety is tolerated during catalysis and does not interfere with the observed photochemistry. When taken together, these results provide a clear roadmap for the development of advanced rhenium bipyridine complexes bearing ancillary BODIPY groups for the efficient photocatalytic reduction of CO2 using visible light. PMID:24015374

  19. e-Cadherin in 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-Induced Parkinson Disease

    Directory of Open Access Journals (Sweden)

    Samuela Cataldi

    2016-01-01

    Full Text Available Today a large number of studies are focused on clarifying the complexity and diversity of the pathogenetic mechanisms inducing Parkinson disease. We used 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP, a neurotoxin that induces Parkinson disease, to evaluate the change of midbrain structure and the behavior of the anti-inflammatory factor e-cadherin, interleukin-6, tyrosine hydroxylase, phosphatase and tensin homolog, and caveolin-1. The results showed a strong expression of e-cadherin, variation of length and thickness of the heavy neurofilaments, increase of interleukin-6, and reduction of tyrosine hydroxylase known to be expression of dopamine cell loss, reduction of phosphatase and tensin homolog described to impair responses to dopamine, and reduction of caveolin-1 known to be expression of epithelial-mesenchymal transition and fibrosis. The possibility that the overexpression of the e-cadherin might be implicated in the anti-inflammatory reaction to MPTP treatment by influencing the behavior of the other analyzed molecules is discussed.

  20. Time trend of butyl- and phenyl-tin contamination in organisms of the Lagoon of Venice (1999-2003).

    Science.gov (United States)

    Zanon, F; Rado, N; Centanni, E; Zharova, N; Pavoni, B

    2009-05-01

    In the period 1999-2003 a monitoring study on the accumulation of organotin compounds in edible organisms in the Lagoon of Venice was conducted. Butyl and Phenyl derivatives were determined in pooled samples of Mytilus galloprovincialis and Tapes spp. with the aims of assessing organotin contamination in the Lagoon of Venice in the period just preceding their ban in Europe, monitoring the concentrations in organisms with a high commercial use, evaluating a potential hazard for human health due to seafood and identifying the possible contamination sources. Sampling stations (up to 20) were distributed around the Lagoon and particularly concentrated in the area close to the town of Chioggia. Significantly higher (analysis of variance (ANOVA), p 0.05) in either species. Furthermore, by analyzing the entire data set, it is evident that most stations show analogous concentrations in the 3 years for both species, whereas few have anomalously higher concentrations. If organotin concentrations in specimens from some sites are compared with the Tolerable Average Residue Level, a possible risk for human health must be considered.

  1. Crystal structure, vibrational, spectral investigation, quantum chemical DFT calculations and thermal behavior of Diethyl [hydroxy (phenyl) methyl] phosphonate

    Science.gov (United States)

    Ouksel, Louiza; Chafaa, Salah; Bourzami, Riadh; Hamdouni, Noudjoud; Sebais, Miloud; Chafai, Nadjib

    2017-09-01

    Single Diethyl [hydroxy (phenyl) methyl] phosphonate (DHPMP) crystal with chemical formula C11H17O4P, was synthesized via the base-catalyzed Pudovik reaction and Lewis acid as catalyst. The results of SXRD analyzes indicate that this compound crystallizes into a mono-clinic system with space group P21/n symmetry and Z = 4. The crystal structure parameters are a = 9.293 Å, b = 8.103 Å, c = 17.542 Å, β = 95.329° and V = 1315.2 Å3, the structure displays one inter-molecular O-H⋯O hydrogen bonding. The UV-Visible absorption spectrum shows that the crystal exhibits a good optical transmission in the visible domain, and strong absorption in middle ultraviolet one. The vibrational frequencies of various functional groups present in DHPMP crystal have been deduced from FT-IR and FT-Raman spectra and then compared with theoretical values performed with DFT (B3LYP) method using 6-31G (p, d) basis sets. Chemical and thermodynamic parameters such as: ionization potential (I), electron affinity (A), hardness (σ), softness (η), electronegativity (χ) and electrophilicity index (ω), are also calculated using the same theoretical method. The thermal decomposition behavior of DHPMP, studied by using thermogravimetric analysis (TDG), shows a thermal stability until to 125 °C.

  2. Thioxanthone based 9-[2-(methyl-phenyl-amino)-acetyl]-thia-naphthacene-12-one as a visible photoinitiator

    International Nuclear Information System (INIS)

    Doğruyol, Sevnur Keskin; Doğruyol, Zekeriya; Arsu, Nergis

    2013-01-01

    Photoinitiators that operate in the visible range of the electromagnetic spectrum have widespread applications. Thioxanthone based 9-[2-(methyl-phenyl-amino)-acetyl]-thia-naphthacene-12-one (TX-MPA) was synthesized and the characterization of this initiator was confirmed by spectral analysis methods. TX-MPA has excellent absorption properties in the visible range (ε 480 nm =3576 L/mol.cm). Photophysical studies; fluorescence quantum yield (φ f =0.22, DPA), phosphorescence lifetime (τ p =115 ms) and triplet lifetime (τ=190 ns) were explored. To explore the initiation mechanism of TX-MPA, besides the photophysical and photochemical studies, the polymer (PMMA) obtained from the photopolymerization studies was subjected to a phosphorescence study and τ p was found to be 105 ms compared to 115 ms for the initiator TX-MPA which proved attachment of the initiator to the polymer. Possibly both intermolecular and intramolecular hydrogen abstraction, occur during the initiation stage depending on the concentration of the initiator. Highlights: ► Synthesis and photophysical properties of a visible photoinitiator (TX-MPA) are proposed. ► TX-MPA has high molar absorption values in the visible region. ► TX-MPA can initiate photopolymerization of methylmethacrylate monomer under UV and sunlight. ► Inter or intramolecular hydrogen abstraction mechanisms occur depending on initiator concentration

  3. Thioxanthone based 9-[2-(methyl-phenyl-amino)-acetyl]-thia-naphthacene-12-one as a visible photoinitiator

    Energy Technology Data Exchange (ETDEWEB)

    Doğruyol, Sevnur Keskin [Department of Chemistry, Yıldız Technical University, Davutpasa Campus, Esenler, 34220 Istanbul (Turkey); Doğruyol, Zekeriya [Department of Engineering Science, Istanbul University, 34850, Avcılar, Istanbul (Turkey); Arsu, Nergis, E-mail: narsu@yildiz.edu.tr [Department of Chemistry, Yıldız Technical University, Davutpasa Campus, Esenler, 34220 Istanbul (Turkey)

    2013-06-15

    Photoinitiators that operate in the visible range of the electromagnetic spectrum have widespread applications. Thioxanthone based 9-[2-(methyl-phenyl-amino)-acetyl]-thia-naphthacene-12-one (TX-MPA) was synthesized and the characterization of this initiator was confirmed by spectral analysis methods. TX-MPA has excellent absorption properties in the visible range (ε{sub 480} {sub nm}=3576 L/mol.cm). Photophysical studies; fluorescence quantum yield (φ{sub f}=0.22, DPA), phosphorescence lifetime (τ{sub p}=115 ms) and triplet lifetime (τ=190 ns) were explored. To explore the initiation mechanism of TX-MPA, besides the photophysical and photochemical studies, the polymer (PMMA) obtained from the photopolymerization studies was subjected to a phosphorescence study and τ{sub p} was found to be 105 ms compared to 115 ms for the initiator TX-MPA which proved attachment of the initiator to the polymer. Possibly both intermolecular and intramolecular hydrogen abstraction, occur during the initiation stage depending on the concentration of the initiator. Highlights: ► Synthesis and photophysical properties of a visible photoinitiator (TX-MPA) are proposed. ► TX-MPA has high molar absorption values in the visible region. ► TX-MPA can initiate photopolymerization of methylmethacrylate monomer under UV and sunlight. ► Inter or intramolecular hydrogen abstraction mechanisms occur depending on initiator concentration.

  4. Phenyl Propionate and Sex Pheromone for Monitoring Navel Orangeworm (Lepidoptera: Pyralidae) in the Presence of Mating Disruption.

    Science.gov (United States)

    Burks, Charles S; Kuenen, L P S Bas; Daane, Kent M

    2016-04-01

    The recent availability of sex pheromone lures for the navel orangeworm, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), improves options for monitoring this key pest in conventionally managed almonds. These lures are, however, minimally effective in the presence of mating disruption. Experiments were conducted to determine if phenyl propionate (PPO), an attractant for the navel orangeworm, acts in an additive or synergistic manner when presented together with the pheromone. In the absence of mating disruption, traps baited with PPO captured significantly fewer adults than traps baited with a sex pheromone lure. There was no difference in the number of adults captured in traps with both attractants when mating disruption was not used. In the presence of mating disruption, pheromone traps were completely suppressed, yet traps with both pheromone and PPO captured significantly more adults than traps baited with only PPO. Traps with only PPO captured equal numbers of both sexes, whereas traps with both attractants had significantly more males. These findings demonstrate that PPO is likely to be useful for monitoring navel orangeworm in fields treated with mating disruption.

  5. Optimization of antiproliferative activity of substituted phenyl 4-(2-oxoimidazolidin-1-yl) benzenesulfonates: QSAR and CoMFA analyses.

    Science.gov (United States)

    Masand, Vijay H; Mahajan, Devidas T; Alafeefy, Ahmed M; Bukhari, Syed Nasir Abbas; Elsayed, Nahed N

    2015-09-18

    Multiple separate quantitative structure-activity relationships (QSARs) models were built for the antiproliferative activity of substituted Phenyl 4-(2-Oxoimidazolidin-1-yl)-benzenesulfonates (PIB-SOs). A variety of descriptors were considered for PIB-SOs through QSAR model building. Genetic algorithm (GA), available in QSARINS, was employed to select optimum number and set of descriptors to build the multi-linear regression equations for a dataset of PIB-SOs. The best three parametric models were subjected to thorough internal and external validation along with Y-randomization using QSARINS, according to the OECD principles for QSAR model validation. The models were found to be statistically robust with high external predictivity. The best three parametric model, based on steric, 3D- and finger print descriptors, was found to have R(2)=0.91, R(2)ex=0.89, and CCCex=0.94. The CoMFA model, which is based on a combination of steric and electrostatic effects and graphically inferred using contour plots, gave F=229.34, R(2)CV=0.71 and R(2)=0.94. Steric repulsion, frequency of occurrence of carbon and nitrogen at topological distance of seven, and internal electronic environment of the molecule were found to have correlation with the anti-tumor activity of PIB-SOs. Copyright © 2015 Elsevier B.V. All rights reserved.

  6. Conformational studies on the four stereoisomers of the novel anticholinergic 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide

    Science.gov (United States)

    Oyasu, Hitoshi; Nakanishi, Isao; Tanaka, Akito; Murano, Kenji; Matsuo, Masaaki

    1995-04-01

    To interpret differences in the anticholinergic activity among the four steroisomers of 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide ( 1-4), we performed conformational studies using the semiempirical molecular orbital method. The structures of the global minimum-energy conformations obtained for 1-4, however, could not explain the different activities, particularly in terms of distances between the essential pharmacophores. We thus implemented superimposition studies, using the energetically stable conformations of the most active stereoisomer, 1( 2S,4R), as a template. The energy penalties for a conformation change of the less active stereoisomers 2-4 from their global minimum-energy structure to a new conformation, fitting onto the global minimum-energy conformation of 1, appear to account for the differences in the pharmacological potency better than using the other conformations of 1 as a template. We thus presume that the global minimum-energy conformation of 1 is closely related to the bioactive conformation for these anticholinergics, and also that the pharmacological potency is linked to how readily these substances can change their conformations to fit the muscarinic receptor.

  7. Synthesis and Bioactivity of N-Benzoyl-N'-[5-(2'-substituted phenyl-2-furoyl] Semicarbazide Derivatives

    Directory of Open Access Journals (Sweden)

    Zining Cui

    2010-06-01

    Full Text Available In order to find novel chitin synthesis inhibitors (CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl-2-furoyl hydrazine, and the structures were confirmed by IR, 1H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2. The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60, and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402, human gastric carcinoma cell line (BGC-823, and human nasopharyngeal carcinoma cell line (KB. The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates.

  8. DPPC/poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) chimeric nanostructures as potential drug nanocarriers

    International Nuclear Information System (INIS)

    Pippa, Natassa; Kaditi, Eleni; Pispas, Stergios; Demetzos, Costas

    2013-01-01

    In this study, we report on the self assembly behavior and on stability studies of mixed (chimeric) nanosystems consisting of dipalmitoylphosphatidylcholine (DPPC) and poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) (MPOx) gradient copolymer in aqueous media and in fetal bovine serum (FBS). A gamut of light scattering techniques and fluorescence spectroscopy were used in order to extract information on the size and morphological characteristics of the nanoassemblies formed, as a function of gradient block copolymer content, as well as temperature. The hydrodynamic radii (R h ) of nanoassemblies decreased in the process of heating up to 50 °C, while the fractal dimension (d f ) values, also increased. Indomethacin was successfully incorporated into these chimeric nanocarriers. Drug release was depended on the components ratio. The present studies show that there are a number of parameters that can be used in order to alter the properties of chimeric nanosystems, and this is advantageous to the development of “smart” nanocarriers for drug delivery.

  9. Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea.

    Science.gov (United States)

    Liu, Chunhui; Cui, Zining; Yan, Xiaojing; Qi, Zhiqiu; Ji, Mingshan; Li, Xinghai

    2016-06-24

    Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22) were synthesized, and their structures were confirmed by ¹H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA), and compound III-3 on potato dextrose agar (PDA) indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM) and transmission electron micrography (TEM) were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

  10. Crystal structures and fungicidal activities of anti-2,4-bis(X-phenyl)pentane-2,4-diols

    Science.gov (United States)

    Jiao, Yinchun; Cao, Chenzhong; Zhao, Xiaolin

    2012-11-01

    The 1,3-diol moiety is present in a number of natural products and has some biological activity. Four symmetric anti-2,4-bis(X-phenyl)pentane-2,4-diols (a, X = p-F; b, X = p-CF3; c, X = m-OMe; d, X = m-CF3) have been characterized by X-ray diffraction, and the results indicated that the dihedral angles between the every two benzene rings in the systems are 34.38(10)°, 39.46(13)°, 23.42(7)°(A), 30.42(7)°(B) and 44.74(9)°, respectively. All of the structures were stabilized by classical intra- and intermolecular hydrogen bonding and some other weak interactions. It was observed that the hydrogen bonding patterns were formed between each single-molecule in compounds a-d, whereas H-bonding dimers were formed in the crystal lattices of both the anti- and syn-2,4-bisphenylpentane-2,4-diols. The four symmetric diaryl 1,3-diols were evaluated alongside several other 1,3-diols as potential antifungal agents, and their in vitro antifungal activities were measured against several fungal species, including Gibberella zeae, Botrytis cinerea, Alternaria alternata and Sclerotonia sclerotiorum.

  11. Interaction of SF6 and O2 plasma with porous poly phenyl methyl silsesquioxane low-κ films

    International Nuclear Information System (INIS)

    Cherunilam, J F; Rajani, K V; Daniels, S; Byrne, C; Heise, A; McNally, P J

    2015-01-01

    A reduction in the κ-value of dielectric materials is of great interest today as it leads to the reduction of resistance–capacitance delays and parasitic capacitances within integrated circuits, thereby improving device performance. We have recently reported our studies on the great potential of the Poly phenyl methyl silsesquioxane (PMSQ) low-κ films (κ = 2.7  ±  0.2) for interlayer dielectric applications. Here we report on the deposition and characterisation of porous PMSQ thin films using Heptakis (2,3,6-tri-O-methyl)-β-cyclodextrin as the porogen. A reduction in the κ-value of the films was achieved as a function of the increase in porogen loading in the film. The removal of the thermally liable porogen material from the hybrid films was studied using thermogravimetric analysis (TGA) and Fourier transform infrared spectroscopy (FTIR). The change in density as a function of the porosity was studied using x-ray reflectivity techniques. The interaction of the films with pure SF 6 and O 2 plasmas was studied and the surface modification that occurs in the films as a result of the interaction was studied using FTIR and x-ray photoelectron spectroscopy. A change in the κ-value of the films was observed after plasma treatment which is attributed to the chemical modification of the film surface due to plasma interaction. (paper)

  12. In vitro cytotoxicity assessment of a West Virginia chemical spill mixture involving 4-methylcyclohexanemethanol and propylene glycol phenyl ether.

    Science.gov (United States)

    Han, Alice A; Fabyanic, Emily B; Miller, Julie V; Prediger, Maren S; Prince, Nicole; Mouch, Julia A; Boyd, Jonathan

    2017-04-01

    Thousands of gallons of industrial chemicals, crude 4-methylcyclohexanemethanol (MCHM) and propylene glycol phenyl ether (PPh), leaked from industrial tanks into the Elk River in Charleston, West Virginia, USA, on January 9, 2014. A considerable number of people were reported to exhibit symptoms of chemical exposure and an estimated 300,000 residents were advised not to use or drink tap water. At the time of the spill, the existing toxicological data of the chemicals were limited for a full evaluation of the health risks, resulting in concern among those in the impacted regions. In this preliminary study, we assessed cell viability and plasma membrane degradation following a 24-h exposure to varying concentrations (0-1000 μM) of the two compounds, alone and in combination. Evaluation of different cell lines, HEK-293 (kidney), HepG2 (liver), H9c2 (heart), and GT1-7 (brain), provided insight regarding altered cellular responses in varying organ systems. Single exposure to MCHM or PPh did not affect cell viability, except at doses much higher than the estimated exposure levels. Certain co-exposures significantly reduced metabolic activity and increased plasma membrane degradation in GT1-7, HepG2, and H9c2 cells. These findings highlight the importance of examining co-exposures to fully understand the potential toxic effects.

  13. Synthesis and spectral properties of Methyl-Phenyl pyrazoloquinoxaline fluorescence emitters: Experiment and DFT/TDDFT calculations

    Science.gov (United States)

    Gąsiorski, P.; Matusiewicz, M.; Gondek, E.; Uchacz, T.; Wojtasik, K.; Danel, A.; Shchur, Ya.; Kityk, A. V.

