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Sample records for 3-cyclohexene carboxaldehyde lyral

  1. Recommendation to include fragrance mix 2 and hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyral) in the European baseline patch test series

    DEFF Research Database (Denmark)

    Bruze, Magnus; Andersen, Klaus Ejner; Goossens, An;

    2008-01-01

    BACKGROUND: The currently used fragrance mix in the European baseline patch test series (baseline series) fails to detect a substantial number of clinically relevant fragrance allergies. OBJECTIVE: To investigate whether it is justified to include hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyr...

  2. Hydroxyisohexyl 3-cyclohexene carboxaldehyde- known as Lyral: quantitative aspects and risk assessment of an important fragrance allergen

    DEFF Research Database (Denmark)

    Johansen, Jeanne Duus; Frosch, Peter J; Svedman, C;

    2003-01-01

    as an allergen. It has been used without restrictions in cosmetic products, until now. In the present study, the dose-response relationship of Lyral contact allergy was studied with doses relevant for normal exposure in cosmetic products. 18 eczema patients, who previously had given a positive patch test...... to Lyral 5% petrolatum, were included along with 7 control subjects. All cases were tested with a serial dilution of Lyral in ethanol 6% to 6 p.p.m and subjected to a 2-week, repeated open application test with a low dose of Lyral in ethanol. In the case of no reaction, this was followed by another 2 weeks...

  3. Application of Purpald® for determination of 3-cyclohexene-1-carboxaldehyde and hydroxyisohexyl 3-cyclohexene carboxaldehyde.

    Science.gov (United States)

    Zakrzewski, Robert; Skowron, Monika; Rembisz, Zaneta; Ciesielski, Witold

    2013-01-01

    A spectrophotometric method for determination of 3-cyclohexene-1-carboxaldehyde and hydroxyisohexyl 3-cyclohexene carboxaldehyde was developed. This procedure is based on the reaction of carbonyl compounds with the selective derivatization reagent Purpald® in alkaline solution. The product of reaction is a colored compound with maximum absorption at 538 nm. The linear relationship is in the range of (2.5-30) × 10-5 mol·l-1 for 3-cyclohexene-1-carboxaldehyde and (2.0-20) × 10-5 mol·l-1 for hydroxyisohexyl 3-cyclohexene carboxaldehyde. The proposed method was successfully used for determination of hydroxyisohexyl 3-cyclohexene carboxaldehyde in a cosmetic product. PMID:24139437

  4. Management of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone-induced methemoglobinemia

    Science.gov (United States)

    Kunos, Charles A; Radivoyevitch, Tomas; Ingalls, Stephen T; Hoppel, Charles L

    2012-01-01

    The anticancer agent 3-aminopyridine-2-carboxaldehyde thiosemicarbazone is a ribonucleotide reductase inhibitor. It inactivates ribonucleotide reductase by disrupting an iron-stabilized radical in ribonucleotide reductase's small subunits, M2 and M2b (p53R2). Unfortunately, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone also alters iron II (Fe2+) in hemoglobin. This creates Fe3+ methemoglobin that does not deliver oxygen. Fe2+ in hemoglobin normally auto-oxidizes to inactive Fe3+ methemoglobin at a rate of nearly 3% per day and this is counterbalanced by a reductase system that normally limits methemoglobin concentrations to less than 1% of hemoglobin. This balance may be perturbed by symptomatic toxicity levels during 3-aminopyridine-2-carboxaldehyde thiosemicarbazone therapy. Indications of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone sequelae attributable to methemoglobinemia include resting dyspnea, headaches and altered cognition. Management of methemoglobinemia includes supplemental oxygen, ascorbate and, most importantly, intravenously administered methylene blue as a therapeutic antidote. PMID:22335579

  5. Management of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone-induced methemoglobinemia

    OpenAIRE

    Kunos, Charles A.; Radivoyevitch, Tomas; Ingalls, Stephen T.; Hoppel, Charles L.

    2012-01-01

    The anticancer agent 3-aminopyridine-2-carboxaldehyde thiosemicarbazone is a ribonucleotide reductase inhibitor. It inactivates ribonucleotide reductase by disrupting an iron-stabilized radical in ribonucleotide reductase's small subunits, M2 and M2b (p53R2). Unfortunately, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone also alters iron II (Fe2+) in hemoglobin. This creates Fe3+ methemoglobin that does not deliver oxygen. Fe2+ in hemoglobin normally auto-oxidizes to inactive Fe3+ methemog...

  6. Metal complexes of 4,5-dimethylpyrazole-3-carboxaldehyde phenylthiosemicarbazone

    Science.gov (United States)

    El-Dissouky, Ali

    Several new transition metal complexes derived from 4,5-dimethyl-3-carboxaldehyde phenyl- thiosemicarbazone, LH, have been synthesized. The complexes are of stoichiometry, [CoL 2]X, X = Cl -, Br -, ClO -4 or NO -3, [MnL 2] and [CuX nL m], X = Cl -, Br -, NCS - or N -3; n = 1 or 0; m = 1 or 2 and L = the anion of LH. All complexes have been characterized by elemental analysis, spectral (i.r., electronic, NMR, ESR) and magnetic measurements. The ligand acts as tridentate monobasic co-ordinated to the metal ion via azomethine, pyrazole (N 2) nitrogen atoms and the thiolo-sulphur. The ligand field and ESR parameters are used to interpret the nature of bonding of LH with the metal ion, ground state and the ligand field strength of LH and the various co-ordinated simple ions. The coupling constants of various co-ordinated nuclei with copper (II) are estimated from ESR spectra of copper (II) complexes.

  7. Spectrophotometric Determination of Arsenic in Water Samples by Thiophene-2-Carboxaldehyde Thiosemicarbazone impregnated with alumina

    OpenAIRE

    Md. Faridur Rahman; Aniruddha Chakraborty; Tanmoy Das

    2015-01-01

    Thiophene-2-carboxaldehyde thiosemicarbazone has been successfully applied as an analytical reagent for micro level solid phase spectrophotometric determination of As (III) at pH 3.5. Here it can be seen that arsenic reacts with the new chelating ligand in acidic medium to form the As (III)-tctsc complex. The complex showed maximum absorbance at λ max 281 nm for As (III) ions. The Beer’s law range was 0.1-1.0 mg/L. Job’s method and Mole-ratio method showed that As (III)-ligand ratio in the co...

  8. Outer-Sphere Mechanism in the Oxidation of Pyrrole-2- Carboxaldehyde by Hexacyanoferrate (III Complex.

    Directory of Open Access Journals (Sweden)

    Abd-Alhakeem H. Abu-Nawwas

    2014-01-01

    Full Text Available The kinetics and mechanism of base-catalyzed oxidation of pyrrole-2-carboxaldehyde with hexacyanoferrate (III is reported. The reaction showed first order with respect to aldahyde , alkali and hexaeyanoferrate(III. The kinetic data suggest that the oxidation involves the formation of an anion of the substrate undergoes oxidation with hexaeyanoferrate(III via outer sphere mechanism process. The free radical thus produced is further oxidized to form the final products. A suitable mechanism was proposed and rate law was derived as − d[Fe CN 6 ] 3− = 2k1k2 RC(OH2 [Fe CN 6 ] 3−[OH−] k−1 H2O

  9. Inclusion behaviour of Indole-7-Carboxaldehyde inside β-cyclodextrin: A nano cage

    Science.gov (United States)

    Singla, Nidhi; Chowdhury, Papia

    2014-09-01

    Encapsulation of Indole-7-Carboxaldehyde (I7C) inside nano sized cyclodextrin (α-, β-, γ-) cavities have been investigated by theoretical (PM3, HF, DFT, ONIOM methods) and experimental (UV-VIS, IR spectroscopy) results. β- cyclodextrin (CD) provides best trapping ability as its cavity size matches perfectly with the dimension of I7C. It is shown that in two specific orientations (P, Q), I7C can be encapsulated inside hydrophobic β-CD cavity by forming 1:1 inclusion complex. Intermolecular hydrogen bonding is observed to play a vital role in this encapsulation process. Present study on complexation mechanism is expected to provide a better knowledge on the reactivity of β-CD as drug carrier.

  10. Ribonucleotide reductase inhibition by metal complexes of Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone): A combined experimental and theoretical study

    OpenAIRE

    Popović-Bijelić, Ana; Kowol, Christian R.; Lind, Maria E S; Luo, Jinghui; Himo, Fahmi; Enyedy, Éva A.; Arion, Vladimir B.; Gräslund, Astrid

    2011-01-01

    Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone, 3-AP) is currently the most promising chemotherapeutic compound among the class of α-N-heterocyclic thiosemicarbazones. Here we report further insights into the mechanism(s) of anticancer drug activity and inhibition of mouse ribonucleotide reductase (RNR) by Triapine. In addition to the metal-free ligand, its iron(III), gallium(III), zinc(II) and copper (II) complexes were studied, aiming to correlate their cytotoxic activities wi...

  11. Structure and Luminescence Property of a Hexanuclear Silver(I) Cluster Containing Pyridine-3-carboxaldehyde Thiosemicarbazone

    Institute of Scientific and Technical Information of China (English)

    SUN Qiao-Zhen; CHAI Li-Yuan

    2012-01-01

    A new hexanuclear silver(I) compound containing thiosemicarbazone with group of 3-pyridine was synthesized and structurally characterized by single-crystal X-ray diffraction,elemental analysis and fluorescence spectrum.The title compound 3 crystallizes in monoclinic,space group C2/m with a = 18.6523(9),b = 24.7519(11),c = 22.4542(15) ,β = 93.4960(10)°,V = 10347.4(10)3,C68H104Ag6N30O8S6,Mr = 2309.39,Dc = 1.482g/cm3,μ(MoKα) = 1.293 mm-1,F(000) = 4656,Z = 4,the final R = 0.0544 and wR = 0.1580 for 6733 observed reflections(I 〉 2σ(I)).In the structure,two Ag6L36(L3 = pyridine-3-carboxaldehyde thiosemicarbazone) clusters are contained.In each cluster,the S atom of ligand L3 served as a triply bridged chelator to connect the six silver atoms into a Ag6L36 cluster.Luminescence investigation revealed that the band at 630 nm was attributed to cluster-centered(CC) electron transfer,and those at 493 and 530 nm to the LMCT and CC transitions,respectively.

  12. Spectrophotometric Determination of Arsenic in Water Samples by Thiophene-2-Carboxaldehyde Thiosemicarbazone impregnated with alumina

    Directory of Open Access Journals (Sweden)

    Md. Faridur Rahman

    2015-12-01

    Full Text Available Thiophene-2-carboxaldehyde thiosemicarbazone has been successfully applied as an analytical reagent for micro level solid phase spectrophotometric determination of As (III at pH 3.5. Here it can be seen that arsenic reacts with the new chelating ligand in acidic medium to form the As (III-tctsc complex. The complex showed maximum absorbance at λ max 281 nm for As (III ions. The Beer’s law range was 0.1-1.0 mg/L. Job’s method and Mole-ratio method showed that As (III-ligand ratio in the complex is 1:2. The Molar absorptivity and Sandell’s sensitivity were 5.96 x 104 L mol-1 cm-1 and 0.01μg/cm2 respectively for As (III ions. The proposed method has been successfully applied to the determination of arsenic in drinking water samples of Kaliachak, in the district of Malda, West Bengal, India.

  13. Heterogeneous photochemistry of imidazole-2-carboxaldehyde: HO2 radical formation and aerosol growth

    Science.gov (United States)

    González Palacios, Laura; Corral Arroyo, Pablo; Aregahegn, Kifle Z.; Steimer, Sarah S.; Bartels-Rausch, Thorsten; Nozière, Barbara; George, Christian; Ammann, Markus; Volkamer, Rainer

    2016-09-01

    The multiphase chemistry of glyoxal is a source of secondary organic aerosol (SOA), including its light-absorbing product imidazole-2-carboxaldehyde (IC). IC is a photosensitizer that can contribute to additional aerosol ageing and growth when its excited triplet state oxidizes hydrocarbons (reactive uptake) via H-transfer chemistry. We have conducted a series of photochemical coated-wall flow tube (CWFT) experiments using films of IC and citric acid (CA), an organic proxy and H donor in the condensed phase. The formation rate of gas-phase HO2 radicals (PHO2) was measured indirectly by converting gas-phase NO into NO2. We report on experiments that relied on measurements of NO2 formation, NO loss and HONO formation. PHO2 was found to be a linear function of (1) the [IC] × [CA] concentration product and (2) the photon actinic flux. Additionally, (3) a more complex function of relative humidity (25 % cycle. OH does not appear to be formed as a primary product but is produced from the reaction of NO with HO2 in the gas phase. Further, seed aerosols containing IC and ammonium sulfate were exposed to gas-phase limonene and NOx in aerosol flow tube experiments, confirming significant PHO2 from aerosol surfaces. Our results indicate a potentially relevant contribution of triplet state photochemistry for gas-phase HO2 production, aerosol growth and ageing in the atmosphere.

  14. A time-resolved study of the multiphase chemistry of excited carbonyls: Imidazole-2-carboxaldehyde and halides

    OpenAIRE

    Tinel, Liselotte; Dumas, Stéphane; George, Christian

    2014-01-01

    CARE+LTI:SDU:CGO International audience Imidazole-2-carboxaldehyde (IC) reactivity in the presence of halide anions (Cl-, Br-, I-) has been studied by laser flash photolysis in aqueous solution at room temperature. The absorption spectrum of the triplet state of IC has been measured with a maximum absorption at 330 nm and a weaker absorption band around 650 nm. Iodide anions proved to be efficient quenchers of the triplet state IC, with a rate coefficient kg of (5.33 +/- 0.25) x 10(9) M...

  15. Synthesis, thermal and antitumour studies of Th(IV complexes with furan-2-carboxaldehyde4-phenyl-3-thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    VINO T. CHERIYAN

    2010-06-01

    Full Text Available Thorium(IV complexes with the Schiff base furan-2-carboxaldehyde4-phenyl-3-thiosemicarbazone (L were synthesised and characterized. The composition and structure of the metal complexes were proposed based on elemental analysis, molar conductivity measurements, FTIR and 1H-NMR spectroscopy. The Schiff base behaves as a neutral bidentate ligand coordinating through the azomethine N and the thioketo S atoms. From various studies, complexes were ascertained the general formula [ThL2X4] and [ThL2Y2], where X represents NO3–, NCS–, CH3COO–, CH3CHOHCOO–, ClO4– and Y SO42–and C2O42–. The thermal behaviour of the nitrato and oxalato complexes was studied and kinetic and thermodynamic parameters were calculated using the Coats-Redfern Equation. The ligand and a representative complex [ThL2(NO34] were screened in vitro for their antitumour activity against the human cervical cancer cell line (HeLa.

  16. Quinoline-2-carboxaldehyde thiosemicarbazones and their Cu(II) and Ni(II) complexes as topoisomerase IIa inhibitors.

    Science.gov (United States)

    Bisceglie, Franco; Musiari, Anastasia; Pinelli, Silvana; Alinovi, Rossella; Menozzi, Ilaria; Polverini, Eugenia; Tarasconi, Pieralberto; Tavone, Matteo; Pelosi, Giorgio

    2015-11-01

    A series of quinoline-2-carboxaldehyde thiosemicarbazones and their copper(II) and nickel(II) complexes were synthesized and characterized. In all complexes the ligands are in the E configuration with respect to the imino bond and behave as terdentate. The copper(II) complexes form square planar derivatives with one molecule of terdentate ligand and chloride ion. A further non-coordinated chloride ion compensates the overall charge. Nickel(II) ions form instead octahedral complexes with two ligands for each metal ion, independently from the stoichiometric metal:ligand ratio used in the synthesis. Ligands and complexes were tested for their antiproliferative properties on histiocytic lymphoma cell line U937. Copper(II) derivatives are systematically more active than the ligands and the nickel complexes. All copper derivatives result in inhibiting topoisomerase IIa in vitro. Computational methods were used to propose a model to explain the different extent of inhibition presented by these compounds. The positive charge of the dissociated form of the copper complexes may play a key role in their action. PMID:26335598

  17. WITTIG REACTION APPROACH FOR THE SYNTHESIS OF 7-METHOXY-2-[4- ALKYL/ARYL]-L-BENZOFURAN-5-CARBOXALDEHYDE Wittig-Reaktion Ansatz für die Synthese von 7-Methoxy-2-[4 - ALKYL / ARYL]-L-BENZOFURAN-5-CARBOXALDEHYDE

    Directory of Open Access Journals (Sweden)

    Bapu R Thorata, Dyneshwar Shelke, Ramdas Atram and Ramesh Yamgar

    2013-07-01

    Full Text Available Vanillin undergoes sequence of reaction forming phosphonium salt through dimethyaminomethyl derivative (Mannich reaction. The synthesis of phosphonium salt can be achieved by sequence of three steps which was condense with series of aliphatic/aromatic acid chlorides by refluxing in toluene in presence of triethylamine (Wittig reaction as key step resulting 7-methoxy-2-alkyl/aryl-l-benzofuran-5-carboxaldehyde. The crude product was purified by using column chromatography and characterized by FTIR, NMR and Mass spectroscopy.

  18. Pterostilbene carboxaldehyde thiosemicarbazone, a resveratrol derivative inhibits 17β-Estradiol induced cell migration and proliferation in HUVECs.

    Science.gov (United States)

    Nikhil, Kumar; Sharan, Shruti; Wishard, Rohan; Palla, Srinivasa Rao; Krishna Peddinti, Rama; Roy, Partha

    2016-04-01

    Angiogenesis plays important roles in tumor growth and metastasis, thus development of a novel angiogenesis inhibitor is essential for the improvement of therapeutics against cancer. Thrombospondins-1 (TSP-1) is a potent endogenous inhibitor of angiogenesis that acts through direct effects on endothelial cell migration, proliferation, survival, and activating apoptotic pathways. TSP-1 has been shown to disrupt estrogen-induced endothelial cell proliferation and migration. Here we investigated the potential of pterostilbene carboxaldehyde thiosemicarbazone (PTERC-T), a novel resveratrol (RESV) derivative, to inhibit angiogenesis induced by female sex steroids, particularly 17β-Estradiol (E2), on Human umbilical vein endothelial cells (HUVECs) and to elucidate the involvement of TSP-1 in PTERC-T action. Our results showed that PTERC-T significantly inhibited 17β-E2-stimulated proliferation of HUVECs and induced apoptosis as determined by annexin V/propidium iodide staining and cleaved caspase-3 expression. Furthermore, PTERC-T also inhibited endothelial cell migration, and invasion in chick chorioallantoic membrane (CAM) assay. In contrast, RESV failed to inhibit 17β-E2 induced HUVECs proliferation and invasion at similar dose. PTERC-T was also found to increase TSP-1 protein expression levels in a dose-dependent manner which, however, was counteracted by co-incubation with p38MAPK or JNK inhibitors, suggesting involvement of these pathways in PTERC-T action. These results suggest that the inhibitory effect of PTERC-T on 17β-E2 induced angiogenesis is associated, at least in part, with its induction of endothelial cell apoptosis and inhibition of cell migration through targeting TSP-1. Thus, PTERC-T could be considered as a potential lead compound for developing a class of new drugs targeting angiogenesis-related diseases. PMID:26850466

  19. Radiochemotherapy plus 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in Advanced-Stage Cervical and Vaginal Cancers

    Science.gov (United States)

    Kunos, Charles A.; Radivoyevitch, Tomas; Waggoner, Steven; Debernardo, Robert; Zanotti, Kristine; Resnick, Kimberly; Fusco, Nancy; Adams, Ramon; Redline, Raymond; Faulhaber, Peter; Dowlati, Afshin

    2013-01-01

    Objective Cervical and vaginal cancers have virally-mediated or mutated defects in DNA damage repair responses, making these cancers sensible targets for ribonucleotide reductase inhibition during radiochemotherapy. Methods We conducted a phase II study evaluating 3x weekly 2-hour intravenous 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, 25 mg/m2) co-administered with 1x weekly intravenous cisplatin (40 mg/m2) and daily pelvic radiation (45 Gy) in women with stage IB2-IVB cervical (n = 22) or stage II-IV vaginal (n = 3) cancers. Brachytherapy followed (40 Gy). Toxicity was monitored by common terminology criteria for adverse events (version 3.0). The primary end point of response was assessed by 3-month posttherapy 2-[18F] fluoro-2-deoxy-D-glucose positron emission tomography (PET/CT) and clinical examination. Results 3-AP radiochemotherapy achieved clinical responses in 24 (96% [95% confidence interval: 80-99%]) of 25 patients (median follow-up 20 months, range 2-35 months). 23 (96% [95% confidence interval: 80-99%]) of 24 patients had 3-month posttherapy PET/CT scans that recorded metabolic activity in the cervix or vagina equal or less than that of the cardiac blood pool, suggesting complete metabolic responses. The most frequent 3-AP radiochemotherapy-related adverse events included fatigue, nausea, diarrhea, and reversible hematological and electrolyte abnormalities. Conclusions The addition of 3-AP to cisplatin radiochemotherapy was tolerable and produced high rates of clinical and metabolic responses in women with cervical and vaginal cancers. Future randomized phase II and III clinical trials of 3-AP radiochemotherapy are warranted. PMID:23603372

  20. Ribonucleotide reductase inhibition by metal complexes of Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone): A combined experimental and theoretical study

    Science.gov (United States)

    Popović-Bijelić, Ana; Kowol, Christian R.; Lind, Maria E.S.; Luo, Jinghui; Himo, Fahmi; Enyedy, Éva A.; Arion, Vladimir B.; Gräslund, Astrid

    2012-01-01

    Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone, 3-AP) is currently the most promising chemotherapeutic compound among the class of α-N-heterocyclic thiosemicarbazones. Here we report further insights into the mechanism(s) of anticancer drug activity and inhibition of mouse ribonucleotide reductase (RNR) by Triapine. In addition to the metal-free ligand, its iron(III), gallium(III), zinc(II) and copper (II) complexes were studied, aiming to correlate their cytotoxic activities with their effects on the diferric/tyrosyl radical center of the RNR enzyme in vitro. In this study we propose for the first time a potential specific binding pocket for Triapine on the surface of the mouse R2 RNR protein. In our mechanistic model, interaction with Triapine results in the labilization of the diferric center in the R2 protein. Subsequently the Triapine molecules act as iron chelators. In the absence of external reductants, and in presence of the mouse R2 RNR protein, catalytic amounts of the iron(III)–Triapine are reduced to the iron(II)–Triapine complex. In the presence of an external reductant (dithiothreitol), stoichiometric amounts of the potently reactive iron (II)–Triapine complex are formed. Formation of the iron(II)–Triapine complex, as the essential part of the reaction outcome, promotes further reactions with molecular oxygen, which give rise to reactive oxygen species (ROS) and thereby damage the RNR enzyme. Triapine affects the diferric center of the mouse R2 protein and, unlike hydroxyurea, is not a potent reductant, not likely to act directly on the tyrosyl radical. PMID:21955844

  1. Pterostilbene carboxaldehyde thiosemicarbazone, a resveratrol derivative inhibits 17β-Estradiol induced cell migration and proliferation in HUVECs.

    Science.gov (United States)

    Nikhil, Kumar; Sharan, Shruti; Wishard, Rohan; Palla, Srinivasa Rao; Krishna Peddinti, Rama; Roy, Partha

    2016-04-01

    Angiogenesis plays important roles in tumor growth and metastasis, thus development of a novel angiogenesis inhibitor is essential for the improvement of therapeutics against cancer. Thrombospondins-1 (TSP-1) is a potent endogenous inhibitor of angiogenesis that acts through direct effects on endothelial cell migration, proliferation, survival, and activating apoptotic pathways. TSP-1 has been shown to disrupt estrogen-induced endothelial cell proliferation and migration. Here we investigated the potential of pterostilbene carboxaldehyde thiosemicarbazone (PTERC-T), a novel resveratrol (RESV) derivative, to inhibit angiogenesis induced by female sex steroids, particularly 17β-Estradiol (E2), on Human umbilical vein endothelial cells (HUVECs) and to elucidate the involvement of TSP-1 in PTERC-T action. Our results showed that PTERC-T significantly inhibited 17β-E2-stimulated proliferation of HUVECs and induced apoptosis as determined by annexin V/propidium iodide staining and cleaved caspase-3 expression. Furthermore, PTERC-T also inhibited endothelial cell migration, and invasion in chick chorioallantoic membrane (CAM) assay. In contrast, RESV failed to inhibit 17β-E2 induced HUVECs proliferation and invasion at similar dose. PTERC-T was also found to increase TSP-1 protein expression levels in a dose-dependent manner which, however, was counteracted by co-incubation with p38MAPK or JNK inhibitors, suggesting involvement of these pathways in PTERC-T action. These results suggest that the inhibitory effect of PTERC-T on 17β-E2 induced angiogenesis is associated, at least in part, with its induction of endothelial cell apoptosis and inhibition of cell migration through targeting TSP-1. Thus, PTERC-T could be considered as a potential lead compound for developing a class of new drugs targeting angiogenesis-related diseases.

  2. Antioxidation and DNA-binding properties of binuclear lanthanide(III) complexes with a Schiff base ligand derived from 8-hydroxyquinoline-7-carboxaldehyde and benzoylhydrazine.

    Science.gov (United States)

    Liu, Yongchun; Zhang, Kejun; Wu, Yun; Zhao, Junying; Liu, Jianning

    2012-08-01

    8-Hydroxyquinoline-7-carboxaldehyde (8-HQ-7-CA), Schiff-base ligand 8-hydroxyquinoline-7-carboxaldehyde benzoylhydrazone, and binuclear complexes [LnL(NO(3))(H(2)O)(2)](2) were prepared from the ligand and equivalent molar amounts of Ln(NO(3))·6H(2)O (Ln=La(3+), Nd(3+), Sm(3+), Eu(3+), Gd(3+), Dy(3+), Ho(3+), Er(3+), Yb(3+), resp.). Ligand acts as dibasic tetradentates, binding to Ln(III) through the phenolate O-atom, N-atom of quinolinato unit, and C=N and -O-C=N- groups of the benzoylhydrazine side chain. Dimerization of this monomeric unit occurs through the phenolate O-atoms leading to a central four-membered (LnO)(2) ring. Ligand and all of the Ln(III) complexes can strongly bind to CT-DNA through intercalation with the binding constants at 10(5)-10(6) M(-1). Moreover, ligand and all of the Ln(III) complexes have strong abilities of scavenging effects for hydroxyl (HO·) radicals. Both the antioxidation and DNA-binding properties of Ln(III) complexes are much better than that of ligand.

  3. Rational design of carbonitrile-carboxaldehyde cation receptor models: probing the nature of the heteroatom-metal interaction.