    2018-01-01

    Paper reports the synthesis and spectroscopic studies of two novel 1-Methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoxaline (PQX) derivatives with 6-substituted methyl (MeMPPQX) or methoxy (MeOMPPQX) side groups. The optical absorption and fluorescence emission spectra are recorded in solvents of different polarity. Steady state and time-resolved spectroscopy provide photophysical characterization of MeMPPQX and MeOMPPQX dyes as materials for potential luminescence or electroluminescence applications. Measured optical absorption and fluorescence emission spectra are compared with quantum-chemical DFT/TDDFT calculations using long-range corrected xc-functionals, LRC-BLYP and CAM-B3LYP in combination with self-consistent reaction field model based on linear response (LR), state specific (SS) or corrected linear response (CLR) solvations. Performances of relevant theoretical models and approaches are compared. The reparameterized LRC-BLYP functional (ω = 0.231 Bohr-1) in combination with CLR solvation provides most accurate prediction of both excitation and emission energies. The MeMPPQX and MeOMPPQX dyes represent efficient fluorescence emitters in blue-green region of the visible spectra.

  14. Alternating current conductivity and dielectrical properties of -5-sulfono-7-(4-x phenyl azo)-8-hydroxy quinoline derivatives

    Science.gov (United States)

    Zeyada, H. M.; El-Ghamaz, N. A.; Gaml, Eman A.

    2017-08-01

    The influence of NO2, CH3 and Cl substitutions on structure, dielectric constants and alternating current conductivity, σac, of -5-sulfono-7-(4-x phenyl azo)-8-hydroxy quinoline (SAHQ) ligands is investigated in the frequency range 1-100 kHz and in the temperature range 200-373 K. SAHQ-x; x = -NO2 or -CH3 or -Cl ligands have monoclinic crystal system with different lattice parameters and crystallite size depending on the substitutions. The thermal behavior of SAHQ-x depends on the substitution. The AC electrical conduction mechanism for (SAHQ- NO2) and (SAHQ- Cl) ligands are found to follow the correlated barrier hopping model (CBH). The parameters such as barrier height, hopping distance, density of states near Fermi level and relaxation time have been reported. Overlapping large polaron tunneling model has been applied for explaining conduction behavior of SAHQ-CH3 ligand. The hopping energy and the polaron radius have been determined.

  15. Effect of Solvent Additives on the Solution Aggregation of Phenyl-C61-Butyl Acid Methyl Ester (PCBM)

    KAUST Repository

    Tummala, Naga Rajesh

    2015-11-24

    High-boiling-point solvent additives, employed during the solution processing of active-layer formulations, impact the efficiency of bulk hetero-junction (BHJ) organic solar cells by influencing the morphological / topological features of the multicomponent thin film. Here, we aim at a better understanding of how these additives change the aggregation landscape in the casting solution prior to film deposition via a multi-scale computational study of the aggregation phenomena of phenyl-C61-butyric-acid methyl ester (PCBM) in various solutions. The energetic landscape of PCBM-solvent / solvent-additive intermolecular interactions is evaluated at the electronic-structure level through symmetry-adapted perturbation theory to determine the nature and strength of non-covalent forces important to aggregation. Molecular dynamics simulations highlight how the choice of solvent and solvent additives control the formation of molecular aggregates. Our results indicate that high-boiling-point solvent additives change the effective interactions among the PCBM and casting-solvent molecules and alter the equilibrium PCBM aggregate sizes in solution.

  16. Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea

    Directory of Open Access Journals (Sweden)

    Chunhui Liu

    2016-06-01

    Full Text Available Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22 were synthesized, and their structures were confirmed by 1H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA, and compound III-3 on potato dextrose agar (PDA indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM and transmission electron micrography (TEM were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

  17. 3′-(4-Chlorophenyl-4′-phenyl-3H,4′H-spiro[benzo[b]thiophene-2,5′-isoxazol]-3-one

    Directory of Open Access Journals (Sweden)

    Mohamed Bakhouch

    2017-05-01

    Full Text Available The molecule of the title compound, C22H14ClNO2S, is built up from an isoxazole ring linked to a benzothiophene ring system with additional phenyl and 4-chlorophenyl substituents. The benzothiophene system is virtually planar with the largest deviation from the mean plane being 0.041 (2 Å, while the isoxazole ring adopts an envelope conformation. The plane of the benzothiophene ring system is almost perpendicular to those of the phenyl and the 4-chlorophenyl rings, with dihedral angles of 64.76 (10 and 82.81 (10°, respectively, between them. The phenyl ring is inclined by 85.76 (12° to the plane of the 4-chlorophenyl ring, which in turn lies close to the plane of the isoxazole ring. In the crystal, molecules are linked by weak C—H...O hydrogen bonds and offset π–π interactions between the aromatic rings of adjacent benzothiophene ring systems. These combine to form a three-dimensional network structure.

  18. Crystal structure of {2,6-bis[(dimethylaminomethyl]phenyl-κ3N,C1,N′}(bromido/chloridomercury(II

    Directory of Open Access Journals (Sweden)

    Anand Gupta

    2017-11-01

    Full Text Available In the molecular structure of the title compound, {2,6-bis[(dimethylaminomethyl]phenyl-κ3N,C1,N′}[bromido/chlorido(0.30/0.70]mercury(II–{2,6-bis[(dimethylaminomethyl]phenyl-κ3N,C1,N′}[bromido/chlorido(0.24/0.76]mercury(II (1/1, [HgBr0.30Cl0.70(C12H19N2]·[HgBr0.24Cl0.76(C12H19N2], there are two molecules in the asymmetric unit of formula LHgX {L = 2,6-bis[(dimethylaminomethyl]phenyl and X = Cl/Br}. In each molecule, the halide site is mixed Cl/Br, with occupancies of 0.699 (7:0.301 (7 and 0.763 (7:0.237 (7, respectively. The two molecules are linked into dimers by a combination of Hg...Hg [Hg...Hg = 3.6153 (3 Å] and C—H...Cl and C—H...π interactions.

  19. Oxidation of phenyl and hydride ligands of bis(pentamethylcyclopentadienyl)hafnium derivatives by nitrous oxide via selective oxygen atom transfer reactions: insights from quantum chemistry calculations.

    Science.gov (United States)

    Xie, Hujun; Liu, Chengcheng; Yuan, Ying; Zhou, Tao; Fan, Ting; Lei, Qunfang; Fang, Wenjun

    2016-01-21

    The mechanisms for the oxidation of phenyl and hydride ligands of bis(pentamethylcyclopentadienyl)hafnium derivatives (Cp* = η(5)-C5Me5) by nitrous oxide via selective oxygen atom transfer reactions have been systematically studied by means of density functional theory (DFT) calculations. On the basis of the calculations, we investigated the original mechanism proposed by Hillhouse and co-workers for the activation of N2O. The calculations showed that the complex with an initial O-coordination of N2O to the coordinatively unsaturated Hf center is not a local minimum. Then we proposed a new reaction mechanism to investigate how N2O is activated and why N2O selectively oxidize phenyl and hydride ligands of . Frontier molecular orbital theory analysis indicates that N2O is activated by nucleophilic attack by the phenyl or hydride ligand. Present calculations provide new insights into the activation of N2O involving the direct oxygen atom transfer from nitrous oxide to metal-ligand bonds instead of the generally observed oxygen abstraction reaction to generate metal-oxo species.

  20. Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent.

    Science.gov (United States)

    Radulović, Niko S; Mladenović, Marko Z; Stojanović-Radić, Zorica; Bogdanović, Goran A; Stevanović, Dragana; Vukićević, Rastko D

    2014-08-01

    A library of 16 2-substituted methyl acetoacetates containing ferrocenyl or phenyl units was designed to disclose differences in the antimicrobial activity of ferrocene-containing compounds and their phenyl analogs. Two methyl acetoacetates, whose structures do not contain an aromatic nucleus, were also included in order to probe the inherent activity of the scaffold itself. The acetoacetates were synthesized (low-to-good yields) and fully characterized by spectral (MS, IR, UV-Vis, 1D and 2D NMR) and electrochemical (cyclic voltammetry) techniques. Single-crystal X-ray analysis has been performed for methyl 2-acetyl-2-(ferrocenylmethyl)-5-methylhex-4-enoate. All compounds have demonstrated in vitro antimicrobial activity against six bacterial (three Gram-positive and three Gram-negative) and two fungal strains with minimal inhibitory concentration values of 0.0050-20.6 μmol mL(-1). The most active compound was 2-acetyl-2-(ferrocenylmethyl)-4-methylpent-4-enoate whose activity was comparable to that of nystatin against the yeast Candida albicans. Agglomerative hierarchical clustering statistical analysis of the antimicrobial assay data demonstrated that ferrocene-containing compounds have statistically different and greater antimicrobial activity when compared to their phenyl analogs.

  1. Study on the metabolism of 15 p-131iodine phenyl pentadecanoic acid [p-iodine phenyl pentadecanoic acid] as a tracer of free fatty acids in comparison to 1-14C-palmitic acid (C-palmitic acid)

    International Nuclear Information System (INIS)

    Sauer, J.W.

    1986-01-01

    In an animal experiment under identical metabolic influences the metabolism of a new radiopharmaceutical, 15 p- 131 iodine phenyl pentadecanoic acid (IPPA), was compared to the marked physiological fatty acid, 1- 14 C-palmitic acid (PA). The pharmacological kinetics of both tracers in tissues with widely varied turnover rates of fatty acids (heart, lung, liver, kidney, spleen, small intestine, skeletal muscle) was studied. By alkali extraction of the tissue lipids and then a chromatographic separation of the lipid fractions quantitatively comparable statements about the metabolism of PA and IPPA were made possible. The analyses of autoradiographs of the chromatographically separated lipids show a qualitatively congruous assimilation of both markers in the major lipid fractions. The quantitative evaluation shows minor differences as a result of a preferred assimilation of IPPA in triglycerides and of PA in phospholipids. The fractionated separation of tissue lipids which had been marked with PA and IPPA in vivo agrees very well with values which have been determined by other authors using 14 C- or 3 H-marked fatty acids. The close correlation of the tissue-specific metabolism kinetics of both markers makes it clear that both fatty acids are metabolized by similar, respectively, primarily identical metabolic pathyways. In conclusion, this study makes clear the extensive congruence of the metabolism kinetics of IPPA and the kinetics of the physiological palmitic acid. As a result of the presented results of the γ-radiating radiopharmaceutical IPPA as a free fatty acid analog new possibilities for the non-invasive external comprehension of lipid metabolism are opened up, whose use especially in the diagnostic of heart diseases promises success. (orig./MG) [de

  2. Evaluation of the potential application of 2-acetylpyridine N4- phenyl thiosemicarbazones derivatives for cancer therapy and diagnosis

    International Nuclear Information System (INIS)

    Soares, Marcella Araugio

    2013-01-01

    Despite the wide range of antineoplastic agents available, resistance of some types of cancer and toxicity to normal cells have been identified as the main causes of treatment failure and death. The lack of early and precise diagnosis is also responsible for reducing survival of cancer patients. In this context, the development of substances with low toxicity and therapeutic potential and/or diagnosis purpose, is the major tool in an attempt to increase the survival of patients and assure the safety and efficacy of treatment. Thiosemicarbazones (TSC) are a class of synthetic compounds that have several biological activities, including antitumor. Although several studies have shown the great potential of TSC as therapeutic and / or diagnostic agents, different chemical modifications performed on this class of molecules indicate new possibilities for applications and still require further studies. The objective of this study was to evaluate the potential applicability of 2-acetylpyridine N-4-phenyl thiosemicarbazones derivatives for cancer therapy and diagnosis. The results showed that all 13 TSC tested were cytotoxic to breast and glioblastoma tumor cell lines, presenting higher in vitro antitumor activity than etoposide, an antineoplastic and inhibitor of topoisomerase II frequently used for cancer therapy. The TSC that have halogen or nitro on ortho position showed higher antitumor activity in vitro than their isomers with halogen or nitro on meta or para position of the phenyl group. H2Ac4oFPh and H2Ac4oClPh compounds showed the highest antitumor activity among all tested compounds, with IC 50 in nanomolar order. These TSC induced cell death by apoptosis and oxidative stress was responsible, at least in part, for this type of cell death. The 5 mg.kg -1 H2Ac4oFPh dose, administered s.c., for 4 consecutive days, did not induce important toxicity; however, the same treatment protocol was not effective for tumor growth reduction in an animal model of brain tumor

  3. The pharmacology of 1-phenyl-2-propylamino-pentane (PPAP), a deprenyl-derived new spectrum psychostimulant.

    Science.gov (United States)

    Knoll, J; Knoll, B; Török, Z; Timár, J; Yasar, S

    1992-01-01

    The peculiar tyramine uptake inhibitory effect of (-)deprenyl prompted structure-activity relationship studies aiming to develop new spectrum central nervous system stimulants which are devoid of MAO inhibitory potency and operate de facto as indirectly acting, nonreleasing sympathomimetics. Of the derivatives synthesized for this purpose, 1-phenyl-2-propylaminopentane (PPAP) was selected as the reference substance and its pharmacological spectrum is presented. PPAP is taken up by the catecholamine axon terminal membrane and the vesicular membrane but it is devoid of catecholamine-releasing property. As a result, PPAP is, by interference, a potent inhibitor of the uptake of indirectly acting sympathomimetic releasers and of the catecholamine transmitters. This was proved, on the one hand, by measuring the uptake of [14C]PPAP into the catecholaminergic axon terminals and the inhibition of the uptake of [3H]noradrenaline and [3H]dopamine by PPAP in the rat brain, and, on the other hand, on the pulmonary artery strip of the rabbit and, in vivo, using the rat nictitating membrane as a detector. PPAP increases motility at 2 mg/kg and, in contrast to amphetamine, inhibits it at very high doses (50 mg/kg) only. A two-sided antagonism in the motility-increasing effect between PPAP and amphetamine and, more pronounced, between PPAP and mazindol was detected. PPAP is substantially less effective in inducing stereotyped behavior than either amphetamine or methamphetamine. PPAP facilitates learning and retention, is highly potent in antagonizing the tetrabenazine-induced depression in behavioral tests and is very effective in the forced swimming test. Whereas amphetamines facilitate performance in a very narrow range of low doses, which turns, at a modest elevation of the dose, into the opposite effect, PPAP improves performance within a reasonably broad dose range. Based on the peculiar pharmacological profile of PPAP, its potential usefulness in depression, in Alzheimer

  4. Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives.

    Science.gov (United States)

    Kim, Do Hyun; Kim, Su Jeong; Ullah, Sultan; Yun, Hwi Young; Chun, Pusoon; Moon, Hyung Ryong

    2017-01-01

    The authors designed and synthesized 17 (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives to find a new chemical scaffold, showing excellent tyrosinase-inhibitory activity. Their tyrosinase-inhibitory activities were evaluated against mushroom tyrosinase at 50 μM, and five of the PDTM derivatives (PDTM3, PDTM7-PDTM9, and PDTM13) were found to inhibit mushroom tyrosinase more than kojic acid or arbutin, the positive controls. Of seventeen PDTMs, PDTM3 (half-maximal inhibitory concentration 13.94±1.76 μM), with a 2,4-dihydroxyphenyl moiety, exhibited greatest inhibitory effects (kojic acid half-maximal inhibitory concentration 18.86±2.14 μM). Interestingly, PDTM compounds with no hydroxyl group, PDTM7-PDTM9, also had stronger inhibitory activities than kojic acid. In silico studies of interactions between tyrosinase and the five PDTMs suggested their binding affinities were closely related to their tyrosinase-inhibitory activities. Cell-based experiments performed using B16F10 mouse-skin melanoma cells showed that PDTM3 effectively inhibited melanogenesis and cellular tyrosinase activity. A cell-viability study conducted using B16F10 cells indicated that the antimelanogenic effect of PDTM3 was not attributable to its cytotoxicity. Kinetic studies showed PDTM3 competitively inhibited tyrosinase, indicating binding to the tyrosinase-active site. We found that PDTM3 with a new chemical scaffold could be a promising candidate for skin-whitening agents, and that the 1,3-dithiolane ring could be used as a chemical scaffold for potent tyrosinase inhibition.

  5. Revealing charge carrier dynamics in squaraine:[6, 6]-phenyl-C 71-butyric acid methyl ester based organic solar cells

    Science.gov (United States)

    Rana, Aniket; Sharma, Chhavi; Prabhu, Deepak D.; Kumar, Mahesh; Karuvath, Yoosaf; Das, Suresh; Chand, Suresh; Singh, Rajiv K.

    2018-04-01

    Ultrafast charge carrier dynamics as well as the generation of polaron pair in squaraine (SQ) and squaraine:[6,6]-phenyl-C 71-butyric acid methyl ester (SQ:PCBM71) have been studied using ultrafast transient absorption spectroscopy (UTAS). The current study reveals that the pure SQ exhibits the creation of singlet and triplet states; however, incorporation of PCBM71 in SQ results in the formation of polaron pairs with ˜550ps lifetime, which in turn leads to the creation of free electrons in the device. We show that the considerable increment in monomolecular and bimolecular recombination in SQ:PCBM71 compared to pure SQ which describes the interfacial compatibility of SQ and PCBMC71 molecules. The present work not only provides the information about the carrier generation in SQ and SQ:PCBM71 but also gives the facts relating to the effect of PCBM71 mixing into the SQ which is very significant because the SQ has donor-acceptor-donor (D-A-D) structure and mixing one more acceptor can introduce more complex recombinations in the blend. These findings have been complimented by the charge transport study in the device using impedance spectroscopy. The various important transport parameters are transit time (τt), diffusion constant (Dn), global mobility (μ) and carrier lifetime (τr). The values of these parameters are 26.38 μs, 4.64x10-6 cm2s-1, 6.12x10-6 cm2V-1s-1 and 399 μs, respectively. To the best of our knowledge such study related to SQ is not present in the literature comprehensively.

  6. Complexes of palladium(II with 1-phenyl-1-hydroxymethylene bisphosphoniс acid and their antitumor activity

    Directory of Open Access Journals (Sweden)

    O. M. Kozachkova

    2017-02-01

    Full Text Available Complex formation of K2[PdCl4] with 1-phenyl-1-hydroxymethylene bisphosphonic acid (PhHMBP, H4L has been studied by pH potentiometry, electron and NMR spectroscopy. It was found that in aqueous solution with physiological concentration of chlorine anions (0.15 mol/l KCl, anionic complexes of the equimolar compositions [PdHLCl2]3- (lgβ = 24.51 (0.3 and [PdLCl2]4- (lgβ = 20.74 (0.02 are formed. In the first coordination sphere palladium was surrounded by two oxygen atoms of two phosphonic groups of the bidentately coordinated ligand with closure of six-membered [O, O] ring, and two chlorine anions. The formation of palladium(II equimolar complexes with PhHMBP and bidentate coordination of the ligand to the central metal cation was confirmed by 31P NMR spectroscopy. Cytotoxic activity (IC50 based on metal content of the synthesized Pd(II complexes with PhHMBP against human MG-63 osteosarcoma and MCF-7 mammary tumor cells was compared with cisplatin on in vitro models. It was established that cytotoxic activity of the Pd complexes was lower than that of cisplatin. The acute toxicity (LD50 based on metal content of solutions of Pd(II complexes with PhHMBP was found to be lower compared to cisplatin. It was shown that the use of solutions of palladium(II complexes with PhHMBP inhibited tumor growth in mice with sarcoma 180.

  7. Preparation of N-1 -naphthyl benzo- and N-phenyl benzo hydroxamic acids and study of their extractability towards Fe (III), Cr (VI) and U (VI)

    International Nuclear Information System (INIS)

    Mohamed, Eltoum Elnour

    1997-12-01

    Two aryl hydroxamic acids were prepared; The N-phenyl benzo hydroxamic acid and the N-1- naphthyl benzohydroxamic acid the first one was prepared by the partial reduction of nitrobenzene to the β-phenyl hydroxylamine and coupling the latter with benzyl chloride. The reduction was carried out using ammonium chloride and zinc dust; this pair failed after so many attempts to give the N-1- naphthyl hydroxylamine. So the latter was prepared by using a somewhat milder reducing agent; hydrogen sulphide and ammonia gas in absolute alcohol. The two acids were obtained using the modified procedure of Tandon coupling the hydroxylamine with benzoyl chloride. The two acids were characterized by their melting points, elemental analysis, their I.R functional group frequencies and by their characteristic colour tests with vanadium (VI) and Iron (III). The acids were used for the extraction and spectrophotometric determination for iron (III), Chromium (VI), and Uranium (VI) from different molar solution, PH and from synthetic sea water. The maximum recovery of iron (III) occurred at PH 4 and PH 5 giving 92.25 and 91.25% when using N-1-naphthyl benzo hydroxamic acid and a maximum recovery of 100% at PH 5 with other acid. The maximum recovery of Chromium (VI) occurred at 3MH 2 SO 4 of 97.50% when using N-1-naphthyl benzohydroxamic acid and a maximum of 94.25% at the same molar concentration with N-phenyl benzo hydroxamic acid. The maximum recovery for Uranium (VI) was occurred at PH 7 giving 100% when using N-1-naphthyl benzo hydroxamic acid and a maximum recovery of 85% at PH 7 and PH* with the other acid. The two reagents give sharp colour with both iron (III) and chromium (VI), so trials were carried out to compare the curves obtained with that of the original reagent i.e. Thiocynate and diphenylcarbazide, which give a smaller slope.(Author)

  8. High-Resolution Rovibrational Spectroscopy of Jet-Cooled Phenyl Radical: The ν19 Out-of-Phase Symmetric CH Stretch

    Science.gov (United States)

    Buckingham, Grant T.; Chang, Chih-Hsuan; Nesbitt, David J.

    2013-10-01

    Phenyl radical has been studied via sub-Doppler infrared spectroscopy in a slit supersonic discharge expansion source, with assignments for the highest frequency b2 out-of-phase C-H symmetric stretch vibration (-19) unambiguously confirmed by ≤6 MHz (0.0002 cm-1) agreement with microwave ground state combination differences of McMahon et al. [Astrophys. J. 2003, 590, L61-64]. Least squares analysis of over 100 resolved rovibrational peaks in the sub-Doppler spectrum to a Watson Hamiltonian yields precision excited-state rotational constants and a vibrational band origin (-0 = 3071.8915(4) cm-1) consistent with a surprisingly small red-shift (0.9 cm-1) with respect to Ar matrix isolation studies of Ellison and co-workers [J. Am. Chem. Soc. 2001, 123, 1977]. Nuclear spin weights and inertial defects confirm the vibrationally averaged planarity and 2A1 rovibronic symmetry of phenyl radical, with analysis of the rotational constants consistent with a modest C2v distortion of the carbon backbone frame due to partial sp rehybridization of the σ C radical-center. Most importantly, despite the number of atoms (N = 11) and vibrational modes (3N - 6 = 27), phenyl radical exhibits a remarkably clean jet cooled high-resolution IR spectrum that shows no evidence of intramolecular vibrational relaxation (IVR) phenomena such as local or nonlocal perturbations due to strongly coupled nearby dark states. This provides strong support for the feasibility of high-resolution infrared spectroscopy in other aromatic hydrocarbon radical systems.

  9. High Resolution Rovibrational Spectroscopy of Jet-Cooled Phenyl Radical: the ν_{19} Out-Of Symmetric C-H Stretch

    Science.gov (United States)

    Buckingham, Grant T.; Chang, Chih-Hsuan; Nesbitt, David J.

    2013-06-01

    Phenyl radical has been studied via sub-Doppler infrared spectroscopy in a slit supersonic discharge expansion source, with assignments for the highest frequency b_{2} out-of-phase C-H symmetric stretch vibration (ν_{19}) unambiguously confirmed by ≤ 6 MHz (0.0002 cm^{-1}) agreement with microwave ground state combination differences of McMahon et al. [Astrophys. J. 590, L61-64 (2003)]. Least squares analysis of > 100 resolved rovibrational peaks in the sub-Doppler spectrum to a Watson Hamiltonian yields precision exited-state rotational constants and a vibrational band origin (ν_{0} = 3071.8915(4) cm^{-1}) consistent with a surprisingly small red-shift (0.9 cm^{-1}) with respect to Ar matrix isolation studies of Ellison and coworkers [J. Am. Chem. Soc. 123, 1977 (2001)]. Nuclear spin weights and inertial defects confirm the vibrationally averaged planarity and ^{2}A_{1} rovibronic symmetry of phenyl radical, with analysis of the rotational constants consistent with a modest C_{2v} distortion of the carbon backbone frame due to partial sp rehybridization of the σ C radical-center. Most importantly, despite the number of atoms (N = 11) and vibrational modes (3N-6 = 27), phenyl radical exhibits a remarkably clean jet cooled high resolution IR spectrum that shows no evidence of intramolecular vibrational relaxation (IVR) phenomena such as local or non-local perturbations due to strongly coupled nearby dark states. This provides strong support for the feasibility of high resolution infrared spectroscopy in other cyclic aromatic hydrocarbon radical systems.

  10. Novel 2-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,3,4-oxadiazole and 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole derivatives as dengue virus inhibitors targeting NS5 polymerase.

    Science.gov (United States)

    Benmansour, Fatiha; Eydoux, Cécilia; Querat, Gilles; de Lamballerie, Xavier; Canard, Bruno; Alvarez, Karine; Guillemot, Jean-Claude; Barral, Karine

    2016-02-15

    Using a functional high-throughput screening (HTS) and subsequent SAR studies, we have discovered a novel series of non-nucleoside dengue viral polymerase inhibitors. We report the elaboration of SAR around hit compound 1 as well as the synthesis and antiviral evaluation of 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole and 5-phenyl-2-[2-(2-thienyl)ethenyl]-1,3,4-oxadiazole analogues derived from a rapid and easily accessible chemical pathway. A large number of compounds prepared by this method were shown to possess in vitro activity against the polymerase of dengue virus. The most potent inhibitors were tested against Dengue virus clinical isolates on infected cells model and exhibit submicromolar activity on the four dengue virus serotypes. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  11. A computational study of pyrolysis reactions of lignin model compounds

    Science.gov (United States)

    Thomas Elder

    2010-01-01

    Enthalpies of reaction for the initial steps in the pyrolysis of lignin have been evaluated at the CBS-4m level of theory using fully substituted b-O-4 dilignols. Values for competing unimolecular decomposition reactions are consistent with results previously published for phenethyl phenyl ether models, but with lowered selectivity. Chain propagating reactions of free...

  12. Synthesis and anticonvulsant activity of Schiff’s bases of 3-{[2-({(E-[(substituted phenyl] methylidene} amino ethyl] amino} quinoxalin-2(1H-one

    Directory of Open Access Journals (Sweden)

    Ratnadeep V. Ghadage

    2011-06-01

    Full Text Available In an effort to develop potent anticonvulsant agents, we have synthesized some novel schiff’s bases of 3-{[2-({(E-[substituted phenyl] methylidene} amino ethyl] amino} quinoxalin-2(1H-one and evaluated for in vivo anticonvulsant activity. All the compounds were characterized by IR, 1H NMR data. This activity was carried out on pentylenetetrazole-induced seizure model. Compounds (IIIb and (IIIc Showed maximum time for straub tail and clonic convulsions. That means they possess good activity compared with standard. Animals treated with compounds (IIIb and (IIIe were recovered from this activity.

  13. catena-Poly[[(5-phenyl-2,2′-bipyridine-κ2N,N′copper(I]-μ-thiocyanido-κ2N:S

    Directory of Open Access Journals (Sweden)

    Shuxin Cui

    2012-02-01

    Full Text Available The title compound, [Cu(NCS(C16H12N2]n, was synthesised under hydrothermal conditions. The CuI ion shows distorted tetrahedral geometry being coordinated by two N atoms from a 5-phenyl-2,2′-bipyridine ligand and by the N and S atoms from two different thiocyanate anions. The CuI ions are bridged by thiocyanide groups, forming a one-dimensional coordination polymer along the b axis. The crystal packing is through van der Waals contacts and C—H...π interactions.

  14. (2E-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl-1-(2,5-dimethyl-3-thienylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Salman A. Khan

    2010-04-01

    Full Text Available The title compound, (2E-3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl-1-(2,5-dimethyl-3-thienylprop-2-en-1-one (3 was synthesized in high yield by aldol condensation of 3-acetyl-2,5-dimethylthiophene and 3,5-dimethyl-1-phenylpyrazole-4-carboxaldehyde in ethanolic NaOH at room temperature. Its structure was fully characterized by elemental analysis, IR, 1H NMR, 13C NMR and EI-MS spectral analysis.

  15. Synthesis, crystal structures and spectral properties of 6'-phenyl-2,2'-bipyridine derivatives and their CdLI(2) complexes.

    Science.gov (United States)

    Zhao, Xuesong; Chen, Yanxin; Luo, Junshan; Wang, Hui; Li, Shengli; Zhou, Hongping; Wu, Jieying; Tian, Yupeng

    2014-04-05

    Two novel 6'-phenyl-2,2'-bipyridine ligands (L1, L2) and their CdL(1,2)I2 complexes (1, 2) were synthesized and characterized by elemental analysis, (1)H NMR, IR, MALDI-TOF spectroscopy, and single crystal X-ray diffraction analysis. The results reveal that the central cadmium(II) atom in the complexes was coordinated by two iodide ions and two nitrogen atoms from L1, L2, forming a distorted coordination geometry. The electronic absorption properties of them were investigated on the basis of theoretical calculations (TD-DFT). Copyright © 2013 Elsevier B.V. All rights reserved.

  16. Crystal structures and hydrogen bonding in the isotypic series of hydrated alkali metal (K, Rb and Cs) complexes with 4-amino-phenyl-arsonic acid.

    Science.gov (United States)

    Smith, Graham; Wermuth, Urs D

    2017-02-01

    The structures of the alkali metal (K, Rb and Cs) complex salts with 4-amino-phenyl-arsonic acid ( p -arsanilic acid) manifest an isotypic series with the general formula [ M 2 (C 6 H 7 AsNO 3 ) 2 (H 2 O) 3 ], with M = K {poly[di-μ 3 -4-amino-phenyl-arsonato-tri-μ 2 -aqua-dipotassium], [K 2 (C 6 H 7 AsNO 3 ) 2 (H 2 O) 3 ], (I)}, Rb {poly[di-μ 3 -4-amino-phenyl-arsonato-tri-μ 2 -aqua-dirubidium], [Rb 2 (C 6 H 7 AsNO 3 ) 2 (H 2 O) 3 ], (II)}, and Cs {poly[di-μ 3 -4-amino-phenyl-arsonato-tri-μ 2 -aqua-dirubidium], [Cs 2 (C 6 H 7 AsNO 3 ) 2 (H 2 O) 3 ], (III)}, in which the repeating structural units lie across crystallographic mirror planes containing two independent and different metal cations and a bridging water mol-ecule, with the two hydrogen p -arsanilate ligands and the second water mol-ecule lying outside the mirror plane. The bonding about the two metal cations in all complexes is similar, one five-coordinate, the other progressing from five-coordinate in (I) to eight-coordinate in both (II) and (III), with overall M -O bond-length ranges of 2.694 (5)-3.009 (7) (K), 2.818 (4)-3.246 (4) (Rb) and 2.961 (9)-3.400 (10) Å (Cs). The additional three bonds in (II) and (III) are the result of inter-metal bridging through the water ligands. Two-dimensional coordination polymeric structures with the layers lying parallel to (100) are generated through a number of bridging bonds involving the water mol-ecules (including hydrogen-bonding inter-actions), as well as through the arsanilate O atoms. These layers are linked across [100] through amine N-H⋯O hydrogen bonds to arsonate and water O-atom acceptors, giving overall three-dimensional network structures.

  17. Crystal structures and hydrogen bonding in the isotypic series of hydrated alkali metal (K, Rb and Cs) complexes with 4-amino­phenyl­arsonic acid

    Science.gov (United States)

    Smith, Graham; Wermuth, Urs D.

    2017-01-01

    The structures of the alkali metal (K, Rb and Cs) complex salts with 4-amino­phenyl­arsonic acid (p-arsanilic acid) manifest an isotypic series with the general formula [M 2(C6H7AsNO3)2(H2O)3], with M = K {poly[di-μ3-4-amino­phenyl­arsonato-tri-μ2-aqua-dipotassium], [K2(C6H7AsNO3)2(H2O)3], (I)}, Rb {poly[di-μ3-4-amino­phenyl­arsonato-tri-μ2-aqua-dirubidium], [Rb2(C6H7AsNO3)2(H2O)3], (II)}, and Cs {poly[di-μ3-4-amino­phenyl­arsonato-tri-μ2-aqua-dirubidium], [Cs2(C6H7AsNO3)2(H2O)3], (III)}, in which the repeating structural units lie across crystallographic mirror planes containing two independent and different metal cations and a bridging water mol­ecule, with the two hydrogen p-arsanilate ligands and the second water mol­ecule lying outside the mirror plane. The bonding about the two metal cations in all complexes is similar, one five-coordinate, the other progressing from five-coordinate in (I) to eight-coordinate in both (II) and (III), with overall M—O bond-length ranges of 2.694 (5)–3.009 (7) (K), 2.818 (4)–3.246 (4) (Rb) and 2.961 (9)–3.400 (10) Å (Cs). The additional three bonds in (II) and (III) are the result of inter-metal bridging through the water ligands. Two-dimensional coordination polymeric structures with the layers lying parallel to (100) are generated through a number of bridging bonds involving the water mol­ecules (including hydrogen-bonding inter­actions), as well as through the arsanilate O atoms. These layers are linked across [100] through amine N—H⋯O hydrogen bonds to arsonate and water O-atom acceptors, giving overall three-dimensional network structures. PMID:28217343

  18. Tris(1,10-phenanthroline-κ2N,N′zinc(II chloride 2-phenyl-4-selenazole-5-carboxylate decahydrate

    Directory of Open Access Journals (Sweden)

    Jin-Bei Shen

    2011-02-01

    Full Text Available The asymmetric unit of the title salt, [Zn(C12H8N23](C10H6NO2SeCl·10H2O, contains a [Zn(phen3]2+ cation (phen is 1,10-phenanthroline, uncoordinated chloride and 2-phenyl-4-selenazole-5-carboxylate anions and ten uncoordinated water molecules. The central ZnII ion is six-coordinated by six N atoms from three phen ligands in a distorted octahedral geometry. An extensive O—H...O, O—H...N and O—H...Cl hydrogen-bonding network stabilizes the crystal structure.

  19. N′-[(4Z-1-(3-Methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidenehexyl]benzenesulfonohydrazide

    Directory of Open Access Journals (Sweden)

    Nkechinyere N. Ukwueze

    2014-06-01

    Full Text Available In the title compound, C22H26N4O3S, the dihedral angle between the pyrazoloneand phenyl rings is 21.73 (4°. The benzensulfonohydrazide group adopts a gauche conformation about the N—N vector. The C—N—N—S torsion angle is −109.88 (13°. The molecule exists as the enamine tautomeric form (C=C—NH. An intramolecular N—H...O=C hydrogen bond occurs. In the crystal, molecules are linked by pairs of N—H...O=C hydrogen bonds, forming centrosymmetric dimers.

  20. Electric field-induced hole injection-enhanced photoluminescence in a N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine-based emitter

    International Nuclear Information System (INIS)

    Xu-Xie Hui-Na; Li Wen-Bin; Peng Huan; He Yun; Yu Hao-Miao; Hou Xiao-Yuan

    2014-01-01

    Non-monotonic, asymmetrical electric field dependence of photoluminescence (PL) intensity is observed in a monolayer sample of tris-(8-hydroxyquinoline) aluminum (AlQ) doped N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine (TPD). A possible model is proposed: the charge separation from the dissociated photoexcited excitons causes energy band bending in the organic films and improves the hole injection from the electrode, which brings about the extra fluorescence. This mechanism is further verified by a series of experiments using a series of samples, variously featuring symmetrical electrodes, block layers, and hosts with lower hole mobilities. (condensed matter: electronic structure, electrical, magnetic, and optical properties)

  1. Spectrophotometric analysis of Cis-platin injection and Lead containing cosmetics using 2-acetylpyridine-4 - phenyl -3- thiosemicarbazone as complexing reagent

    International Nuclear Information System (INIS)

    Arain, G.M.; Laghari, A.J.; Khuhawar, M.Y.