    Science.gov (United States)

    Rosli, Ahmad Nazmi; Abu Bakar, Maizathul Akmam; Lee, Vannajan Sanghiran; Zain, Sharifuddin Md; Ahmad, Mohd Rais; Abdul Manan, Ninie Suhana; Alias, Yatimah; Woi, Pei Meng

    2014-09-01

    In this work, hybrid functional and G4 methods were employed in the rational design of carbonitrile-carboxaldehyde receptor models for cation recognition. Electron-sharing and ionic interactions between the models and the cations were analyzed utilizing the concepts of overlap population, atomic valence, electrostatic potential, and CHELPG charge in order to elucidate the nature of the heteroatom-metal interaction, the N versus O disparity, and the effect of pH. Receptor fragment models from ionomycin were employed to rationalize the selection of receptor models for discriminating group I cations and enhancing the selectivity for Mg(II) rather than Ca(II), and to examine the effects of keto-enol forms and negatively charged sites. The changes in geometries, overlap population, metal valence, and CHELPG charge upon solvation in heptane medium as compared to the gas phase were negligible. The optimized geometries reveal that the interaction between group II cations and the keto, enol, and enolate forms of 2-cyanoethanal causes 12 % bending of the C-C-N angle from linearity. Overlap populations show that the electron-sharing interaction favors group II cations but that the same mechanism allows Li(I) to compete. The total spin of Li(I) is 17 % greater than that of Ca(II), but the G4 binding energies of the two are separated by more than 50 kcal/mol, favoring group II cations, which may eliminate interference from Li(I). 1,2-Dicyanoethylene, which has only one form, shows similar characteristics. CHELPG analysis shows that Mg(II) transfers 25 and 18 % of its positive charge to 2-cyanoethanal enolate and 1,2-dicyanoethylene, respectively. Hydrogen atoms receive most of the positive charge in both receptors, but the N-termini exhibit strikingly different characteristics. Electrostatic potential contour profiles were found to be in good agreement with the atomic charge distributions. The application of uncharged 1,3-dicarbonyl and 2-cyanocarbonyl receptors and a judicious

  4. Cytotoxic evaluation of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone in peripheral blood lymphocytes of patients with refractory solid tumors using electron paramagnetic resonance

    Science.gov (United States)

    KOLESAR, JILL M.; SACHIDANANDAM, KAMAKSHI; SCHELMAN, WILLIAM R.; EICKHOFF, JENS; HOLEN, KYLE D.; TRAYNOR, ANNE M.; ALBERTI, DONA B.; THOMAS, JAMES P.; CHITAMBAR, CHRISTOPHER R.; WILDING, GEORGE; ANTHOLINE, WILLIAM E.

    2011-01-01

    3-Aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) is a metal chelator that potently inhibits the enzyme ribonucleotide reductase (RR), which plays a key role in cell division and tumor progression. A subunit of RR has a non-heme iron and a tyrosine-free radical, which are required for the enzymatic reduction of ribonucleotides to deoxyribonucleotides. The objective of the present study was to determine whether 3-AP affects its targeted action by measuring electron paramagnetic resonance (EPR) signals formed either directly or indirectly from low molecular weight ferric-3-AP chelates. Peripheral blood lymphocytes were collected from patients with refractory solid tumors at baseline and at 2, 4.5 and 22 h after 3-AP administration. Using EPR spectra, our study identified signals from high-spin Fe-transferrin, high-spin heme and low-spin iron or copper ions. An increase in the Fe-transferrin signal was observed, suggesting blockage of Fe uptake. It is hypothesized that formation of reactive oxygen species by FeT2 or CuT damages the transferrin or the transferrin receptor. An increase in the heme signal was also observed, which was a probable source of cytochrome c release from the mitochondria and potential apoptosis. In addition, increased levels of Fe and Cu were identified. These results, which were consistent with our previous study validating 3-AP-mediated signals by EPR, provide valuable insights into the in vivo mechanism of action of 3-AP. PMID:21373381

  5. Phase I study of the ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) in combination with high dose cytarabine in patients with advanced myeloid leukemia

    Science.gov (United States)

    Larson, Richard A.; Gajria, Devika; Dolan, M. Eileen; Delaney, Shannon M.; Karrison, Theodore G.; Ratain, Mark J.; Stock, Wendy

    2014-01-01

    Summary Purpose This Phase I dose escalation study was based on the hypothesis that the addition of 3-aminopyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) to cytarabine would enhance cytarabine cytotoxicity. The primary objective of the study was to establish the maximum tolerated dose of 3-AP when given in combination with a fixed dose of cytarabine. Experimental design Twenty-five patients with relapsed or refractory myeloid leukemia were enrolled to three dose levels of 3-AP. Cytarabine was administered as a 2 h infusion at a fixed dose of 1,000 mg/m2/day for 5 consecutive days. Escalating doses of 3-AP as a 2 h infusion were administered on days 2 through 5. The 3-AP infusion preceded the start of the cytarabine infusion by 4 h. Results In general, the toxicities observed with the combination were similar to the expected toxicity profile for cytarabine when utilized as a single agent at this dose and schedule. However, two of three patients developed dose-limiting methemoglobinemia at the highest 3-AP dose studied (100 mg/m2). Transient reversible methemoglobinemia was documented in 11 of 15 patients enrolled at the 75 mg/m2 dose level. Objective evidence of clinical activity was observed in four patients. Conclusions The combination of 3-AP and cytarabine given on this schedule is feasible in advanced myeloid leukemia. The recommended Phase II dose is 75 mg/m2/day of 3-AP on days 2–5 given prior to cytarabine administered at a dose of 1,000 mg/m2/day over 5 consecutive days. Methemoglobinemia is a common toxicity of this combination and requires close monitoring. PMID:18217206

  6. A phase 2 consortium (P2C) trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) for advanced adenocarcinoma of the pancreas

    Science.gov (United States)

    Attia, Steven; Kolesar, Jill; Mahoney, Michelle R.; Pitot, Henry C.; Laheru, Daniel; Heun, James; Huang, Wei; Eickhoff, Jens; Erlichman, Charles

    2015-01-01

    Summary 3-Aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine®) is a novel small molecule inhibitor of ribonucleotide reductase (RR) with clinical signs of activity in pancreatic cancer. Therefore, the Phase 2 Consortium (P2C) initiated a trial (two single stage studies with planned interim analysis) of 3-AP at 96 mg/m2 intravenously days 1–4 and 15–18 of a 28-day cycle in both chemotherapy-naive and gemcitabine-refractory (GR) patients with advanced pancreatic cancer. The primary endpoint was survival at six months (chemotherapy-naive) and four months (GR). Secondary endpoints were toxicity, response, overall survival, time to progression and mechanistic studies. Fifteen patients were enrolled including one chemotherapy-naïve and 14 GR. The chemotherapy-naïve patient progressed during cycle 1 with grade 3 and 4 toxicities. Of 14 GR patients, seven received two cycles, six received one cycle and one received eight cycles. Progression precluded further treatment in 11 GR patients. Additionally, one died of an ileus in cycle 1 considered related to treatment and two stopped treatment due to toxicity. Five GR patients had grade 4 toxicities possibly related to 3-AP and six GR patients had grade 3 fatigue. Toxicities and lack of meaningful clinical benefit prompted early study closure. Four-month survival in GR patients was 21% (95% CI: 8–58%). Correlative studies confirmed that 3-AP increased the percentage of S-phase buccal mucosal cells, the presence of multidrug resistance gene polymorphisms appeared to predict leukopenia, and baseline pancreatic tumor RR M2 expression was low relative to other tumors treated with 3-AP. In conclusion, this regimen appears inactive against predominantly GR pancreatic cancer. RR M2 protein may not have a critical role in the malignant potential of pancreatic cancer. PMID:18278438

  7. Phase I trial of pelvic radiation, weekly cisplatin, and 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) for locally advanced cervical cancer

    Science.gov (United States)

    Kunos, Charles A.; Waggoner, Steven; von Gruenigen, Vivian; Eldermire, Elisa; Pink, John; Dowlati, Afshin; Kinsella, Timothy J.

    2009-01-01

    Purpose This study assessed the safety/tolerability, pharmacokinetics, and clinical activity of three-times weekly intravenous 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in combination with once weekly intravenous cisplatin and daily pelvic radiation in patients with gynecologic malignancies. 3-AP is a novel small molecule inhibitor of ribonucleotide reductase (RNR) and is being tested as a potential radiosensitizer and chemosensitizer. Experimental Design Patients with stage IB2-IVB cervical cancer (n=10) or recurrent uterine sarcoma (n=1) were assigned to dose-finding cohorts of 2-hour 3-AP infusions during five weeks of cisplatin chemoradiation. Pharmacokinetic and methemoglobin samples and tumor biopsy for RNR activity were obtained on days 1 and 10. Clinical response was assessed. Results The maximum tolerated 3-AP dose is 25mg/m2 given three-times weekly during cisplatin and pelvic radiation. Two patients experienced manageable 3-AP-related grade 3 or 4 electrolyte abnormalities. 3-AP pharmacokinetics showed a 2-hour half-life, with median peak plasma concentrations of 277ng/mL (25mg/m2) and 467ng/mL (50mg/m2). Median methemoglobin levels peaked at 1% (25mg/m2) and 6% (50mg/m2) at 4 hours after initiating 3-AP infusions. No change in RNR activity was found on day 1 versus 10 in six early complete responders, while elevated RNR activity was seen on day 10 as compared to day 1 in four late complete responders (P =0.02). Ten (100%) patients with stage IB2-IVB cervical cancer achieved complete clinical response and remain without disease relapse with a median 18 months of follow-up (6-32 months). Conclusions 3-AP was well tolerated at a three-times weekly intravenous 25mg/m2 dose during cisplatin and pelvic radiation. PMID:20145183

  8. Studies on coordination chemistry and bioactivity of metal complexes of a bidentate NN schiff base, (2-pyridyl-methylene)(phenyl) hydrazine, produced from the condensation of pyridine-2-carboxaldehyde with phenylhydrazine

    International Nuclear Information System (INIS)

    A bidentate Schiff base, (2-pyridyl-methylene)(phenyl) hydrazine, with NN donor sequence, was isolated from the condensation of pyridine-2-carboxaldehyde with phenylhydrazine in ethanol. Metal complexes of this ligand with Ni(II), Zn(It), and Cu(n) ions were synthesized and characterized by a variety of physico-chemical techniques. The structure of the Schiff base was solved by X-ray diffraction studies, which indicated that it was monoclinic with a space group of C2/c. The complexes were all four coordinated. The compounds were tested against four pathogenic bacteria and fungi. The nickel complex, [Ni(NN)2Cl2], in particular, was found to be active against all the fungi tested. The complexes were however inactive against leukemic cell lines (CEM-SS). (author)

  9. Lyral is an important sensitizer in patients sensitive to fragrances

    DEFF Research Database (Denmark)

    Frosch, P J; Johansen, Jeanne Duus; Menné, T;

    1999-01-01

    Contact allergy to fragrances is a common problem world-wide. The currently used fragrance mix (FM) for patch testing has only eight constituents and does not identify all fragrance-allergic patients. As perfumes may contain 100 or more substances, the search for markers for allergy continues...

  10. Simple,Selective,and Sensitive Spectrophotometric Method for Determination of Trace Amounts of Nickel(Ⅱ),Copper(Ⅱ), Cobalt(Ⅱ),and Iron(Ⅲ)with a Novel Reagent 2-Pyridine Carboxaldehyde Isonicotinyl Hydrazone

    Institute of Scientific and Technical Information of China (English)

    Sajid H.Guzar; JIN Qin-han

    2008-01-01

    A selective and sensitive reagent of 2-pyridine carboxaldehyde isonicotinyl hydrazone(2-PYAINH)was synthesized and studied for the spectrophotometric determination of nickel,copper,cobalt,and iron in detail.At a pH value of 7.0,9.0,9.0,and 8.0,respectively,which greatly increased the selectivity;nickel,copper,cobalt, and iron reacted with 2-PYAINH to form a 1:2 yellow-orange,1:2 yellow-green,1:2 yellow and 1:1 yellow complexes,with absorption peaks at 363,352,346,and 359 nm,respectively.Under the optimal conditions,Beer's law was obeyed over the ranges of 0.01-1.4,0.01-1.5,0.01-2.7,and 0.01-5.4 mg/L,respectively.The apparent molar absorptivity and Sandell's sensitivities were 8.4×104,5.2x104,7.1×104,and 3.9×104L·mol-1.cm-1,respectively,and 0.00069,0.0012,0.00078,and 0.0014 μ g·cm-2,respectively.The detection limits were found to be 0.001,O.002,0.003,and 0.01 mg/L,respectively.The detailed study of various interfering ions to make the method more sensitive was carried out and selective and several real samples were analyzed with satisfactory results.

  11. A phase I and pharmacokinetic study of oral 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in the treatment of advanced stage solid cancers – A California Cancer Consortium Study

    Science.gov (United States)

    Chao, Joseph; Synold, Timothy W.; Morgan, Robert J.; Kunos, Charles; Longmate, Jeff; Lenz, Heinz-Josef; Lim, Dean; Shibata, Stephen; Chung, Vincent; Stoller, Ronald G.; Belani, Chandra P.; Gandara, David R.; McNamara, Mark; Gitlitz, Barbara J.; Lau, Derick H.; Ramalingam, Suresh S.; Davies, Angela; Espinoza-Delgado, Igor; Newman, Edward M.; Yen, Yun

    2012-01-01

    Background 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) is a novel small molecule ribonucleotide reductase inhibitor. This study was designed to estimate the maximum-tolerated dose (MTD) and oral bioavailability of 3-AP in patients with advanced stage solid tumors. Methods Twenty patients received one dose of intravenous and subsequent cycles of oral 3-AP following a 3+3 patient dose-escalation. Intravenous 3-AP was administered to every patient at a fixed dose of 100 mg over a 2-hour infusion 1 week prior to the first oral cycle. Oral 3-AP was administered every 12 hours for 5 consecutive doses on days 1–3, days 8–10, and days 15–17 of every 28-day cycle. 3-AP was started at 50 mg with a planned dose escalation to 100, 150, and 200 mg. Dose-limiting toxicities (DLT) and bioavailability were evaluated. Results Twenty patients were enrolled. For dose level 1 (50mg), the second of three treated patients had a DLT of grade 3 hypertension. In the dose level 1 expansion cohort, three patients had no DLTs. No further DLTs were encountered during escalation until the 200 mg dose was reached. At the 200 mg 3-AP dose level, two treated patients had DLTs of grade 3 hypoxia. One additional DLT of grade 4 febrile neutropenia was subsequently observed at the de-escalated 150 mg dose. One DLT in 6 evaluable patients established the MTD as 150 mg per dose on this dosing schedule. Responses in the form of stable disease occurred in 5 (25%) of 20 patients. The oral bioavailability of 3-AP was 67 ± 29%, and was consistent with the finding that the MTD by the oral route was 33% higher than by the intravenous route. Conclusions Oral 3-AP is well-tolerated and has an MTD similar to its intravenous form after accounting for the oral bioavailability. Oral 3-AP is associated with a modest clinical benefit rate of 25% in our treated patient population with advanced solid tumors. PMID:22105720

  12. Fragrance mix II in the baseline series contributes significantly to detection of fragrance allergy

    DEFF Research Database (Denmark)

    Heisterberg, Maria S Vølund; Andersen, Klaus E.; Avnstorp, Christian;

    2010-01-01

    Background: Fragrance mix II (FM II) is a relatively new screening marker for fragrance contact allergy. It was introduced in the patch test baseline series in Denmark in 2005 and contains six different fragrance chemicals commonly present in cosmetic products and which are known allergens. Aim......: To investigate the diagnostic contribution of including FM II in the baseline series by comparing it with other screening markers of fragrance allergy: fragrance mix I (FM I), Myroxylon pereirae and hydroxyisohexyl 3-cyclohexene carboxaldehyde (HICC). Method: Retrospective study of 12 302 patients consecutively...

  13. Essential Oil Composition of the Dracocephalum moldavica L from Xinjiang in China

    Directory of Open Access Journals (Sweden)

    Tian Shuge

    2009-01-01

    Full Text Available The essential oil of Dracocephalum moldavica L from Xinjiang in China was isolated by hydrodistillation in yield of 0.15 %(w/w. The chemical composition of the essential oil was analyzed by GC and GCMS. Fifty-one compounds accounting for 99.45% of the total oil were identified. The major components werea-Citral (32.55%, β-Citral (23.53%, Acetic acid, geranial ester(21.32%, Trans-Geraniol(3.38%, Nerolacetate(3.38%, Octane(2.14%, and 2,4,6-Trimethyl -3-cyclohexene-1-carboxaldehyde (1.3%. Monotenepers were the main group of compounds.

  14. 噻吩-N-4甲基缩氨基硫脲及其银离子配合物对EC109增殖和凋亡影响%Effects of thiophene-2-carboxaldehyde N(4)-methylthiosemicarbazone and its Ag(Ⅰ)complex on proliferation and apoptosis of EC109

    Institute of Scientific and Technical Information of China (English)

    李晓娟; 曹更生; 刘广超; 李明雪; 张洪

    2011-01-01

    Aim To study the anti-tumor activity and the possible mechanism of thiophene-2-carboxaldehydeN( 4 )-methylthiosemicarbazone and its Ag( Ⅰ ) complex for esophageal EC109 in vitro. Methods The effect of the thiophene-2-carboxaldehydeN( 4 ) -methyl thiosemicarbazone and its Ag( Ⅰ ) complex on cell proliferation for esophageal EC109 in vitro was tested by MTT method. Ciemsa staining and acridine orange ( AO ) fluorescence staining were used to observe the morphological changes of the esophageal EC109. Cell apoptosis and cell cycle distribution were detected by flow cytometry. Results The results indicated its Ag ( Ⅰ ) complex had strong inhibitory effect on EC109 cell proliferation in a dose-and-time dependent manner;Typical morphological changes of apoptosis were also observed in the esophageal EC109. The result of flow cytometry showed the Ag( Ⅰ ) complex led to cell apoptosis partly in lower concentrations . And the apoptosis increased in a concentration dependent manner, and inhibited G0/G1 phase from entering S phase. Conclusions The ligand N has no anti-tumor effect at all on esophageal EC109 , but the Ag( Ⅰ )complex N-Ag exhibits significant anti-tumor activity after introducing Ag ion, and possibly induces cell apoptosis by blocking cell cycle.%目的 用食管癌细胞EC109体外鉴定噻吩-N-4甲基缩氨基硫脲(N)及其过渡金属配合物噻吩-N-4甲基缩氨基硫脲银(N-Ag)的抗肿瘤生物活性,探讨其可能机制.方法 采用四甲基偶氮唑法(MTT法)测定上述两种药物体外对食道癌细胞EC109生长抑制率;采用吖啶橙荧光染色和吉姆萨染色观察药物对食道癌细胞EC109形态影响;采用流式细胞仪检测细胞周期的改变和细胞的凋亡情况.结果 N-Ag对食道癌EC109的增殖有较强的抑制作用,且成量效和时效关系;实验组能观察到细胞凋亡形态;流式细胞仪检测结果表明在低剂量N-Ag作用下食道癌细胞EC109部分凋亡,且随着

  15. A second monoclinic polymorph of (pyridine-2-carboxaldehyde oximato-κ2N,N′(pyridine-2-carboxaldehyde oxime-κ2N,N′palladium(II chloride

    Directory of Open Access Journals (Sweden)

    Kwang Ha

    2012-02-01

    Full Text Available The asymmetric unit of the title compound, [Pd(C6H5N2O(C6H6N2O]Cl, contains one half of a cationic PdII complex and a Cl− anion, with a crystallographic mirror plane parallel to the ac plane passing through the Pd and Cl atoms. In the complex, the PdII ion is four-coordinated in a distorted square-planar environment by four N atoms derived from the two chelating ligands. The hydroxy H atom lies on the mirror plane and so is equidistant from the O atoms. This indicates that the negative charge is delocalized over the two O atoms. The complex molecules are stacked in columns along the c axis and are connected by C—H...O hydrogen bonds, forming a three-dimensional network. The structure reported herein represents a new monoclinic polymorph of the previously reported monoclinic (C2/c form [Torabi et al. (2007. Z. Kristallogr. New Cryst. Struct. 222, 197–198].

  16. Population Pharmacokinetics of 3-Aminopyridine-2-Carboxaldehyde Thiosemicarbazone (Triapine®) in Cancer Patients

    Science.gov (United States)

    Kolesar, Jill; Brundage, Richard C.; Pomplun, Marcia; Alberti, Dona; Holen, Kyle; Traynor, Anne; Ivy, Percy; Wilding, George

    2011-01-01

    Purpose The purpose of this study was to develop a population pharmacokinetic (PK) model for 3-AP pharmacokinetics and to evaluate the effect of ABCB1 polymorphisms on the pharmacokinetic profile of 3-AP and to assess the relationship between 3AP disposition and patient covariates. Methods A total of 40 patients with advanced cancer from two phase 1 studies were included in the population PK model building. Patients received 3-AP 25–105 mg/m2 IV on day 1. 3-AP plasma and erythrocyte levels were sampled at 10 timepoints over a 24-hour period and measured by a validated HPLC method. Data were analyzed by a nonlinear mixed-effects modeling approach using the NONMEM system. Results 3AP pharmacokinetics were described as a 3-compartment model with first-order elimination. One compartment representing the plasma and another representing erythrocyte concentrations. Gender was associated with volume of distribution, in which women had a lower V2. The number of cycles administered was associated with clearance; those with decreased clearance were more likely to receive less than 2 cycles before going off study. Conclusion This study suggests that monitoring 3-AP plasma concentrations in the first cycle and dose adjustment in those with decreased clearance may be helpful in decreasing toxicity associated with the 3-AP. PMID:20440618

  17. One-pot synthesis of cyclic aldol tetramer and,β-unsaturated aldol from linear aldehydes using quaternary ammonium combined with sodium hydroxide as catalysts

    Institute of Scientific and Technical Information of China (English)

    许海峰; 钟宏; 王帅; 李方旭

    2015-01-01

    One-pot synthesis of cyclic aldol tetramer anda,β-unsaturated aldol from C3−C8 linear aldehydes using phase-transfer catalyst (PTC), quaternary ammonium, combined with sodium hydroxide as catalysts was investigated. Butanal was subjected for detail investigations to study the effect of parameters. It was found that the selectivity of cyclic aldol tetramer depends greatly on the operating conditions of the reaction, especially the PTC/butanal molar ratio. The average selectivity of 2-hydroxy-6-propyl-l, 3, 5-triethyl-3-cyclohexene-1-carboxaldehyde (HPTECHCA) was 54.41% using tetrabutylammonium chloride combined with 14% (mass fraction) NaOH as catalysts at 60 °C for 2 h with a PTC-to-butanal molar ratio of 0.09:1. Pentanal was more likely to generate cyclic aldol tetramer compared with other aldehydes under the optimum experimental conditions. Recovery of the PTC through water washing followed by adding enough sodium hydroxide from the washings was also demonstrated.

  18. SYNTHESIS, SPECTRAL CHARACTERIZATION OF Cu (II AND Ni (II COMPLEXES WITH THIOSEMICARBAZONES AND SEMICARBAZONES DERIVED FROM PYRIDINE-2- CARBOXALDEHYDE

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2013-08-01

    Full Text Available Ni (II and Cu (II complexes were synthesized with L1(Pyridine-2-carboxaldehydethiosemicarbazones and L2 (Pyridine-2-carboxaldehydesemicarbazones. These complexes were characterized by elemental analysis, molar conductance measurements, magnetic susceptibility measurements, mass, IR, electronic and EPR spectral studies. The molar conductance measurements on the complexes in DMSO correspond to non electrolytes nature with L1. The molar conductance measurements with L2 lie in the range 210-226 Ω-1cm2mol-1 indicating the complexes were 1:2 electrolyte thus the complexes may be formulated as [M(L2]X2 where M= Ni (II and Cu (II complexes. On the basis of spectral studies an octahedral geometry has been assigned for Ni (II complexes. A tetragonal geometry suggested for Cu (II complexes.

  19. SYNTHESIS, SPECTRAL CHARACTERIZATION OF Cu (II) AND Ni (II) COMPLEXES WITH THIOSEMICARBAZONES AND SEMICARBAZONES DERIVED FROM PYRIDINE-2- CARBOXALDEHYDE

    OpenAIRE

    Sulekh Chandra; Prem Ballabh; S.K Choudhary

    2013-01-01

    Ni (II) and Cu (II) complexes were synthesized with L1(Pyridine-2-carboxaldehydethiosemicarbazones) and L2 (Pyridine-2-carboxaldehydesemicarbazones). These complexes were characterized by elemental analysis, molar conductance measurements, magnetic susceptibility measurements, mass, IR, electronic and EPR spectral studies. The molar conductance measurements on the complexes in DMSO correspond to non electrolytes nature with L1. The molar conductance measurements with L2 lie in the range 210-2...

  20. Synthesis, characterization, molecular docking and biological studies of self assembled transition metal dithiocarbamates of substituted pyrrole-2-carboxaldehyde.

    Science.gov (United States)

    Nami, Shahab A A; Ullah, Irfan; Alam, Mahboob; Lee, Dong-Ung; Sarikavakli, Nursabah

    2016-07-01

    A series of self assembled 3d transition metal dithiocarbamate, M(pdtc) [where M=Mn(II), Fe(II), Co(II), Ni(II) and Cu(II)] have been synthesized and spectroscopically characterized. The bidentate dithiocarbamate ligand Na2pdtc (Disodium-1,4-phenyldiaminobis (pyrrole-1-sulfino)dithioate) was prepared by insertion reaction of carbondisulfide with Schiff base, N,N'-bis-(1H-pyrrol-2-ylmethylene)-benzene-1,4-diamine (L1) in basic medium. The simple substitution reaction between the metal halide and Na2pdtc yielded the title complexes in moderate yields. However, the in situ procedure gives high yield with the formation of single product as evident by TLC. Elemental analysis, IR, (1)H and (13)C NMR spectra, UV-vis., magnetic susceptibility and conductance measurements were done to characterize the complexes, M(pdtc). All the evidences suggest that the complexes have tetrahedral geometry excepting Cu(II) which is found to be square planar. A symmetrical bidentate coordination of the dithiocarbamato moiety has been observed in all the complexes. The conductivity data show that the complexes are non-electrolyte in nature. The anti-oxidant activity of the ligand, Na2pdtc and its transition metal complexes, M(pdtc) have been carried out using DPPH and Cu(pdtc) was found to be most effective. The anti-microbial activity of the Na2pdtc and M(pdtc) complexes have been carried out and on this basis the molecular docking study of the most effective complex, Cu(pdtc) has also been reported. PMID:27197060

  1. Synthetic, structural and biological studies of organosilicon(IV complexes of Schiff bases derived from pyrrole-2-carboxaldehyde

    Directory of Open Access Journals (Sweden)

    KIRAN SING

    2010-07-01

    Full Text Available Selected new organosilicon(IV complexes having the general formula R2SiCl[L] and R2Si[L] 2 were synthesized by the reactions of Me2SiCl2 with Schiff bases (5-mercapto-4-[(1H-pyrrol-2ylmethyleneamino]-s-triazole, 5-mercapto-3-methyl-4-[(1H-pyrrol-2ylmethyleneamino]-s-triazole and 3-ethyl-5-mercapto-4-[(1H-pyrrol-2ylmethyleneamino]-s-triazole in 1:1 and 1:2 molar ratios. All of the compounds were characterized by elemental analysis, molar conductance, and IR, UV, 1H-, 13C- and 29Si-NMR spectral studies. All the spectral data suggest an involvement with an azomethine nitrogen in coordination to the central silicon atom. With the help of above-mentioned spectral studies, penta and hexacoordinated environments around the central silicon atoms in the 1:1 and 1:2 complexes, respectively, are proposed. Finally, the free ligands and their metal complexes were tested in vitro against some pathogenic bacteria and fungi to assess their antimicrobial properties.

  2. Synthesis and structure-activity correlation studies of metal complexes of alpha-N-heterocyclic carboxaldehyde thiosemicarbazones in Shewanella oneidensis.