    2003-01-01

    The reaction of reagent 2- acetylpyridine - 4 - phenyl -3 -thiosemicarbazone (APPT) was examined towards platinum (ii), gold (III), vanadium (V), ruthenium (IV), Tellurium (VI), arsenic (III) and lead (II) spectrophotometrically. The reaction were carried out in slightly acidic to neutral media and indicated molar absorptivity in range 9.6 x 10/sup 2/ to 2.2 x 10/sup 4/ L. mole/sup -1/ cm/sup -1/ between 370 to 435 nm. Each of the complex obeyed the beer's Law. The method was used for analysis of anticancer drug cis-platin and cosmetic (Surma) for the contents of platinum (II) and lead (II) respectively. (author)

  2. Synthesis, spectral characteristics, and the crystal and molecular structures of 2,3-dimethyl-1-phenyl-4-(N-phthalimido)pyrazolone-5

    International Nuclear Information System (INIS)

    Sokol, V. I.; Strashnova, S. B.; Kovalchukova, O. V.; Sergienko, V. S.; Davydov, V. V.; Zaitsev, B. E.; Evtushenko, Yu. M.

    2008-01-01

    2,3-Dimethyl-1-phenyl-4-(N-phthalimido)pyrazolone-5 (I) is synthesized and isolated in the form of single crystals. The crystal structure of compound I is determined using X-ray diffraction. The phthalimide and pyrazolone rings in the molecule are not coplanar: the angle between their median planes is 56.4 o . The bond lengths in the rings level off, which indicates the delocalization of the electron density. The spectral characteristics (IR and electronic spectra) of molecule I are determined.

  3. Solution-processable polymer solar cells from a poly(3-hexylthiophene)/[6,6]-phenyl C61-butyric acidmethyl ester concentration graded bilayers

    International Nuclear Information System (INIS)

    Wang, Dong Hwan; Lee, Hang Ken; Park, O Ok; Choi, Dae-Geun; Park, Jong Hyeok

    2009-01-01

    Polymer photovoltaic (PV) device prepared with a vertical phase separation has intensified the research on the effectiveness of the concentration graded active layer. In this paper, a polymer PV device with a poly(3-hexylthiophene)/[6,6]-phenyl C 61 -butyric acidmethyl ester (P3HT/PCBM) bilayers active film with a concentration gradient has been fabricated via solution process. The concentration variation has been confirmed by the Auger spectroscopy. The devices showed an enhanced photocurrent density and power conversion efficiency compared to those of the bulk heterojunction PV prepared under the same fabrication condition.

  4. Synthesis and antiestrogenic activity of [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)ethoxy]-phenyl]methanone, methanesulfonic acid salt.

    Science.gov (United States)

    Jones, C D; Suarez, T; Massey, E H; Black, L J; Tinsley, F C

    1979-08-01

    Acylation of the sodio anion of beta-tetralone with phenyl anisoate, followed by a Grignard reaction of the resultant 4 with 4-methoxyphenylmagnesium bromide, gave rise to two novel dihydronaphthalene isomers 5 and 6. Regioselective demethylation of either 5 or 6 by NaSEt produced [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl](4-hydroxyphenyl)methanone (7). Etherification of the phenolic group of 7 by N-(2-chloroethyl)pyrrolidine and subsequent methanesulfonate salt formation provided [3,4-dihydro-2-(4-methoxyphenyl)-1-maphthalenyl

  5. Synthesis and Antifungal Activities of 5-(o-Hydroxy phenyl-2-[4'aryl-3'chloro-2'azetidinon-1-yl]-1,3,4-thiadiazole

    Directory of Open Access Journals (Sweden)

    Shiv K. Gupta

    2011-01-01

    Full Text Available New series of 5-(o-hydroxy phenyl-2-[4'aryl-3'chloro-2'azetidinon-1-yl]-1,3,4-thiadiazole have been synthesized and the structures of the new compounds were established on the basis of IR, 1H NMR spectral data. In vitro antifungal activity (MIC activity was evaluated and compared with standard drugs of ketoconazole. Compounds 3c in the series has shown interesting antifungal activity against both C. albicans and A. niger fungus. In the gratifying result, most of the compounds were found to have moderate antifungal activity.

  6. Aspartic protease inhibitory and nematocidal activity of phenyl-4-(2-phenylhydrazonohexahydrofuro[3,2-c]pyridazin-7-ol (Percival dianhydroosazone

    Directory of Open Access Journals (Sweden)

    El Sayed H. El Ashry

    2014-04-01

    Full Text Available We synthesized Phenyl-4-(2-phenylhydrazonohexahydrofuro[3,2-c]pyridazin-7-ol (compound 3. The structure compound 3 was elucidated with IR, 1H NMR, 13C NMR and EIMS spectra. Compound 3 showed potent inhibitory activity against aspartic proteases, human cathepsin D and Plasmodium falciparum plasmepsin-II with IC50 = 20 μM. Enzyme-inhibitor complexes were predicted to stabilize by electrostatic and hydrophobic interactions between the side chains of amino acid residues at the active center and compound 3. Moreover, compound 3 displayed good nematocidal activity against all developmental stages of C. elegans.

  7. Activation of human ether-a-go-go-related gene potassium channels by the diphenylurea 1,3-bis-(2-hydroxy-5-trifluoromethyl-phenyl)-urea (NS1643)

    DEFF Research Database (Denmark)

    Hansen, Rie Schultz; Diness, Thomas Goldin; Christ, Torsten

    2005-01-01

    increased both steady-state and tail current at all voltages tested. The EC(50) value for HERG channel activation was 10.5 microM. These results were reproduced on HERG channels expressed in mammalian human embryonic kidney 293 cells. In guinea pig cardiomyocytes, studied by patch clamp, application of 10......-a-go-go-related gene (ERG) potassium channels. We have developed the diphenylurea compound 1,3-bis-(2-hydroxy-5-trifluoromethyl-phenyl)-urea (NS1643) and tested whether this small organic molecule could increase the activity of human ERG (HERG) channels expressed heterologously. In Xenopus laevis oocytes, NS1643...

  8. The fragment ion C13H9O2 m/z 197 in the mass spectra of 2-(2'-R-phenyl)benzoic acids

    International Nuclear Information System (INIS)

    Gills, R.G.; Porter, Q.N.

    1990-01-01

    In the electron impact mass spectrum of 2-( ' -R-phenyl)benzoic acids where R = H, NO 2 , OCH 3 , COOH, or Br, and abundant fragment ion m/z 197 is formed by an ipso substitution in which R is expelled as a radical. The structure of the ion m/z 197 has been shown by collision-activated dissociation to be identical with that of the protonated molecule formed by methane chemical ionization of 6H-dibenzo[b,d]pyran-6-one. 11 refs., 1 fig., ills

  9. Plasma microbiome-modulated indole- and phenyl-derived metabolites associate with advanced atherosclerosis and postoperative outcomes.

    Science.gov (United States)

    Cason, Cori A; Dolan, Kyle T; Sharma, Gaurav; Tao, Ming; Kulkarni, Rohan; Helenowski, Irene B; Doane, Brendan M; Avram, Michael J; McDermott, Mary M; Chang, Eugene B; Ozaki, C Keith; Ho, Karen J

    2017-12-13

    Multiple studies have shown that gut microbes contribute to atherosclerosis, and there is mounting evidence that microbial metabolism of dietary nutrients influences pathophysiology. We hypothesized that indole- and phenyl-derived metabolites that originate solely or in part from bacterial sources would differ between patients with advanced atherosclerosis and age- and sex-matched controls without clinically apparent atherosclerosis. Plasma from the advanced atherosclerosis cohort (n = 100) was from patients who underwent carotid endarterectomy, open infrainguinal leg revascularization, or major leg amputation for critical limb ischemia. The controls (n = 22) were age- and sex-matched participants who had no peripheral arterial disease or history of stroke or myocardial infarction. Patients with chronic kidney disease were excluded. Metabolites and internal standards were measured using high-performance liquid chromatography and tandem mass spectrometry. Plasma metabolite concentrations differed significantly between the advanced atherosclerosis and control cohorts. After adjustment for traditional atherosclerosis risk factors, indole (odds ratio [OR], 0.84; 95% confidence interval [CI], 0.75-0.95; P = .004), tryptophan (OR, 999; P = .02) was positively associated. Furthermore, tryptophan and indole-3-propionic acid concentrations (Spearman coefficients of 0.63 and 0.56, respectively; P < .001) correlated with the ankle-brachial index, a surrogate for overall atherosclerotic disease burden. Fourteen patients experienced a major postoperative cardiac complication within 30 days in the advanced atherosclerosis cohort, which was associated with baseline kynurenine/tryptophan ratio (P = .001) and hippuric acid (P = .03). In a multivariate analysis, only the kynurenine/tryptophan ratio remained significantly associated with a postoperative cardiac complication (OR, 44.1; 95% CI, 3.3-587.1; P = .004). Twenty patients in the advanced atherosclerosis cohort

  10. Spectroscopic (FT-IR, FT-Raman, UV and NMR) investigation on 1-phenyl-2-nitropropene by quantum computational calculations.

    Science.gov (United States)

    Xavier, S; Periandy, S

    2015-01-01

    In this paper, the spectral analysis of 1-phenyl-2-nitropropene is carried out using the FTIR, FT Raman, FT NMR and UV-Vis spectra of the compound with the help of quantum mechanical computations using ab-initio and density functional theories. The FT-IR (4000-400 cm(-1)) and FT-Raman (4000-100 cm(-1)) spectra were recorded in solid phase, the (1)H and (13)C NMR spectra were recorded in CDCl3 solution phase and the UV-Vis (200-800 nm) spectrum was recorded in ethanol solution phase. The different conformers of the compound and their minimum energies are studied using B3LYP functional with 6-311+G(d,p) basis set and two stable conformers with lowest energy were identified and the same was used for further computations. The computed wavenumbers from different methods are scaled so as to agree with the experimental values and the scaling factors are reported. All the modes of vibrations are assigned and the structure the molecule is analyzed in terms of parameters like bond length, bond angle and dihedral angle predicted by both B3LYP and B3PW91 methods with 6-311+G(d,p) and 6-311++G(d,p) basis sets. The values of dipole moment (μ), polarizability (α) and hyperpolarizability (β) of the molecule are reported, using which the non-linear property of the molecule is discussed. The HOMO-LUMO mappings are reported which reveals the different charge transfer possibilities within the molecule. The isotropic chemical shifts predicted for (1)H and (13)C atoms using gauge invariant atomic orbital (GIAO) theory show good agreement with experimental shifts. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. The local reactivity of the molecule has been studied using the Fukui function. The thermodynamic properties (heat capacity, entropy and enthalpy) at different temperatures are also calculated. Copyright © 2015 Elsevier B.V. All rights reserved.

  11. Molecular modeling study of agglomeration of [6,6]-phenyl-C61-butyric acid methyl ester in solvents.

    Science.gov (United States)

    Mortuza, S M; Banerjee, Soumik

    2012-12-28

    The molecular interactions between solvent and nanoparticles during photoactive layer formation in organic photovoltaic (OPV) cells influence the morphology of the photoactive layer and hence determine the power conversion efficiency. Prediction of optimal synthesis parameters in OPVs, such as choice of solvent, processing temperature, and nanoparticle concentration, requires fundamental understanding of the mechanisms that govern the agglomeration of nanoparticles in solvents. In this study, we used molecular dynamics simulations to simulate a commonly used organic nanoparticle, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), in various solvents to correlate solvent-nanoparticle interactions with the size of the agglomerate structure of PCBM. We analyzed the effects of concentration of PCBM and operating temperature on the molecular rearrangement and agglomeration of PCBM in three solvents: (i) toluene, (ii) indane, and (iii) toluene-indane mixture. We evaluated the agglomeration behavior of PCBM by determining sizes of the largest clusters of PCBM and the corresponding size distributions. To obtain further insight into the agglomerate structure of PCBMs, we evaluated radial distribution functions (RDFs) and coordination numbers of the various moieties of PCBMs with respect to solvent atoms as well as with respect to that of other PCBMs. Our simulations demonstrate that PCBMs form larger clusters in toluene while they are relatively dispersed in indane, which indicates the greater solubility of PCBM in indane than in toluene. In toluene-indane mixture, PCBMs are clustered to a greater extent than in indane and less than that in toluene. To correlate agglomerate size to nanoparticle-solvent interactions, we also evaluated the potential of mean force (PMF) of the fullerene moiety of PCBM in toluene and indane. Our results also show that the cluster size of PCBM molecules increases with the increase of concentration of PCBM and the processing temperature. To

  12. Phenyl N-(2-methylphenylcarbamate

    Directory of Open Access Journals (Sweden)

    Durre Shahwar

    2009-07-01

    Full Text Available In the title compound, C14H13NO2, the aromatic rings attached to the O and N atoms make dihedral angles of 62.65 (9 and 38.28 (11°, respectively, with the central carbamate group. The benzene rings are oriented at a dihedral angle of 39.22 (10°. In the crystal, a very weak C—H...π interaction occurs.

  13. Phenyl N-phenylcarbamate

    Directory of Open Access Journals (Sweden)

    Durre Shahwar

    2009-06-01

    Full Text Available In the title compound, C13H11NO2, the aromatic rings are oriented at a dihedral angle of 42.52 (12°. The crystal structure is stabilized by intermolecular N—H...O hydrogen bonds, which form infinite one-dimensional polymeric chains extending along the a axis. C—H...π interactions between the aromatic rings are also present.

  14. 4-(Dimethylaminophenyl phenyl ketone

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2008-08-01

    Full Text Available In the crystal structure of the title compound, C15H15NO, the two benzene rings are twisted from each other by a dihedral angle of 47.97 (4°. The crystal structure is stabilized by weak intermolecular C—H...O and C—H...π interactions, and π–π interactions with a centroid–centroid distance of 3.8493 (5 Å are observed.

  15. (3- (trifluoromethyl)phenyl)

    Indian Academy of Sciences (India)

    Kirk K 2006 J. Fluor. Chem. 127 1013. 6. Sakairi K, Kogami M, Torii M, Makino M, Kataoka. D, Okamoto R, Miyazawa T, Inoue M, Takahashi N,. Harada S and Watanabe N 2012 Chem. Pharm. Bull. 60. 1093. 7. Parikh K and Joshi D 2013 Med. Chem. Res. 22 3688. 8. Amir M and Shikha K 2004 Eur. J. Med. Chem. 39. 535. 9.

  16. Synthesis and Anticancer Activities of 4-[(Halophenyldiazenyl]phenol and 4-[(Halophenyldiazenyl]phenyl Aspirinate Derivatives against Nasopharyngeal Cancer Cell Lines

    Directory of Open Access Journals (Sweden)

    Boon Kui Ho

    2017-01-01

    Full Text Available Aspirin and azo derivatives have been widely studied and have drawn considerable attention due to diverse biological activities. In this study, a series of 4-[(halophenyldiazenyl]phenyl aspirinate derivatives were synthesized from the reaction of aspirin with 4-[(halophenyldiazenyl]phenol via esterification, in the presence of DCC/DMAP in DCM with overall yield of 45–54%. 4-[(Halophenyldiazenyl]phenol was prepared prior to esterification from coupling reaction of aniline derivatives and phenol in basic solution. All compounds were characterized using elemental analysis, FTIR, and 1H and 13C NMR spectroscopies. All compounds were screened for their anticancer activities against nasopharyngeal cancer (NPC HK-1 cell lines and the viability of cultured cells was determined by MTS [3-(4,5-dimethylthiazol-2-yl-5-(3-carboxylmethoxylphenyl-2-(4-sulfophenyl-2H-tetrazolium]-based colorimetric assay. 4-[(E-(Fluorophenyldiazenyl]phenol showed the highest anticancer activity against NPC HK-1 cell lines compared to other synthesized compounds. 4-[(Halophenyldiazenyl]phenyl aspirinate showed low cytotoxicity against NPC HK-1 cell lines compared to 4-[(halophenyldiazenyl]phenol but better anticancer activity than aspirin alone.

  17. The thermal stability and pyrolysis mechanism of boron-containing phenolic resins: The effect of phenyl borates on the char formation

    Science.gov (United States)

    Wang, Shujuan; Wang, Yong; Bian, Cheng; Zhong, Yuhu; Jing, Xinli

    2015-03-01

    Boron-containing phenolic resin (BPR) is a kind of the ablative resins with high-performance. Due to the lack of the exact knowledge concerning the pyrolysis mechanism of BPR, its development and application are greatly impeded. In the present paper, the chemical structure of the cured BPR and its structural evolution at high temperatures are investigated to clarify the reason for the high char yield of BPR. The results indicate that the high char yield of BPR is mainly attributed to the phenyl borates formed during curing, which can block parts of phenolic hydroxyl groups, and effectively inhibit their thermal decomposition reaction. Boron oxide is formed on the surface of carbonization products by the cleavage of O-C bonds from phenyl borates via pyrolysis, which avoids the release of volatile carbon dioxide and reduces the development of micro-structural defects of carbonization products. Introducing boron into PR improves the graphitization degree and graphite crystallites of carbonization products, which promotes the formation of a more ordered glassy carbon during pyrolysis. This study provides a new vision for the understanding of the high char yield of BPR, which makes it possible to develop a new ablative resin through molecular design.

  18. ISOLATION OF NOVEL PARA-PENTYL PHENYL BENZOATE FROMMONDIA WHITEI. (HOOK.F.) SKEELS (PERIPLOCACEAE), ITS STRUCTURE, SYNTHESIS AND NEUROPHARMACOLOGICAL EVALUATION.

    Science.gov (United States)

    Bamigboye J, Taiwo; Josephine Y, Osasan; Olujide O, Olubiyi; A, Oyemitan Idris; Shakir A M, Atoyebi; Mark R J, Elsegood; Raymond C F, Jones

    2017-01-01

    Mondia whitei L. (Hook. F.) Skeels (Periplocaceae) is a medicinal plant used locally in managing pain, fever, loss of appetite and as aphrodiasc in the South-Western states of Nigeria. However, the fruit is consumed habitually in the South-Eastern states of Nigeria, leading to speculation that it may possess some central nervous system effect but which has not been scientifically investigated, hence this study. Fresh fruits of Mondia whitei were collected and identified by a taxonomist. They were chopped into small pieces and extracted with absolute ethanol. The crude extract was subjected to various chromatographic techniques to isolate a novel compound whose structure was elucidated from the analysis of the crystal data and by extensive use of spectroscopy. The structure was confirmed by synthesis. The compound was subjected to anxiolytic and sedative activity assay. Computational analysis of the receptor binding event of isolated compound at the gamma amino butyric acid A receptor was also evaluated. The structure of the compound was elucidated as para pentyl phenyl benzoate. The neuropharmacological evaluation of the compound indicated significant (pchlorpromazine, benzamidine, and is comparable with the affinity obtained for pentobarbitone and diazepam. These present data provide evidence for the role of para pentyl phenyl benzoate in the habitual consumption of the fruit as well as its central nervous system activities.

  19. Interception and characterization of catalyst species in rhodium bis(diazaphospholane)-catalyzed hydroformylation of octene, vinyl acetate, allyl cyanide, and 1-phenyl-1,3-butadiene.

    Science.gov (United States)

    Nelsen, Eleanor R; Brezny, Anna C; Landis, Clark R

    2015-11-11

    In the absence of H2, reaction of [Rh(H) (CO)2(BDP)] [BDP = bis(diazaphospholane)] with hydroformylation substrates vinyl acetate, allyl cyanide, 1-octene, and trans-1-phenyl-1,3-butadiene at low temperatures and pressures with passive mixing enables detailed NMR spectroscopic characterization of rhodium acyl and, in some cases, alkyl complexes of these substrates. For trans-1-phenyl-1,3-butadiene, the stable alkyl complex is an η(3)-allyl complex. Five-coordinate acyl dicarbonyl complexes appear to be thermodynamically preferred over the four-coordinate acyl monocarbonyls at low temperatures and one atmosphere of CO. Under noncatalytic (i.e., no H2 present) reaction conditions, NMR spectroscopy reveals the kinetic and thermodynamic selectivity of linear and branched acyl dicarbonyl formation. Over the range of substrates investigated, the kinetic regioselectivity observed at low temperatures under noncatalytic conditions roughly predicts the regioselectivity observed for catalytic transformations at higher temperatures and pressures. Thus, kinetic distributions of off-cycle acyl dicarbonyls constitute reasonable models for catalytic selectivity. The Wisconsin high-pressure NMR reactor (WiHP-NMRR) enables single-turnover experiments with active mixing; such experiments constitute a powerful strategy for elucidating the inherent selectivity of acyl formation and acyl hydrogenolysis in hydroformylation reactions.

  20. Dibenzyl({1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylmethyl]-1H-1,2,3-triazol-4-yl}methylamine

    Directory of Open Access Journals (Sweden)

    Salaheddine Boukhssas

    2017-06-01

    Full Text Available In the title compound, C28H29N5O, the molecule adopts an approximate U-shape, a conformation imposed at least in part by an intramolecular π–π contact between the two five-membered rings, which display a centroid-to-centroid separation of 3.6522 (7 Å. The planes of these rings are inclined to one another by 66.12 (5°. A weak intramolecular C—H...·N hydrogen bond is also found. The planes of the phenyl rings of the amine unit are inclined at a dihedral angle of 81.10 (4°, while that of the 4,5-dihydrooxazole ring makes an angle of 11.74 (8° with its phenyl substituent. The crystal packing is stabilized by C—H...N hydrogen bonds that form chains parallel to the b axis. Several C—H...π(ring contacts are also present.

  1. Eco-sustainable synthesis and biological evaluation of 2-phenyl 1,3-benzodioxole derivatives as anticancer, DNA binding and antibacterial agents

    Directory of Open Access Journals (Sweden)

    Sayan Dutta Gupta

    2016-11-01

    Full Text Available The current research and development scenario in medicinal chemistry demands small molecules synthesized in a simple, fast and effective way with enhanced activity and fewer side effects than the existing ones. Therefore, one-pot, microwave assisted green and efficient synthesis of a series of derivatives belonging to 2-phenyl 1,3-benzodioxole (1a–14a and 2-phenyl 1,3-benzodioxole-4-ol (1b–14b class were carried out and subsequently investigated for their anticancer, antibacterial and DNA binding potential. Compound 3c proved to be the most active one among the screened derivatives possessing anticancer and antibacterial potency greater than the standard reference compound (cisplatin and cinoxacin for anticancer and antibacterial activity, respectively. The most active compound in terms of DNA binding capacity was found to be 5b. A rewarding feature of the work is a facile, convenient, eco friendly one step synthesis of compounds demonstrating attenuated activity against cancer and bacterial cell with an inherent potential of binding to DNA. Subsequently, a hit molecule for further anticancer, antibacterial (compound 3c and DNA binding studies (compound 5b was also identified.

  2. 2-(Substituted phenyl-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

    Directory of Open Access Journals (Sweden)

    Xin-Juan Yang

    2013-08-01

    Full Text Available The title compounds are a class of structurally simple analogues of quaternary benzo[c]phenanthridine alkaloids (QBAs. In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenyl ring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 μg/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 2–12 exhibited excellent activities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC50 values of 8.88–19.88 µg/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha- and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal agrochemicals. Compounds 8 and 2 should have great potential as new broad spectrum antifungal agents for plant protection.

  3. Molecular modeling of the inhibition of enzyme PLA2 from snake venom by dipyrone and 1-phenyl-3-methyl-5-pyrazolone

    Science.gov (United States)

    Silva, S. L. Da; Comar, M., Jr.; Oliveira, K. M. T.; Chaar, J. S.; Bezerra, E. R. M.; Calgarotto, A. K.; Baldasso, P. A.; Veber, C. L.; Villar, J. A. F. P.; Oliveira, A. R. M.; Marangoni, S.

    Phospholipases A2 (PLA2) are enzymes that trigger the degradation cascade of the arachidonic acid, leading to the formation of pro-inflammatory eicosanoids. The selective inhibition of PLA2s is crucial in the search for a more efficient anti-inflammatory drug with fewer side effects than the drugs currently used. Hence, we studied the influences caused by two pyrazolonic inhibitors: dipyrone (DIP) and 1-phenyl-3-methyl-5-pyrazolone (PMP) on the kinetic behavior of PLA2 from Crotalus adamanteus venom. Molecular modeling results, by DFT and MM approaches, showed that DIP is strongly associated to the active site of PLA2 through three hydrogen bonds, whereas PMP is associated to the enzyme just through hydrophobic interactions. In addition, only PMP presents an intramolecular hydrogen bond that make difficult the formation of more efficient interactions with PLA2. These results help in the understanding of the experimental observations. Experimentally, the results showed that PLA2 from C. adamanteus present a typical Michaelian behavior. In addition, the calculated kinetic parameters showed that, in the presence of DIP or PMP, the maximum enzymatic velocity (VMAX) value was kept constant, whereas the Michaelis constant (KM) values increased and the inhibition constant (KI) decreased, indicating competitive inhibition. These results show that the phenyl-pyrazolonic structures might help in the development and design of new drugs able to selectively inhibit PLA2.

  4. Preparation and characterization of new poly(amide–imide reinforced layer silicate nanocomposite containing N,N′-pyrromellitoyl-bis-l-phenyl acetic acid

    Directory of Open Access Journals (Sweden)

    Khalil Faghihi

    2014-12-01

    Full Text Available Two new samples of poly(amide–imide/montmorillonite reinforced nanocomposites containing N,N′-pyrromellitoyl-bis-l-phenyl acetic acid moiety in the main chain were synthesized by a convenient solution intercalation technique. Poly(amide–imide (PAI 3 as a source of polymer matrix was synthesized by the direct polycondensation reaction of N,N′-pyrromelitoyl-bis-l-phenyl acetic acid 1 with 4,4′-diamino diphenyl ether 2 in the presence of triphenyl phosphite (TPP, CaCl2, pyridine and N-methyl-2-pyrrolidone (NMP. Morphology and structure of the resulting PAI-nanocomposite films 4a and 4b with 10% and 20% silicate particles were characterized by FTIR spectroscopy, X-ray diffraction (XRD and scanning electron microscopy (SEM. The effect of clay dispersion and the interaction between clay and polymeric chains on the properties of nanocomposite films were investigated by using UV–vis spectroscopy, thermogravimetric analysis (TGA and water uptake measurements.

  5. Radioiodinated fatty acid carnitine ester: synthesis and biodistribution of 15-(p-iodo(/sup 131/I)-phenyl)pentadecanoyl-D,L-carnitine chloride

    Energy Technology Data Exchange (ETDEWEB)

    Eisenhut, M.; Liefhold, J.

    After the uptake into heart muscle cells long chain fatty acids enter predominantly into the triglyceride and phospholipid pool before they are degraded in the mitochondria by ..beta..-oxidation. Therefore the formation of fatty acid esters with glycerine obscures the functional ability of the heart namely to catabolize free fatty acids. The sum of the two reaction pathways are visualized by sequential heart scintigraphy with e.g. /sup 131/I labeled 15-(p-iodo-phenyl)-pentadecanoic acid (IPPA). Before the fatty acids can be degraded by ..beta..-oxidation they are bound to carnitine for mitochondrial membrane transport. Thus IPPA would not participate in lipid formation, if it is offered as 15-(p-iodo(/sup 131/I)-phenyl)-pentadecanoyl-D,L-carnitine chloride (IPPA-CE) to the heart muscle cells. Additionally carnitine esters of fatty acids are known to be better substrates for ..beta..-oxidation than free fatty acids. We were therefore interested in the biochemical fate of radioiodinated IPPA-CE in rats.

  6. Synthesis and evaluation of technetium-99m monocationic mixed ligand complexes of phenyl substituted/condensed tetradentate Schiff's bases and trimethylphosphine

    International Nuclear Information System (INIS)

    Goomer, N.C.; Kulkarni, P.V.; Constantinescu, A.; Antich, P.; Parkey, R.W.; Corbett, J.R.

    1992-01-01

    Tc-99m monocationic mixed ligand complexes of phenyl substituted/condensed Schiff's bases, N,N'-ethylene-bis-(benzoylacetone imine) (L b ) or N,N'-ethylene-bis-(salicyladehyde imine) (L c ) or N,N'-ethylene-bis-(2-hydroxyacetophenone imine) (L d ) and trimethylphosphine were synthesized to determine the influence of the presence of a phenyl group in these tracers on their heart uptake in rats. A new formulation procedure using aq. β-hydroxypropylcyclodextrin (HPB) solution was developed for intravenous administration of nonpolar 99m Tc complexes. Comparison of biodistribution data for the reference 99m Tc complex from N,N'-ethylene-bis-(acetylacetone imine) and trimethylphosphine using HPB formulation and alternate formulation (0.9% saline) showed the same results. Biodistribution of the title 99m Tc complexes, [ 99m Tc L b (PMe 3 ) 2 ] + , [ 99m Tc L c (PME 3 ) 2 ] + and [ 99m Tc L d (PME 3 ) 2 + showed heart-to-blood activity ratios of 1.7, 2.1 and 1.7, respectively, at 15 min post-injection in rats. (Author)

  7. In Vitro Studies on a Microfluidic Sensor with Embedded Obstacles Using New Antibacterial Synthetic Compounds (1-TDPPO Mixed Prop-2-en-1-one with Difluoro Phenyl

    Directory of Open Access Journals (Sweden)

    Changhyun Roh

    2017-04-01

    Full Text Available This paper describes the use of an analytical microfluidic sensor for accelerating chemo-repellent response and strong anti-bacterial 1-(Thien-2-yl-3-(2, 6-difluoro phenyl prop-2-en-1-one (1-TDPPO. The chemically-synthesized antimicrobial agent, which included prop-2-en-1-one and difluoro phenyl groups, was moving through an optically transparent polydimethylsiloxane (PDMS microfluidic sensor with circular obstacles arranged evenly. The response, growth and distribution of fluorescent labeling Pseudomonas aeruginosa PAO1 against the antimicrobial agent were monitored by confocal laser scanning microscope (CLSM. The microfluidic sensor along with 1-TDPPOin this study exhibits the following advantages: (i Real-time chemo-repellent responses of cell dynamics; (ii Rapid eradication of biofilm by embedded obstacles and powerful antibacterial agents, which significantly reduce the response time compared to classical methods; (iii Minimal consumption of cells and antimicrobial agents; and (iv Simplifying the process of the normalization of the fluorescence intensity and monitoring of biofilm by captured images and datasets.

  8. Metabolism of aspirin and procaine in mice pretreated with O-4-nitrophenyl methyl(phenyl)phosphinate or O-4-nitrophenyl diphenylphosphinate

    International Nuclear Information System (INIS)

    Joly, J.M.; Brown, T.M.

    1986-01-01

    Concentrations of [carboxyl- 14 C]procaine in blood of mice were increased threefold for 27 min by exposure to O-4-nitrophenyl diphenylphosphinate 2 hr prior to [carboxyl- 14 C]procaine injection ip, while there was no effect of O-4-nitrophenyl methyl(phenyl)phosphinate pretreatment. There was no effect of either organophosphinate on the primary hydrolysis of [acetyl-l- 14 C]aspirin when assessed by the expiration of [ 14 C]carbon dioxide; however, O-4-nitrophenyl diphenylphosphinate pretreatment produced transient increases in blood concentrations of both [carboxyl- 14 C]aspirin and [carboxyl- 14 C]salicylic acid following administration of [carboxyl- 14 C]aspirin. Liver carboxylesterase activity in O-4-nitrophenyl diphenylphosphinate pretreated mice was 11% of control activity. These results indicate the potential for drug interaction with O-4-nitrophenyl diphenylphosphinate but not with O-4-nitrophenyl methyl(phenyl)phosphinate. It appears that liver carboxylesterase activity has a minor role in hydrolysis of aspirin in vivo, but may be more important in procaine metabolism

  9. Contrasting C- and O-Atom Reactivities of Neutral Ketone and Enolate Forms of 3-Sulfonyloxyimino-2-methyl-1-phenyl-1-butanones.

    Science.gov (United States)

    Ning, Yingtang; Otani, Yuko; Ohwada, Tomohiko

    2018-01-05

    The mechanisms of intramolecular cyclization of 3-sulfonyloxyimino-2-methyl-1-phenyl-1-butanones (1) under basic (DABCO and t-BuOK) and acidic (AcOH and TFA) conditions were investigated by means of experimental and computational methods. The ketone, enol, and enolate forms of 1 can afford different intramolecular cyclization products (2, 3, 4), depending on the conditions. The results of the reaction of 1 under basic conditions suggest intermediacy of neutral enol (DABCO) and anionic enolate (t-BuOK), while the results under acidic conditions (AcOH and TFA) indicate involvement of neutral ketones, which exhibit reactivities arising from both the oxygen lone-pair electrons (O atom reactivity) and carbon σ-electrons (C atom reactivity). The neutral enol in DABCO afforded 2H-azirine 4. On the other hand, the products (isoxazole 2 and oxazole 3) generated from the ketone form and from the enolate form are the same, but the reaction mechanisms are apparently different. The results demonstrate ambident-like reactivity of neutral ketone in the 3-sulfonyloxyimino-2-methyl-1-phenyl-1-butanone system.

  10. Anti-leishmanial and structure-activity relationship of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl-2-propen-1-one derivatives

    Directory of Open Access Journals (Sweden)

    Asunción Burguete

    2008-12-01

    Full Text Available A series of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl-2-propen-1-one derivatives were synthesized and tested for in vitro leishmanicidal activity against amastigotes of Leishmania amazonensis in axenical cultures and murine infected macrophages. Structure-activity relationships demonstrated the importance of a radical methoxy at position R3', R4' and R5'. (2E-3-(3,4,5-trimethoxy-phenyl-1-(3,6,7-trimethyl-1,4-dioxy-quinoxalin-2-yl-propenone was the most active. Cytotoxicity on macrophages revealed that this product was almost six times more active than toxic.

  11. (4S)-4-(3,4-Dichloro?phen?yl)-1?-methyl-4?-phenyl-3,4-dihydronaphthalene-2-spiro-3?-pyrrolidine-2?-spiro-1??-acenaphthyl?ene-1,2??(2H,1??H)-dione

    OpenAIRE

    Murugan, R.; Gunasekaran, B.; Narayanan, S. Sriman; Manivannan, V.

    2008-01-01

    In the title compound, C37H27Cl2NO2, the 3,4-dichloro?phenyl ring makes a dihedral angle of 46.66?(6)? with the phenyl ring. The mol?ecular structure is stabilized by weak intra?molecular C?H?O inter?actions and the crystal structure is stabilized by weak inter?molecular C?H?O inter?actions. The C?C?C?C?C five-membered ring is planar, while the C?C?C?C?N five-membered ring adopts a half-chair conformation.

  12. [A new phenethyl alcohol glycoside from Orobanche coerulescens].

    Science.gov (United States)

    Zhang, Qiang-Rong

    2017-03-01

    The constituents of the whole plant of Orobanche coerulescens were isolated and purified by using various column chromatographic techniques including D101, silica gel and ODS. The structures were identified by spectroscopic analyses including NMR and MS. A new phenylethanol glycoside was isolated from the whole plant of O. coerulescens, and was identified as 2-(3-methoxy-4-hydroxyphenyl)-ethanol-1-O- [(1→3)-O-α-L-rhamnopyranosyl-4, 6-O-di-feruloyl]-β-D-glucopyranoside, named as orobancheoside B. Through the antibacterial activity test, orobancheoside B was proved to have certain antibacterial activity, and be one of the main active components of O. coerulescens. The research result will laid a foundation for the medicinal materials and quality control research. Activity screening, broomrape orobancheoside B has certain antibacterial activity, as one of the main active components of O. coerulescens, and to constantly improve the quality of the medicinal materials laid a foundation. Copyright© by the Chinese Pharmaceutical Association.

  13. Effect of Betong Watercress and Phenethyl Isothiocyanate on N ...

    African Journals Online (AJOL)

    watercress once daily for five days, before receiving the same dose of CF as in phase I. Serum concentrations of CF and its ... International Pharmaceutical Abstract, Chemical Abstracts, Embase, Index Copernicus, EBSCO, African. Index Medicus ..... authors investigated the kinetics of a single dose administration of PEITC ...