    Science.gov (United States)

    Wilson, Barbara A; Venkatraman, Ramaiyer; Whitaker, Cedrick; Tillison, Quintell

    2005-04-01

    This investigation involved the synthesis of metal complexes to test the hypothesis that structural changesand metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced reactivity exhibited by metal complexes of heterocyclic thiosemicarbazones, synthesis and structural characterization of di-2-pyridylketone 4N-phenyl thiosemicarbazone and diphenyl tin (Sn) and platinum (Pt) complexes were undertaken. Shewanella oneidensis MR-1, a metal ion-reducing bacterium, was used as a model organism to explore the biological activity under aerobic conditions. A comparision of the cytotoxic potential of selected ligand and metal-complex thiosemicarbazones on cell growth in wild type MR-1 and mutant DSP-010 Shewanella oneidensis strains at various concentrations (0, 5, 10, 15, 20 or 25 ppm) was performed. The wild type (MR-1) grown in the presence of increasing concentrations of Sn- thiosemicarbazone complexes was comparatively more sensitive (mean cell number = 4.8 X 10(8) +/- 4.3 X 10(7) SD) than the DSP-010, a spontaneous rifampicillin derivative of the parent strain (mean cell number = 5.6 x 10(8) +/- 6.4 X 10(7) SD) under comparable aerobic conditions (p = 0.0004). No differences were observed in the sensitivity of the wild and mutant types when exposed to various concentrations of diphenyl Pt- thiosemicarbazone complex (p = 0.425) or the thiosemicarbazone ligand (p = 0.313). Growth of MR-1 in the presence of diphenyl Sn-thiosemicarbazone was significantly different among treatment groups (p = 0.012). MR-1 cell numbers were significantly higher at 5ppm than at 10 to 20ppm (p = 0.05). The mean number of DSP-010 variant strain cells also differed among diphenyl Sn- thiosemicarbazone complex treated groups (p = 0.051). In general, there was an increasing trend in the number of cells from about 5.0 X 10(8) cells (methanol control group) to about 6.0 X 10(8) cells (25ppm). The number of cells in methanol control group was significantly lower than cell numbers at 20ppm and 25ppm (p = 0.05), and numbers at 5ppm treatment were lower than at 20 and 25ppm (p = 0.05). Furthermore, a marginally significant difference in the number of MR-1 cells was observed among diphenyl Pt- thiosemicarbazone complex treatment groups (p = 0.077), and an increasing trend in the number of cells was noted from approximately 5.0 X 10(8) cells (methanol control group) to approximately 5.8 X 10(8) cells (20ppm). In contrast, the DSP-010 variant strain showed no significant differences in cell numbers when treated with various concentrations of diphenyl Pt- thiosemicarbazone complex (p = 0.251). Differences in response to Sn- metal complex between MR-1 and DSP-010 growing cultures indicate that biological activity to thiosemicarbazone metal complexes may be strain specific. PMID:16705815

  3. Synthesis and Structure-Activity Correlation Studies of Metal Complexes of α-N-heterocyclic Carboxaldehyde Thiosemicarbazones in Shewanella oneidensis

    Science.gov (United States)

    Wilson, Barbara A.; Venkatraman, Ramaiyer; Whitaker, Cedrick; Tillison, Quintell

    2005-01-01

    This investigation involved the synthesis of metal complexes to test the hypothesis that structural changes and metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced reactivity exhibited by metal complexes of heterocyclic thiosemicarbazones, synthesis and structural characterization of di-2-pyridylketone 4N-phenyl thiosemicarbazone and diphenyl tin (Sn) and platinum (Pt) complexes were undertaken. Shewanella oneidensis MR-1, a metal ion-reducing bacterium, was used as a model organism to explore the biological activity under aerobic conditions. A comparision of the cytotoxic potential of selected ligand and metal-complex thiosemicarbazones on cell growth in wild type MR-1 and mutant DSP-010 Shewanella oneidensis strains at various concentrations (0, 5, 10, 15, 20 or 25 ppm) was performed. The wild type (MR-1) grown in the presence of increasing concentrations of Sn- thiosemicarbazone complexes was comparatively more sensitive (mean cell number = 4.8 × 108 ± 4.3 × 107 SD) than the DSP-010, a spontaneous rifampicillin derivative of the parent strain (mean cell number = 5.6 × 108 ± 6.4 × 107 SD) under comparable aerobic conditions (p=0.0004). No differences were observed in the sensitivity of the wild and mutant types when exposed to various concentrations of diphenyl Pt- thiosemicarbazone complex (p= 0.425) or the thiosemicarbazone ligand (p=0.313). Growth of MR-1 in the presence of diphenyl Sn- thiosemicarbazone was significantly different among treatment groups (p=0.012). MR-1 cell numbers were significantly higher at 5ppm than at 10 to 20ppm (p = 0.05). The mean number of DSP-010 variant strain cells also differed among diphenyl Sn- thiosemicarbazone complex treated groups (p=0.051). In general, there was an increasing trend in the number of cells from about 5.0 × 108 cells (methanol control group) to about 6.0 × 108 cells (25ppm). The number of cells in methanol control group was significantly lower than cell numbers at 20ppm and 25ppm (p = 0.05), and numbers at 5ppm treatment were lower than at 20 and 25ppm (p = 0.05). Furthermore, a marginally significant difference in the number of MR-1 cells was observed among diphenyl Pt- thiosemicarbazone complex treatment groups (p = 0.077), and an increasing trend in the number of cells was noted from ~5.0 × 108 cells (methanol control group) to ~5.8 × 108 cells (20ppm). In contrast, the DSP-010 variant strain showed no significant differences in cell numbers when treated with various concentrations of diphenyl Pt- thiosemicarbazone complex (p = 0.251). Differences in response to Sn- metal complex between MR-1 and DSP-010 growing cultures indicate that biological activity to thiosemicarbazone metal complexes may be strain specific. PMID:16705815

  4. The maximum tolerated dose and biologic effects of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) in combination with irinotecan for patients with refractory solid tumors

    Science.gov (United States)

    Choi, Brian S.; Alberti, Dona B.; Schelman, William R.; Kolesar, Jill M.; Thomas, James P.; Marnocha, Rebecca; Eickhoff, Jens C.; Ivy, S. Percy; Wilding, George; Holen, Kyle D.

    2010-01-01

    Purpose 3-AP is a ribonucleotide reductase inhibitor and has been postulated to act synergistically with other chemotherapeutic agents. This study was conducted to determine the toxicity and antitumor activity of 3-AP with irinotecan. Correlative studies included pharmacokinetics and the effects of ABCB1 and UGT1A1 polymorphisms. Methods The treatment plan consisted of irinotecan on day 1 with 3-AP on days 1-3 of a 21-day cycle. Starting dose was irinotecan 150 mg/m2 and 3-AP 85 mg/m2/d. Polymorphisms of ABCB1 were evaluated by pyrosequencing. Drug concentrations were determined by HPLC. Results Twenty-three patients were enrolled, 10 men and 13 women. Tumor types included 7 patients with pancreatic cancer, 4 with lung cancer, 2 with cholangiocarcinoma, 2 with mesothelioma, 2 with ovarian cancer, and 6 with other malignancies. Two patients experienced dose-limiting toxicity (DLT) at dose level 1, requiring amendment of the dose escalation scheme. Maximal tolerated dose (MTD) was determined to be 3-AP 60 mg/m2/d and irinotecan 200 mg/m2. DLTs consisted of hypoxia, leukopenia, fatigue, infection, thrombocytopenia, dehydration and ALT elevation. One partial response in a patient with refractory non-small cell lung cancer was seen. Genotyping suggests that patients with wild-type ABCB1 have a higher rate of grade 3 or 4 toxicity than those with ABCB1 mutations. Conclusions The MTD for this combination was 3-AP 60 mg/m2/d on days 1-3 and irinotecan 200 mg/m2 on day 1 every 21 days. Antitumor activity in a patient with refractory non-small cell lung cancer was noted at level 1. PMID:20127092

  5. Microwave Synthesis and Antimicrobial Activity of some Copper (II, Cobalt (II, Nickel (II and Chromium (III Complexes with Schiff Base 2, 6-Pyridinedi carboxaldehyde-Thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Dr.Mohammed.Fakruddin Ali Ahmed

    2014-03-01

    Full Text Available Some novel Schiff base metal complexes of Cr(III, Co(II, Ni(II andCu(II derived from 2, 6-pyridinedicarboxaldehyde-Thiosemicarbazone(PDCTC was synthesized by conventional as well as microwavemethods. This compound wascharacterized by elemental analysis, FT-IR, Mass, molar conductanceand magneticsusceptibilitymeasurements analyses. Analytical data revealed that all the complexesexhibited 1:1 (metal: ligand ratio with a coordination number of six.The IR data showed that the ligand coordinates with the metal ions in ahexa-dentate manner. The solid state electricalconductivity of the metal complexes was also measured. Solid state electricalconductivity studies reflected a semi-conducting nature of the complexes. The Schiff base and metal complexes displayed good activity againstthe Gram-positive bacteria Staphylococcus aureus, the Gram-negative bacteriaEscherichia coli and the fungi AspergillusnigerandCandida albicans. The antimicrobialresults also indicated that the metal complexes displayed betterantimicrobial activity as compared to the Schiff bases.

  6. SYNTHESIS, SPECTRAL CHARACTERIZATION OF Mn(II AND Co(II COMPLEXES WITH THIOSEMICARBAZONES AND SEMICARBAZONES DERIVED FROM PYRIDINE-2- CARBOXALDEHYDE

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2014-02-01

    Full Text Available Mn(II and Co(II complexes are synthesized with L1(Pyridine-2-carboxaldehydethiosemicarbazones and L2 (Pyridne-2-carboxaldehydesemicarbazones. These complexes were characterized by elemental analysis, molar conductance measurements, magnetic suscepectibility measurements, mass, IR, electronic and EPR spectral studies. The molar conductance measurement of the complexes in DMSO corresponds to non electrolytes nature with L1 and formulated as [M(L2X2] where M=Mn(II and Co(II complexes. The molar conductance measurements with L2 lie in the range 208-217 Ω-1cm2mol-1 indicating the electrolytes nature of the complexes thus the complexes formulated as [M(L2]X2 where M=Mn(II and Co(II complexes. On the basis of spectral studies an octahedral geometry has been assigned for Mn(II and Co(II complexes.

  7. Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities

    OpenAIRE

    Karaküçük-İyidoğan, Ayşegül; Taşdemir, Demet; Oruç-Emre, Emine Elçin; Balzarini, Jan

    2011-01-01

    A series of thiosemicarbazones and their platinum(II) and palladium(II) complexes have been synthesized. The chemical structures of ligands and their complexes were characterized by UV-Vis, IR, (1)H NMR, (13)C NMR, MS spectra, elemental analysis and TGA. The antiviral and cytotoxic activities of all compounds have been tested. Results of broad antiviral evaluation showed that none of the compounds evaluated endowed with anti-DNA or -RNA virus activity at subtoxic concentrations except for the...

  8. SYNTHESIS, SPECTRAL CHARACTERIZATION OF Mn(II) AND Co(II) COMPLEXES WITH THIOSEMICARBAZONES AND SEMICARBAZONES DERIVED FROM PYRIDINE-2- CARBOXALDEHYDE

    OpenAIRE

    Sulekh Chandra; Prem Ballabh

    2014-01-01

    Mn(II) and Co(II) complexes are synthesized with L1(Pyridine-2-carboxaldehydethiosemicarbazones) and L2 (Pyridne-2-carboxaldehydesemicarbazones). These complexes were characterized by elemental analysis, molar conductance measurements, magnetic suscepectibility measurements, mass, IR, electronic and EPR spectral studies. The molar conductance measurement of the complexes in DMSO corresponds to non electrolytes nature with L1 and formulated as [M(L)2X2] where M=Mn(II) and Co(II) complexes. The...

  9. Synthesis and Structure-Activity Correlation Studies of Metal Complexes of α-N-heterocyclic Carboxaldehyde Thiosemicarbazones in Shewanella oneidensis

    OpenAIRE

    Quintell Tillison; Cedrick Whitaker; Ramaiyer Venkatraman; Wilson, Barbara A

    2005-01-01

    This investigation involved the synthesis of metal complexes to test the hypothesis that structural changes and metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced r...

  10. Synthesis and Structure-Activity Correlation Studies of Metal Complexes of α-N-heterocyclic Carboxaldehyde Thiosemicarbazones in Shewanella oneidensis

    Directory of Open Access Journals (Sweden)

    Quintell Tillison

    2005-04-01

    Full Text Available This investigation involved the synthesis of metal complexes to test the hypothesis that structural changes and metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced reactivity exhibited by metal complexes of heterocyclic thiosemicarbazones, synthesis and structural characterization of di-2-pyridylketone 4N-phenyl thiosemicarbazone and diphenyl tin (Sn and platinum (Pt complexes were undertaken. Shewanella oneidensis MR-1, a metal ion-reducing bacterium, was used as a model organism to explore the biological activity under aerobic conditions. A comparision of the cytotoxic potential of selected ligand and metal-complex thiosemicarbazones on cell growth in wild type MR-1 and mutant DSP-010 Shewanella oneidensis strains at various concentrations (0, 5, 10, 15, 20 or 25 ppm was performed. The wild type (MR-1 grown in the presence of increasing concentrations of Sn- thiosemicarbazone complexes was comparatively more sensitive (mean cell number = 4.8 X 108 + 4.3 X 107 SD than the DSP-010, a spontaneous rifampicillin derivative of the parent strain (mean cell number = 5.6 x 108 + 6.4 X 107 SD under comparable aerobic conditions (p=0.0004. No differences were observed in the sensitivity of the wild and mutant types when exposed to various concentrations of diphenyl Pt- thiosemicarbazone complex (p= 0.425 or the thiosemicarbazone ligand (p=0.313. Growth of MR-1 in the presence of diphenyl Sn- thiosemicarbazone was significantly different among treatment groups (p=0.012. MR-1 cell numbers were significantly higher at 5ppm than at 10 to 20ppm (p = 0.05. The mean number of DSP-010 variant strain cells also differed among diphenyl Sn- thiosemicarbazone complex treated groups (p=0.051. In general, there was an increasing trend in the number of cells from about 5.0 X 108 cells (methanol control group to about 6.0 X 108 cells (25ppm. The number of cells in methanol control group was significantly lower than cell numbers at 20ppm and 25ppm (p = 0.05, and numbers at 5ppm treatment were lower than at 20 and 25ppm (p = 0.05. Furthermore, a marginally significant difference in the number of MR-1 cells was observed among diphenyl Pt- thiosemicarbazone complex treatment groups (p = 0.077, and an increasing trend in the number of cells was noted from ~5.0 X 108 cells (methanol control group to ~5.8 X 108 cells (20ppm. In contrast, the DSP-010 variant strain showed no significant differences in cell numbers when treated with various concentrations of diphenyl Pt- thiosemicarbazone complex (p = 0.251. Differences in response to Sn- metal complex between MR-1 and DSP-010 growing cultures indicate that biological activity to thiosemicarbazone metal complexes may be strain specific.

  11. Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities.

    Science.gov (United States)

    Karaküçük-İyidoğan, Ayşegül; Taşdemir, Demet; Oruç-Emre, Emine Elçin; Balzarini, Jan

    2011-11-01

    A series of thiosemicarbazones and their platinum(II) and palladium(II) complexes have been synthesized. The chemical structures of ligands and their complexes were characterized by UV-Vis, IR, (1)H NMR, (13)C NMR, MS spectra, elemental analysis and TGA. The antiviral and cytotoxic activities of all compounds have been tested. Results of broad antiviral evaluation showed that none of the compounds evaluated endowed with anti-DNA or -RNA virus activity at subtoxic concentrations except for the palladium complex 1b. This compound exhibited slightly selective inhibition against cytomegalovirus. The platinum complex 4a exhibited the best cytostatic activities against human cervix carcinoma. Ligands 2, 4 and 5 showed cytostatic potential. The palladium complexes were in general less cytostatic than the corresponding platinum complexes or unliganded congeners. PMID:21993152

  12. Hexakis(μ3-2-hydroxynaphthalene-1-carboxaldehyde thiosemicarbazonato-κ3N2:S:Shexasilver(I N,N-dimethylformamide tetrasolvate

    Directory of Open Access Journals (Sweden)

    Qiaozhen Sun

    2013-01-01

    Full Text Available In the title compound, [Ag6(C12H10N3OS6]·4C3H7NO, the hexanuclear complex molecule lies about an inversion center. The six Ag atoms form a distorted octahedron, with Ag...Ag distances in the range 2.933 (1–3.401 (1 Å. Each Ag atom is surrounded by one N atom and two thiolate S atoms from two deprotonated 2-hydroxy-1-naphthaldehyde thiosemicarbazone ligands. Each ligand coordinates three Ag atoms via a bridging thiolate S atom and a monodentate N atom, thus two Ag3S3 hexagonal rings are linked together. Two dimethylformamide solvent molecules are located in four sets of sites with half-occupancy and form O...H—N hydrogen bonds to the complex molecule. Intramolecular O—H...N hydrogen bonds are also present. The discrete hexanuclear clusters are further linked through π–π interactions into layers parallel to (001, the shortest distance between the centroids of aromatic rings being 3.698 (2 Å.

  13. A PHASE I STUDY OF THE NOVEL RIBONUCLEOTIDE REDUCTASE INHIBITOR 3-AMINOPYRIDINE-2-CARBOXALDEHYDE THIOSEMICARBAZONE (3-AP, TRIAPINE®) IN COMBINATION WITH THE NUCLEOSIDE ANALOG FLUDARABINE FOR PATIENTS WITH REFRACTORY ACUTE LEUKEMIAS AND AGGRESSIVE MYELOPROLIFERATIVE DISORDERS

    Science.gov (United States)

    Karp, Judith E.; Giles, Francis J.; Gojo, Ivana; Morris, Lawrence; Greer, Jacqueline; Johnson, Bonny; Thein, Mya; Sznol, Mario; Low, Jennifer

    2009-01-01

    Triapine® is a potent ribonucleotide reductase (RR) inhibitor that depletes intracellular deoxyribonculeotide pools, especially dATP. We designed a Phase I trial of Triapine followed by the adenosine analog fludarabine in adults with refractory acute leukemias and aggressive myeloproliferative disorders (MPD). Two schedules were examined: A. Triapine 105mg/m2/day over 4 hours followed by fludarabine daily × 5 (24 patients, fludarabine 15–30 mg/m2/dose); B. Triapine 200mg/m2 over 24 hours followed by 5 days of fludarabine 30 mg/m2/day (9 patients). Complete and partial responses (CR,PR) occurred in Schedule A (5/24, 21%), with CR occurring at the 2 highest fludarabine doses (2/12, 17%). In contrast, no CR or PR occurred in Schedule B. Four of the 5 responses occurred in patients with underlying MPD (4/14, 29%). Drug-related toxicities included fever and metabolic acidosis. Triapine 105 mg/m2 followed by fludarabine 30mg/m2 daily × 5 is active in refractory myeloid malignancies and warrants continuing study for patients with aggressive MPD. PMID:17640728

  14. Postnatal odorant exposure induces peripheral olfactory plasticity at the cellular level.

    Science.gov (United States)

    Cadiou, Hervé; Aoudé, Imad; Tazir, Bassim; Molinas, Adrien; Fenech, Claire; Meunier, Nicolas; Grosmaitre, Xavier

    2014-04-01

    Mammalian olfactory sensory neurons (OSNs) form the primary elements of the olfactory system. Inserted in the olfactory mucosa lining of the nasal cavity, they are exposed to the environment and their lifespan is brief. Several reports say that OSNs are regularly regenerated during the entire life and that odorant environment affects the olfactory epithelium. However, little is known about the impact of the odorant environment on OSNs at the cellular level and more precisely in the context of early postnatal olfactory exposure. Here we exposed MOR23-green fluorescent protein (GFP) and M71-GFP mice to lyral or acetophenone, ligands for MOR23 or M71, respectively. Daily postnatal exposure to lyral induces plasticity in the population of OSNs expressing MOR23. Their density decreases after odorant exposure, whereas the amount of MOR23 mRNA and protein remain stable in the whole epithelium. Meanwhile, quantitative PCR indicates that each MOR23 neuron has higher levels of olfactory receptor transcripts and also expresses more CNGA2 and phosphodiesterase 1C, fundamental olfactory transduction pathway proteins. Transcript levels return to baseline after 4 weeks recovery. Patch-clamp recordings reveal that exposed MOR23 neurons respond to lyral with higher sensitivity and broader dynamic range while the responses' kinetics were faster. These effects are specific to the odorant-receptor pair lyral-MOR23: there was no effect of acetophenone on MOR23 neurons and no effect of acetophenone and lyral on the M71 population. Together, our results clearly demonstrate that OSNs undergo specific anatomical, molecular, and functional adaptation when chronically exposed to odorants in the early stage of life.

  15. Copper catalyzed synthesis of quinolinopyrano[2,3-]carbazole derivatives via Povarov reaction

    Indian Academy of Sciences (India)

    Subburethinam Ramesh; Rajagopal Nagarajan

    2014-07-01

    An efficient procedure for the synthesis of pyranocarbazole derivatives using copper catalysed Povarov reaction between aromatic amines and -propargyl carbazole carboxaldehyde has been developed. Ionic liquid is found to be a good solvent medium.

  16. Studies on the Synthesis of Some Substituted Flavonyl Thiazolidinedione Derivatives-I

    OpenAIRE

    BOZDAĞ, Oya; AYHAN-KILCIGİL, Gülgün; TUNÇBİLEK, Meral; ERTAN, Rahmiye

    1999-01-01

    Synthesis and some physico-chemical properties of five flavonyl thiazolidinedione derivatives are described. These products were synthesized by Knoevenagel condensation from flavone-6-carboxaldehyde and 3-substituted 2,4-thiazolidinediones.

  17. Safety Evaluation of Chrysanthemum indicum L. Flower Oil by Assessing Acute Oral Toxicity, Micronucleus Abnormalities, and Mutagenicity

    OpenAIRE

    Hwang, Eun-Sun; Kim, Gun-Hee

    2013-01-01

    Chrysanthemum indicum is widely used to treat immune-related and infectious disorders in East Asia. C. indicum flower oil contains 1,8-cineole, germacrene D, camphor, α-cadinol, camphene, pinocarvone, β-caryophyllene, 3-cyclohexen-1-ol, and γ-curcumene. We evaluated the safety of C. indicum flower oil by conducting acute oral toxicity, bone marrow micronucleus, and bacterial reverse mutation tests. Mortality, clinical signs and gross findings of mice were measured for 15 days after the oral s...

  18. 噻吩-2-甲醛缩L-半胱氨酸Schiff碱共价结合CdTe量子点修饰金电极循环伏安法测定柠檬黄%Detection of lemon yellow by cyclic voltammetry method using thiophene-2-carboxaldehyde shrink L-cysteine Schiff base condensation CdTe quantum dot modify gold electrode cyclic voltammetry method

    Institute of Scientific and Technical Information of China (English)

    郭征楠; 刘峥; 魏席; 李巍

    2016-01-01

    将L-半胱氨酸、纳米金、巯基乙胺修饰CdTe量子点、噻吩-2-甲醛缩L-半胱氨酸Schiff碱镍配合物(L5-Ni)通过自组装的方式依次修饰在裸金电极的表面,制备完成的修饰电极利用循环伏安方法和电化学交流阻抗方法进行电化学表征,建立了一种快速测定饮料中柠檬黄含量的新方法,柠檬黄浓度在0~2.5 m/L范围内,阳极峰值电流与柠檬黄浓度间具有良好的线性关系,得到的线性方程为I=(-1.88×10-4)C-4.36×10-5,相关系数r为0.995,检出限为0.37 mg/L,该方法应用于饮料中柠檬黄含量的检测,相对标准偏差RSD在2.15%~3.23%,加标回收率在97.33%~104.02%之间.

  19. Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions

    Directory of Open Access Journals (Sweden)

    Koichi Mitsudo

    2011-10-01

    Full Text Available Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino-2-pyridine-carboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of α-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined.

  20. Coordination chemistry of actinide elements: preparation of new uranium complexes with schiff bases and their characterization (Preprint No. CT-31)

    International Nuclear Information System (INIS)

    The Schiff bases, o-vanillin semicarbazone (oVSC) and 2-pyridine carboxaldehyde isonicotinoyl hydrazone (PCINH) have been prepared and their novel complexes with dioxouranium(VI) have been synthesized and characterized by IR spectra, elemental analysis and other physico-chemical techniques. (author)

  1. Conjugation of a 3-(1H-phenanthro[9,10-d]imidazol-2-yl)-1H-indole intercalator to a triplex oligonucleotide and to a three-way junction

    DEFF Research Database (Denmark)

    Fatthalla, Maha I; Elkholy, Yehya M; Abbas, Nermeen S;

    2012-01-01

    A new intercalating nucleic acid monomer M comprising a 4-(1-indole)-butane-1,2-diol moiety was synthesized via a classical alkylation reaction of indole-3-carboxaldehyde followed by a condensation reaction with phenanthrene-9,10-dione in the presence of ammonium acetate to form a phenanthroimida...

  2. Construction of Ru(II) Polypyridyl Based Macrocycles: Synthesis, Characterization, Electrochemical, Li+ Binding, Antitumour and Anti-HIV properties

    OpenAIRE

    Mishra, Lallan; Sinha, Ragini; Pandey, P. C.

    2001-01-01

    Some ruthenium (II) polypyridyl complexes with a bis-chalcone (obtained by the condensation of 3-methyl-thiophene-2-carboxaldehyde and 4-acetyl pyridine) have been synthesized and characterized spectroscopically (IR, NMR, UV/Vis), conductimetric, elemental analysis and FAB mass data. Their luminescent, redox and Li+ binding properties have been studied. The anti-HIV and antitumour activities have also been reported.

  3. CHEMISTRY OF THIENOPYRIDINES .39. SYNTHESIS OF [1]BENZOTHIENO[2,3-H]ISOQUINOLINE AND RELATED STUDIES

    NARCIS (Netherlands)

    KLEMM, LH; SEVERNS, B; WYNBERG, H

    1991-01-01

    Benzo[b]thiophene-2-carboxaldehyde undergoes condensation with 4-methylpyridine and with 2-methylquinoline to produce trans-diarylethenes (52% and 76%, respectively). The former alkene photocyclizes in cyclohexane to yield [1]benzo[2,3-h]isoquinoline (35%), while the latter alkene does not give succ

  4. The Analysis of Lavender Oil by GC/MS%薰衣草挥发油化学成分的GC-MS分析

    Institute of Scientific and Technical Information of China (English)

    解成喜; 王强; 崔晓明

    2002-01-01

    采用毛细管气质联用法对薰衣草挥发油化学成分进行了研究,共确认了其中21种成分,占精油总含量的96.55%.其主要化学成分为芳樟醇(Linalool),乙酸芳樟酯(Linalyl acetate),4-甲基-1-(1-异丙基)-3-环己烯-1-醇(3-Cyclohexen-1-o1,4-methy1-1-1(1-methykthyl)-),乙酸薰衣草酯(Lavandayl acetate)等.

  5. N1-((1H-Indazol-5-ylmethylene-N2-(2-((2-((2-(((1H-indazol-6-ylmethyleneaminoethylaminoethylaminoethylethane-1,2-diamine

    Directory of Open Access Journals (Sweden)

    Carlos Lodeiro

    2012-08-01

    Full Text Available One novel molecular emissive probe L has been synthesized by classical Schiff-base reaction between 1H-indazole-6-carboxaldehyde and tetraethylenepentamine. The structure of compound L was confirmed by melting point, elemental analysis, ESI-MS spectrometry and by IR and 13C-NMR and 1H-NMR spectroscopy.

  6. Mechanisms underlying reductant-induced reactive oxygen species formation by anticancer copper(II) compounds

    OpenAIRE

    Kowol, Christian R.; Heffeter, Petra; Miklos, Walter; Gille, Lars; Trondl, Robert; Cappellacci, Loredana; Berger, Walter; Keppler, Bernhard K.

    2011-01-01

    Intracellular generation of reactive oxygen species (ROS) via thiol-mediated reduction of copper(II) to copper(I) has been assumed as the major mechanism underlying the anticancer activity of copper(II) complexes. The aim of this study was to compare the anticancer potential of copper(II) complexes of Triapine (3-amino-pyridine-2-carboxaldehyde thiosemicarbazone; currently in phase II clinical trials) and its terminally dimethylated derivative with that of 2-formylpyridine thiosemicarbazone a...

  7. A one-pot hydrothermal synthesis of sulfur and nitrogen doped carbon aerogels with enhanced electrocatalytic activity in the oxygen reduction reaction

    OpenAIRE

    Wohlgemuth, Stephanie-Angelika; White, Robin Jeremy; Willinger, Marc-Georg; Titirici, Maria-Magdalena; Antonietti, Markus

    2012-01-01

    A one-pot, hydrothermal synthesis of nitrogen and sulfur dual doped carbon aerogels is presented, derived from our previously published hydrothermal carbonization approach. Two co-monomers, S-(2-thienyl)-L-cysteine (TC) and 2-thienyl carboxaldehyde (TCA), were used for sulfur incorporation, giving rise to distinct morphologies and varying doping levels of sulfur. Nitrogen-doping levels of 5 wt% and sulfur-doping levels of 1 wt% (using TCA) to 4 wt% (using TC) were obtained. A secondary pyroly...

  8. 1,10-phenanthroline promotes copper complexes into tumor cells and induces apoptosis by inhibiting the proteasome activity

    OpenAIRE

    Zhang, Zhen; Bi, Caifeng; Schmitt, Sara M.; FAN, YUHUA; Dong, Lili; Zuo, Jian; Dou, Q. Ping

    2012-01-01

    Indole-3-acetic acid and indole-3-propionic acid, two potent natural plant growth hormones, have attracted attention as promising prodrugs in cancer therapy. Copper is known to be a cofactor essential for tumor angiogenesis. We have previously reported that taurine, l-glutamine, and quinoline-2-carboxaldehyde Schiff base copper complexes inhibit cell proliferation and proteasome activity in human cancer cells. In the current study, we synthesized two types of copper complexes, dinuclear compl...

  9. Repellents and acaricides as personal protection measures in the prevention of tick-borne diseases.

    Science.gov (United States)

    Cisak, Ewa; Wójcik-Fatla, Angelina; Zając, Violetta; Dutkiewicz, Jacek

    2012-01-01

    A number of preventive measures for the protection of humans against tick-borne diseases were evaluated. Measures involving the avoidance of tick bites with the use of protective clothing and insect repellents are the simplest and most effective. Repellents are applied directly to the skin or clothing and other fabrics, such as bednets, tents and anti-mosquito screens. Currently, DEET (N,N-diethyl-m-toluamide) is considered the most efficient arthropod repellent reference substance. The registered and recommended active repellent ingredients for skin and/or cloths application, among others, are: DEET, 1-methyl-propyl-2- (hydroxyethyl)-1-piperidinecarboxylate (picaridin), p-menthane-3,8-diol (PMD), ethyl butylactyloaminopropionate ( IR3535), 1S,2S-2-methylpiperidinyl-3-cyclohexene-1-carboxamide (SS220), racemic 2-methylpiperidinyl-3-cyclohexene-1-carboxamide (AI3-37220) and synthethic pyrethroid - 3-phenoxybenzyl-cis-trans-3(2,2 dichlorovinyl)-2,2-dimethylcyclopropancarboxylate (permethrin) - an acaricide with repellent properties. To achieve the protection from tick bites by avoiding attachment and/or engorgement by the arthropod, acaricides with repellent properties, such as synthetic pyrethroid-permethrin are used. This pyrethroid is an acaricide of choice used for clothing impregnation, which is effective for personal protection against all three parasitic stages of western black-legged ticks. Products based on natural compounds, e.g. eugenol from Ocimum basilicum, 2-undecanone originally derived from wild tomato, geraniol - a natural product extracted from plants, and many others, represent an interesting alternative to common synthetic repellents and/or acaricides. PMID:23311778

  10. Antimicrobial Activity and the Chemical Composition of the Volatile Oil Blend from Allium sativum (Garlic Clove and Citrus reticulata (Tangerine Fruit

    Directory of Open Access Journals (Sweden)

    OO Johnson

    2013-10-01

    Full Text Available The synergistic effect in the antimicrobial activity of the volatile oil blend from Garlic clove (Allium sativum and tangerine fruits (Citrus reticulata were investigated and compared to antimicrobial activity when the individual volatile oils were used alone. The volatile oils were extracted by steam distillation using Clevenger hydrodistillator apparatus and each oil was tested for antimicrobial activity, while equal volume of these oils were blended and tested for antimicrobial activity. The microorganisms used include, Staphylococcus aureus isolate, Escherichia coli isolate, Pseudomonas aeruginosa, Salmonella typhi, Candida albicans isolate, Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922 and Candida albicans ATCC 90028. The Minimum Inhibitory Concentrations (MICs ranged from 9.31×10-13 – 7.88 mg/ml for garlic oil, 0.16 – 2.66 mg/ml for tangerine oil and 5.95×10-31 – 1.24 mg/ml for the essential oil blend. Minimum Inhibitory Concentration indicated that the Garlic oil and Tangerine oil blend was better at inhibiting the tested microorganisms than the individual oils except for Escherichia coli ATCC 25922 and Staphylococcus aureus ATCC 25923. The Gas Chromatography-Mass Spectrometry revealed Trisulphide, di-2-propenyl (30.32% as the major component in the garlic oil extract and 3-Cyclohexene-1-methanol, alpha 4-trimethyl (33.38% in the tangerine oil. While the equal volume of the oil blend also revealed Trisulphide, di-2-propenyl (15.92% and 3-Cyclohexene-1-methanol, alpha.4-trimethyl (12.02% as the major constituents though in lower concentrations. Hence, the more potent antimicrobial properties demonstrated by the oil blend can be exploited further with a view to generate new effective antimicrobial compounds.

  11. Removal of phytotoxic compounds from torrefied grass fibres by plant-beneficial microorganisms.

    Science.gov (United States)

    Trifonova, Radoslava; Postma, Joeke; Verstappen, Francel W A; Bouwmeester, Harro J; Ketelaars, Jan J M H; van Elsas, Jan-Dirk

    2008-10-01

    We aimed to select microorganisms colonizing torrefied grass fibres (TGF) and simultaneously reducing the phytotoxicity which appeared after heat treatment of the fibres. Eighty-eight bacterial strains and one fungus, previously isolated from a sequential enrichment experiment on torrefied fibres and extracts, were tested separately for their capacity to decrease phytotoxicity. Eleven of the bacterial strains and the fungus significantly reduced phytotoxicity. These organisms were checked for their ability to grow on agar containing phenol, 2-methoxyphenol, 2,6-dimethoxyphenol, 2-furalaldehyde, pyrrole-2-carboxaldehyde and furan-2-methanol as sole carbon sources. The fungus F/TGF15 and the bacterial strain 66/TGF15 were able to grow on all six compounds. Strains 15/TGE5, 23/TGE5, 43/TGE20, 56/TGF10 and 95/TGF15 grew on two to four compounds, and strain 72/TGF15 only on one compound. Strains 31/TGE5, 34/TGE5, 48/TGE20 and 70/TGF15 did not grow on any of the single toxic compounds. GC analyses of torrefied grass extracts (TGE) determined which compounds were removed by the microorganisms. F/TGF15 was the only isolate depleting phenol, 2-methoxyphenol, 2-dihydrofuranone and pyrrole-2,5-dione-3-ethyl-4-methyl. Strains 15/TGE5, 23/TGE5, 31/TGE5 and 56/TGF10, and the fungus depleted 2-furalaldehyde, 2-furan-carboxaldehyde-5-methyl, pyrrole-2-carboxaldehyde, 5-acetoxymethyl-2-furaldehyde and benzaldehyde-3-hydroxy-4-methoxy. These promising candidates for colonizing and simultaneously reducing the phytotoxicity of TGF were affiliated with Pseudomonas putida, Serratia plymuthica, Pseudomonas corrugata, Methylobacterium radiotolerans and Coniochaeta ligniaria. PMID:18537835

  12. Metal based biologically active compounds: design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium(IV) complexes.

    Science.gov (United States)

    Chohan, Zahid H; Sumrra, Sajjad H; Youssoufi, Moulay H; Hadda, Taibi B

    2010-07-01

    A new series of oxovanadium(IV) complexes have been designed and synthesized with a new class of triazole Schiff bases derived from the reaction of 3,5-diamino-1,2,4-triazole with 2-hydroxy-1-naphthaldehyde, pyrrole-2-carboxaldehyde, pyridine-2-carboxaldehyde and acetyl pyridine-2-carboxaldehyde, respectively. Physical (magnetic susceptibility, molar conductance), spectral (IR, (1)H NMR, (13)C NMR, mass and electronic) and analytical data have established the structures of these synthesized Schiff bases and their oxovanadium(IV) complexes. The Schiff bases, predominantly act as bidentate and coordinate with the vanadium(IV) metal to give a stoichiometric ratio of 1:2 [M:L], forming a general formulae, [M(L-H)(2)] and [M(L)(2)]SO(4) where L = (L(1))-(L(4)) and M = VO(IV) of these complexes in a square-pyramidal geometry. In order to evaluate the biological activity of Schiff bases and to assess the role of vanadium(IV) metal on biological activity, the triazole Schiff bases and their oxovanadium(IV) complexes have been studied for in vitro antibacterial activity against four Gram-negative (Escherichia coli, Shigella flexenari, Pseudomonas aeruginosa, Salmonella typhi) and two Gram-positive (Staphylococcus aureus, Bacillus subtilis) bacterial strains, in vitro antifungal activity against Trichophyton longifucus, Candida albican, Aspergillus flavus, Microscopum canis, Fusarium solani and Candida glaberata. The simple Schiff bases showed weaker to significant activity against one or more bacterial and fungal strains. In most of the cases higher activity was exhibited upon coordination with vanadium(IV) metal. Brine shrimp bioassay was also carried out for in vitro cytotoxic properties against Artemia salina. PMID:20338672

  13. Structure and spectroscopic properties of N,S-coordinating 2-methylsulfanyl-N-[(1H-pyrrol-2-ylmethylidene]aniline methanol monosolvate

    Directory of Open Access Journals (Sweden)

    D. Douglas Richards

    2015-10-01

    Full Text Available The reaction of pyrrole-2-carboxaldehyde and 2-(methylsulfanylaniline in refluxing methanol gave an olive-green residue in which yellow crystals of the title compound, C12H12N2S·CH3OH, were grown from slow evaporation of methanol at 263 K. In the crystal, hydrogen-bonding interactions link the aniline molecule and a nearby methanol solvent molecule. These units are linked by a pair of weak C—H...Omethanol interactions, forming inversion dimers consisting of two main molecules and two solvent molecules.

  14. Diastereo- and enantioselective three-component coupling approach to highly substituted pyrrolidines.

    Science.gov (United States)

    Chaulagain, Mani Raj; Felten, Albert E; Gilbert, Kevin; Aron, Zachary D

    2013-09-20

    The enantioselective synthesis of substituted pyrrolidines through a mild Lewis-acid catalyzed three-component coupling reaction between picolinaldehyde, amino acids, and activated olefins is reported. The reaction uses low catalyst loadings of commercially available chiral diamines and copper triflate proposed to self-assemble in conjunction with the chelating aldehydes, 4-substituted-2-picolinaldehydes or 4-methylthiazole-2-carboxaldehyde, to generate a catalyst complex. A model is provided to explain how this complex directs enantioselectivity. This work represents a significant advance in the ease, scope, and cost of producing highly substituted, enantioenriched pyrrolidines.

  15. (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-thienyl)prop-2-en-1-one

    OpenAIRE

    Khan, Salman A.; Asiri, Abdullah M.

    2010-01-01

    The title compound, (2E)-3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-thienyl)prop-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.

  16. (2E-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl-1-(2,5-dimethyl-3-furanylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Abdullah Mohamed Asiri

    2010-06-01

    Full Text Available The title compound, (2E-3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl-1-(2,5-dimethyl-3-furanylprop-2-en-1-one (3 was synthesized in high yield by an aldol condensation between 3-acetyl-2,5-dimethylfuran 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.

  17. (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.

  18. Two Indole Derivatives and Phenolic Compound Isolated from Mushroom Phellinus linteus

    Institute of Scientific and Technical Information of China (English)

    Sorasak Samchai; Prapairat Seephonkai; Chatthai Kaewtong

    2011-01-01

    AIM: To investigate the constituents from the dichloromethane fraction of the mushroom Phellinus lintues. METHODS: Silica gel and Sephadex LH-20 column chromatography were used for the isolation and purification. The structures of isolated compounds were elucidated based on NMR spectroscopic analyses and mass spectrometric data. RESULTS: Two indole derivatives, 7-methoxyindole-3-carboxylic acid methyl ester (1) and l-methylindole-3-carboxaldehyde (2), and a phenolic compound, (E)-4-(3, 4-dihydroxyphenyl)but-3-en-2-one (3) were isolated. CONCLUSION: Compounds 1 and 2 were isolated for the first time from P. linteus.

  19. Schiff base functionalized Organopropylsilatranes: Synthesis and structural characterization

    Indian Academy of Sciences (India)

    Gurjaspreet Singh; Promila; Amandeep Saroa; Jandeep Singh; Raj Pal Sharm; V Ferretti

    2016-02-01

    Synthesis of Schiff bases linked to organopropylsilatranes were performed by condensation reaction of post-functionalized silatranes such as aminopropylsilatrane (4), aminopropyl-3,7,10-trimethylsilatrane (5) and N-substituted aminopropylsilatrane (10) with two different aldehydes viz. pyrrole-2-carboxaldehyde and 2-hydroxy-1-napthaldehyde. The resulting Schiff base substituted silatranes were well characterized by elemental analysis, spectroscopic studies [IR, (1H, 13C) NMR, and MS]. The structures of two silatranes were confirmed by single crystal X-ray diffraction analysis.

  20. White light generation by carbonyl based indole derivatives due to proton transfer: an efficient fluorescence sensor.

    Science.gov (United States)

    Singla, Nidhi; Bhadram, Venkata Srinu; Narayana, Chandrabhas; Chowdhury, Papia

    2013-04-01

    The motivation of the present work is to understand the optical, chemical, and electrical aspects of the proton transfer mechanism of indole (I) and some carbonyl based indole derivatives: indole-3-carboxaldehyde (I3C) and indole-7-carboxaldehyde (I7C) for both powder form and their liquid solution. Structural information for indole derivatives (isolated molecule and in solution) is obtained with density functional theory (DFT) and time dependent DFT (TD-DFT) methods. Calculated transition energies are used to generate UV-vis, FTIR, Raman, and NMR spectra which are later verified with the experimental spectra. The occurrence of different conformers [cis (N(c)), trans (N(t)), and zwitterion (Z*)] have been interpreted by Mulliken charge, natural bond orbital (NBO) analysis, and polarization versus electric field (P-E loop) studies. (1)H and (13)C NMR and molecular vibrational frequencies of the fundamental modes established the stability of Nc due to the presence of intramolecular hydrogen bonding (IHB) in the ground state (S0). Computed/experimental UV-vis absorption/emission studies reveal the creation of new species: zwitterion (Z*) and anion (A*) in the excited state (S1) due to excited state intramolecular and intermolecular proton transfer (ESI(ra)PT and ESI(er)PT). Increased electrical conductivity (σ(ac)) with temperature and increased ferroelectric polarization at higher field verifies proton conduction in I7C.

  1. Metal based new triazoles: Their synthesis, characterization and antibacterial/antifungal activities

    Science.gov (United States)

    Sumrra, Sajjad H.; Chohan, Zahid H.

    2012-12-01

    A series of new triazoles and their oxovanadium(IV) complexes have been synthesized, characterized and evaluated for antibacterial/antifungal properties. The new Schiff bases ligands (L1)-(L5) were prepared by the condensation reaction of 3,5-diamino-1,2,4-triazole with 2-hydroxy-1-naphthaldehyde, pyrrole-2-carboxaldehyde, pyridine-2-carboxaldehyde, 2-acetyl pyridine and 2-methoxy benzaldehyde. The structures of the ligands have been established on the basis of their physical, spectral (IR, 1H and 13C NMR and mass spectrometry) and elemental analytical data. The prepared ligands were used to synthesize their oxovanadium(IV) complexes (1)-(5) which were also characterized by their physical, spectral and analytical data and proposed to have a square pyramidal geometry. The ligands and their complexes were screened for in vitro antibacterial activity against six bacterial species such as, Escherichia coli, Shigella flexneri, Pseudomonas aeruginosa, Salmonella typhi, Staphylococcus aureus, and Bacillus subtilis and for in vitro antifungal activity against six fungal strains, Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani, and Candida glabrata. Cytotoxic nature of the compounds was also reported using brine shrimp bioassay method against Artemia salina.

  2. Design, spectral characterization and biological studies of transition metal(II) complexes with triazole Schiff bases

    Science.gov (United States)

    Hanif, Muhammad; Chohan, Zahid H.

    2013-03-01

    A new series of three biologically active triazole derived Schiff base ligands L1-L3 have been synthesized in equimolar reaction of 3-amino-1H-1,2,4-triazole with pyrrol-2-carboxaldehyde, 4-bromo-thiophene-2-carboxaldehyde, and 5-iodo-2-hydroxy benzaldehyde. The prepared Schiff bases were used for further complex formation reaction with different metal elements like Co(II), Ni(II), Cu(II) and Zn(II) as chlorides by using a molar ratio of ligand:metal as 2:1. The structure and bonding nature of all the compounds were identified by their physical, spectral and analytical data. All the metal(II) complexes possessed an octahedral geometry except the Cu(II) complexes which showed a distorted octahedral geometry. All the synthesized compounds, were studied for their in vitro antibacterial, and antifungal activities, against four Gram-negative (Escherichia coli, Shigella sonnei, Pseudomonas aeruginosa and Salmonella typhi) and two Gram-positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains and against six fungal strains (Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glabrata) by using agar-well diffusion method. It has been shown that all the synthesized compounds showed moderate to significant antibacterial activity against one or more bacterial strains. In vitro Brine Shrimp bioassay was also carried out to investigate the cytotoxic properties of these compounds. The data also revealed that the metal complexes showed better activity than the ligands due to chelation/coordination.

  3. Identification of novel orosensory active molecules in cured vanilla Beans (Vanilla planifolia).

    Science.gov (United States)

    Schwarz, Bernd; Hofmann, Thomas

    2009-05-13

    Sequential application of solvent extraction, gel permeation chromatography, and HPLC in combination with taste dilution analyses, followed by LC-MS and 1D/2D NMR experiments, led to the discovery of seven velvety mouth-coating molecules in cured beans of Vanilla planifolia . Among these, 5-(4-hydroxybenzyl)vanillin, 4-(4-hydroxybenzyl)-2-methoxyphenol, 4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)-5-methoxybenzaldehyde, (1-O-vanilloyl)-(6-O-feruloyl)-beta-d-glucopyranoside, americanin A, and 4',6'-dihydroxy-3',5-dimethoxy-[1,1'-biphenyl]-3-carboxaldehyde were previously not reported in vanilla beans. Sensory studies revealed human recognition thresholds for the velvety mouth-coating sensation between 1.0 and 5.0 mumol/kg (water). Interestingly, the biphenyl derivatives were found to enhance the perception of creaminess and fatty body of sweetened skim milk, among which 4',6'-dihydroxy-3',5-dimethoxy-[1,1'-biphenyl]-3-carboxaldehyde showed the lowest threshold level of 5 mumol/kg. Quantitative analysis of these compounds in cured vanilla beans from different origins as well as in noncured beans revealed that, with the exception of americanin A, all of the other taste compounds are not present in the green vanilla beans and are formed during the bean curing process.

  4. Preparation of zinc sulfide nanocrystallites from single-molecule precursors

    Science.gov (United States)

    Palve, Anil M.; Garje, Shivram S.

    2011-07-01

    Zinc sulfide nanocrystallites were prepared using Zinc(II) thiosemicarbazone complexes of the types Zn(L) 2 and ZnCl 2(LH) 2 (where, LH=thiosemicarbazones of cinnamaldehyde, 4-chlorobenzaldehyde, indol-3-carboxaldehyde and thiophene-2-carboxaldehyde) as single source precursors by solvothermal decomposition in ethylene glycol and ethylene diamine in few cases. The materials were characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), selected area electron diffraction, energy dispersive X-ray analysis and UV-vis and IR spectroscopy. Solvothermal decomposition in ethylene glycol resulted in the formation of hexagonal ZnS (JCPDS: 36-1450) as evident from the XRD patterns. However, XRD shows formation of hybrid material, ZnS 0.5EN in case of solvothermal decomposition in ethylenediamine. Infrared spectra authenticate the capping of ethylene glycol and ethylenediamine on ZnS and ZnS 0.5EN, respectively. TEM images showed formation of spherical nanoparticles for the materials obtained from ethylene glycol, whereas plate-like morphology is observed in case of materials obtained from ethylene diamine. The blue shift of absorption bands compared to bands of bulk materials in the UV-vis spectra supports the formation of smaller particles.

  5. Non-conventional halide oxidation pathways : oxidation by imidazole triplet and surface specific oxidation by ozone

    Science.gov (United States)

    Ammann, Markus; Corral-Arroyo, Pablo; Aellig, Raphael; Orlando, Fabrizio; Lee, Ming-Tao; Artiglia, Luca

    2016-04-01

    Oxidation of halide ions (chloride, bromide, iodide) are the starting point of halogen release mechanisms out of sea water, marine aerosol or other halide containing continental aerosols. Slow oxidation of chloride and bromide by ozone in the bulk aqueous phase is of limited relevance. Faster surface specific oxidation has been suggested based on heterogeneous kinetics experiments. We provide first insight into very efficient bromide oxidation by ozone at the aqueous solution - air interface by surface sensitive X-ray photoelectron spectroscopy indicating significant build-up of an oxidized intermediate at the surface within millisecond time scales. The second source of oxidants in the condensed we have considered is the absorption of light by triplet forming photosensitizers at wavelengths longer than needed for direct photolysis and radical formation. We have performed coated wall flow tube experiments with mixtures of citric acid (CA) and imidazole-2-carboxaldehyde (IC) to represent secondary organic material rich marine aerosol. The halide ions bromide and iodide have been observed to act as efficient electron donors leading to their oxidation, HO2 formation and finally release of molecular halogen compounds. The photosensitization of imidazole-2-carboxaldehyde (IC) involves a well-known mechanism where the triplet excited state of IC is reduced by citric acid to a reduced ketyl radical that reacts with halide ions. A competition kinetics approach has been used to evaluate the rate limiting steps and to assess the significance of this source of halogens to the gas phase.

  6. Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents.

    Science.gov (United States)

    Özdemir, Ahmet; Altintop, Mehlika Dilek; Turan-Zitouni, Gülhan; Çiftçi, Gülşen Akalın; Ertorun, İpek; Alataş, Özkan; Kaplancikli, Zafer Asim

    2015-01-01

    In the present work, new indole-based chalcone derivatives were obtained via the reaction of 5-substituted-1H-indole-3-carboxaldehydes/1-methylindole-3-carboxaldehyde with appropriate acetophenones. The synthesized compounds were investigated for their in vitro COX-1 and COX-2 inhibitory activity. The most effective COX inhibitors were also evaluated for their in vivo antiinflammatory and antioxidant activities in LPS induced sepsis model. Furthermore, the CCK-8 assay was carried out to determine cytotoxic effects of all compounds against NIH/3T3 mouse embryonic fibroblast cells. 3-(5-Bromo-1H-indol-3-yl)-1-(4-cyanophenyl)prop-2-en-1-one (6) can be considered as a non-selective COX inhibitor (COX-1 IC50 = 8.1 ± 0.2 μg/mL, COX-2 IC50 = 9.5 ± 0.8 μg/mL), whereas 3-(5-methoxy-1H-indol-3-yl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one (1) inhibited only COX-1 (IC50 = 8.6 ± 0.1 μg/mL). According to in vivo studies, these compounds also displayed antiinflammatory and antioxidant activities. PMID:25462246

  7. Synthesis and Electrical and Gas Sensing Properties of Some 5-(Quinolinylmethylene-2-thioxodihydropyrimidine-4,6(1H,5H-dione and 5-(Quinolinylmethylenepyrimidine-2,4,6(1H,3H,5H-trione Derivatives

    Directory of Open Access Journals (Sweden)

    H. Kerim Beker

    2013-01-01

    Full Text Available Eight new 5-(quinolinylmethylenebarbituric acid derivatives were synthesized by the reaction of 1,3-dimethylbarbituric acid and 1,3-diethyl-2-thiobarbituric acid with quinoline-4-carboxaldehydes and several quinoline-2-carboxaldehydes via Knoevenagel condensation. The novel compounds were characterized by 1H NMR, 13C NMR, mass, IR, and UV-visible spectral data and elemental analyses. d.c. and a.c. conduction properties of the compounds were investigated in the frequency range of 40–105 Hz and temperature range 295–440 K. The d.c. results showed an activated conductivity dependence on temperature for all films. Obtained data reveal that a.c. conductivity obeys the relation and exponent is found to decrease by increasing temperature. The analysis of the a.c. conduction data showed that the CBH model is the dominant conduction mechanism for the electron transport in the films. Gas sensing properties of the films for the volatile organic compounds (VOCs were also investigated in the same temperature range. Maximum sensitivity to VOCs was observed at around 360 K for compound 6.

  8. Characterization of urinary volatiles in Swiss male mice (Mus musculus): bioassay of identified compounds

    Indian Academy of Sciences (India)

    S Achiraman; G Archunan

    2002-12-01

    The present study was carried out to investigate the chemical nature of the urine of male mice and to assess its bioactivity. Urine of mature male mice was extracted with dichloromethane (1 : 1 ratio v/v) and analysed by gas-chromatography linked mass-spectrometry (GC-MS). Ten different compounds such as alkanes, alcohols, etc. were detected in the urine. Among the ten, five compounds are specific to males, namely 3-cyclohexene-1-methanol (I), 3-amino-s-triazole (II), 4-ethyl phenol (III), 3-ethyl-2,7-dimethyl octane (IV) and 1-iodoundecane (V). The compound, 4-ethylphenol, has been previously reported in several strains of male mice. Furthermore, the compounds (II) and (IV) are similar to 2-sec-butylthiazole and dehydro-exo-brevicomin compounds which have already been reported in male mice. Bioassay revealed that compounds (II), (III) and (IV) were responsible for attracting females and in inducing aggression towards males, as compared to the other compounds, i.e. (I) and (V). The results indicate that these three volatiles (II, III and IV) of male mice appear to act as attractants of the opposite sex.

  9. Antimicrobial activities of essential oil from Artemisiae argyi leaves

    Institute of Scientific and Technical Information of China (English)

    WANG Wei; ZHANG Xue-ke; WU Nan; FU Yu-jie; ZU Yuan-gang

    2006-01-01

    A study was conducted to determine the antimicrobial activities of essential oil from Artemisiae argyi leaves. The sample of the essential oil was analyzed by GC-MS. From 18 compounds representing the oils, Eucalyptole (18.42%), Spathulenol (14.32), 4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol (3.10%), 3-Carene (2.64%) appeared as the main components. The screening of antimicro bial activity of the essential oil was evaluated using agar diffusion and broth microdilution methods. Gram-positive bacterial were more sensitive than gram-negative bacterial of the 8 microorganisms, and Staphylococcus aureus ATCC 6538 showed the lowest MIC (0.3125%) and MBC (0.625%). In the disc diffusion assay, Staphylococcus epidermidis ATCC 49134 and Bacillus subtilis ATCC 6633 showed obvious inhibitory activity. Survival curve showed that, 2MIC ofArtemisiae argyi essential oil had a lethal effect on Candida albicans within the first 1 h. Results presented here suggest that the essential oil of Artemisiae argyi leaves possesses antimicrobial properties, and provides scientific foundations for exploition ofArtemisiae argyi.