  14. Chemistry of phosphorylmethyl isocyanides, 6 - Cis- and trans-2-(Isocyanomethyl)-5,5-dimethyl-2-oxo-4-phenyl-1,3,2-dioxaphosphorinane - Synthesis and structure of the first chiral isocyanomethylphosphonate synthons

    NARCIS (Netherlands)

    Weener, JW; Versleijen, JPG; Meetsma, A; ten Hoeve, W; van Leusen, A.M.

    Both cis-2-(isocyanomethyl)-5,5-dimethyl-2-oxo-4-phenyl-1,3,2-dioxaphosphorinane (1a) and the trans epimer 1b have been prepared as potentially useful chiral isocyanomethylphosphonate synthons. 2-Methoxy-1,3,2-dioxaphosphorinanes 5 and the corresponding 2-ethoxy analog 6 were prepared from

  15. Synthesis of Some New 2-(3-Aryl-1-phenyl-4-pyrazolyl-benzoxazoles Using Hypervalent Iodine Mediated Oxidative Cyclization of Schiff’s Bases

    Directory of Open Access Journals (Sweden)

    Ajay Kumar

    2006-01-01

    Full Text Available Ten new 2-(3-aryl-1-phenyl-4-pyrazolylbenzoxazoles have been synthesized by oxidative intramolecular cyclization of the corresponding Schiff’s bases using iodobenzene diacetate in methanol as an oxidant.

  16. Synthesis, crystal structure, and spectra of 3,3- dimethyl-1-N-(1'-phenyl-2',3'-dimethyl-5'-oxo-3'- pyrazolin-4'-yl)imino-1,2,3,4-tetrahydroisoquinoline

    International Nuclear Information System (INIS)

    Sokol, V.I.; Ryabov, M.A.; Merkur'eva, N.Yu.; Davydov, V.V.; Zaitsev, B.E.; Shklyaev, Yu.V.; Sergienko, V.S.; Zaitsev, B.E.

    1996-01-01

    The synthesis and the crystal and molecular structure of 3,3-dimethyl-1-N-(1'-phenyl-2',3'- dimethyl-5'-oxo-3'-pyrazolin-4'-yl)imino-1,2,3,4-tetrahydroisoquinoline are reported. As is evidenced by the 1H NMR, IR, and electron spectra, the tautomeric form of the compounds observed in the crystal is also retained in solutions

  17. KINETICS OF UNCATALYZED HYDROLYSIS OF 1-BENZOYL-3-PHENYL-1,2,4-TRIAZOLE AND P-METHOXYPHENYL DICHLOROETHANOATE IN AQUEOUS-SOLUTION CONTAINING UREAS, CARBOXAMIDES, SULFONAMIDES, SULFONES AND SULFOXIDES

    NARCIS (Netherlands)

    Kerstholt, René P V; Engberts, Jan B F N; Blandamer, Michael J

    Rate constants are reported for the hydrolysis of 1-benzoyl-3-phenyl-1,2,4-triazole and p-methoxyphenyl dichloroethanoate in aqueous solutions containing formamide, acetamide, propionamide, isobutyramide, N-methylformamide, N,N-dimethylformamide, n-butyramide, N-methylacetamide,

  18. Candida Rugosa Lipase-catalyzed Kinetic Resolution of 3-(Isobutyryloxy)methyl 4-[2-(Difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate

    NARCIS (Netherlands)

    Sobolev, A.; Zhalubovskis, R.; Franssen, M.C.R.; Vigante, B.; Chekavichus, B.; Duburs, G.; Groot, de Æ.

    2004-01-01

    The lipase-catalyzed kinetic resolution of 3-(isobutyryloxy)methyl 4-[2-(difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate has been performed. The most enantioselective reaction (E = 28) was transesterification with n-butanol in water-saturated toluene at

  19. Application of an octa-anionic 5,10,15,20-tetra[3,5-(nido-carboranylmethyl)phenyl]porphyrin (H2OCP) as dual sensitizer for BNCT and PDT

    Science.gov (United States)

    The applications of the octa-anionic 5,10,15,20-tetra[3,5-(nidocarboranylmethyl) phenyl]porphyrin (H2OCP) as a boron delivery agent in boron neutron capture therapy (BNCT) and a photosensitizer in photodynamic therapy (PDT) have been investigated. Using F98 Rat glioma cells, we evaluated the cytotox...

  20. Synthesis and Characterization of Ferroelectric Liquid Crystalline Organosiloxanes Containing 4-(4-undecanyloxy bi-phenyl-1-carboxyloxyphenyl (2S,3S-2-chloro-3-methylvalerate and 4-(4-undecanyloxybenzoyloxybiphenyl (2S,3S-2-chloro-3-methylvalerate

    Directory of Open Access Journals (Sweden)

    Chih-Hung Lin

    2013-10-01

    Full Text Available A series of new organosiloxane ferroelectric liquid crystalline (FLC materials have been synthesized, and their mesomorphic and physical properties have been characterized. Four new disiloxanes and trisiloxanes, containing biphenyl 4-hydroxybenzoate and phenyl 4-hydroxybiphenylcarboxylate as mesogenic units and eleven methylene unit as spacers and (2S,3S-2-chloro-3-methylvalerate unit as chiral end groups. The molecule, using three phenyl ring as a mesogenic unit, formulates much wider liquid crystalline phase temperature ranges than that of a two phenyl ring unit. The phenyl arrangement differences of mesogenic unit result in the greater differences of the liquid crystal phase formation. The siloxane molecule induction is helpful to the more regular smectic phase formation and smectic phase stabilization, such as chiral SC (SC* and SB phases. The siloxane molecule is helpful to reduce the phase transition temperature and broaden the liquid crystal temperature range of the SC* phase and, simultaneously, it will not induce chain crystallization phenomenon and dilute the Ps value. The synthesis and characterization of the new FLCs materials, which exhibit a room temperature SC* phase and higher spontaneous polarization are presented.

  1. Synthesis, characterization, and crystal structure of 2-amino-7-methyl-5-oxo-4-phenyl-4,5-dihydropyrano[3,2-c] pyran-3-carbonitrile

    Energy Technology Data Exchange (ETDEWEB)

    Sharma, S. [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics (India); Banerjee, B.; Brahmachari, G. [Visva-Bharati (a Central University), Laboratory of Natural Products & Organic Synthesis, Department of Chemistry (India); Kant, Rajni; Gupta, V. K., E-mail: vivek-gupta2k2@hotmail.com [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics (India)

    2015-12-15

    2-Amino-7-methyl-5-oxo-4-phenyl-4,5-dihydropyrano[3,2-c] pyran-3-carbonitrile, C{sub 16}H{sub 12}N{sub 2}O{sub 3} is synthesized via one-pot multi-component reaction at room temperature using commercially available urea as inexpensive and environmentally benign organo-catalyst. Its structure is determined by single-crystal X-ray diffraction technique The crystals are monoclinic, a = 10.7357(12), b = 8.7774(8), c = 15.0759(16) Å, β = 103.575(11)°, Z = 4, sp. gr. P2{sub 1}/n, R = 0.0551 for 1696 observed reflections. The crystal structure is stabilized by N–H···N, C–H···O, and C–H···π interactions.

  2. Study on the inhibition of mild steel corrosion by 1,3-bis-(morpholin-4-yl-phenyl-methyl-thiourea in hydrochloric acid medium

    Directory of Open Access Journals (Sweden)

    Devaraj Karthik

    2014-12-01

    Full Text Available 1,3-Bis-(morpholin-4-yl-phenyl-methyl-thiourea (MBT was synthesized and their influence on the inhibition of corrosion on mild steel in various hydrochloric acid concentrations has been investigated by weight loss, potentiodynamic polarization, electrochemical impedance (EI, Tafel polarization, scanning electron microscope (SEM and FT-IR methods. The result of weight loss study shows that the corrosion inhibition efficiency (IE is directly proportional to the concentration of the inhibitor and inversely proportional to the temperature. Electrochemical study proved that the inhibitor acts as a mixed type inhibitor. SEM shows the formation of a protective film of the inhibitor on the mild steel. The IR data also provide evidence for the anticorrosion effect of the inhibitor.

  3. Bis(4-acetyl-3-methyl-1-phenyl-1H-pyrazol-5-olato-κO,O')bis-(N,N-dimethyl-formamide-κO)nickel(II).

    Science.gov (United States)

    Zhu, Hualing; Wei, Zhen; Bu, Luxia; Xu, Xiaoping; Shi, Jun

    2010-07-10

    The title complex, [Ni(C(12)H(11)N(2)O(2))(2)(C(3)H(7)NO)(2)], lies on on an inversion center. The Ni(II) ion is coordinated in a slightly distorted octa-hedral coordination enviroment by four O atoms from two bis-chelating 4-acety-3-methyl-1-phenyl-1H-pyrazol-5-olate ligands in the equatorial plane and two O atoms from two N,N-dimethyl-formamide ligands in the axial sites. In the crystal structure, weak inter-molecular π-π stacking inter-actions with centroid-centroid distances of 3.7467 (13) Å link mol-ecules into chains extending alongthe b axis.

  4. Bis(2-ethylhexyl)-N,N-diethylcarbamoylmethyl phosphonate as a synergist in the extraction of trivalent lanthanides by 1-phenyl-3-methyl-4-trifluoroacetyl-pyrazolone-5

    International Nuclear Information System (INIS)

    Luxmi Varma, R.; Sujatha, S.; Reddy, M.L.P.; Prasada Rao, T.; Iyer, C.S.P.; Damodaran, A.D.

    1996-01-01

    Synergism in the extraction of trivalent lanthanides such as Nd. Eu and Lu has been investigated using mixtures of 1-phenyl-3-methyl-4-trifluoroacetyl-pyrazolone-5 (HPMTFP) and bis(2-ethylhexyl)-N,N-diethylcarbamoylmethyl phosphonate (CMP) in chloroform. Lanthanides are found to be extracted from 0.01 mol/dm 3 chloroacetate medium with HPMTFP as Ln(PMTFP) 3 or Ln(PMTFP) 3 . CMP in the absence or presence of CMP, respectively. The equilibrium constants of these synergistic species do not increase monotonically with atomic number but have a maximum at Eu. The addition of a synergist, CMP to the metal chelate system not only enhances the extraction efficiency but also improves the selectivities among these trivalent lanthanides. The IR results indicate that CMP acts as a bidentate ligand in these mixed-ligand systems. (orig.)

  5. The Inhibitive Effect of 2-Phenyl-3-nitroso-imidazo [1, 2-a]pyridine on the Corrosion of Steel in 0.5 M HCl Acid Solution

    Directory of Open Access Journals (Sweden)

    K. Bouhrira

    2010-01-01

    Full Text Available The effect of 2-phenyl-3-nitroso-imidazo[1,2-a]pyridine (PNIP on the corrosion inhibition of carbon-steel in 0.5 M HCl was studied by weight loss and different electrochemical techniques such as electrochemical impedance spectroscopy (EIS, potentiodynamic polarization. The obtained results showed that PNIP effectively reduces the corrosion rate of carbon steel. Inhibition efficiency (E% increases with inhibitor concentration to attain 88% at 10-3 M. Adsorption of that PNIP on the carbon steel surface in 0.5 M HCl follows the Langmuir isotherm model. E% values obtained from various methods used are in good agreement. SEM characterization of the steel surface is made.

  6. Analytical recovery of Cr (VI), Mo (VI), Ti (IV) and Co (II) by N-phenyl-meta-nitro-benzohydroxamic and N-P-tolyl-meta-nitro-benzohydroxamic acids

    International Nuclear Information System (INIS)

    Ahmed, Abdul Aziz Malik Mohamed

    2000-05-01

    Two hydroxamic acids were prepared; N-phenyl-m-nitro-benzohydroxamic and N-p-tolyl-m-nitro-benzo hydroxamic acids. N-phenyl-m-nitro-benzohydroxamic was prepared by coupling the β-phenyl hydroxylamine with m-nitro-benzoyl chloride in ratio 1:1 in alkaline medium at zero degree centigrade. It recrystallized from a mixture of benzene and petroleum ether (2:1) with the yield of 67%. The product was characterized by: A-nitrogen content which was found to be 10.7% (lit. 10.9%). B-infra-red spectroscopy. C-the molecular weight which was determined by titration, was found to be 257.7 gram (lit. 257 gram). D-the molecular weight which was determined by elevation of the boiling point, was found to be 253.7 gram (lit. 257 gram). E-characteristic violet color reaction with vanadium and blood-red reaction with ferric chloride solutions. F-melting point 117 degree centigrade. N-p-tolyl-m-nitro benzo hydroxamic acid was prepared by coupling the p-tolyl-hydroxylamine with m-nitro benzoyl chloride using the same procedure. It was recrystallized from a mixture of benzene and petroleum ether (2:1) with the yield of 63%. The product was characterized by: A-nitrogen content which was found to be 10.1% (lit. 10.3). B-infra-red spectroscopy. C-the molecular weight which was determined by titration, was found to be 271.6 gram (lit. 272). D-the molecular weight which was determined by elevation of the boiling point, was found to be 269.9 gram (lit. 272 gram). E.characteristic violet color reaction with vanadium and blood-red color with ferric chloride solutions. F-melting point which was found to be 105 degree centigrade (lit. 106 degree c). the two hydroxamic acids were used as analytical reagents for extraction of metal ions Ti (IV), Cr (VI), Mo (VI) and Co (II). With an equal volume of the organic and aqueous phase, and only one extraction, N-phenyl-m-nitro-benzohydroxamic acid was found to have a maximum extraction of 30.18% for Ti (IV) at pH 2.0, of 97.06% for Cr (VI) at 3MH 2 SO 4

  7. Rolipram improves facilitation of contextual fear extinction in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse model of Parkinson's disease

    Directory of Open Access Journals (Sweden)

    Ken-ichi Kinoshita

    2017-05-01

    Full Text Available Cognitive impairment often occurs in Parkinson's disease (PD, but the mechanism of onset remains unknown. Recently, we reported that PD model mice produced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP show facilitation of hippocampal memory extinction, which may be the cause of cognitive impairment in PD. When we examined the cAMP/CREB signaling in the hippocampus, decreased levels of cAMP and phosphorylated CREB were observed in the dentate gyrus (DG of MPTP-treated mice. Administration of rolipram improved the memory deficits with concomitant recovery of cAMP and phosphorylated CREB levels, suggesting that reduced cAMP/CREB signaling in the DG leads to cognitive impairment in MPTP-treated mice.

  8. 6-Chloro-3-[5-(3-methoxy-8-methyl-4-quinolyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenylquinoline

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2009-11-01

    Full Text Available In the title compound, C36H29ClN4O, the dihydropyrazole ring adopts an envelope conformation. The two quinoline ring systems (r.m.s. deviations = 0.029 and 0.018 Å are oriented at a dihedral angle of 71.43 (4°. One of the quinoline rings makes a dihedral angle of 65.40 (7° with the phenyl substituent. In the crystal, molecules are linked into chains along the b axis by intermolecular C—H...N hydrogen bonds. In addition, C—H...π and π–π [centroid–centroid distance = 3.7325 (8 Å] interactions are observed.

  9. Crystal structure of (3S*,4R*-4-fluoro-3-(4-methoxyphenyl-1-oxo-2-phenyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid

    Directory of Open Access Journals (Sweden)

    Anna Lehmann

    2017-06-01

    Full Text Available The title compound, C23H18FNO4, crystallized as a racemate. It exhibits a cis conformation with respect to the F atom and the methine H atom. The piperidine ring has a screw-boat conformation. The methoxyphenyl ring and the phenyl ring are inclined to the mean plane of the isoquinoline ring system by 89.85 (4 and 46.62 (5°, respectively, and by 78.15 (5° to one another. In the crystal, molecules are linked by an O—H...O hydrogen bond forming chains propagating along the a-axis direction. The chains are linked by C—H...F hydrogen bonds, forming layers lying parallel to the ab plane.

  10. {sup 1} H and {sup 13} C NMR of phenyl barbiturilidene; RMN de H-1 e C-13 de fenil barbiturilidenos

    Energy Technology Data Exchange (ETDEWEB)

    Villar, Jose Daniel Figueroa; Santos, Nedina Lucia dos; Cruz, Elizabete Rangel [Instituto Militar de Engenharia (IME), Rio de Janeiro, RJ (Brazil). Secao de Quimica

    1991-12-31

    The condensation of barbituric acids with aromatic aldehydes gives the phenyl barbiturilidenes, which are studied as intermediary compounds in the synthesis of new heterocyclic compounds for pharmaceutical use. One of the most characteristic reactions of these compounds is the Michael type addition reaction, in the exocyclic carbon-carbon double binding. The reaction with 2,4-di nitrophenyl hydrazine reaction is been used as a test of this type of reactivity, which supplies the respective hydrazone and barbituric acid. In this work, preliminary studies have been performed for establishing correlations between the Brown parameter ({sigma}{sup +}), the chemical shifts ({delta}) of the barbiturilidene atoms involved in the reaction, and their reactivities 3 refs., 1 fig., 6 tabs.

  11. Stability constant for thorium(IV) complexes with aryl bis-(5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl)-methane ligands

    Energy Technology Data Exchange (ETDEWEB)

    Stefan, L.S. [Ain Shams Univ., Cairo (Egypt)

    1995-09-01

    Chelate stability constants of aryl bis(5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl)methane (ABPM) derivatives with thorium(IV) ion were determined by the potentiometric method at 30 C and 0.1 mol dm{sup -3} (KNO{sub 3}) in 75% (v/v) dioxane-water solvent. The computation of the titration data indicated that four kinds of complexes [ThL]{sup 2+}, [ThL(OH)]{sup +}, [ThL{sub 2}] and [ThL(OH){sub 2}] were formed. The appropriate formation constants for all of the 1:1 species and 2:1 complexes have been calculated are probable ligand-banding sites of the complexes were proposed. In addition, the applicability of the Hammett equation for correlation of the stability constants of [Th(IV)-ABPM] complexes was discussed. (author). 19 refs, 5 figs, 1 tab.

  12. Stability constant for thorium(IV) complexes with aryl bis-(5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl)-methane ligands

    International Nuclear Information System (INIS)

    Stefan, L.S.

    1995-01-01

    Chelate stability constants of aryl bis(5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl)methane (ABPM) derivatives with thorium(IV) ion were determined by the potentiometric method at 30 C and 0.1 mol dm -3 (KNO 3 ) in 75% (v/v) dioxane-water solvent. The computation of the titration data indicated that four kinds of complexes [ThL] 2+ , [ThL(OH)] + , [ThL 2 ] and [ThL(OH) 2 ] were formed. The appropriate formation constants for all of the 1:1 species and 2:1 complexes have been calculated are probable ligand-banding sites of the complexes were proposed. In addition, the applicability of the Hammett equation for correlation of the stability constants of [Th(IV)-ABPM] complexes was discussed. (author). 19 refs, 5 figs, 1 tab

  13. 2-r-(4-Chlorophenyl-6-c-phenyl-3,4,5,6-tetrahydro-2H-thiopyran-4-one 1-oxide

    Directory of Open Access Journals (Sweden)

    D. Devanathan

    2008-12-01

    Full Text Available The thiopyran unit of the title molecule, C17H15ClO2S, is in chair form. A crystallographic mirror plane bisects the molecule, passing through the O=S and the opposite C=O atoms of the central ring, with statistical disorder of the Cl atom. The geometry around the S atom is tetrahedral and the carbonyl C is planar. The 4-chlorophenyl group at the 2 position and the phenyl ring at the 6 position have equatorial orientations. Intermolecular C—H...O and C—H...Cl hydrogen bonds are found in the crystal structure. In addition, there is a short O...C intermolecular contact [2.970 (5 Å].

  14. Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities.

    Science.gov (United States)

    Sakane, Rie; Kimura, Kimito; Hirota, Yoshihisa; Ishizawa, Michiyasu; Takagi, Yuta; Wada, Akimori; Kuwahara, Shigefumi; Makishima, Makoto; Suhara, Yoshitomo

    2017-11-01

    Vitamin K is an essential cofactor of γ-glutamylcarboxylase as related to blood coagulation and bone formation. Menaquinone-4, one of the vitamin K homologues, is biosynthesized in the body and has various biological activities such as being a ligand for steroid and xenobiotic receptors, protection of neuronal cells from oxidative stress, and so on. From this background, we focused on the role of menaquinone in the differentiation activity of progenitor cells into neuronal cells and we synthesized novel vitamin K derivatives with modification of the ω-terminal side chain. We report here new vitamin K analogues, which introduced an alkylated phenyl group at the ω-terminal side chain. These compounds exhibited potent differentiation activity as compared to control. Copyright © 2017 The Author(s). Published by Elsevier Ltd.. All rights reserved.

  15. Assessing the suitability of 1,2,3-triazole linkers for covalent immobilization of chiral ligands: application to enantioselective phenylation of aldehydes.

    Science.gov (United States)

    Bastero, Amaia; Font, Daniel; Pericàs, Miquel A

    2007-03-30

    Alkynyl-functionalized amino alcohols have been covalently supported on azidomethylpolystyrene resins with different levels of functionalization through Cu(I)-catalyzed 1,3-dipolar cycloadditions ("click chemistry"). The resulting 1,2,3-triazole-substituted resins, characterized by different levels of ligand loading and, depending on the nature of the alkynyl-functionalized amino alcohol, the presence of a one-carbon, four-carbon, or eight-carbon linear spacer, have been tested as catalysts in the enantioselective phenyl transfer from zinc to aldehydes. High catalytic activities and enantioselectivities (up to 82% ee) have been recorded. The influence of structural characteristics of the resin on enantioselectivity are discussed, and the limitations in enantiocontrol inherent to the use of a 1,2,3-triazole linker have been rationalized with the help of DFT calculations on model systems.

  16. Crystal structure of ethyl (2Z-2-cyano-3-[(3-methyl-1-phenyl-1H-pyrazol-5-ylamino]prop-2-enoate

    Directory of Open Access Journals (Sweden)

    Joel T. Mague

    2014-11-01

    Full Text Available The title compound, C16H16N4O2, crystallizes with two molecules in the asymmetric unit, one of which shows disorder of the acetate group over two sets of sites in a 0.799 (2:0.201 (2 ratio. The phenyl group has a similar but opposite sense of twist relative to the pyrazole ring in the two molecules, as indicated by the syn N—N—Car—Car (ar = aromatic torsion angles of 39.7 (2 and −36.9 (2°. Each molecule features an intramolecular N—H...O hydrogen bond, which closes an S(6 ring. In the crystal, C—H...O and C—H...N interactions direct the packing into a layered structure parallel to (110.

  17. Copper(II Complexes with Ligands Derived from 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Synthesis and Biological Activity

    Directory of Open Access Journals (Sweden)

    Raluca Cernat

    2006-11-01

    Full Text Available The synthesis of Cu(II complexes derived from Schiff base ligands obtainedby the condensation of 2-hydroxybenzaldehyde or terephtalic aldehyde with 4-amino-antipyrine (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one is presented. The newlyprepared compounds were characterized by 1H-NMR, UV-VIS, IR and ESRspectroscopy. The determination of the antimicrobial activity of the ligands and of thecomplexes was carried out on samples of Escherichia coli, Klebsiella pneumoniae,Acinetobacter boumanii, Pseudomonas aeruginosa, Staphylococcus aureus and Candidasp. The qualitative and quantitative antimicrobial activity test results proved that all theprepared complexes are very active, especially against samples of Ps. aeruginosa, A.Boumanii, E. coli and S. aureus.

  18. Investigation into atomic tritium reactions with amino acids. 3. Low-temperature reactions of tritium atoms with phenyl alanine and tyrozine

    International Nuclear Information System (INIS)

    Orlova, M.A.; Simonov, E.F.; Filatov, Eh.S.

    1979-01-01

    The yields of products obtained under the effect of tritium atoms on amino acids (β-phenyl-α alanine and tyrozine) at ZZ K and tritium distribution in molecules of these amino acids are investigated. Vessels of two types are used. In the first atom source incandescent tungsten spiral has been placed in the middle of the reaction vessel; in the second one-tritium atoms fell on the target from the source separately placed through the curved pipe. It has been found that in the first case reactions take place caused by atomic tritium as well as by the luminous radiation effect of the source; in the case of ''cold'' atoms the same reaction products are fixed but with different distribution. The mechanism of the reaction of tritium atoms with amino acids is discussed

  19. N-phenyl-1-naphthylamine/β-cyclodextrin inclusion complex as a new fluorescent probe for rapid and visual detection of Pd(2+).

    Science.gov (United States)

    Maniyazagan, Munisamy; Mohandoss, Sonaimuthu; Sivakumar, Krishnamoorthy; Stalin, Thambusamy

    2014-12-10

    Inclusion complex between N-phenyl-1-naphthylamine (NPN) and β-cyclodextrin (β-CD) was studied by FT-IR, (1)H and 2D NMR, XRD, FT-Raman, SEM and DSC techniques. The formation of 1:1 stoichiometric inclusion complex of NPN with β-CD was proposed based on the Nuclear magnetic resonance spectroscopy and Molecular docking study. The molecular encapsulation of host-guest inclusion complex based on simple chemosensor has high selectivity and sensitivity for the determination of Pd(2+) ion. Host-guest inclusion complex as a spectroscopic probe is used for the detection of transition metal cation Pd(2+). Coordination of this Pd(2+) with (NPN/β-CD) inclusion complex exhibited a noticeable color change in the solution state it used for naked-eye detection. Copyright © 2014 Elsevier B.V. All rights reserved.

  20. Synthesis and structure of new 4-amino-5-(2-R1-phenyl-1,2,4-triazole-3-thiol alkilderivatives

    Directory of Open Access Journals (Sweden)

    Ye. S. Pruglo

    2017-08-01

    Full Text Available Chemistry of heterocyclic systems is a separate branch of organic chemistry with a long history and future prospects. The ring system of 1,2,4-triazole continuously attracts the interest of chemists, pharmacologists and pharmacists in finding medicinal compounds through its universal potential interactions with biological systems. Today it is known that 1,2,4-triazole derivatives have antibacterial, antifungal, antiinflammatory, anticonvulsant, antiviral, antituberculosis, antioxidant, anticancer and antitumor activities. They also have analgesic, local anesthetic, antimalarial, antiproliferative effects, antihypertensive, antidepressant, sedative, antihistamine, hepatoprotective, hypoglycemic, diuretic, antipyretic and countless number of action types. Therefore, the search of biologically active remedies and creating of new drugs on its base is highly efficient topical issue of medical and pharmaceutical work. The purpose of these studies is the synthesis, establishment of physical-chemical parameters of new 4-amino-5-(2-R1-phenyl-1,2,4-triazole-3-thiol alkylderivatives. Materials and methods. The studying of physical and chemical properties of compounds was made in accordance with the methods described in the State Pharmacopoeia of Ukraine 2.0. The melting point was determined on an automatic gear MPA100. The elemental composition of the compounds was set on the analyzer Elementar Vario EL cube. 1H NMR spectra were recorded using the spectrometer Varian Mercury VX-200 (1H, 200 MHz and decrypted by a computer program SpinWorks 3.1.8. Chromatography-mass spectral studies were carried out in the gas-liquid chromatograph Agilent 1260 Infinity HPLC equipped with a mass spectrometer Agilent 6120 (in electrospray ionization (ESI. Results. 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol and 4-amino-5-(2-bromophenyl-4H-1,2,4-triazol-3-thiol were used as the initial materials. These compounds were obtained by reaction of benzoic acid hydrazide and 2

  1. Synthesis and Antifungal Activity of N-(Substituted pyridinyl-1-methyl(phenyl-3-(trifluoromethyl-1H-pyrazole-4-carboxamide Derivatives

    Directory of Open Access Journals (Sweden)

    Zhibing Wu

    2012-11-01

    Full Text Available A series of N-(substituted pyridinyl-1-methyl(phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide derivatives were synthesized. All target compounds were characterized by spectral data (1H-NMR, 13C-NMR, IR, MS and elemental analysis and were bioassayed in vitro against three kinds of phytopathogenic fungi (Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica. The results showed that some of the synthesized N-(substituted pyridinyl-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamides exhibited moderate antifungal activities, among which compounds 6a, 6b and 6c displayed more than 50% inhibition activities against G. zeae at 100 µg/mL, which was better than that of the commercial fungicides carboxin and boscalid.

  2. 1H NMR spectra of N-methyl-4-tolyl-1-(4-bromonaphthylamine and N-phenyl-1-(4-bromonaphthylamine: a combined experimental and theoretical study

    Directory of Open Access Journals (Sweden)

    Sergiy I. Okovytyy

    2014-03-01

    Full Text Available Theoretical investigations of the conformational properties and 1H NMR chemical shifts for N-methyl-4-tolyl-1-(4-bromonaphthylamine and N-phenyl-1-(4-bromonaphthylamine are reported. The calculations were performed at the DFT level (PBE1PBE functional using magnetically consistent 6-31G## and STO##-3Gmag basis sets. Conformational properties of the amines were studied using potential energy surface scanning. Chemical shifts were calculated using the GIAO and CSGT methods and averaged in proportion to the population of the corresponding conformations. Solvent effects (CDCl3 were accounted via PCM method. The obtained results allowed to assign the 1H NMR signals for the naphthalene moiety, which could not be done based on the experimental data alone.

  3. Preconcentration and atomic absorption spectrometric determination of cadmium, cobalt, copper, iron, lead, manganese, nickel and zinc in water samples using 6-methyl-2-pyridinecarboxaldehyde-4-phenyl-3-thiosemicarbazone

    International Nuclear Information System (INIS)

    Khuhawar, M.Y.; Das, P.; Dewani, V.K.

    2005-01-01

    The reagent 6-methyl-2-pyridinecarboxaldehyde-4-phenyl-3-thiosemicarbazone (MPAPT) has been examined for the pre-concentration of metal ions and determination using air acetylene flame atomic absorption spectrometer. The method is based on the complexation and extraction of cadmium (II), cobalt(III), copper(II), lead(II), nickel(II), iron(II), iron(II), manganese(II) and zinc(II) in chloroform. The metal iron are back extracted in nitric acid (1:1) or after evaporation of solvent the residue is digested in nitric acid. After necessary adjustment of volume the metal ions were determined in aqueous solution. Pre-concentration is obtained 10-25 times. Metal ions recovery was 95.4-100.8% with coefficient of variation 0.2-7.5%. The method used for the determination of metals in canal and sewerage waters, within 2-6433 mu g/L with C. V 0.-5.2%. (author)

  4. Design, synthesis and biological evaluation of 1-hydroxy-2-phenyl-4-pyridyl-1H-imidazole derivatives as xanthine oxidase inhibitors.

    Science.gov (United States)

    Zhang, Tingjian; Lv, Yunying; Lei, Yu; Liu, Dan; Feng, Yao; Zhao, Jiaxing; Chen, Shaolei; Meng, Fanhao; Wang, Shaojie

    2018-02-25

    In our previous study, we reported a series of 1-hydroxy-2-phenyl-1H-imidazole-5-carboxylic acid derivatives that presented excellent in vitro xanthine oxidase inhibitory potency. As a continuation study, a series of 1-hydroxy-2-phenyl-1H-imidazole derivatives containing a pyridine moiety (4a-g and 5a-g) at the 4-position was designed and synthesized. Evaluation of in vitro xanthine oxidase inhibition demonstrated that the 4a-g series was more potent than the 5a-g series. Compound 4f was the most promising derivative in the series with an IC 50 value of 0.64 μM. A Lineweaver-Burk plot revealed that compound 4f acted as a mixed-type xanthine oxidase inhibitor. An iso-pentyloxy group at the 4'-position improved the inhibitory potency. More interestingly, structure-activity relationship analysis indicated that the pyridine para-N atom played a crucial role in the inhibition. Molecular modeling provided a reasonable explanation for the structure-activity relationships observed in this study. In addition, a three dimensional quantitative structure-activity relationships model which possessed reasonable statistics (q 2  = 0.885 and r 2  = 0.993) was conducted to further understand the structural basis of these compounds as xanthine oxidase inhibitors. These compounds, especially compound 4f, have good potential for further investigations. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

  5. 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes inhibit proliferation of estrogen receptor-negative breast cancer cells by activation of multiple pathways.

    Science.gov (United States)

    Vanderlaag, Kathy; Su, Yunpeng; Frankel, Arthur E; Grage, Henry; Smith, Roger; Khan, Shaheen; Safe, Stephen

    2008-05-01

    1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes containing para-trifluoromethyl (DIM-C-pPhCF(3)), t-butyl (DIM-C-pPhtBu), and phenyl (DIM-C-pPhC(6)H(5)) groups are methylene-substituted diindolylmetyhanes (C-DIMs) that activate peroxisome proliferator-activated receptor gamma (PPARgamma) in estrogen receptor alpha-negative MDA-MB-231 and MDA-MB-453 breast cancer cells. C-DIMs inhibit breast cancer cell proliferation; however, inhibition of G(0)/G(1) to S phase progression and cyclin D1 downregulation was observed in MDA-MB-231 but not MDA-MB-453 cells. Nonsteroidal anti-inflammatory drug-activated gene 1 (NAG-1), a transforming growth factor beta-like peptide, was also induced by these compounds, and the response was dependent on cell-context dependent activation of kinase pathways. However, inhibition of cell growth, induction of NAG-1 and activation of kinases by C-DIMs were not inhibited by PPARgamma antagonists. Despite the induction of NAG-1 and downregulation of the antiapoptotic protein survivin by C-DIMs in both MDA-MB-231 and MDA-MB-453 cells, apoptotic cell death was not observed. Nevertheless, the cytotoxicity of C-DIMs in vitro was complemented by inhibition of tumor growth in athymic nude mice bearing MDA-MB-231 cells as xenografts and treated with DIM-C-pPhC(6)H(5) (40 mg/kg/day). The growth inhibition of tumors derived from highly aggressive MDA-MB-231 cells suggests a potential role for the C-DIM compounds in the clinical treatment of ER-negative breast cancer.

  6. 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes induce autophagic cell death in estrogen receptor negative breast cancer.

    Science.gov (United States)

    Vanderlaag, Kathy; Su, Yunpeng; Frankel, Arthur E; Burghardt, Robert C; Barhoumi, Rola; Chadalapaka, Gayathri; Jutooru, Indira; Safe, Stephen

    2010-12-03

    A novel series of methylene-substituted DIMs (C-DIMs), namely 1,1-bis(3'-indolyl)-1-(p-substituted phenyl)methanes containing t-butyl (DIM-C-pPhtBu) and phenyl (DIM-C-pPhC6H5) groups inhibit proliferation of invasive estrogen receptor-negative MDA-MB-231 and MDA-MB-453 human breast cancer cell lines with IC50 values between 1-5 uM. The main purpose of this study was to investigate the pathways of C-DIM-induced cell death. The effects of the C-DIMs on apoptotic, necrotic and autophagic cell death were determined using caspase inhibitors, measurement of lactate dehydrogenase release, and several markers of autophagy including Beclin and light chain associated protein 3 expression (LC3). The C-DIM compounds did not induce apoptosis and only DIM-C-pPhCF3 exhibited necrotic effects. However, treatment of MDA-MB-231 and MDA-MB-453 cells with C-DIMs resulted in accumulation of LC3-II compared to LC3-I protein, a characteristic marker of autophagy, and transient transfection of green fluorescent protein-LC3 also revealed that treatment with C-DIMs induced a redistribution of LC3 to autophagosomes after C-DIM treatment. In addition, the autofluorescent drug monodansylcadaverine (MDC), a specific autophagolysosome marker, accumulated in vacuoles after C-DIM treatment, and western blot analysis of lysates from cells treated with C-DIMs showed that the Beclin 1/Bcl-2 protein ratio increased. The results suggest that C-DIM compounds may represent a new mechanism-based agent for treating drug-resistant ER-negative breast tumors through induction of autophagy.

  7. Impact of a heteroatom in a structure-activity relationship study on analogues of phenyl glycidyl ether (PGE) from epoxy resin systems.