  10. Larvicidal efficacies and chemical composition of essential oils of Pinus sylvestris and Syzygium aromaticum against mosquitoes

    Institute of Scientific and Technical Information of China (English)

    Kehinde Adenike Fayemiwo; Monsuru Adebayo Adeleke; Ovie Princewill Okoro; Shola Hezekiah Awojide; Ilias Olufemi Awoniyi

    2014-01-01

    Objective:To assess the chemical composition and mosquito larvicidal potentials of essential oils of locally sourced Pinus sylvestris (P. sylvestris) and Syzygium aromaticum (S. aromaticum) against Aedes aegypti (A. aegypti) and Culex quinquefasciatus (C. quinquefasciatus). Method:The chemical composition of the essential oils of both plants was determined using GC-MS while the larvicidal bioassay was carried out using different concentrations of the oils against the larvae of A. aegypti and C. quinquefasciatus in accordance with the standard protocol. Results:The results as determined by GC-MS showed that oil of S. aromaticum has eugenol (80.5%) as its principal constituent while P. sylvestris has 3-Cyclohexene-1-methanol, .alpha., .alpha.4-trimethyl (27.1%) as its dominant constituent. Both oils achieved over 85%larval mortality within 24 h. The larvae of A. aegypti were more susceptible to the oils [LC50 (S. aromaticum)=92.56 mg/L, LC50(P. sylvestris)=100.39 mg/L] than C. quinquefasciatus [LC50(S. aromaticum)=124.42 mg/L;LC50(P. sylvestris)=128.00 mg/L]. S. aromaticum oil was more toxic to the mosquito larvae than oil of P. sylvestris but the difference in lethal concentrations was insignificant (P>0.05). Conclusion: The results justify the larvicidal potentials of both essential oils and the need to incorporate them in vector management and control.

  11. Patch test results in patients with allergic contact dermatitis in Yozgat

    Directory of Open Access Journals (Sweden)

    Emine Çölgeçen Özel

    2013-09-01

    Full Text Available Background and Design: Patch testing is valuable in the diagnosis of allergic contact dermatitis (ACD as well as in determining the causative agent and thus is helpful in prevention of the disease and also provides information for the patient Material and Method: Hundred and sixty-eight patients (94 female and 74 male with ACD were patch tested with European standard series. Patch test result were assessed according to suggestion of International Contact Dermatitis Research Group at 48 and 72 hours after initial application. Results: Of the patients, 64.3% were between 16-45 years of age and majority of the lesions (57.1% were localized on the hands. A total of 86 (51.1% patients had one or more positive patch test reactions. The most common allergens were nickel sulfate (20.2% followed by potassium dichromate (8.3%, cobalt chloride (7.1%, fragrance mix (7.1%, paraphenylendiamine base (6%, paraben mix 3.6%, N-isopropyl-N-phenyl-p-phenylenediamine (3.6%, wool alcohols (3.6%, formaldehyde (3.6%, quaternium-15 (3.6%. Positive reactions to nickel sulfate were more common among women, especially those in younger group. Frequency of contact allergy to neomycin sulfate, epoxy resin, 4-tert-butylphenolformaldehyde resin, sesquiterpenelactone mix, primin, 5-chloro-2-methyl-4-isothiazolin-3-1, budesonide, lyral were relatively low (1.2%, while no positive reaction was obtained to clioquinol and methyldibromoglutaronitrile in any case. Conclusion: Since no similar study has been previously performed in our area, this study provides information about contact allergen profile in patients underwent skin patch test with a diagnosis of AKD at Yozgat. The most frequent allergens detected with ASS and frequency rates may vary among different facilities at various cities of Turkey. A standard series for our country may be created after assessment of regional variability by new studies conducted in same time zone.

  12. Deposition of rod-shaped antimony sulfide thin films from single-source antimony thiosemicarbazone precursors

    Energy Technology Data Exchange (ETDEWEB)

    Biswal, Jasmine B.; Sawant, Narayan V. [Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (East), Mumbai - 400 098 (India); Garje, Shivram S., E-mail: ssgarje@chem.mu.ac.i [Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (East), Mumbai - 400 098 (India)

    2010-04-02

    Antimony sulfide thin films were deposited on glass substrates by aerosol assisted chemical vapour deposition technique using single source precursors, namely, antimony(III) thiosemicarbazones, SbCl{sub 3}(L) (L = thiosemicarbazones of thiophene-2-carboxaldehyde (1) and cinnamaldehyde (2)). The deposited films were characterized by X-ray diffraction, scanning electron microscopy, energy dispersive X-ray analysis and UV-visible spectroscopy in order to identify their phases, morphologies, compositions and optical properties respectively. These characterizations revealed that the films were comprised of rod-shaped particles of orthorhombic stibnite (Sb{sub 2}S{sub 3}) with a Sb:S stoichiometry of {approx} 1:1.3. The calculated optical band gap from UV-vis absorption spectrum is found to be 3.48 eV.

  13. Flavonoides e outros compostos isolados de Mimosa artemisiana Heringer e Paula

    Directory of Open Access Journals (Sweden)

    Ildomar Alves do Nascimento

    2012-01-01

    Full Text Available This the first phytochemical investigation of Mimosa artemisiana (Leguminosae-Mimosoideae describing the isolation and identification of quercitrin, myricitrin, 3,5,4´-trihydroxi-6,7-dimethoxyflavone (6,7-dimethylkaepferol, flavolignans, 3-O-β-D-glucopyranosil sitosterol, lupeol, sitostenone, stigmastenone, campestenone, sitosterol, stigmasterol, campesterol, methyl indole-3-carboxilate and indole-3-carboxaldehyde in the extracts from the leaves and wood of this plant. This is the first registry of 6,7-dimethoxy,4'-hydroxy-flavona and the flavonolignans in this genera. The isolation of all metabolites was made by chromatographic methods and the structures were established on the basis of IR, MS, ¹H and 13C NMR spectra analysis, comparison with literature data and GC-MS of mixtures analysis.

  14. "Synthesis and smooth muscle Calcium channel antagonist effects of new derivatives of 1,4-Dihydropyridine containing Nitroimidazol substituent "

    Directory of Open Access Journals (Sweden)

    Miri R

    2002-09-01

    Full Text Available A group of racemic 3-[(2-hydroxyethyl, (2-Methoxyethyl, (2-acetylethyl or (2-cyanoethyl], 5- methyl, ethyl or isopropyl-1, 4-dihydro-2, 6-dimethyl-4-(1-methyl-5-nitro-2-imidazolyl-3, 5-pyridinedicarboxylates [XIV-XXV] were prepared by the reaction of 1-methyl-5-nitroimidazol-2-carboxaldehyde [X] with acetoacetic esters [VI-IX] and alkys 3-aminocrotonate [XI-XIII]. In vitro calcium channel antagonist activities of the tested compounds were determined by their effects on contraction of Guinea Pig Ileal Longitudinal Smooth Muscle (GPILSM which was induced by carbacol (1.67 χ 10^-7 M. All compounds exhibited calcium channel antagonist activity (IC50=10^-12 to 10^-13 M range comparable to nifedipine as reference drug (IC50=1.07±0.12x 10^-11 M.

  15. Antibacterial and Enzyme Inhibition Studies of N'-Substituted Benzylidene-2-(2, 4-Dimethylphenoxy Acetatohydrazides

    Directory of Open Access Journals (Sweden)

    1S. Nadeem

    2014-09-01

    Full Text Available The molecules bearing azomethine group are known to possess biological activities. In the present work, the synthesis of N'-Substitutedbenzylidene-2-(2, 4-dimethylphenoxy acetatohydrazide (5a-d has been elaborated using 2,4-Dimethylphenol (1 as precursor. The molecule, 1, was converted to ethyl 2-(2,4-dimethylphenoxyacetate (2 on refluxing with ethyl 2-bromoacetate in ethanol in the presence of KOH. Ethyl ester, 2, was refluxed with hydrated hydrazine (80% in ethanol to yield 2-(2,4-dimethylphenoxy acetohydrazide (3. The target molecules, 5a-d, were synthesized by stirring 3 with phenyl/aryl carboxaldehyde (4a-d in methanol in the presence of glacial acetic acid. The synthesized molecules were characterized by spectral data and evaluated for antibacterial and anti-enzymatic activities.

  16. Semicarbazonas e tiossemicarbazonas: o amplo perfil farmacológico e usos clínicos

    Directory of Open Access Journals (Sweden)

    Beraldo Heloisa

    2004-01-01

    Full Text Available This article shows that thiosemicarbazones, semicarbazones and their metal complexes can exhibit target selectivity along with a wide pharmacological profile. Complexes of thiosemicarbazones with cytotoxic or antitumoral activity are presented, some of which show activity against cisplatinum-resistant cells. The inhibition mechanism of the enzyme ribonucleoside diphosphate reductase (RDR, involved in DNA syntheses, by alpha(N-heterocyclic thiosemicarbazones is discussed. The encouraging results of clinical trials with the RDR inhibitor 3-aminopyridine-2-carboxaldehyde thiosemicarbazone ("Triapine" against rapidly growing tumors are outlined. Examples are also given of thiosemicarbazones with antiviral and antimicrobial activity. The possible applications of semicarbazones as anticonvulsants with low toxicity and good therapeutic index are presented.

  17. Synthesis, antioxidant and antimicrobial evaluation of thiazolidinone, azetidinone encompassing indolylthienopyrimidines

    Indian Academy of Sciences (India)

    Anand Raghunath Saundane; Manjunatha Yarlakatti; Prabhaker Walmik; Vijaykumar Katkar

    2012-03-01

    Various 2-amino-N'-{3-(2',5'-disubstituted-1H-indol-3'-yl)methylene}-4,5-dimethylthieno-3-carbohydrazides (3) synthesized by condensation of 2-amino-4,5-dimethyl thiophene-3-carbohydrazide (2) with 2,5- disubstituded indole-3-carboxaldehyde (1). The Schiff’s base (3) on cyclocondensation with acetic anhydride and triethyl orthoformate afforded thienopyrimidine analogues (4) and (7), respectively. Compounds 4 or 7 on cyclization with thioglycolic acid and chloroacetyl chloride gave thiazolidin-4-ones (5) or (8) and azitidin-2-ones (6) or (9) respectively. The structures of these newly synthesized compounds have been established on the basis of their spectral data and elemental analysis. Some of the compounds exhibited promising antioxidant and antimicrobial activities.

  18. Schiff bases of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane and its silatranes: Synthesis and characterization

    Indian Academy of Sciences (India)

    Gurjaspreet Singh; Amandeep Saroa; Sadhika Khullar; Sanjay K Mandal

    2015-04-01

    This paper aims at the introduction of azomethine group by the condensation reaction of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane with different compounds containing carbonyl group such as 2’-hydroxyacetophenone, salicylaldehyde, pyrrole-2-carboxaldehyde, acetylacetone and ethyl acetoacetate. Further, transesterification reaction of these Schiff base modified silanes with triethanolamine as a tripodal ligand leads to the synthesis of corresponding silatranes 1–5 bearing Schiff base functionalized long chain in the axial position. All the synthesized compounds are characterized by spectroscopic methods, elemental analysis and mass spectrometry. The authentication of Schiff base modified silatranes is scrutinized by single X-ray crystal structure of silatrane 1. The thermal stability of the five silatranes is studied by thermo-gravimetric analysis (TGA).

  19. SYNTHESIS OF 1-({7-METHOXY-2-[4-(METHYLSULFANYL PHENYL]-1- BENZOFURAN-5-YL}-N-[(N-ETHYLPYRROLIDIN-2-YL METHYL]METHANAMINE BY REDUCTIVE AMINATION. Synthese von 1 - ({7-methoxy-2-[4 - (methylsulfanyl phenyl] -1 - BENZOFURAN-5-yl}-N-[(N-Ethylpyrrolidin-2-yl methyl] MethanaMine Durch reduktive LAMINATION.

    Directory of Open Access Journals (Sweden)

    Bapu R Thorata, Dyneshwar Shelke, Ramdas Atram and Ramesh Yamgar

    2013-07-01

    Full Text Available Vanillin undergoes sequence of reaction forming phosphonium salt through dimethyaminomethyl derivative (Mannich reaction. The synthesis of phosphonium salt can be achieved by sequence of three steps. A solution of Mannich base in acetic anhydride was refluxed for 24 hrs to give crude diacetate which is purified and treated with HCl to give chloromethyl derivative. It is further treated with triphenylphosphine in dry benzene under reflux condition. The phosphonium salt undergoes condensation with 4-methylsulfanylbenzoyl chloride by refluxing in toluene in presence of triethylamine. The reaction was completed in 6 hrs. The crude product was purified by using column chromatography. The resulting 7-methoxy-2-[4- (methylsulfanylphenyl]-l-benzofuran-5-carboxaldehyde was subjected to reductive amination and the final product 1-({7-methoxy-2-[4-(methylsulfanylphenyl]-1-benzofuran-5-yl}-N-[(Nethylpyrrolidin- 2-ylmethyl]methan amine was purified by column chromatography and characterized by FT-IR, NMR and Mass spectroscopy.

  20. Analysis of volatile chemical components of Radix Paeoniae Rubra by gas chromatography-mass spectrometry and chemometric resolution

    Institute of Scientific and Technical Information of China (English)

    LI Xiao-ru; LAN Zheng-gang; LIANG Yi-zeng

    2007-01-01

    The volatile chemical components of Radix Paeoniae Rubra (RPR) were analyzed by gas chromatography-mass spectrometry with the method of heuristic evolving latent projections and overall volume integration.The results show that 38 volatile chemical components of RPR are determined.accounting for 95.21% of total contents of volatile chemical components of RPR.The main volatile chemical components of RPR are(Z,Z)-9, 12-octadecadienoic acid, n-hexadecanoic acid, 2-hydroxy benzaldehyde, 1-(2-hydroxy-4-methoxyphenyl)-ethanone, 6,6-dimethyl-bicyclo[3.1.1]heptane-2-methanol, 4,7-dimethyl-benzofuran, 4-(1-methylethenyl)-1-cyclohexene-1-carboxaldehyde, and cyclohexadecane.

  1. An efficient synthesis of 3'-indolyl substituted pyrido[1,2-]benzimidazoles as potential antimicrobial and antioxidant agents

    Indian Academy of Sciences (India)

    Harshad G Kathrotiya; Manish P Patel

    2013-09-01

    A new class of indole-based pyrido[1,2-]benzimidazole derivatives 4a-r have been synthesized by one-pot cyclocondensation reaction of 2-phenyl-1-indole-3-carboxaldehyde 1a-i, malononitrile 2 and 2-cyanomethylbenzimidazole 3a-b in the presence of catalytic amount of NaOH. In vitro antimicrobial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically three Gram-positive bacteria (Streptococcus pneumoniae, Clostridium tetani, Bacillus subtilis), three Gram-negative bacteria (Salmonella typhi, Vibrio cholerae, Escherichia coli) and two fungi (Aspergillus fumigatus, Candida albicans) using broth microdilution MIC (minimum inhibitory concentration) method. In vitro antioxidant activity was evaluated by ferric-reducing antioxidant power (FRAP) assay method. Compounds 4c, 4e, 4l and 4q have been found to be most efficient antimicrobial members while compounds 4h and 4p possess better ferric reducing antioxidant power.

  2. Biological and Spectral Studies of Newly Synthesized Triazole Schiff Bases and Their Si(IV, Sn(IV Complexes

    Directory of Open Access Journals (Sweden)

    Kiran Singh

    2011-01-01

    Full Text Available The Schiff bases HL1-3 have been prepared by the reaction of 5-bromothiophene-2-carboxaldehyde with 4-amino-5-mercapto-3-methyl/propyl/isopropyl-s-triazole, respectively. Organosilicon(IV and organotin(IV complexes of formulae (CH32MCl(L1-3, (CH32M(L1-32 were synthesized from the reaction of (CH32MCl2 and the Schiff bases in 1 : 1 and 1 : 2 molar ratio, where M=Si and Sn. The synthesized Schiff bases and their metal complexes have been characterized with the aid of various physicochemical techniques like elemental analyses, molar conductance, UV, IR, 1H, 13C, 29Si, and 119Sn NMR spectroscopy. Based on these studies, the trigonal bipyramidal and octahedral geometries have been proposed for these complexes. The ligands and their metal complexes have been screened in vitro against some bacteria and fungi.

  3. Flavonolignoids and other compounds isolated from Mimosa artemisiana Heringer and Paula; Flavonoides e outros compostos isolados de Mimosa artemisiana Heringer e Paula

    Energy Technology Data Exchange (ETDEWEB)

    Nascimento, Ildomar Alves do [Universidade Federal Rural do Rio de Janeiro, Seropedica, RJ (Brazil). Dept. de Quimica; Braz-Filho, Raimundo; Mathias, Leda [Universidade Estadual do Norte Fluminense (UENF), Campos dos Goytacases, RJ (Brazil). Centro de Ciencias Tecnologicas. Lab. de Ciencias Quimicas; Carvalho, Mario Geraldo de [Universidade Federal do Rio de Janeiro (NPPN/UFRJ), RJ (Brazil). Centro de Ciencias da Saude. Nucleo de Pesquisa em Produtos Naturais; Fonseca, Fabio de Alcantara [Instituto Estadual de Florestas (IEF), Belo Horizonte, MG (Brazil)

    2012-07-01

    This the first phytochemical investigation of Mimosa artemisiana (Leguminosae-Mimosoideae) describing the isolation and identification of quercitrin, myricitrin, 3,5,4'-trihydroxy-6,7-dimethoxyflavone (6,7-dimethylkaempferol), flavolignans, 3-O-{beta}-D-glucopyranosyl sitosterol, lupeol, sitostenone, stigmastenone, campestenone, sitosterol, stigmasterol, campesterol, methyl indole-3-carboxylate and indole-3-carboxaldehyde in the extracts from the leaves and wood of this plant. This is the first registry of 6,7-dimethoxy,4'-hydroxy-flavone and the flavonolignans in this genera. The isolation of all metabolites was made by chromatographic methods and the structures were established on the basis of IR, MS, {sup 1}H and {sup 13}C NMR spectra analysis, comparison with literature data and GC-MS of mixtures analysis. (author)

  4. Is copper(I) really soft? Probing the hardness of Cu(I) with pyridinecarboxaldehyde ligands

    Indian Academy of Sciences (India)

    D Saravanabharathi; M Nethaji; A G Samuelson

    2002-08-01

    Cu(I) complexes of formula Cu(PPh3)2LClO4 [L = 2 or 3 pyridine carboxaldehyde] are synthesised and characterised to explore the coordination of an aldehyde, a hard and neutral oxygen donor to a soft Cu(I) centre. The structural and spectroscopic results illustrate that only in 2-pyridinecarboxaldehyde, the `C=O' group coordinates to soft Cu(I) centres due to a favourable chelate effect, while in 3-pyridinecarboxaldehyde, it remains uncoordinated. Upon chelation via N and O donors, 2-pyridinecarboxaldehyde resembles bipyridine or phenanthroline in terms of its bite angle and spectroscopic features. Such chelation can be easily challenged with coordinating anions like bromide, or more basic pyridines. A drastic change in the MLCT absorption signals the decomplexation of the `C=O’ group. The observed results point out that the Cu(I) centre can readily exchange the hard `O’ donor for softer ligands.

  5. [Chemical constituents in higher polar substances from Desmodium caudatum].

    Science.gov (United States)

    Zhu, Dan; Wang, Di; Wang, Guang-Hui; Guo, Zhi-Jian; Zou, Xiu-Hong; Lin, Ting; Chen, Hai-Feng

    2014-08-01

    In this study the chemical constituents of the higher polar sustances from Desmodium caudatum were investigated.The compounds were isolated by using column chromatographies over silicagel, polyamide, ODS, Sephadex LH-20, and preparative HPLC. The structures of these compounds were identified on the basis of NMR and MS spectra. Thirteen compounds were obtained and their structures were identified as vanillin(1), loliolide(2), indole-3-carboxaldehyde(3), salicylic acid(4), swertisin(5), saccharumoside C(6), isosinensin (7), kaempferol 3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside (8), isovitexin (9), vitexin (10), nothofagin(11), resveratroloside (12), and 2"-α-rhamnopyranosyl-7-O-methylvitexin (13). Except for compound 5, the remaining compounds were isolated from D. caudatum for the first time. Compounds 2, 3, 6-8, 11-13 were separated from the genus Desmodium for the first time. PMID:25509297

  6. Synthesis and antitubercular activity of new N,N-diaryl-4-(4,5-dichloroimidazole-2-yl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxamides

    Directory of Open Access Journals (Sweden)

    Amini M.

    2008-03-01

    Full Text Available Background and the purpose of the study: Dihydropyridines having carboxamides in 3 and 5 positions show anti-tuberculosis activity. The purpose of the present study was to synthesize new DHPs having possible anti-tuberculosis activity. Methods: 4,5-Dichloroimidazole-2-carboxaldehyde was condensed with N-arylaceto-acetamides and ammonium acetate in methanol to give N,N-diaryl-4-(4,5-dichloroimid-azole-2-yl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxamides. All compounds were screened for their antitubercular activity against Mycobacterium tuberculosis (H37Rv. Results and major conclusion: Some of the new synthesized compounds exhibited a moderate activity in comparison to rifampicin.

  7. High-performance liquid chromatographic determination of methyl anthranilate, hydroxymethylfurfural and related compounds in honey.

    Science.gov (United States)

    Nozal, M J; Bernal, J L; Toribio, L; Jiménez, J J; Martín, M T

    2001-05-11

    A high-performance liquid chromatographic method for determining 5-hydroxymethyl-2-furaldehyde (hydroxymethylfurfural), 2-furaldehyde (furfural), furan-2-carboxylic acid (2-furoic acid), furan-3-carboxylic acid (3-furoic acid), furan-3-carboxaldehyde (3-furaldehyde) and 2-aminobenzoic acid methyl ester (methyl anthranilate) in honey and honeydew samples is described. To prevent matrix interference and to isolate the compounds, a clean-up step which implies a solid-phase extraction on polymeric cartridges and an elution with 0.5 ml methanol is recommended. The compounds are separated on a reversed-phase column with a gradient of (A) 1% aqueous acetic acid-acetonitrile (97:3, v/v) and (B) acetonitrile-water (50:50, v/v), with UV detection at 250 nm. The method is applied to the analysis of samples from different botanical origin. PMID:11403496

  8. Copper(II) complexes with aroylhydrazones

    Indian Academy of Sciences (India)

    Samudranil Pal

    2002-08-01

    The coordination chemistry of copper(II) with tridentate aroylhydrazones is briefly discussed in this article. Two types of aroylhydrazones derived from aroylhydrazines and ortho-hydroxy aldehydes or 2-pyridine-carboxaldehyde have been used. The characterization of the complexes has been performed with the help of various physico-chemical techniques. Solid state structural patterns have been established by X-ray crystallography. In the solid state, structural varieties of these complexes are seen to range from monomeric, dimeric, polymeric and onedimensional self-assembly via hydrogen bonds and - interactions. EPR spectroscopy and variable temperature magnetic susceptibility measurements have been used to reveal the nature of the coordination geometry and magnetic characteristics of these complexes.

  9. Fluorescent-magnetic Janus particles prepared via seed emulsion polymerization.

    Science.gov (United States)

    Kaewsaneha, Chariya; Bitar, Ahmad; Tangboriboonrat, Pramuan; Polpanich, Duangporn; Elaissari, Abdelhamid

    2014-06-15

    Anisotropic polymeric colloidal or Janus particles possessing simultaneous magnetic and fluorescent properties were successfully prepared via the swelling-diffusion or the in situ emulsion polymerization method. In the swelling-diffusion process, magnetic emulsions (an organic ferrofluid dispersed in aqueous medium) were synthesized and used for seeds of submicron magnetic Janus particles. After swelling the anisotropic particles obtained by 1-pyrene-carboxaldehyde fluorescent dye dissolved in tetrahydrofuran, well-defined fluorescent-magnetic Janus particles were produced. In the in situ emulsion polymerization, styrene monomer mixed with fluorescent dye monomers, i.e., 1-pyrenylmethyl methacrylate (PyMMA) or fluorescein dimethacrylate (FDMA), and an oil-soluble initiator (2,2'-azobis(2-isobutyronitrile)) were emulsified in the presence of magnetic seed emulsions. The confocal microscopic images showed the fluorescent-magnetic Janus particles with high fluorescent intensity when a fluorescent crosslinker monomer FDMA was employed. PMID:24767504

  10. Chemical Constituents of the Sponge Mycale Sp ecies from South China Sea

    Directory of Open Access Journals (Sweden)

    Xuefeng Zhou

    2013-03-01

    Full Text Available Chemical investigation of the sponge Mycale species from the South China Sea afforded eleven known compounds, henicosanoic acid methyl ester (1 , hexadecyl ethers of glycerol ( 2 , N-docosanoyl-D-erythro-(2S,3R-16-methyl-heptadecasphing-4(E-enine ( 3 , dibutyl phthalate ( 4 , cholesterol ( 5 , 5α,8α-epidioxycholest-6,22-dien-3β-ol ( 6 , 5-hexadecyl-pyrrole-2-carboxaldehyde ( 7 , benzoic acid ( 8 , 4-hydroxybenzoic acid ( 9 , thymine ( 10 ,and uracil ( 11 . Compounds 1 – 4 , 6 – 9 were obtained from the sponge of the genus Mycale for the first time, and 4 and 6 showed toxicity in the brine shrimp lethality test with the LD 50 values at 2.9 μg/mL and 4. 7 μg/mL, respectively .

  11. Pattern recognition analysis of chromatographic fingerprints of Crocus sativus L. secondary metabolites towards source identification and quality control.

    Science.gov (United States)

    Aliakbarzadeh, Ghazaleh; Sereshti, Hassan; Parastar, Hadi

    2016-05-01

    Chromatographic fingerprinting is an effective methodology for authentication and quality control of herbal products. In the presented study, a chemometric strategy based on multivariate curve resolution-alternating least squares (MCR-ALS) and multivariate pattern recognition methods was used to establish a gas chromatography-mass spectrometry (GC-MS) fingerprint of saffron. For this purpose, the volatile metabolites of 17 Iranian saffron samples, collected from different geographical regions, were determined using the combined method of ultrasound-assisted solvent extraction (UASE) and dispersive liquid-liquid microextraction (DLLME), coupled with GC-MS. The resolved elution profiles and the related mass spectra obtained by an extended MCR-ALS algorithm were then used to estimate the relative concentrations and to identify the saffron volatile metabolites, respectively. Consequently, 77 compounds with high reversed match factors (RMFs > 850) were successfully determined. The relative concentrations of these compounds were used to generate a new data set which was analyzed by multivariate data analysis methods including principal component analysis (PCA) and k-means. Accordingly, the saffron samples were categorized into five classes using these techniques. The results revealed that 11 compounds, as biomarkers of saffron, contributed to the class discrimination and characterization. Eleven biomarkers including nine secondary metabolites of saffron (safranal, α- and β-isophorone, phenylethyl alcohol, ketoisophorone, 2,2,6-trimethyl-1,4-cyclohexanedione, 2,6,6-trimethyl-4-oxo-2-cyclohexen-1-carbaldehyde, 2,4,4-trimethyl-3-carboxaldehyde-5-hydroxy-2,5-cyclohexadien-1-one, and 2,6,6-trimethyl-4-hydroxy-1-cyclohexene-1-carboxaldehyde (HTCC)), a primary metabolite (linoleic acid), and a long chain fatty alcohol (nanocosanol) were distinguished as the saffron fingerprint. Finally, the individual contribution of each biomarker to the classes was determined by the

  12. Pattern recognition analysis of chromatographic fingerprints of Crocus sativus L. secondary metabolites towards source identification and quality control.

    Science.gov (United States)

    Aliakbarzadeh, Ghazaleh; Sereshti, Hassan; Parastar, Hadi

    2016-05-01

    Chromatographic fingerprinting is an effective methodology for authentication and quality control of herbal products. In the presented study, a chemometric strategy based on multivariate curve resolution-alternating least squares (MCR-ALS) and multivariate pattern recognition methods was used to establish a gas chromatography-mass spectrometry (GC-MS) fingerprint of saffron. For this purpose, the volatile metabolites of 17 Iranian saffron samples, collected from different geographical regions, were determined using the combined method of ultrasound-assisted solvent extraction (UASE) and dispersive liquid-liquid microextraction (DLLME), coupled with GC-MS. The resolved elution profiles and the related mass spectra obtained by an extended MCR-ALS algorithm were then used to estimate the relative concentrations and to identify the saffron volatile metabolites, respectively. Consequently, 77 compounds with high reversed match factors (RMFs > 850) were successfully determined. The relative concentrations of these compounds were used to generate a new data set which was analyzed by multivariate data analysis methods including principal component analysis (PCA) and k-means. Accordingly, the saffron samples were categorized into five classes using these techniques. The results revealed that 11 compounds, as biomarkers of saffron, contributed to the class discrimination and characterization. Eleven biomarkers including nine secondary metabolites of saffron (safranal, α- and β-isophorone, phenylethyl alcohol, ketoisophorone, 2,2,6-trimethyl-1,4-cyclohexanedione, 2,6,6-trimethyl-4-oxo-2-cyclohexen-1-carbaldehyde, 2,4,4-trimethyl-3-carboxaldehyde-5-hydroxy-2,5-cyclohexadien-1-one, and 2,6,6-trimethyl-4-hydroxy-1-cyclohexene-1-carboxaldehyde (HTCC)), a primary metabolite (linoleic acid), and a long chain fatty alcohol (nanocosanol) were distinguished as the saffron fingerprint. Finally, the individual contribution of each biomarker to the classes was determined by the

  13. “Turn on/off” proton transfer based fluorescent sensor for selective detection of environmentally hazardous metal ions (Zn{sup 2+}, Pb{sup 2+}) in aqueous media

    Energy Technology Data Exchange (ETDEWEB)

    Singla, Nidhi; Tripathi, Ashish; Rana, Meenakshi [Department of Physics and Materials Science & Engineering, Jaypee Institute of Information Technology, Noida 201307, Uttar Pradesh (India); Kishore Goswami, Sudipta [Bruker India Scientific Pvt. Ltd., 22B Ruby Park South, Kolkata 700078, West Bengal (India); Pathak, Anirban [Department of Physics and Materials Science & Engineering, Jaypee Institute of Information Technology, Noida 201307, Uttar Pradesh (India); RCPTM, Joint Laboratory of Optics of Palacky University and Institute of Physics of Academy of Science of the Czech Republic, Faculty of Science, Palacky University, 17. listopadu 12, 771 46 Olomouc (Czech Republic); Chowdhury, Papia, E-mail: papia.chowdhury@jiit.ac.in [Department of Physics and Materials Science & Engineering, Jaypee Institute of Information Technology, Noida 201307, Uttar Pradesh (India)

    2015-09-15

    Sensing ability of fluorescence based chemosensor: Indole-7-carboxaldehyde (I7C) for environmentally hazardous metal ions (X{sup n+}=Zn{sup 2+}, Pb{sup 2+}, Co{sup 2+}, Ni{sup 2+}, Cu{sup 2+}, Cd{sup 2+}, Cr{sup 3+}, and Fe{sup 3+}) has been investigated. Based on excited state proton transfer (ESPT) phenomenon, the sensing capability of I7C is verified experimentally (UV–vis, FTIR, NMR) and theoretically (DFT, TD-DFT) in aqueous media. Chemical hardness (η), electrophilicity (ω) and electronic chemical potentials (μ) confirm the selective reactivity of I7C (N{sub c} and N{sub t} conformers) in the presence of metal ions by the formation of (1:1) metal ion: I7C complex (M{sub X}, M{sub X}{sup ⁎}). M{sub X}, M{sub X}{sup ⁎} are found to display excellent sensing capability for Zn{sup 2+} and Pb{sup 2+} ions. “Turn-On” response for Zn{sup 2+} is observed through the appearance of a new enhanced fluorescence at ~430 nm. By strong blue emission I7C establishes its strong candidature as “blue emitter”. “Turn-Off” response is observed for Pb{sup 2+} through the quenching of the existing fluorescence peak. - Highlights: • Indole-7-carboxaldehyde (I7C) shows “Turn-on” and “Turn-off” sensing for Zn{sup 2+} and Pb{sup 2+} ions. • I7C forms complex with metal ions (M{sub X}{sup ⁎}). • 27-Fold strong blue fluorescence due to M{sub Zn}{sup ⁎} formation indicates I7C as a good candidature to be used as blue emitter. • Computed (UV–vis absorption/emission, FTIR, NMR) data validate the experimental facts.

  14. “Turn on/off” proton transfer based fluorescent sensor for selective detection of environmentally hazardous metal ions (Zn2+, Pb2+) in aqueous media

    International Nuclear Information System (INIS)

    Sensing ability of fluorescence based chemosensor: Indole-7-carboxaldehyde (I7C) for environmentally hazardous metal ions (Xn+=Zn2+, Pb2+, Co2+, Ni2+, Cu2+, Cd2+, Cr3+, and Fe3+) has been investigated. Based on excited state proton transfer (ESPT) phenomenon, the sensing capability of I7C is verified experimentally (UV–vis, FTIR, NMR) and theoretically (DFT, TD-DFT) in aqueous media. Chemical hardness (η), electrophilicity (ω) and electronic chemical potentials (μ) confirm the selective reactivity of I7C (Nc and Nt conformers) in the presence of metal ions by the formation of (1:1) metal ion: I7C complex (MX, MX⁎). MX, MX⁎ are found to display excellent sensing capability for Zn2+ and Pb2+ ions. “Turn-On” response for Zn2+ is observed through the appearance of a new enhanced fluorescence at ~430 nm. By strong blue emission I7C establishes its strong candidature as “blue emitter”. “Turn-Off” response is observed for Pb2+ through the quenching of the existing fluorescence peak. - Highlights: • Indole-7-carboxaldehyde (I7C) shows “Turn-on” and “Turn-off” sensing for Zn2+ and Pb2+ ions. • I7C forms complex with metal ions (MX⁎). • 27-Fold strong blue fluorescence due to MZn⁎ formation indicates I7C as a good candidature to be used as blue emitter. • Computed (UV–vis absorption/emission, FTIR, NMR) data validate the experimental facts

  15. Volatile emissions during storing of green food waste under different aeration conditions.

    Science.gov (United States)

    Agapiou, A; Vamvakari, J P; Andrianopoulos, A; Pappa, A

    2016-05-01

    Controlled field experiments were carried out for monitoring the emissions of three plastic commercial household waste bins, which were adapted for studying the effect of aeration process in the evolved volatiles, during house storing of green food waste for 2 weeks, prior to collection. Three experimental scenarios were examined based on no aeration ("NA," closed commercial waste bin), diffusion-based aeration ("DA," closed commercial waste bin with tiny holes), and enforced aeration ("EA," closed commercial waste bin with tiny holes and enforced aeration). The monitoring of volatile organic compounds (VOCs) emitted from organic household kitchen waste was performed using solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) analysis. Portable sensors were also used for monitoring selected gases and parameters of environmental, bioprocess, and health interest (e.g., CO2, O2, H2S, CH4, NH3, % RH, waste temperatures). VOC emissions are strongly dependent on the waste material. The most frequent VOCs identified over the storing waste, showing over 50 % appearance in all examined samples, were terpenes (e.g., di-limonene, beta-myrcene, delta-3-carene, alpha-pinene, alpha-terpinolene, linalool, etc.), sulfides (dimethyl disulfide), aromatics (benzene, 1-methyl-2-(2-propenyl)), alkanes (e.g., decane, dodecane), ketones (2-propanone), esters (e.g., acetic acid ethyl ester, acetic acid methyl ester), and alcohols (e.g., 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)). The prominent role of terpenes in the "pre-compost" odor and especially that of di-limonene was highlighted. In all examined scenarios, the emitted volatiles were increased at raised temperatures and later decreased in time. Aeration of waste bins slightly affected the volatilization process resulting in higher profiles of VOCs; uniformity in the composition of VOCs was also noted. Slight modifications of commercial waste bins may favor the initiation of home composting. PMID

  16. Volatile emissions during storing of green food waste under different aeration conditions.

    Science.gov (United States)

    Agapiou, A; Vamvakari, J P; Andrianopoulos, A; Pappa, A

    2016-05-01

    Controlled field experiments were carried out for monitoring the emissions of three plastic commercial household waste bins, which were adapted for studying the effect of aeration process in the evolved volatiles, during house storing of green food waste for 2 weeks, prior to collection. Three experimental scenarios were examined based on no aeration ("NA," closed commercial waste bin), diffusion-based aeration ("DA," closed commercial waste bin with tiny holes), and enforced aeration ("EA," closed commercial waste bin with tiny holes and enforced aeration). The monitoring of volatile organic compounds (VOCs) emitted from organic household kitchen waste was performed using solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) analysis. Portable sensors were also used for monitoring selected gases and parameters of environmental, bioprocess, and health interest (e.g., CO2, O2, H2S, CH4, NH3, % RH, waste temperatures). VOC emissions are strongly dependent on the waste material. The most frequent VOCs identified over the storing waste, showing over 50 % appearance in all examined samples, were terpenes (e.g., di-limonene, beta-myrcene, delta-3-carene, alpha-pinene, alpha-terpinolene, linalool, etc.), sulfides (dimethyl disulfide), aromatics (benzene, 1-methyl-2-(2-propenyl)), alkanes (e.g., decane, dodecane), ketones (2-propanone), esters (e.g., acetic acid ethyl ester, acetic acid methyl ester), and alcohols (e.g., 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)). The prominent role of terpenes in the "pre-compost" odor and especially that of di-limonene was highlighted. In all examined scenarios, the emitted volatiles were increased at raised temperatures and later decreased in time. Aeration of waste bins slightly affected the volatilization process resulting in higher profiles of VOCs; uniformity in the composition of VOCs was also noted. Slight modifications of commercial waste bins may favor the initiation of home composting.

  17. A Solvent Switch for the Stabilization of Multiple Hemiacetals on an Inorganic Platform: Role of Supramolecular Interactions.

    Science.gov (United States)

    Kalita, Alok Ch; Gupta, Sandeep K; Murugavel, Ramaswamy

    2016-05-10

    Reaction of Zn(OAc)2 ⋅2 H2 O with 2,6-diisopropylphenyl phosphate (dippH2 ) in the presence of pyridine-4-carboxaldehyde (Py-4-CHO) in methanol resulted in the isolation of a tetrameric zinc phosphate cluster [Zn(dipp)(Py-4-CH(OH)(OMe))]4 ⋅4 MeOH (1) with four hemiacetal moieties stabilized on the double-4-ring inorganic cubane cluster. The change of solvent from methanol to acetonitrile leads to the formation of [Zn(dipp)(Py-4-CHO)]4 (2), in which the coordinated Py-4-CHO retains its aldehydic form. Dissolution of 1 in CD3 CN readily converts it to the aldehydic form and yields 2. Similarly 2, which exists in the aldehyde form in CD3 CN, readily converts to the hemiacetal form in CD3 OD/CH3 OH. Compound 1 is an unprecedented example in which four hemiacetals have been stabilized on a single molecule in the solid state retaining its stability in solution as revealed by its (1) H NMR spectrum in CD3 OD. The solution stability of 1 and 2 has further been confirmed by ESI-MS studies. To generalize the stabilization of multiple hemiacetals on a single double-four-ring platform, pyridine-2-carboxaldehyde (Py-2-CHO) was used as the auxiliary ligand in the reaction between zinc acetate and dippH2 , leading to isolation of [Zn(dipp)(Py-2-CH(OH)(OMe))]4 (3). Understandably, recrystallization of 3 from acetonitrile yields the parent aldehydic form, [Zn(dipp)(Py-2-CHO)]4 (4). Single-crystal X-ray diffraction studies reveal that supramolecular bonding, aided by hydrogen-bonding interactions involving the hemiacetal functionalities (C-OH, C-OMe, and C-H), are responsible for the observed stabilization. The hemiacetal/aldehyde groups in 1 and 2 readily react with p-toluidine, 2,6-dimethylaniline, and 4-bromoaniline to yield the corresponding tetra-Schiff base ligands, [Zn(dipp)(L)]4 (L=4-methyl-N-(pyridin-4-ylmethylidene)aniline (5), 2,6-dimethyl-N-(pyridin-4-ylmethylene)-aniline (6), and 4-bromo-N-(pyridin-4-ylmethylene)aniline (7)). Isolation of 5-7 opens up further

  18. How polar are choline chloride-based deep eutectic solvents?

    Science.gov (United States)

    Pandey, Ashish; Rai, Rewa; Pal, Mahi; Pandey, Siddharth

    2014-01-28

    Developing and characterizing green solvents with low toxicity and cost is one of the most important issues in chemistry. Deep Eutectic Solvents (DESs), in this regard, have shown tremendous promise. Compared to popular organic solvents, DESs possess negligible VOCs and are non-flammable. Compared to ionic liquids, which share many characteristics but are ionic compounds and not ionic mixtures, DESs are cheaper to make, much less toxic and mostly biodegradable. An estimate of the polarity associated with DESs is essential if they are to be used as green alternatives to common organic solvents in industries and academia. As no one physical parameter can satisfactorily represent solute-solvent interactions within a medium, polarity of DESs is assessed through solvatochromic optical spectroscopic responses of several UV-vis absorbance and molecular fluorescence probes. Information on the local microenvironment (i.e., the cybotactic region) that surrounds several solvatochromic probes [betaine dye, pyrene, pyrene-1-carboxaldehyde, 1-anilino-8-naphthalene sulfonate (ANS), p-toluidinyl-6-naphthalene sulfonate (TNS), 6-propionyl-2-(dimethylaminonaphthalene) (PRODAN), coumarin-153, and Nile Red] for four common and popular DESs formed from choline chloride combined with 1,2-ethanediol, glycerol, urea, and malonic acid, respectively, in 1 : 2 molar ratios termed ethaline, glyceline, reline, and maline is obtained and used to assess the effective polarity afforded by each of these DESs. The four DESs as indicated by these probe responses are found to be fairly dipolar in nature. Absorbance probe betaine dye and fluorescence probes ANS, TNS, PRODAN, coumarin-153, and Nile Red, whose solvatochromic responses are based on photoinduced charge-transfer, imply ethaline and glyceline, DESs formed using alcohol-based H-bond donors, to be relatively more dipolar in nature as compared to reline and maline. The pyrene polarity scale, which is based on polarity-induced changes in

  19. Electromeric effect of substitution at 6th position in 2-(Furan-2-yl)-3-hydroxy-4 H-chromen-4-one (FHC) on the absorption and emission spectra

    Indian Academy of Sciences (India)

    Manisha Bansal; Ranbir Kaur

    2015-03-01

    Five 3-Hydroxychromones (3HCs), namely, 2-(furan-2-yl)-3-hydroxy-4H-chromen-4-one (FHC) and its four derivatives by substitution of -CH3, -OH, -NO2 and -Cl at 6th position were synthesized from their corresponding 2’-hydroxyacetophenone and furan-2-carboxaldehyde. Various spectral transitions of all these 3-hydroxychromones (3-HCs) have been assigned by interpreting their absorption spectra in cyclohexane, acetonitrile and methanol. It has been shown that the electromeric effects of substitution at 2nd and 6th positions on the 2–3 double bond in `C’ ring are similar but the effect on the double bond of 4-carbonyl group is opposite. It has been found that the substitution at 2nd position changes mainly the electron density directly at the 4-carbonyl group and substitution at 6th position changes the electron density of the `C’ ring, changing the overall dipole moment of the molecule, which in turn changes the electron density at the 4-carbonyl group. Emission spectral studies showed that the increase and decrease in dipole moment by substitution at 6th position with electron withdrawing group like NO2 and electron donating group like -CH3 and -OH, stabilizes and destabilizes the N* state in the polar solvents respectively

  20. 2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis.

    Science.gov (United States)

    Jallapally, Anvesh; Addla, Dinesh; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas

    2014-12-01

    Here a series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids were designed by combining three different pharmacophoric fragments in single molecular architecture. 2-Butyl-4-chloro-1-(3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes (4a-p) prepared by reacting carboxaldehyde 2 with N-alkyl piperazines 3a-p which were condensed with thiosemicarbazine to give desired compounds 5a-p in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl) piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5e and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene) hydrazine carbothioamide 5f were found to be the most potent antitubercular agents (MIC: 3.13 μg/mL) with low toxicity profile. PMID:25451998

  1. Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: indolenyl sulfonamide derivatives.

    Science.gov (United States)

    Chohan, Zahid H; Youssoufi, Moulay H; Jarrahpour, Aliasghar; Ben Hadda, Taibi

    2010-03-01

    Synthesis of seven new indolenyl sulfonamides, have been prepared by the condensation reaction of indole-3-carboxaldehyde with different sulfonamides such as, sulphanilamide, sulfaguanidine, sulfathiazole, sulfamethoxazole, sulfisoxazole, sulfadiazine and sulfamethazine. These synthesized compounds have been used as potential ligands for complexation with some selective divalent transition metal ions (cobalt, copper, nickel & zinc). Structure of the synthesized ligands has been deduced from their physical, analytical (elemental analyses) and spectral (IR, (1)H NMR and (13)C NMR & UV-vis) data. All the compounds have also been assayed for their in vitro antibacterial and antifungal activities examining six species of pathogenic bacteria (Escherichia coli, Shigella flexneri, Pseudomonas aeruginosa, Salmonella typhi, Staphylococcus aureus and Bacillus subtilis) and six of fungi (Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium soloni and Candida glabrata). Antibacterial and antifungal results showed that all the compounds showed significant antibacterial activity whereas most of the compounds displayed good antifungal activity. Brine shrimp bioassay was also carried out for in vitro cytotoxic properties against Artemia salina. PMID:20005022

  2. Antioxidants and α-glucosidase inhibitors from Ipomoea batatas leaves identified by bioassay-guided approach and structure-activity relationships.

    Science.gov (United States)

    Zhang, Lu; Tu, Zong-Cai; Yuan, Tao; Wang, Hui; Xie, Xing; Fu, Zhi-Feng

    2016-10-01

    Sweet potato (Ipomoea batatas) leaf (SPL) is an underused commercial vegetable with considerable bio-activities. By means of DPPH scavenging ability and α-glucosidase inhibitory oriented isolation, 9 and 7 compounds were isolated and identified, respectively. Among them, trans-N-(p-coumaroyl)tyramine (1), trans-N-feruloyltyramine (2), cis-N-feruloyltyramine (3), 4,5-feruloylcourmaoylquinic acid (8), caffeic acid ethyl ester (10), 7-hydroxy-5-methoxycoumarin (11), 7,3'-dimethylquercetin (13) and indole-3-carboxaldehyde (15), were firstly identified from SPL, and four of them (1, 2, 3 and 10) were firstly identified from genus Ipomoea. Phenethyl cinnamides and 3,4,5-triCQA exhibited the strongest α-glucosidase inhibition, while 3,4,5-triCQA and diCQAs were the dominant antioxidants. Structure-activity relationship revealed that higher caffeoylation of quinic acid and lower methoxylation of flavonols resulted in stronger antioxidant activity, and methylation and cis-configuration structure of phenethyl cinnamides weaken the α-glucosidase inhibition. Aforementioned results could help to explain the antioxidant activity and anti-diabetic activity of SPL, and provide theoretical basis for its further application. PMID:27132824

  3. Synthesis, optical and photoelectrical characterizations of the novel 10-chloro-6H,8H-dichromeno[2,3-b:3‧,4‧-e]pyridine-6,8-dione (CDPD) and its photodiode application

    Science.gov (United States)

    Ibrahim, Magdy A.; Farag, A. A. M.; Roushdy, N.; El-Gohary, Nasser M.

    2016-01-01

    Friedländer condensation of 2-amino-6-chlorochromone-3-carboxaldehyde (1) with 4-hydroxycoumarin (2) under basic conditions afforded 10-chloro-6H,8H-dichromeno[2,3-b:3‧,4‧-e]pyridine-6,8-dione (3) (CDPD). Structure of CDPD was deduced based on its correct elemental analysis and spectral data (IR, 1H NMR, 13C NMR and mass spectra). Crystalline structure by using X-ray diffraction confirms a polycrystalline nature of the powder and films with monoclinic system. A flower-like morphology was resolved for the high magnification images of scanning electron microscopy. Three direct optical band gaps were obtained and found to be 1.17, 2.24 and 3.40 eV, respectively. A sharp single peak of photoluminescence in the visible region was observed and centered at around 683 nm as well as another two peaks at 417 and 386 nm. Rectification characteristics of the device based CDPD indicates that the device behaves as a diode. A maximum value of photosensitivity of the device was obtained under effect of 60 mW/cm2 and bias voltage of 1.25 V. The phototransient characteristics of the device confirm that the device can be operated as a photodiode.

  4. Ruthenium (II) complexes of thiosemicarbazone: synthesis, biosensor applications and evaluation as antimicrobial agents.

    Science.gov (United States)

    Yildirim, Hatice; Guler, Emine; Yavuz, Murat; Ozturk, Nurdan; Kose Yaman, Pelin; Subasi, Elif; Sahin, Elif; Timur, Suna

    2014-11-01

    A conformationally rigid half-sandwich organoruthenium (II) complex [(η(6)-p-cymene)RuClTSC(N-S)]Cl, (1) and carbonyl complex [Ru(CO)Cl(PPh3)2TSC(N-S)] (2) have been synthesized from the reaction of [{(η(6)-p-cymene)RuCl}2(μ-Cl)2] and [Ru(H)(Cl)(CO)(PPh3)3] with thiophene-2-carboxaldehyde thiosemicarbazon (TSC) respectively and both novel ruthenium (II) complexes have been characterized by elemental analysis, FT-IR and NMR spectroscopy. The peripheral TSC in the complexes acts as an electrochemical coupling unit providing the ability to carry out electrochemical deposition (ED) and to form an electro-deposited film on a graphite electrode surface. The biosensing applicability of complexes 1 and 2 was investigated by using glucose oxidase (GOx) as a model enzyme. Electrochemical measurements at -0.9V versus Ag/AgCl electrode by following the ED Ru(II) reduction/oxidation due to from the enzyme activity, in the presence of glucose substrate. The designed biosensor showed a very good linearity for 0.01-0.5mM glucose. The in vitro antimicrobial activities of complexes 1 and 2 were also investigated against nine bacterial strains and one fungus by the disc diffusion test method. No activity was observed against the Gram-negative strains and fungus, whereas complex 1 showed moderate antibacterial activities against Gram-positive bacterial strains. PMID:25280673

  5. Application of Porous Nickel-Coated TiO2 for the Photocatalytic Degradation of Aqueous Quinoline in an Internal Airlift Loop Reactor

    Directory of Open Access Journals (Sweden)

    Mingxin Huo

    2012-02-01

    Full Text Available P25 film, prepared by a facile dip-coating method without any binder, was further developed in a recirculating reactor for quinoline removal from synthetic wastewater. Macroporous foam Ni, which has an open three-dimensional network structure, was utilized as a substrate to make good use of UV rays. Field emission scanning electron microscopy and X-ray diffraction analysis showed that the coated/calcinated P25 films consisted of two crystal phases, and had a number of uniform microcracks on the surface. The effects of initial quinoline concentration, light intensity, reaction temperature, aeration, and initial pH were studied. Increased reaction time, light intensity, environmental temperature, and gas aeration were found to significantly improve the quinoline removal efficiency. The aeration effect of oxygen dependency on the quinoline degradation had the trend pure oxygen > air > no gas > pure nitrogen with free O2. The solution pH crucially affected quinoline photodegradation; the high electrostatic adsorption of quinoline molecules on the TiO2 surface was strongly pH dependent. 2-Pyridine-carboxaldehyde, 3-pyridinecarboxaldehyde, and 2(1H-quinolinone were identified as the major intermediates of quinoline degradation. Based on these intermediates, a primary degradation mechanism was proposed. This reusable P25 film benefits the photodegradation of water contaminants and has potential in other various applications.

  6. Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines.

    Science.gov (United States)

    Almansour, Abdulrahman I; Arumugam, Natarajan; Suresh Kumar, Raju; Soliman, Saied M; Altaf, Mohammad; Ghabbour, Hazem A

    2016-01-01

    A series of benzimidazole-tethered oxazepine heterocyclic hybrids has been synthesized in good to excellent yields from an N-alkylated benzimidazole 2-carboxaldehyde, which in turn was accomplished from o-phenylenediamine in three good yielding steps. The calculated molecular structure of compounds 2-methyl-4-(2-((phenylimino)methyl)-1H-benzo-[d]imidazol-1-yl)-butan-2-ol 9 and 10 3,3-dimethyl-N-phenyl-1,2,3,5-tetrahydrobenzo-[4,5]imidazo[2,1-c][1,4]oxazepin-5-amine using the B3LYP/6-31 G(d, p) method were found to agree well with their X-ray structures. The charge distributions at the different atomic sites were computed using the natural bond orbital (NBO) method. The regions of electrophilic and nucleophilic reactivity were shown using a molecular electrostatic potential (MEP) map. In addition, the frontier molecular orbitals of these compounds were discussed at the same level of theory. Nonlinear optical (NLO) properties have also been investigated by computational hyperpolarizability studies, and it was found that Compound 9 is the best candidate for NLO applications. PMID:27271585

  7. Synthesis of Novel Ferrocenyl Quinoxaline Piperazines and Their Relevant Antimalarial Activities%新型二茂铁基喹喔啉哌嗪的合成及其抗疟活性研究

    Institute of Scientific and Technical Information of China (English)

    谭平; 吴超; 向建南

    2013-01-01

    A series of novel ferrocenyl-substituted pyrrolo [1,2-α] quinoxaline piperazines 1a-h were synthe-sized from ferrocene-carboxaldehyde by six-step reactions .All of the compounds were screened for their antimalarial activities against plasmodium falciparum FcB1, K1, F32 strains.The results revealed that compounds 1 exhibited some inhibitory activities against the plasmodium falciparum strains.Among them, nitro substituted 1h was best. This work laid a foundation for further study of new antimalarial drugs .%以二茂铁甲醛为起始原料,经过6步反应合成得到新型的二茂铁吡咯并[1,2-α]喹喔啉哌嗪类衍生物1a-h.产物针对恶性疟原虫FcB1, K1, F32等菌株进行了体外抑制活性实验.实验结果表明,新合成的化合物具有一定的抗疟活性,其中芳环上4-位硝基取代的化合物1h体外抗疟活性最优.本工作为进一步研究具有更好活性的抗疟药物打下一定的基础.

  8. Degradation of carbofuran-contaminated water by the Fenton process.

    Science.gov (United States)

    Ma, Ying-Shih; Kumar, Mathava; Lin, Jih-Gaw

    2009-07-15

    In this study, the Fenton process was applied for the degradation of carbofuran from aqueous system. Batch experiments were conducted at two different carbofuran concentrations i.e., 10 and 50 mg/L, and at pH 3. Batch experiments at each carbofuran concentration were designed by central composite design (CCD) with two independent variables i.e. Fe2+ and H2O2. Experimental results indicate that more than 90% of carbofuran removal was observed within 5 mins of Fenton reaction at 5 mg/L of Fe2+ concentration and 100 mg/L of H202 concentration. Increases in Fe2+ and/or H2O2 concentrations beyond 5 and 100 mg/L, respectively produced 100% carbofuran removal. Based on the experimental observations, the optimal Fe2+ and H2O2 dosages required for 10 mg/L of aqueous carbofuran removal were estimated as 7.4 and 143 mg/L, respectively. During this study, three carbofuran intermediates such as 7-benzofuranol,2,3,-dihydro-2,2-dimethyl, 7-hydroxy-2,2-dimethyl-benzofuran-3-one and 1,4-Benzene-di-carboxaldehyde were identified using GC/MS analyses.