    Science.gov (United States)

    Niklasson, Ida B; Delaine, Tamara; Luthman, Kristina; Karlberg, Ann-Therese

    2011-04-18

    Epoxy resins are among the most common causes of occupational contact dermatitis. They are normally used in so-called epoxy resin systems (ERS). These commercial products are combinations of epoxy resins, curing agents, modifiers, and reactive diluents. The most frequently used resins are diglycidyl ethers based on bisphenol A (DGEBA) and bisphenol F (DGEBF). In this study, we have investigated the contact allergenic properties of a series of analogues to the reactive diluent phenyl glycidyl ether (PGE), all with similar basic structures but with varying heteroatoms or with no heteroatom present. The chemical reactivity of the compounds in the test series toward the hexapeptide H-Pro-His-Cys-Lys-Arg-Met-OH was investigated. All epoxides were shown to bind covalently to both cysteine and proline residues. The percent depletion of nonreacted peptide was also studied resulting in ca. 60% depletion when using either PGE, phenyl 2,3-epoxypropyl sulfide (2), or N-(2,3-epoxypropyl)aniline (3), and only 15% when using 1,2-epoxy-4-phenylbutane (4) at the same time point. The skin sensitization potencies of the epoxides using the murine local lymph node assay (LLNA) were evaluated in relation to the observed physicochemical and reactivity properties. To enable determination of statistical significance between structurally closely related compounds, a nonpooled LLNA was performed. It was found that all investigated compounds containing a heteroatom in the α-position to the epoxide were strong sensitizers, congruent with the reactivity data, indicating that the impact of a heteroatom is crucial for the sensitizing capacity for this type of epoxides.

  8. Spectral Analysis and Crystal Structures of 4-(4-Methylphenyl)-6-Phenyl-2,3,3a, 4-Tetrahydro-1H-Pyrido[3,2,1-jk]Carbazole and 4-(4-Methoxyphenyl)-6-Phenyl-2,3,3a, 4-Tetrahydro-1H-Pyrido[3,2,1-jk]Carbazole.

    Science.gov (United States)

    Kalyana Sundar, J; Natarajan, S; Chitra, S; Paul, Nidhin; Manisankar, P; Muthusubramanian, S; Suresh, J

    2011-01-01

    The crystal structures of 4-(4-methylphenyl)-6-phenyl-2,3,3a,4-tetrahydro-1H-pyrido[3,2,1-jk]carbazole (IIa) and 4-(4-methoxyphenyl)-6-phenyl-2,3,3a,4-tetrahydro-1H-pyrido[3,2,1-jk]carbazole (IIb) were elucidated by single crystal X-ray diffraction. Compound (IIa), C28H25N, crystallizes in the triclinic system, space group P-1, with a = 8.936(2) Å, b = 10.490(1) Å, c = 11.801(1) Å, α = 102.69(5) (°) ,  β = 103.27(3) (°) , γ = 93.80(1) (°) , and Z = 2. The compound (IIb), C28H25NO, crystallizes in the monoclinic system, space group P21/a, with a = 11.376(5) Å, b = 14.139(3) Å, c = 13.237(4) Å, β = 97.41(3) (°) , and Z = 4. In both the structures, the pyrido ring adopts a twist boat conformation and the carbazole molecule has the twisted envelope structure with C3 and C13 at the flap. No classical hydrogen bonds are observed in the crystal structures. Details of the preparation, structures, and spectroscopic properties of the new compounds are discussed.

  9. Synthesis and Antimicrobial Activity of 2-[2-(2,6-dichloro phenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H)ones.

    Science.gov (United States)

    Patel, Nb; Patel, Jc; Barat, Gg

    2010-04-01

    A series of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H) ones 6a-m have been synthesized by the reaction of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-substituted phenylacrylamido-6,8-dibromoquinazolin-4(3H) ones 5a-m with hydrazine hydrate in the presence of glacial acetic acid. The chalcones 5a-m were prepared by the condensation of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-acetamido-6,8-dibromoquinazolin-4(3H)one 4 with different substituted aromatic aldehyde. The benzoxazinone 2 was synthesized from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetyl chloride 1 on treatment with 3,5-dibromoanthranilic acid in pyridine, which on reaction with hydrazine hydrate and then on acetylation reaction yielded 4. The structures of these compounds have been elucidated by elemental analyses, IR, and NMR spectral data. The title compounds pyrazolyl-quinazolin-4(3H)ones 6a-m were evaluated for their antibacterial and antifungal activities in vitro.

  10. Capillary microextraction of volatiles device for enhanced BTEX vapors sampling based on a phenyl modified PDMS sol-gel adsorption phase.

    Science.gov (United States)

    Gura, Sigalit; Tarifa, Anamary; Mulloor, Jerome; Torres, Michelle N; Almirall, José R

    2018-07-19

    A novel phenyl modified PDMS (PhPDMS) sol-gel adsorption phase was developed for use with the capillary microextraction of volatiles (CMV) device, and determined to provide significant enhancement in BTEX recoveries when sampling trace (ng) amounts of these volatiles at ambient conditions. The previously reported reusable PDMS-CMV device has been demonstrated to rapidly and efficiently extract target compound's vapors in forensic and environmental applications. An improved recovery for VOCs was achieved with a cryofocusing system while extracting at -10  ° C, but it was found to be impractical for field sampling. This report details a modification to the CMV's chemistry, by the successful introduction of phenyl groups to the PDMS sol-gel adsorption phase, allowing enhanced performance at ambient extraction conditions. Higher average recoveries, determined through a broad concentration range, were demonstrated for PhPDMS-CMV over its original PDMS-CMV, from cans simulating a closed space set-up. Within 7.8 (±10%) and 3.5 (±6%) folds higher for benzene and toluene, respectively and 2 (±2%) folds for ethylbenzene and xylenes. Significant higher retaining capabilities were demonstrated also at the more challenging set-up, simulating an open space environment. Whereas, benzene had completely breakthrough the PDMS-CMV, its reliable detection was still confirmed with PhPDMS-CMV pumping at 2 L or 6 L air, concentration dependent. At least 50 folds (±26%) more toluene was retained with PhPDMS-CMV at 6 L air than with PDMS-CMV. The enhanced overall performance lead to determination of trace LODs with the new CMV of 0.002, 0.00035 and 0.00015 ppm for benzene, toluene, ethyl benzene and xylenes, respectively. As proof of concept, for the first time solvent extraction is presented for the new CMV as an alternative to thermal desorption extraction. Extraction efficiencies of 60% for TEX, and lower concentration dependent for benzene, were demonstrated with the

  11. High resolution spectroscopy of jet cooled phenyl radical: The ν1 and ν2 a1 symmetry C-H stretching modes

    Science.gov (United States)

    Chang, Chih-Hsuan; Nesbitt, David J.

    2016-07-01

    A series of CH stretch modes in phenyl radical (C6H5) has been investigated via high resolution infrared spectroscopy at sub-Doppler resolution (˜60 MHz) in a supersonic discharge slit jet expansion. Two fundamental vibrations of a1 symmetry, ν1 and ν2, are observed and rotationally analyzed for the first time, corresponding to in-phase and out-of-phase symmetric CH stretch excitation at the ortho/meta/para and ortho/para C atoms with respect to the radical center. The ν1 and ν2 band origins are determined to be 3073.968 50(8) cm-1 and 3062.264 80(7) cm-1, respectively, which both agree within 5 cm-1 with theoretical anharmonic scaling predictions based on density functional B3LYP/6-311g++(3df,3dp) calculations. Integrated band strengths for each of the CH stretch bands are analyzed, with the relative intensities agreeing remarkably well with theoretical predictions. Frequency comparison with previous low resolution Ar-matrix spectroscopy [A. V. Friderichsen et al., J. Am. Chem. Soc. 123, 1977 (2001)] reveals a nearly uniform Δν ≈ + 10-12 cm-1 blue shift between gas phase and Ar matrix values for ν1 and ν2. This differs substantially from the much smaller red shift (Δν ≈ - 1 cm-1) reported for the ν19 mode, and suggests a simple physical model in terms of vibrational mode symmetry and crowding due to the matrix environment. Finally, the infrared phenyl spectra are well described by a simple asymmetric rigid rotor Hamiltonian and show no evidence for spectral congestion due to intramolecular vibrational coupling, which bodes well for high resolution studies of other ring radicals and polycyclic aromatic hydrocarbons. In summary, the combination of slit jet discharge methods with high resolution infrared lasers enables spectroscopic investigation of even highly reactive combustion and interstellar radical intermediates under gas phase, jet-cooled (Trot ≈ 11 K) conditions.

  12. Exploring selectivity requirements for COX-2 versus COX-1 binding of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines using topological and physico-chemical parameters.

    Science.gov (United States)

    Chakraborty, Santanu; Sengupta, Chandana; Roy, Kunal

    2005-04-01

    Considering the current need for development of selective cyclooxygenase-2 (COX-2) inhibitors, an attempt has been made to explore physico-chemical requirements of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines for binding with COX-1 and COX-2 enzyme subtypes and also to explore the selectivity requirements. In this study, E-states of different common atoms of the molecules (calculated according to Kier & Hall), first order valence connectivity and physicochemical parameters (hydrophobicity pi, Hammett sigma and molar refractivity MR of different ring substituents) were used as independent variables along with suitable dummy parameters in the stepwise regression method. The best equation describing COX-1 binding affinity [n = 25, Q2 = 0.606, R(a)2 = 0.702, R2 = 0.752, R = 0.867, s = 0.447, F = 15.2 (df 4, 20)] suggests that the COX-1 binding affinity increases in the presence of a halogen substituent at R1 position and a p-alkoxy or p-methylthio substituent at R2 position. Furthermore, a difluoromethyl group is preferred over a trifluoromethyl group at R position for the COX-1 binding. The best equation describing COX-2 binding affinity [n = 32, Q2 = 0.622, R(a)2= 0.692, R2 = 0.732, R = 0.856, s = 0.265, F = 18.4 (df 4, 27)] shows that the COX-2 binding affinity increases with the presence of a halogen substituent at R1 position and increase of size of R2 substituents. However, it decreases in case of simultaneous presence of 3-chloro and 4-methoxy groups on the phenyl nucleus and in the presence of highly lipophilic R2 substituents. The best selectivity relation [n = 25, Q2 = 0.455, R(a)2 = 0.605, R2 = 0.670, R = 0.819, s = 0.423, F = 10.2 (df 4, 20)] suggests that the COX-2 selectivity decreases in the presence of p-alkoxy group and electron-withdrawing para substituents at R2 position. Again, a trifluoro group is conductive for the selectivity instead of a difluoromethyl group at R position. Furthermore, branching may also play significant role in

  13. Synthesis and characterisation of iron, cobalt and gallium complexes wit the redox-active amide ligand systems pyridinocarboxiamidobenzene and hydroxy phenyl oxamide; Synthese und Charakterisierung von Eisen-, Cobalt- und Galliumkomplexen mit den redoxaktiven Amidligandsystemen Pyridincarboxamidobenzol und Hydroxyphenyloxamid

    Energy Technology Data Exchange (ETDEWEB)

    Beckmann, U.

    2001-07-01

    The interactions of the redox-active ligand systems piridinocarboxamidobenzene and hydroxy phenyl oxamide with the metals iron, cobalt and gallium were investigated. It was found that metal complexes with ligands of the pyridinocarboxamidobenzene and hydroxy phenyl oxamide type can be redox-active in the sense of a ligand-centered reaction. This may provide a better understanding of natural catalysis mechanisms and redox processes. [German] In dieser Arbeit wurde die Wechselwirkung der redoxaktiven Ligandsysteme Pyridincarboxamidobenzol und Hydroxyphenyloxamid mit den Metallen Eisen, Cobalt und Gallium untersucht. Es konnte gezeigt werden, dass Metallkomplexe mit Liganden vom Typ Pyridincarboxamidobenzol und Hydroxyphenyloxamid auch im Sinne einer ligandzentrierten Reaktion redoxaktiv sein koennen. Dies kann dazu beitragen, Katalysemechanismen und Redoxprozesse in der Natur besser zu verstehen. (orig.)

  14. 1,3,5-Tris(phenyl-2-benzimidazole)-benzene cathode buffer layer thickness dependence in solution-processable organic solar cell based on 1,4,8,11,15,18,22,25-octahexylphthalocyanine

    Science.gov (United States)

    De Roméo Banoukepa, Gilles; Fujii, Akihiko; Shimizu, Yo; Ozaki, Masanori

    2015-04-01

    Studies on the insertion effects of a cathode buffer layer on bulk heterojunction organic solar cell based on 1,4,8,11,15,18,22,25-octahexylphthalocyanine (C6PcH2) and 1-(3-methoxy-carbonyl)-propyl-1-1-phenyl-(6,6)C61 (PCBM) by using 1,3,5-tris(phenyl-2-benzimidazole)-benzene (TPBi) as a cathode buffer layer material have been carried out. The external quantum efficiency and the short-circuit current markedly increased, resulting in the enhancement of the power conversion efficiency. The solar cell performance has been discussed from the atomic force microscopy, photoelectron yield spectroscopy and X-ray photoelectron spectroscopy measurements.

  15. Crystal structure of (E-2-benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-ylmethyl]-2H-benzo[b][1,4]thiazin-3(4H-one

    Directory of Open Access Journals (Sweden)

    Nada Kheira Sebbar

    2015-06-01

    Full Text Available In the title compound, C25H20N2O2S, the dihydroisoxazole ring exhibits an envelope conformation with the methine atom being the flap, while the 1,4-thiazine ring displays a screw-boat conformation. The six-membered ring fused to the 1,4-thiazine ring makes dihedral angles of 63.04 (2 and 54.7 (2° with the mean planes through the five-membered heterocycle and the attached phenyl ring, respectively. The phenyl group connected to the 1,4-thiazine ring is disordered over two sites [major component = 0.57 (2]. The most prominent interactions in the crystal structure are C—H...O hydrogen bonds that link molecules, forming inversion dimers, and C—H...N hydrogen bonds that link the dimers into columns parallel to the b axis.

  16. PEG1000-Based Dicationic Acidic Ionic Liquid Catalyzed One-Pot Synthesis of 4-Aryl-3-Methyl-1-Phenyl-1H-Benzo[h]pyrazolo [3,4-b]quinoline-5,10-Diones via Multicomponent Reactions

    Directory of Open Access Journals (Sweden)

    Yi-Ming Ren

    2015-09-01

    Full Text Available A novel and green approach for efficient and rapid synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-diones has been accomplished by the one-pot condensation reaction of aromatic aldehydes, 3-methyl-1-phenyl-1H-pyrazol-5-amine and 2-hydroxynaphthalene-1,4-dione using PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL as a catalyst was reported. Recycling studies have shown that the PEG1000-DAIL can be readily recovered and reused several times without significant loss of activity. The key advantages are the short reaction time, high yields, simple workup, and recovered catalyst.

  17. Recyclable Keggin Heteropolyacids as an Environmentally Benign Catalyst for the Synthesis of New 2-Benzoylamino-N-phenyl-benzamide Derivatives under Microwave Irradiations at Solvent-Free Conditions and the Evaluation of Biological Activity.

    Science.gov (United States)

    Ighilahriz-Boubchir, Karima; Boutemeur-Kheddis, Baya; Rabia, Cherifa; Makhloufi-Chebli, Malika; Hamdi, Maamar; Silva, Artur M S

    2017-12-21

    2-Benzoylamino- N -phenyl-benzamide derivatives ( 5a - h ) were prepared from 2-phenyl-3,1-(4 H )-benzoxazin-4-one 3 and substituted anilines 4a - h in the presence of a Keggin-type heteropolyacids series (H₃PW 12 O 40 ·13H₂O; H₄SiW 12 O 40 ·13H₂O; H₄SiMo 12 O 40 ·13H₂O; and H₃PMo 12 O 40 ·13H₂O) as catalysts without solvent and under microwave irradiation. We found that the use of H₃PW 12 O 40 ·13H₂O acid coupled to microwave irradiation allowed obtaining a high-yielding reaction with a short time. The compound structures were established by ¹H-NMR and 13 C-NMR. The antibacterial and antifungal activities of the synthesized compounds exhibited an inhibition of the growth of bacteria and fungi.

  18. 2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl-octa-hydro-pyrrolo-[3,4-c]pyrrol-1-yl]acetamide.

    Science.gov (United States)

    Kudryavtsev, Konstantin V; Churakov, Andrei V; Dogan, Ozdemir

    2011-12-01

    In the title compound, C(21)H(21)N(3)O(3), the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7)°. In the crystal, ribbons spread along the a axis are formed by N-H⋯O hydrogen bonds. C-H⋯π inter-actions also occur.

  19. 2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl­octa­hydro­pyrrolo­[3,4-c]pyrrol-1-yl]acetamide

    Science.gov (United States)

    Kudryavtsev, Konstantin V.; Churakov, Andrei V.; Dogan, Ozdemir

    2011-01-01

    In the title compound, C21H21N3O3, the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7)°. In the crystal, ribbons spread along the a axis are formed by N—H⋯O hydrogen bonds. C—H⋯π inter­actions also occur. PMID:22199707

  20. Separation Studies of Pd(II from Acidic Chloride Solutions of Pt(IV, Ni(II and Rh(III by Using 4-Aroyl-3-Phenyl-5-Isoxazolones

    Directory of Open Access Journals (Sweden)

    Koduru Janardhan Reddy

    2012-01-01

    Full Text Available This study examined the effect influence of various factors on the extraction of Pd(II to develop a new liquid-liquid extraction mechanism for the selective separation of palladium(II from its acidic chloride solutions using 4-aroyl-3-phenyl-5-isoxazolones (HA, such as 3-phenyl-4-(4-fluorobenzoyl-5- isoxazolone (HFBPI, 3-phenyl-4-benzoyl-5-isoxazolone (HPBI and 3-phenyl-4- (4-toluoyl-5-isoxazolone (HTPI. The extraction strength of Pd(II with HA were in the following order: HFBPI > HPBI > HTPI, which is opposite to that observed with their pKa values. HPBI was used to separate Pd(II from Pt(IV, Ni(II and Rh(III metal ions and calculated their separation factors (S.F. were followed in the order: Pd/Ni (40±0.4 > Pd/Pt (25±0.2 > Pd/Rh (15±0.3 > Rh/Ni (2.7±0.3 > Pt/Ni ≈ Rh/Pt (1.7±0.2. The loading and striping of Pd(II (1.12×10-4 mol L-1 were also examined using 1.0×10-3 mol L-1 HPBI in CHCl3 and 1.0 mol L-1 HCl, respectively. The results demonstrated that the maximum (97.5% extraction and desorption (89% of metal required at least 3.0 cycles. The developed method was applied successfully to the separation of palladium from synthetic water samples.