  9. Hydroxypyridyl Imines: Enhancing Chromatographic Separation and Stereochemical Analysis of Chiral Amines via Circular Dichroism.

    Science.gov (United States)

    Joyce, Leo A; Regalado, Erik L; Welch, Christopher J

    2016-09-16

    Imine-bond formation between chiral amines and commercially available 3-hydroxypyridine-2-carboxaldehyde (HCA) was exploited for rapid determination of stereochemical composition. Chiral supercritical fluid chromatography (SFC) screening of the derivatized imine compounds led to the elucidation of multiple combinations of mobile and stationary phases that gave resolution of all members of a series of chiral amines. The first eluting enantiomer was generally the derivative of the (R)-amine enantiomer across the series that was studied, indicating that the imine formed from the (S)-amine has more favorable interaction with the chiral stationary phase of the column. These conditions were then applied to more challenging compounds, namely amino alcohols and diastereomers possessing more than one stereocenter. The approach was utilized to monitor stereoselective biocatalytic transamination and assign the absolute configuration of the enantiomeric products. Finally, hydrolysis of the imine bond of the derivative was shown to generate enantiopure amine starting materials without racemization. This further highlights the value of this approach for creating readily reversed derivatives that enhance chromatographic separation and aid in the determination of absolute configuration.

  10. A family of indoles regulate virulence and Shiga toxin production in pathogenic E. coli.

    Directory of Open Access Journals (Sweden)

    Bettina Bommarius

    Full Text Available Enteropathogenic Escherichia coli (EPEC, enterohemorrhagic E. coli (EHEC and enteroaggregative E. coli (EAEC are intestinal pathogens that cause food and water-borne disease in humans. Using biochemical methods and NMR-based comparative metabolomics in conjunction with the nematode Caenorhabditis elegans, we developed a bioassay to identify secreted small molecules produced by these pathogens. We identified indole, indole-3-carboxaldehyde (ICA, and indole-3-acetic acid (IAA, as factors that only in combination are sufficient to kill C. elegans. Importantly, although lethal to C. elegans, these molecules downregulate several bacterial processes important for pathogenesis in mammals. These include motility, biofilm formation and production of Shiga toxins. Some pathogenic E. coli strains are known to contain a Locus of Enterocyte Effacement (LEE, which encodes virulence factors that cause "attaching and effacing" (A/E lesions in mammals, including formation of actin pedestals. We found that these indole derivatives also downregulate production of LEE virulence factors and inhibit pedestal formation on mammalian cells. Finally, upon oral administration, ICA inhibited virulence and promoted survival in a lethal mouse infection model. In summary, the C. elegans model in conjunction with metabolomics has facilitated identification of a family of indole derivatives that broadly regulate physiology in E. coli, and virulence in pathogenic strains. These molecules may enable development of new therapeutics that interfere with bacterial small-molecule signaling.

  11. "Synthesis and smooth muscle Calcium channel antagonist effect of Alkyl, Aminoalkyl 1,4-Dihydro-2,6-Dimethyl-4-Nitroimidazole-3,5 Pyridine Dicarboxylates "

    Directory of Open Access Journals (Sweden)

    Miri R

    2001-08-01

    Full Text Available The discovery that 1,4-dihydropyridine (DHP class of calcium channel antagonist inhibits the Ca+² influx represented a major therapeutic advance in the treatment of cardiovascular diseases such as hypertension, angina pectoris and other spastic smooth muscle disorders. A novel class of calcium channel antagonist of flunarizine containing arylpiperazinyl moiety has recently been reported. It was therefore of interest to determine the effect that selected C-3 substituents contained amino alkyl and arylpiperazine, in conjunction with a C-4 1-methyl-5-nitro-2-imidazolyl substituents on calcium channel antagonist activity. The unsymmetrical analogues were prepared by a procedure reported by Meyer in which 1-methyl-5-nitro-imidazol-2-carboxaldehyde was reacted with acetoacetic esters and alkyl 3-aminocrotonate. In vitro calcium channel antagonist activities were determined by the use of high K+ contraction of guinea pig ileal longitudinal smooth muscle. All compounds exhibited comparable calcium channel antagonist activity (IC50=10^-9 to 10^-11 M against reference drug nifedipine (IC50=2.75±0.36 x 10^-10 M.

  12. 1,10-Phenanthroline promotes copper complexes into tumor cells and induces apoptosis by inhibiting the proteasome activity.

    Science.gov (United States)

    Zhang, Zhen; Bi, Caifeng; Schmitt, Sara M; Fan, Yuhua; Dong, Lili; Zuo, Jian; Dou, Q Ping

    2012-12-01

    Indole-3-acetic acid and indole-3-propionic acid, two potent natural plant growth hormones, have attracted attention as promising prodrugs in cancer therapy. Copper is known to be a cofactor essential for tumor angiogenesis. We have previously reported that taurine, L-glutamine, and quinoline-2-carboxaldehyde Schiff base copper complexes inhibit cell proliferation and proteasome activity in human cancer cells. In the current study, we synthesized two types of copper complexes, dinuclear complexes and ternary complexes, to investigate whether a certain structure could easily carry copper into cancer cells and consequently inhibit tumor proteasome activity and induce apoptosis. We observed that ternary complexes binding with 1,10-phenanthroline are more potent proteasome inhibitors and apoptosis inducers than dinuclear complexes in PC-3 human prostate cancer cells. Furthermore, the ternary complexes potently inhibit proteasome activity before induction of apoptosis in MDA-MB-231 human breast cancer cells, but not in nontumorigenic MCF-10A cells. Our results suggest that copper complexes binding with 1,10-phenanthroline as the third ligand could serve as potent, selective proteasome inhibitors and apoptosis inducers in tumor cells, and that the ternary complexes may be good potential anticancer drugs.

  13. Synthesis of (plus or minus) [5-{sup 3}H] N'-Nitrosoanatabine, a tobacco-specific nitrosamine

    Energy Technology Data Exchange (ETDEWEB)

    Desai, Dhimant; Lin, Guoying; Morimoto, Hiromi; Williams, Philip G.; El-Bayoumy, Karam; Amin, Shantu

    2002-06-14

    Tobacco-specific N'-nitrosamines (TSNA) are a unique class of systemic organ-specific carcinogens. The TSNA are formed by N-nitrosation of nicotine and of the minor tobacco alkaloids after harvesting of tobacco and during smoking. The N-nitrosation of anatabine leads to N'-nitrosoanatabine (NAT; 1-nitroso-1,2,3,4-tetrahydro-2,3'-bipyridyl) which requires in-depth assays in laboratory animals other than the rat. Furthermore, delineation of its tissue distribution and metabolism is needed for structure:activity comparisons with other TSNA and for the assessment of potential human risk from this TSNA. We have, therefore, synthesized (+)[5-3H]NAT. 5-Bromo-3-pyridine-carboxaldehyde was condensed with ethyl carbamate prior to Diels-Alder reaction with 1,4-butadiene to give the racemic anatabine ring system. Hydrolysis followed by reduction with LiAlT4 and nitrosation, led to (+)[5-3H]NAT (60 percent yield, specific activity 266 mCi/mmol, radiochemical purity of >99 percent).

  14. 1,10-Phenanthroline promotes copper complexes into tumor cells and induces apoptosis by inhibiting the proteasome activity.

    Science.gov (United States)

    Zhang, Zhen; Bi, Caifeng; Schmitt, Sara M; Fan, Yuhua; Dong, Lili; Zuo, Jian; Dou, Q Ping

    2012-12-01

    Indole-3-acetic acid and indole-3-propionic acid, two potent natural plant growth hormones, have attracted attention as promising prodrugs in cancer therapy. Copper is known to be a cofactor essential for tumor angiogenesis. We have previously reported that taurine, L-glutamine, and quinoline-2-carboxaldehyde Schiff base copper complexes inhibit cell proliferation and proteasome activity in human cancer cells. In the current study, we synthesized two types of copper complexes, dinuclear complexes and ternary complexes, to investigate whether a certain structure could easily carry copper into cancer cells and consequently inhibit tumor proteasome activity and induce apoptosis. We observed that ternary complexes binding with 1,10-phenanthroline are more potent proteasome inhibitors and apoptosis inducers than dinuclear complexes in PC-3 human prostate cancer cells. Furthermore, the ternary complexes potently inhibit proteasome activity before induction of apoptosis in MDA-MB-231 human breast cancer cells, but not in nontumorigenic MCF-10A cells. Our results suggest that copper complexes binding with 1,10-phenanthroline as the third ligand could serve as potent, selective proteasome inhibitors and apoptosis inducers in tumor cells, and that the ternary complexes may be good potential anticancer drugs. PMID:23053530

  15. Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of some new 4,6-dimethoxy-5-(heterocyclesbenzofuran starting from naturally occurring visnagin

    Directory of Open Access Journals (Sweden)

    E.R. El-Sawy

    2014-12-01

    Full Text Available Novel 3-(4,6-dimethoxybenzofuran-5-yl-1-phenyl-1H-pyrazole-4-carboxaldehyde (3 and 3-chloro-3-(4,6-dimethoxybenzofuran-5-ylpropenal (4 were prepared via Vilsmeier–Haack reaction of 1-(4,6-dimethoxybenzofuran-5-ylethanone (1 and its hydrazone derivative 2. Reaction of compound 4 with some hydrazine derivatives, namely hydrazine hydrate, phenylhydrazine and benzylhydrazine hydrochloride led to the formation of pyrazole derivatives 5–8, respectively. On the other hand, reaction of compound 4 with thiourea, urea or guanidine gave the pyrimidine derivatives 9–11, respectively. Reaction of amino compound 11 with acetic anhydride, benzoyl chloride and benzenesulphonyl chloride yielded N-substituted pyrimidine derivatives 12–14, respectively. Reaction of diazonium salt of compound 11 with sodium azide afforded azidopyrimidine derivative 15, which upon reaction with ethyl acetoacetate gave 1,2,3-triazole derivative 16. Acid catalyzed reaction of 11 with p-nitrobenzaldehyde gave Schiff base 17, which cyclized upon reaction with thioglycolic acid or chloroacetyl chloride to give thiazolidin-4-one 18 and azetidin-2-one 19, respectively. The newly synthesized compounds were tested for their anti-inflammatory, analgesic and anticonvulsant activities. Depending on the obtained results, the newly synthesized compounds possess significant anti-inflammatory, analgesic and anticonvulsant activities.

  16. A virus-MIPs fluorescent sensor based on FRET for highly sensitive detection of JEV.

    Science.gov (United States)

    Liang, Caishuang; Wang, Huan; He, Kui; Chen, Chunyan; Chen, Xiaoming; Gong, Hang; Cai, Changqun

    2016-11-01

    Major stumbling blocks in the recognition and detection of virus are the unstable biological recognition element or the complex detection means. Here a fluorescent sensor based on virus-molecular imprinted polymers (virus-MIPs) was designed for specific recognition and highly sensitive detection of Japanese encephalitis virus (JEV). The virus-MIPs were anchored on the surface of silica microspheres modified by fluorescent dye, pyrene-1-carboxaldehyde (PC). The fluorescence intensity of PC can be enhanced by the principle of fluorescence resonance energy transfer (FRET), where virus acted as energy donor and PC acted as energy acceptor. The enhanced fluorescence intensity was proportional to the concentration of virus in the range of 24-960pM, with a limit of detection (LOD, 3σ) of 9.6pM, and the relative standard deviation was 1.99%. In additional, the specificity study confirmed the resultant MIPs has high-selectivity for JEV. This sensor would become a new key for the detection of virus because of its high sensitive, simple operation, high stability and low cost. PMID:27591625

  17. SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL STUDIES ON Co (II, Ni (II, Cu (II AND Zn (II COMPLEXES OF N, O, DONAR HETEROCYCLIC SCHIFF BASES Synthese, Charakterisierung und antimikrobiellen STUDIES ON Co (II, Ni (II, Cu (II und Zn (II-Komplexe von N, O, DONAR HETEROCYCLISCHE SCHIFF BASES

    Directory of Open Access Journals (Sweden)

    R.Shakru, N.J.P.Subhashini, Acharyanagarjuna,Shivaraj

    2011-08-01

    Full Text Available The Schiff base ligands L1 4-allyl-2-{[(5'-methyl-3'-isoxazolylimino]methyl}phenol [AMIIMP] and L2 N-[5'-methyl-3'-isoxazolyl]-[(EPyridine]methylidine]amine[MIPMA] have been synthesized by the condensation of 4-allyl 2- hydroxyl 1-benzaldehyde and Pyridine 3- carboxaldehyde with 3- amino 5-methy isoxazole. The metal chelates of L1 and L2 with Cobalt (II, Nickel (II, Copper (II and Zn (II metal ions have been synthesised and characterized on the basis of elemental analysis, IR, 1H- NMR, Mass, Electronic spectra and magnetic moment studies. From these studies it is found that ligands act as bivalent chelating agents coordinating through oxygen and nitrogen donor atoms in the case of AMIIMP, and pyridine nitrogen and imino nitrogen donar atoms of in the case of MIPMA. The chelates of Co (II, Ni (II and Zn (II appear to be octahedral geometry and Cu (II appears to be tetragonal geometry. Antimicrobial activity of the ligands and their metal complexes against bacteria (Bacillus, Pseudomonas and fungus (R. Solani, A. Niger has been carried out. It is found that the metal complexes have higher activities than those of free ligands.

  18. 商品肉豆蔻挥发油化学组成及抑菌活性研究∗%Composition and Antimicrobial Activity of the Volatile Oil from Nutmeg

    Institute of Scientific and Technical Information of China (English)

    唐裕芳; 曾永德; 张妙玲

    2014-01-01

    气相色谱-质谱(GC-MS)联用分析了肉豆蔻挥发油的化学组成.平板扩散法研究了肉豆蔻挥发油对6种细菌和6种真菌的抑菌活性,同时研究了高温对挥发油抑菌活性的影响和肉豆蔻挥发油对煮熟土豆的防腐保鲜效果.结果表明:从肉豆蔻挥发油中分离并鉴定出31种化合物,主要含有肉豆蔻醚(35.84%),4-松油醇(19.36%),细辛脑(11.19%)等物质.挥发油对6种细菌具有较强的抑菌活性,对6种真菌的抑制效果较弱.高温加热减弱肉豆蔻挥发油的抑菌活性.肉豆蔻挥发油对煮熟的土豆保鲜10 d不变质.%The composition of the volatile oil extracted from Nutmeg was analyzed by GC-MS.Anti-mi-crobial activity against 6 bacteria and 6 fungi were investigated by plate diffusion.The effect of temperature on anti-microbial activity of the volatile oil and keeping the cooked potato flesh were also investigated.The results indicated that 3 1 compounds were separated and identified from the volatile oil ,the volatile oil is mainly composed of 4-methoxy-6-(2-propenyl)-1,3-Benzodioxole(35.84%),4-methyl-1-[1-methylethyl]-3-Cyclohexen-1-ol(19.36%),1,2,4-trimethoxy-5-(1-propenyl)Benzene(11.19%).The volatile oil showed more significant antimicrobial activity against tested bacteria than against tested fungi.The anti-microbial activity of the volatile oil was weakened by being treated in high temperature.The cooked potato was keep-ing fresh for days when Nutmeg volatile oil was used as preservative for cooked potato.

  19. Changes in the composition of aroma components in blue honeysuckle fruit at different developmental stages%蓝果忍冬果实不同发育期香气成分构成及对比分析

    Institute of Scientific and Technical Information of China (English)

    刘朋; 赵毅; 赵利娟; 辛秀兰; 娄爽; 霍俊伟; 秦栋; 马旿晛; 刘煜池

    2016-01-01

    were identified from the two cultivars.During fruit ripening,the total relative content of hydrocarbons rose,and aldehydes decreased first and then increased,while alcohol content displayed an opposite pattern with aldehydes.Butylated hydroxytoluene,(E)-2-hexenal,hexanal,alpha-4-trimethyl,1-butanol,trimethylamine,compd with borane (1:1) and eucalyptol were the major aroma components in ripe fruit.Composition of aroma components differed in different periods of fruit.developments.In ‘Berel' fruit,a total of 20 species of compounds were detected at fruit setting stage,and aldehydes [(E)-2-hexenal and hexanal] and alcohols (3,7-dimethyl-1,6-octadien-3-ol) were prevailing compounds.19 aroma components were identified at color break including alcohols such as 1-butanol,(E)-3-hexen-1-ol,2-ethyl-1-hexanol,3,7-dimethyl-1,6-octadien-3-ol,and 2-hexen-1-ol.A total of 24 aroma components were identified in the mature fruit,and aldehydes such as hexanal and (E)-2-hexenal) and hydrocarbons such as butylated hydroxytoluene were the dominant.In ‘ C-1' fruit,25 aroma components were detected in fruit at setting period,and the main components were aldehydes such as (E)-2-hexenal and hexanal.A total of 25 aroma components,chiefly alcohols (1-Butanol,(Z)-3-hexen-1-ol,3,7-dimethyl-1,6-octadien-5-ol,α-4-trimethyl,α-3-cyclohexene-1-methano) and hydrocarbons (butylated,hydroxytoluene,eucalyptol) were identified at color break stage.In ripe fruit,25 aroma compounds were indentified including chiefly alcohols (3,7-dimethyl-1,6-octadien-3-ol,α-4-trimethyl,α-3-cyclohexene-1-methanol),aldehydes [(E)-2-hexenal and hexanal],hydrocarbons (butylated hydroxytoluene,eucalyptol) and others (1-methoxy-1-propene).There were 11 compounds detected in mature fruit of both cultivars.They were 1-butanol,3-methylpenta-1,4-diene-3-ol,alpha-4-trimethyl,hexanal,(E)-2-hexenal,nonanal,eucalyptol,tridecane,tetradecane,butylatcd hydroxytoluene and 2-(1,1-dimethylethyl)-4-methyl-phenol.The contents of aroma

  20. 5,6-Dimethoxybenzofuran-3-one Derivatives: a Novel Series of Dual Acetylcholinesterase/Butyrylcholinesterase Inhibitors Bearing Benzyl Pyridinium Moiety

    Directory of Open Access Journals (Sweden)

    Mohammad Abdollahi

    2013-02-01

    Full Text Available Several studies have been focused on design and synthesis of multi-target anti Alzheimer compounds. Utilizing of the dual Acetylcholinesterase/Butyrylcholinesterase inhibitors has gained more interest to treat the Alzheimer’s disease. As a part of a research program to find a novel drug for treating Alzheimer disease, we have previously reported 6-alkoxybenzofuranone derivatives as potent acetylcholinesterase inhibitors. In continuation of our work, we would like to report the synthesis of 5,6-dimethoxy benzofuranone derivatives bearing a benzyl pyridinium moiety as dual Acetylcholinesterase/Butyrylcholinesterase inhibitors.MethodsThe synthesis of target compounds was carried out using a conventional method. Bayer-Villiger oxidation of 3,4-dimethoxybenzaldehyde furnished 3,4-dimethoxyphenol. The reaction of 3,4-dimethoxyphenol with chloroacetonitrile followed by treatment with HCl solution and then ring closure yielded the 5,6-dimethoxy benzofuranone. Condensation of the later compound with pyridine-4-carboxaldehyde and subsequent reaction with different benzyl halides afforded target compounds. The biological activity was measured using standard Ellman’s method. Docking studies were performed to get better insight into interaction of compounds with receptor.ResultsThe in vitro anti acetylcholinesterase/butyrylcholinesterase activity of compounds revealed that, all of the target compounds have good inhibitory activity against both Acetylcholinesterase/Butyrylcholinesterase enzymes in which compound 5b (IC50 = 52 ± 6.38nM was the most active compound against acetylcholinesterase. The same binding mode and interactions were observed for the reference drug donepezil and compound 5b in docking study.ConclusionsIn this study, we presented a new series of benzofuranone-based derivatives having pyridinium moiety as potent dual acting Acetylcholinesterase/Butyrylcholinesterase inhibitors.

  1. Ruthenium (II) complexes of thiosemicarbazone: Synthesis, biosensor applications and evaluation as antimicrobial agents

    International Nuclear Information System (INIS)

    A conformationally rigid half-sandwich organoruthenium (II) complex [(η6-p-cymene)RuClTSCN–S]Cl, (1) and carbonyl complex [Ru(CO)Cl(PPh3)2TSCN–S] (2) have been synthesized from the reaction of [{(η6-p-cymene)RuCl}2(μ-Cl)2] and [Ru(H)(Cl)(CO)(PPh3)3] with thiophene-2-carboxaldehyde thiosemicarbazon (TSC) respectively and both novel ruthenium (II) complexes have been characterized by elemental analysis, FT-IR and NMR spectroscopy. The peripheral TSC in the complexes acts as an electrochemical coupling unit providing the ability to carry out electrochemical deposition (ED) and to form an electro-deposited film on a graphite electrode surface. The biosensing applicability of complexes 1 and 2 was investigated by using glucose oxidase (GOx) as a model enzyme. Electrochemical measurements at − 0.9 V versus Ag/AgCl electrode by following the ED Ru(II) reduction/oxidation due to from the enzyme activity, in the presence of glucose substrate. The designed biosensor showed a very good linearity for 0.01–0.5 mM glucose. The in vitro antimicrobial activities of complexes 1 and 2 were also investigated against nine bacterial strains and one fungus by the disc diffusion test method. No activity was observed against the Gram-negative strains and fungus, whereas complex 1 showed moderate antibacterial activities against Gram-positive bacterial strains. - Highlights: • Novel Ru (II) thiosemicarbazone complexes were synthesized and characterized. • Electrochemical depositions were performed. • Rigid half-sandwich Ru (II) complex showed enhanced antibacterial activity

  2. Use of volatile organic solvents in headspace liquid-phase microextraction by direct cooling of the organic drop using a simple cooling capsule.

    Science.gov (United States)

    Ghiasvand, Ali Reza; Yazdankhah, Fatemeh; Hajipour, Somayeh

    2016-08-01

    A low-cost and simple cooling-assisted headspace liquid-phase microextraction device for the extraction and determination of 2,6,6-trimethyl-1,3 cyclohexadiene-1-carboxaldehyde (safranal) in Saffron samples, using volatile organic solvents, was fabricated and evaluated. The main part of the cooling-assisted headspace liquid-phase microextraction system was a cooling capsule, with a Teflon microcup to hold the extracting organic solvent, which is able to directly cool down the extraction phase while the sample matrix is simultaneously heated. Different experimental factors such as type of organic extraction solvent, sample temperature, extraction solvent temperature, and extraction time were optimized. The optimal conditions were obtained as: extraction solvent, methanol (10 μL); extraction temperature, 60°C; extraction solvent temperature, 0°C; and extraction time, 20 min. Good linearity of the calibration curve (R(2) = 0.995) was obtained in the concentration range of 0.01-50.0 μg/mL. The limit of detection was 0.001 μg/mL. The relative standard deviation for 1.0 μg/mL of safranal was 10.7% (n = 6). The proposed cooling-assisted headspace liquid-phase microextraction device was coupled (off-line) to high-performance liquid chromatography and used for the determination of safranal in Saffron samples. Reasonable agreement was observed between the results of the cooling-assisted headspace liquid-phase microextraction high-performance liquid chromatography method and those obtained by a validated ultrasound-assisted solvent extraction procedure. PMID:27311349

  3. Quantifying the ionic reaction channels in the Secondary Organic Aerosol formation from glyoxal

    Science.gov (United States)

    Maxut, Aurelia; Nozière, Barbara; Rossignol, Stéphanie; George, Christian; Waxman, Eleanor Marie; Laskin, Alexander; Slowik, Jay; Dommen, Josef; Prévôt, André; Baltensperger, Urs; Volkamer, Rainer

    2014-05-01

    Glyoxal, a common organic gas in the atmosphere, has been identified in recent years as an important Secondary Organic Aerosol (SOA) precursor (Volkamer et al., 2007). But, unlike with other precursors, the SOA is largely produced by particle-phase reactions (Volkamer et al., 2009) and equilibria (Kampf et al. 2013) that are still not entirely characterized. Since 2009 series of smog chamber experiments have been performed within the Eurochamp program at the Paul Scherrer Institute, Switzerland, to investigate SOA formation from glyoxal. In these experiments, glyoxal was produced by the gas-phase oxidation of acetylene in the presence of seeds, the seed composition and other conditions being varied. The 2011 campaign resulted in the identification of salting processes controlling the glyoxal partitioning in the seeds (Kampf et al. 2013). This presentation will report results of the 2013 campaign focusing on the identification of the various reactions (ionic or photo-induced) contributing to the SOA mass. In particular, the contribution of the ionic reactions, i.e. mediated by NH4+, were investigated by quantifying the formation of imidazoles (imidazole, imidazole-2-carboxaldehyde, 2,2'-biimidazole) from the small condensation channel of glyoxal with ammonia. For this, the SOA produced were collected on quartz filters and analyzed by Orbitrap LC/MS (Q-Exactive Thermo Fisher). The formation of other products such as organic acids was also investigated to determine potential competing reactions. Time-resolved MOUDI sampling coupled with nano-DESY/ESI-MS/MS analysis was also used to identify nitrogen- and sulphur-containing products from all the reactions. The results obtained for a range of conditions will be presented and compared with recent mechanistic information on the ionic reaction channels (Nozière et al., in preparation, 2013). The implementation of all this new information into a glyoxal-SOA model will be discussed.

  4. Fluorescence, Photophysical Behaviour and DFT Investigation of E,E-2,5-bis[2-(3-pyridyl)ethenyl]pyrazine (BPEP).

    Science.gov (United States)

    Al-Soliemy, Amerah M; Osman, Osman I; Hussein, Mahmoud A; Asiri, Abdullah M; El-Daly, Samy A

    2016-07-01

    E,E-2,5-bis[2-(3-pyridyl)ethenyl]pyrazine (BPEP) has been prepared by aldol condensation between 2,5-dimethylpyrazine and pyridine-3-carboxaldehyde. It is characterized by IR, (1)H NMR, and (13)C NMR. The electronic absorption and emission properties of BPEP were studied in different solvents. BPEP displays a slight solvatochromic effect of the absorption and emission spectrum, indicating a small change in dipole moment of BPEP upon excitation. The dye solutions (1 × 10(-4) M) in CHCl3, EtOH and dioxane give laser emission in blue region upon excitation by a 337.1 nm nitrogen pulse (λ = 337 nm). The tuning range, gain coefficient (α) and emission cross - section (σe) have been determined. Ground and excited states electronic geometric optimizations were performed using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively. A DFT natural bond analysis complemented the ICT. The simulated maximum absorption and emission wavelengths are in line the observed ones in trend, and are proportionally red-shifted with the increase of the solvent polarity. The stability, hardness and electrophilicity of BPEP in different solvents were correlated with the polarity of the elected solvents. BPEP dye displays fluorescence quenching by colloidal silver nanoparticles (AgNPs). The fluorescence data reveal that radiative and non-radiative energy transfer play a major role in the fluorescence quenching mechanism. PMID:27079457

  5. Kinetic Spectrophotometric Determination of Propellant Grade Hydrazines using Thiophenes with Active Carbonyl Groups

    Directory of Open Access Journals (Sweden)

    Selvakumar Subramanian

    2014-01-01

    Full Text Available A simple, cost effective, highly sensitive and rapid kinetic spectrophotometric method was developed for hydrazines by using Thiophene-3-carboxaldehyde (3-Thienaldehyde and 3-Butenone (E-1,1,1-trifluoro-4-(3-thienyl (CF3 enone. CF3 enone was prepared by crossed aldol condensation of 3-Thienaldehyde and characterized by UV-Vis, FT-IR and NMR spectra. Reactions of 3-Thienaldehyde (with catalyst and CF3 enone (in acetonitrile medium without catalyst with hydrazines were followed spectrophotometrically and compared. Variables such as temperature and concentration were optimized to determine hydrazines in the concentration range of 0.1 mM to 0.1 M for 3-Thienaldehyde and 0.1 mM to 1 mM for CF3 enone. Minimum detectable limits were found to be 0.2 mM (Hydrazine and 0.1 mM (MMH for 3-Thienaldehyde. For CF3 enone, Minimum detectable limits were found to be 0.007 mM (Hydrazine and 0.01 mM (MMH. Rate of the CF3 enone reaction was studied as there is gradual decrease in absorbance for the peak at 320 nm for the interaction of hydrazines. Initial rate and fixed time methods were adopted for kinetic study. CF3 enone based kinetic spectrophotometric method is rapid and sensitive with no catalyst requirement for interaction of hydrazines when compared with the classical CHO functional group based method.Defence Science Journal, Vol. 64, No. 1, January 2014, DOI:10.14429/dsj.64.3092

  6. Synthesis, characterization, electronic structure and catalytic activity of new ruthenium carbonyl complexes of N-[(2-pyridyl)methylidene]-2-aminothiazole

    Science.gov (United States)

    Kundu, Subhankar; Sarkar, Deblina; Jana, Mahendra Sekhar; Pramanik, Ajoy Kumar; Jana, Subrata; Mondal, Tapan Kumar

    2013-03-01

    Reaction of ruthenium carbonyls, [Ru(CO)2Cl2]n/[Ru(CO)4I2] with bidentate Schiffs base ligands derived by the condensation of pyridine-2-carboxaldehyde with 2-aminothiazole in a 1:1 mole ratio in acetonitrile led to the formation of complexes having general formula [Ru(CO)2(L)X2] (X = Cl (1) and I (2)) (L = N-[(2-pyridyl)methylidene]-2-aminothiazole). The compounds have been characterized by various analytical and spectroscopic (IR, electronic and 1H NMR) studies. In acetonitrile solution the complexes exhibit a weak broad metal-ligand to ligand charge transfer (MLLCT) band along with ILCT transitions. The compounds are emissive in room temperature upon excitation in the ILCT band. The complexes exhibit a quasi-reversible one electron Ru(II)/Ru(III) oxidation couple at 1.44 V for 1 and 0.94 V for 2. Catalytic activity of these compounds is investigated to the oxidation of PhCH2OH to PhCHO, 2-butanol (C4H9OH) to 2-butanone, 1-phenylethanol (PhC2H4OH) to acetophenone, cyclopentanol (C5H9OH) to cyclopentanone, cyclohexanol to cyclohexanone, cycloheptanol to cycloheptanone and cycloctanol to cycloctanone using N-methylmorpholine-N-oxide (NMO) as oxidant. The catalytic efficiency of 2 is greater than complex 1 and well correlate with the metal oxidation potential of the complexes. DFT, NBO and TDDFT calculations are employed to explain the structural and electronic features and to support the spectroscopic assignments.

  7. Ruthenium (II) complexes of thiosemicarbazone: Synthesis, biosensor applications and evaluation as antimicrobial agents

    Energy Technology Data Exchange (ETDEWEB)

    Yildirim, Hatice [Dokuz Eylul University, The Graduate School of Natural and Applied Sciences, Department of Chemistry, 35160 Buca, Izmir (Turkey); Guler, Emine [Ege University, Faculty of Science, Department of Biochemistry, 35100 Bornova, Izmir (Turkey); Yavuz, Murat, E-mail: myavuz@dicle.edu.tr [Ege University, Faculty of Science, Department of Biochemistry, 35100 Bornova, Izmir (Turkey); Dicle University, Faculty of Science, Department of Chemistry, 21280 Diyarbakir (Turkey); Ozturk, Nurdan; Kose Yaman, Pelin [Dokuz Eylul University, The Graduate School of Natural and Applied Sciences, Department of Chemistry, 35160 Buca, Izmir (Turkey); Subasi, Elif; Sahin, Elif [Dokuz Eylul University, Faculty of Science, Department of Chemistry, 35160 Buca, Izmir (Turkey); Timur, Suna [Ege University, Faculty of Science, Department of Biochemistry, 35100 Bornova, Izmir (Turkey); Ege University, Institute on Drug Abuse, Toxicology and Pharmaceutical Science (BATI), 35100 Bornova, Izmir (Turkey)

    2014-11-01

    A conformationally rigid half-sandwich organoruthenium (II) complex [(η{sup 6}-p-cymene)RuClTSC{sup N–S}]Cl, (1) and carbonyl complex [Ru(CO)Cl(PPh{sub 3}){sub 2}TSC{sup N–S}] (2) have been synthesized from the reaction of [{(η"6-p-cymene)RuCl}{sub 2}(μ-Cl){sub 2}] and [Ru(H)(Cl)(CO)(PPh{sub 3}){sub 3}] with thiophene-2-carboxaldehyde thiosemicarbazon (TSC) respectively and both novel ruthenium (II) complexes have been characterized by elemental analysis, FT-IR and NMR spectroscopy. The peripheral TSC in the complexes acts as an electrochemical coupling unit providing the ability to carry out electrochemical deposition (ED) and to form an electro-deposited film on a graphite electrode surface. The biosensing applicability of complexes 1 and 2 was investigated by using glucose oxidase (GOx) as a model enzyme. Electrochemical measurements at − 0.9 V versus Ag/AgCl electrode by following the ED Ru(II) reduction/oxidation due to from the enzyme activity, in the presence of glucose substrate. The designed biosensor showed a very good linearity for 0.01–0.5 mM glucose. The in vitro antimicrobial activities of complexes 1 and 2 were also investigated against nine bacterial strains and one fungus by the disc diffusion test method. No activity was observed against the Gram-negative strains and fungus, whereas complex 1 showed moderate antibacterial activities against Gram-positive bacterial strains. - Highlights: • Novel Ru (II) thiosemicarbazone complexes were synthesized and characterized. • Electrochemical depositions were performed. • Rigid half-sandwich Ru (II) complex showed enhanced antibacterial activity.

  8. Characterization of acute biliary hyperplasia in Fisher 344 Rats administered the Indole-3-Carbinol Analog, NSC-743380

    Energy Technology Data Exchange (ETDEWEB)

    Eldridge, Sandy R.; Covey, Joseph; Morris, Joel [Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Rockville, MD, 20892 (United States); Fang, Bingliang [The University of Texas MD Anderson Cancer Center, Houston, TX, 77030 (United States); Horn, Thomas L. [IIT Research Institute, Chicago, IL, 60616 (United States); Elsass, Karen E. [Battelle Columbus, Columbus, OH, 43201 (United States); Hamre, John R. [Investigative Toxicology Laboratory, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 21702 (United States); McCormick, David L. [IIT Research Institute, Chicago, IL, 60616 (United States); Davis, Myrtle A., E-mail: myrtledavis@mail.nih.gov [Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Rockville, MD, 20892 (United States)

    2014-12-15

    NSC-743380 (1-[(3-chlorophenyl)-methyl]-1H-indole-3-carbinol) is in early stages of development as an anticancer agent. Two metabolites reflect sequential conversion of the carbinol functionality to a carboxaldehyde and the major metabolite, 1-[(3-chlorophenyl)-methyl]-1H-indole-3-carboxylic acid. In an exploratory toxicity study in rats, NSC-743380 induced elevations in liver-associated serum enzymes and biliary hyperplasia. Biliary hyperplasia was observed 2 days after dosing orally for 2 consecutive days at 100 mg/kg/day. Notably, hepatotoxicity and biliary hyperplasia were observed after oral administration of the parent compound, but not when major metabolites were administered. The toxicities of a structurally similar but pharmacologically inactive molecule and a structurally diverse molecule with a similar efficacy profile in killing cancer cells in vitro were compared to NSC-743380 to explore scaffold versus target-mediated toxicity. Following two oral doses of 100 mg/kg/day given once daily on two consecutive days, the structurally unrelated active compound produced hepatic toxicity similar to NSC-743380. The structurally similar inactive compound did not, but, lower exposures were achieved. The weight of evidence implies that the hepatotoxicity associated with NSC-743380 is related to the anticancer activity of the parent molecule. Furthermore, because biliary hyperplasia represents an unmanageable and non-monitorable adverse effect in clinical settings, this model may provide an opportunity for investigators to use a short-duration study design to explore biomarkers of biliary hyperplasia. - Highlights: • NSC-743380 induced biliary hyperplasia in rats. • Toxicity of NSC-743380 appears to be related to its anticancer activity. • The model provides an opportunity to explore biomarkers of biliary hyperplasia.

  9. DFT and experimental study of the structure and vibrational spectra of 2-(benzylthio)-N-{pyridinylmethylidene}anilines

    Science.gov (United States)

    Alberto Acosta-Ramirez, J.; Larade, Mathew C.; Lloy, Samantha M.; Cross, Edward D.; McLellan, Beth M.; Martell, Jaime M.; McDonald, Robert; Bierenstiel, Matthias

    2013-02-01

    2-(Benzylthio)-N {pyridine-4-ylmethylidene}aniline was prepared by reaction of S-benzyl ortho-aminothiophenol with 4-pyridine carboxaldehyde and characterized by NMR, IR and Raman spectroscopy and mass spectrometry. The structure and the vibrational analysis of the series of 2-, 3-, and 4-pyridine derivatives was performed based on a comparative computational methodology study with the density functionals B3LYP and B3PW91 and the basis sets LanZ2DZ and 6-31++G(d,p). Comparison of computational results with single crystal X-ray diffraction results of 2-(benzylthio)-N {pyridine-3-ylmethylidene}aniline allowed the evaluation of structure predictions and confirmed B3PW91/6-31++G(d,p) as most accurate for structure determination of the four investigated levels of theories. B3LYP and B3PW91 with the LanL2DZ basis set consistently outperformed calculations for IR and Raman vibrational estimations when compared to level of theories using the 6-31++G(d,p) basis set. Application of scaling factors for IR and Raman frequency predictions showed excellent agreement with experimental values and supported the assignment of the major contributors of the vibration modes of the three pyridine pendant compounds. Overall, B3PW91/LanL2DZ level of theory showed best performance in accuracy and low computational cost for structural and vibrational analysis for the series of 2-(benzylthio)-N-{pyridinylmethylidene}anilines.

  10. Synthesis, X-ray crystal structures and catecholase activity investigation of new chalcone ligands

    Science.gov (United States)

    Thabti, Salima; Djedouani, Amel; Rahmouni, Samra; Touzani, Rachid; Bendaas, Abderrahmen; Mousser, Hénia; Mousser, Abdelhamid

    2015-12-01

    The reaction of dehydroacetic acid DHA carboxaldehyde and RCHO derivatives (R = quinoleine-8-; indole-3-; pyrrol-2- and 4-(dimethylamino)phenyl - afforded four new chalcone ligands (4-hydroxy-6-methyl-3-[(2E)-3-quinolin-8-ylprop-2-enoyl]-2H-pyran-2-one) L1, (4-hydroxy-3-[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]-6-methyl-2H-pyran-2-one) L2, (4-hydroxy-6-methyl-3-[(2E)-3-(1H-pyrrol-2-yl)prop-2-enoyl]-2H-pyran-2-one) L3, and (3-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-4-hydroxy-6-methyl-2H-pyran-2-one) L4. L3 and L4 were characterized by X-ray crystallography. Molecules crystallize with four and two molecules in the asymmetric unit, respectively and adopt an E conformation about the Cdbnd C bond. Both structures are stabilized by an extended network O-H … O. Furthermore, N-H … O and C-H … O hydrogen bonds are observed in L3 and L4 structures, respectively. The in situ generated copper (II) complexes of the four compounds L1, L2, L3 and L4 were examined for their catalytic activities and were found to catalyze the oxidation reaction of catechol to o-quinone under atmospheric dioxygen. The rates of this oxidation depend on three parameters: ligand, ion salts and solvent nature and the combination L2[Cu (CH3COO)2] leads to the faster catalytic process.

  11. 天福号酱香鸡挥发性香成分的提取与分析%Extraction and Analysis of Volatile Aroma Components in Tianfuhao-Branded Sauce Fragrant Chicken

    Institute of Scientific and Technical Information of China (English)

    徐晓兰; 张宁; 綦艳梅; 陈海涛; 孙宝国

    2012-01-01

    In order to explore the volatile aroma composition of Tianfuhao-branded Sauce fragrant chicken, volatile aroma components were isolated and identified by simultaneous distillation extraction-gas chromatography-mass spectrometry (SDE- GC-MS). 84 and 72 volatile aromatic compounds were identified from the ethyl ether and dichloromethane extracts from Tianfuhao- branded Sauce fragrant chicken, respectively. Altogether, 85 flavor compounds were found in both extracts, including 10 hydrocarbons, 24 aldehydes, 12 ketones, 2 ethers, 2 phenols, 19 alcohols, 4 acids, 4 ester and 8 nitrogen-containing or sulfur- containing or heterocyclic compounds. The major volatile aroma components with relatively higher peak area (〉 1%) were hexanal, 1- methoxy-4-(1-propenyl)-benzene, hexadecanal, nonanal, eucalyptol, heptanal, 2-pentyl-furan, (E,E)-2,4-decadienal, octanal, 1-octen- 3-ol, (E)-2-octenal, (E)-2-decenal, 3,7-dimethyl-1,6-octadien-3-ol, (S)-alpha, a/pha-4-trimethyl-3-cyclohexene-1-methanol and 2,3- octanedione. Among these aroma components, aldehydes, ethers and nitrogen-containing and sulfur-containing and heterocyclic compounds were considered as the major flavor components in Tianfuhao Sauce fragrant chicken.%为探究北京传统肉制品——天福号酱香鸡的挥发性风味成分,采用同时蒸馏萃取法对酱香鸡的香成分进行提取,并采用气相色谱-质谱联用法对香成分进行分离鉴定。结果表明:以乙醚作溶剂共鉴定出84种风味化合物,以二氯甲烷作溶剂共鉴定出72种风味化合物,两者共计鉴定出85种风味化合物,可分为9类,即烃类10种、醛类24种、酮类12种、醚类2种、酚类2种、醇类19种、酸类4种、酯类4种、含氮含硫及杂环化合物8种;含量较高(峰面积大于1%)的化合物有己醛、茴香脑、棕榈醛、壬醛、桉叶油醇、庚醛、2-正戊基呋喃、(反,反)-2,4-癸二烯醛、正辛醛、1-辛烯-3-醇、反-2-

  12. Analysis of volatile compounds in oleoresin obtained from wind-dried and baked chilli (Capsicum annuum L.) using solid-phase micro-extraction coupled with gas chromatography-mass%固相微萃取-气相色谱质谱联用分析辣椒油树脂挥发性成分

    Institute of Scientific and Technical Information of China (English)

    曹雁平; 张东

    2011-01-01

    Volatile components emitted from oleoresin of wind-dried and baked Capsicum annuum L. with cultivation place of Wangdu of Hebei were analyzed by using solid- phase micro- extraction coupled with gas chromatography-mass. 28 Volatile components were identified in oleoresin from wind-dried chilli. Acetic acid ( 14.43 % ) ,2 ,4a,5,6 ,7 ,8,9,9a- octahydro-3,5,5 - trimethyl-9- methylene- 1H- benzocycloheptene ( 5.74% ), 1 -methoxy-4- (1-propenyl) - benzene ( 5.67% ) and 10s, 11 s- himachala-3 ( 12 ) ,4- diene (41.14%) were the primary volatile components. On the other hand,32 volatile components were identified in oleoresin from baked chilli, beta-Myrcene(3.14% ) ,2,6- dimethyl-2,6-octadiene(5.54% ) ,2-isopropyl-5-methyl-3-cyclohexen-1-one( 10.15% ),1 a,2,3,4,4a,5,6, 7 b- octahydro- 1,1, 4,7- tetramethyl- 1H- cycloprop [ e ] azulene ( 3.51% ) ,4- ( 1 - methylethyl ) -benzaldehyde ( 6.54% ), phenyl ethyl tiglate( 8.12% ), 1 - methoxy-4- ( 1 - propenyl ) - benzene ( 23.45 % ) and 1, 6-dimethyl-4 - ( 1 - methylethyl ) - naphthalene ( 3.69% ) were the primary volatile components. The composition of volatile components clearly differed between wind-dried and baked chilli.%以河北望都产朝天椒为原料,利用固相微萃取-气相色谱质谱联用技术分析风干辣椒和焙烤辣椒油树脂挥发性成分.从风干辣椒中共鉴定出28种挥发性成分,其中主要挥发性成分为:乙酸(14.43%),2,4a,5,6,7,8,9,9a-八氢-3,5,5-三甲基-9-亚甲基1H-苯(并)环庚烯(5.74%),1-甲氧基-4-(1-丙烯基)-笨(5.67%),10s,11s-Himachala-3(12),4-diene(41.14%).从焙烤辣椒中共鉴定出32种挥发性成分,其中主要挥发性成分为:β-月桂烯(3.14%),2,6-二甲基-2,6-辛二烯(5.54%),2-异丙基-5-甲基-3-环己烯-1-酮(10.15%),1a,2,3,4,4a,5,6,7b-八氢-1,1,4,7-四甲基-环丙苷菊(3.51%),4-(1-甲乙基)-苯甲醛(6.54%),苯基乙酸酯(8.12%),1-甲氧基-4-(1-丙烯基)-苯(23.45%),1,6-二甲基-4-(1-甲乙基)-萘(3.69%).风干

  13. Solvatochromic probe response within ionic liquids and their equimolar mixtures with tetraethylene glycol.

    Science.gov (United States)

    Rai, Rewa; Pandey, Siddharth

    2014-09-25

    Synergism in a probe response within a mixture hints at the presence of strong interactions involving the solvent constituents of the mixture and possibly the probe. Unusual and rare "hyperpolarity" resulting from the synergism in probe response exhibited by ionic liquid (IL) mixtures with glycol family solvents is investigated in detail for equimolar mixtures of tetraethylene glycol (TEG) with many structurally different ILs using several UV-vis absorbance and fluorescence solvatochromic probes. Thirteen different ILs, of the same cation 1-butyl-3-methylimidazolium and different anions, of the same anion bis(trifluoromethylsulfonyl)imide and different cations, and of C2 methyl-substituted imidazolium cations, are used to assess the structural dependence of the IL on synergism exhibited by (IL + TEG) mixture. Responses from UV-vis absorbance probes are used to obtain ET [dipolarity/polarizability and/or H-bond donating (HBD) acidity] and Kamlet-Taft parameters [π* (dipolarity/polarizability), α (HBD acidity), and β (HB accepting basicity)] within (IL + TEG) mixtures. The band I-to-band III fluorescence intensity ratio of dipolarity probe pyrene along with the lowest energy fluorescence band maxima of pyrene-1-carboxaldehyde (PyCHO, a probe for the permittivity of the medium), coumarin-153 and N,N-dimethyl-6-propionyl-2-naphthylamine PRODAN (neutral photoinduced charge-transfer fluorescence probes), and 6-p-toluidine-2-naphthalenesulfonic acid (TNS) and l-anilinonaphthalene-8-sulfonate (ANS) (ionic photoinduced charge-transfer fluorescence probes) are used to assess whether synergism is exhibited by (IL + TEG) equimolar mixtures. Probe responses within TEG equimolar mixtures with ILs are compared to those with common organic solvents. An attempt is made to establish a correlation between the synergism observed in the probe response within an (IL + TEG) mixture and the structural features of the cation and anion of the IL, such as acidity of the protons of the

  14. Radical production from photosensitization of imidazoles

    Science.gov (United States)

    Corral Arroyo, P.; Gonzalez, L.; Steimer, S.; Aellig, R.; Volkamer, R. M.; George, C.; Bartels-Rausch, T.; Ammann, M.

    2015-12-01

    Reactions promoted by light are key in atmospheric chemistry. Some of them occur in the condensed phase of aerosols containing light absorbing organic compounds (George et al., 2015). This work explores the radical reactions initiated by near-UV light in mixtures of citric acid (CA) and imidazole-2-carboxaldehyde (IC) using NO as a probe molecule for HO2, by means of coated wall flow tube experiments. Citric acid may act as H atom or electron donor in condensed phase radical cycles. IC may act as a photosensitizer. The loss of NO was measured by a chemiluminescence detector. The dependence of the NO loss on the NO concentration, the IC/CA ratio in the film, relative humidity, light intensity, oxygen molar fraction were investigated as well as the HONO and NO2 yields. We also added halide salts to investigate the effect of a competing electron donor in the system and the output of halogens to the gas phase. We found a correlation between the loss of NO above the film and the molar ratio of IC/CA and the light intensity. The variation of the NO loss with oxygen corroborates a mechanism, in which the triplet excited state of IC is reduced by citric acid, to a reduced ketyl radical that transfers an electron to molecular oxygen, which in turn leads to production of HO2 radicals. Therefore, the NO loss in the gas phase is related to the production of HO2 radicals. Relative humidity had a strong impact on the HO2 output, which shows a maximum production rate at around 30%. The addition of halide ions (X- = Cl-, Br-, I-) increases the HO2 output at low concentration and decrease it at higher concentration when X2- radical ions likely scavenge HO2. We could preliminarily quantify for the first time the contribution of these processes to the oxidative capacity in the atmosphere and conclude that their role is significant for aerosol aging and potentially a significant source of halogen compounds to the gas phase.

  15. Synthesis and antiproliferative activity of some A- and B modified D-homo lactone androstane derivatives

    Directory of Open Access Journals (Sweden)

    Savić Marina P.

    2013-01-01

    Full Text Available An efficient synthesis of several A- and B-modified D-homo lactone androstane derivatives from 3β-hydroxy-17-oxa-D-homoandrost-5-en-16-one (1 is reported. 17-Oxa-Dhomoandrost- 4-ene-3,16-dione (2, obtained by the Oppenauer oxidation of compound 1, was converted via the unstable intermediate 3,16-dioxo-4,17-dioxa-D-homoandrostane- 5α-carboxaldehyde (3 to 17-oxa-D-homo-3,5-seco-4-norandrostan-5-one-3-carboxylic acid (4, which was also obtained directly from compound 2. Compound 1 was acetylated to give 17-oxa-D-homoandrost-5-en-16-on-3β-yl acetate (5 which was then oxidized with chromium(VI-oxide in 50% acetic acid or with meta-chlorperbenzoic acid and chromium(VI-oxide to yield compounds 6-8 and 5α-hydroxy-17-oxa-D-homoandrostane- 6,16-dion-3β-yl acetate (9, respectively. The oximination of compound 9 gave a mixture of 6(E-hydroximino-5α-hydroxy-17-oxa-D-homoandrostan-16-on-3β-yl acetate (10 and 6(Z-hydroximino-5α-hydroxy-17-oxa-D-homoandrostan-16-on-3β-yl acetate (11, the hydrolysis of which gave 6(E-hydroximino-3β,5α-dihydroxy-17-oxa-D-homoandrostan- 16-one (12 and 6(Z-hydroximino-3β,5α-dihydroxy-17-oxa-D-homoandrostan-16-one (13. 6-Nitrile-17-oxa-5,6-seco-D-homoandrostane-5,16-dion-3β-yl acetate (14 was obtained under the Beckmann fragmentation of compounds 10 and 11. Only pure and stable compounds (1, 2, 4, 5, 9 and 14 were tested in vitro on six malignant cell lines (MCF-7, MDA-MB-231, PC-3, HeLa, HT-29, K562 and one non-tumor MRC-5 cell line. Significant antiproliferative activity against MDA-MB-231 cells showed compounds 1, 5 and 9, while compound 2 exhibited a strong antiproliferative activity. Only compound 14 showed weak antiproliferative activity against MCF-7 cells. All tested compounds were not toxic on MRC-5 cells, whereas Doxorubicin was highly toxic on these cells. [Projekat Ministarstva nauke Republike Srbije, br. 172021

  16. Oviposition Preferences of Major Lepidoptera Pest of Pinus kesiya var.langbianensis%思茅松主要鳞翅目害虫的产卵选择性

    Institute of Scientific and Technical Information of China (English)

    马惠芬; 刘凌; 闫争亮; 刘云彩

    2013-01-01

    )-caryophyllene, isocaryophyllene, α-muurolene, guaiane-1(5), 11-diene and bicyclogermacrene are the main components.In addition to some terpenoids (egα-pinene), lots of green leaf volatile compounds are in volatileof Betula alon ides, such as 2-exenal, 1-hexenol, (Z)-3-cyclohexene-1-ol and (Z)-2-cyclohexene-1-ol.Tests of oviposition preferences show that three species prefers Pinus kesiya var.langbianensis as their egg dropping sites, and oviposition amounts are greatly reduced when volatile extracts of Altingia chinensi or Betula al-noides spray over leaves of Pinus kesiya var.langbianensis.Plant volatileas play important roles in oviposition host selec-tion for the pine pest, and R.crstata, D.rueb lla, D.kikuchii, pine volatile can provide some chemical cues of suitability for females to oviposit.Whereas, the broadleaf volatiles are repellent to the oviposition.

  17. 超高效液相色谱荧光法检测贝类中三种高毒性麻痹性贝毒%Analysis of three paralytic shellfish poisoning toxins with high toxicity in shellfish by UPLC with fluorescence detection

    Institute of Scientific and Technical Information of China (English)

    张晓玲; 杨桥; 惠芸华; 冯兵; 马丽艳; 于慧娟

    2012-01-01

    Establishing sensitive and reliable analytical methods for inspection on paralytic shellfish poisoning (PSP) toxins in shellfish foods is an effective mean to ensure the quality and safety of aquatic products in China. In this paper, the suitability of the ultra performance liquid chromatography (UPLC) and precolumn derivatization for the analysis of three PSP toxins (STX,GTX1 and NEO) with high toxicity in shellfish was investigated by choosing 3-(2-furoyl)quinoline-2-carboxaldehyde (FQ) as the derivatization reagent. Various parameters affecting the derivatization reaction and the UPLC separation were respectively optimized. Under the optimal conditions, the correlation coefficients (r) of three calibration equations were more than 0. 998, the relative standard deviations (RSD) values of the intra-day and inter-day precision for the retention time and peak area of the three targeted analyses were less than 3.1% and 5. 6% , respectively. The limits of detection (LOD) were 7 -14 μg · kg-1. The spiked recoveries were determined as in the range of 82 -92% with the RSDs value less than 5. 2%. The proposed method has proven sensitive and reliable, and can be used for the routine analysis of three PSP toxins in shellfish.%建立灵敏可靠的麻痹性贝类毒素(PSP)检测技术是保障我国贝类水产品质量安全的有力手段.本研究选取3-(2-呋喃甲酰基)-喹啉-2-羰醛(FQ)为荧光衍生试剂,利用超高效液相色谱(UPLC)和柱前衍生荧光检测技术,建立了贝类中3种高毒性PSP毒素成分(STX、GTX1及NEO)的检测方法,对影响荧光衍生效率和色谱分离效果的各主要实验因素分别进行了优化.结果表明,在优化后的最佳实验条件下,3种PSP毒素成分线性方程的相关系数(r)均大于0.998,保留时间(tm)及峰面积(PA)的日内及日间精密度RSD值分别小于3.1%和5.6%,当信噪比(S/N)等于3时,检测限范围为7~14 μg· kg-1,样品加标回收率为82% ~92%,RSD值小于5