WorldWideScience

Sample records for benzyl monohydrazone-3-hydrazine 4-benzyl-6-phenyl

  1. Benzyl Alcohol Topical

    Science.gov (United States)

    Benzyl alcohol lotion is used to treat head lice (small insects that attach themselves to the skin) in adults ... children less than 6 months of age. Benzyl alcohol is in a class of medications called pediculicides. ...

  2. Single Pot Benzylation of O-Xylene with Benzyl Chloride and Benzyl Alcohol Over Pillared Montmorillonites

    Directory of Open Access Journals (Sweden)

    Kurian Manju

    2014-09-01

    Full Text Available Improvement of product selectivity is a major concern of the day. Presence of a coreactant can alter the rate as well as product selectivity of many key reactions like Friedel-Crafts benzylation. Single pot benzylation of o-xylene with benzyl chloride and benzyl alcohol was studied over transition metal exchanged pillared clay catalysts. Complete conversion of benzyl alcohol occured within one hour with 100% monoalkylated product selectivity. The reaction of o-xylene with benzyl alcohol was found to proceed fast in presence of benzyl chloride in single pot, than when present alone as the benzylating species. This enhancement occurs at the expense of no reaction of benzyl chloride, which when present alone reacts faster than benzyl alcohol. Existence of a second transition metal exchanged between the pillars increased the rate of the reaction. A detailed investigation of the reaction variables suggested preferential adsorption of benzyl alcohol to catalyst active sites as the reason.

  3. Benzyl 2-((E-Tosyliminomethylphenylcarbamate

    Directory of Open Access Journals (Sweden)

    Kwang Min Ko

    2016-10-01

    Full Text Available Benzyl 2-((E-tosyliminomethylpenylcarbamate was prepared in good yield and characterized by the condensation reaction of benzyl 2-formylphenylcarbamate with p-toluenesulfonyl amine. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR and mass spectral data.

  4. Beyond benzyl grignards: facile generation of benzyl carbanions from styrenes.

    Science.gov (United States)

    Grigg, R David; Rigoli, Jared W; Van Hoveln, Ryan; Neale, Samuel; Schomaker, Jennifer M

    2012-07-23

    Benzylic functionalization is a convenient approach towards the conversion of readily available aromatic hydrocarbon feedstocks into more useful molecules. However, the formation of carbanionic benzyl species from benzyl halides or similar precursors is far from trivial. An alternative approach is the direct reaction of a styrene with a suitable coupling partner, but these reactions often involve the use of precious-metal transition-metal catalysts. Herein, we report the facile and convenient generation of reactive benzyl anionic species from styrenes. A Cu(I)-catalyzed Markovnikov hydroboration of the styrenic double bond by using a bulky pinacol borane source is followed by treatment with KOtBu to facilitate a sterically induced cleavage of the C-B bond to produce a benzylic carbanion. Quenching this intermediate with a variety of electrophiles, including CO(2), CS(2), isocyanates, and isothiocyanates, promotes C-C bond formation at the benzylic carbon atom. The utility of this methodology was demonstrated in a three-step, two-pot synthesis of the nonsteroidal anti-inflammatory drug (±)-flurbiprofen. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. Optimized Formation of Benzyl Isothiocyanate by Endogenous ...

    African Journals Online (AJOL)

    Purpose: To use endogenous myrosinase in Carica papaya seed to convert benzyl glucosinolate (BG) to benzyl isothiocyanate (BITC) and then extract it for further studies. Methods: Process variables including seed powder particle size, sample-to-solvent ratio, pH of buffer solution, enzymolysis temperature, enzymolysis ...

  6. Electron impact study of molecular ions of some benzyl derivatives

    International Nuclear Information System (INIS)

    Selim, E.T.; Rabia, M.A.; Fahmy, M.A.

    1992-01-01

    The ionization energies at threshold and values of higher energy levels for the molecular ions of benzyl alcohol, benzyl amine and benzyl cyanide are reported using electron impact technique. The first ionization energy values are found to be 8.26 eV (benzyl alcohol), 8.49 eV(benzyl amine)and 9.32 eV (benzyl cyanide). Some of the reported higher energy levels for the molecular ions are tentatively explained. The differences in the relative abundances for the main fragment ions are discussed and attributed to the effect of the different substituents - OH, -NH2 and -CN groups

  7. Resonance Raman study of benzyl radical

    DEFF Research Database (Denmark)

    Langkilde, F.W.; Bajdor, K.; Wilbrandt, R.

    1992-01-01

    symmetric a1 modes. The remaining observed bands are tentatively assigned to fundamental modes of b1, a2, and b2 symmetry, and to overtones and combinations. The resonance Raman spectra are found to be quite different from previous fluorescence spectra of benzyl, and the origins of these differences...

  8. Experimental and theoretical investigation of benzyl- ...

    Indian Academy of Sciences (India)

    Home; Journals; Journal of Chemical Sciences; Volume 128; Issue 1. Experimental and theoretical investigation of benzyl--pyrrolylketene, one- step procedure for preparing of new -lactams by [2+2] cycloaddition reaction. Masoumeh Behzadi Kazem Saidi Mohammad Reza Islami Hojatollah Khabazzadeh. Regular ...

  9. Palladium-Catalyzed Asymmetric Benzylic Substitution of Secondary Benzyl Carbonates with Nitrogen and Oxygen Nucleophiles.

    Science.gov (United States)

    Najib, Atifah; Hirano, Koji; Miura, Masahiro

    2017-05-05

    A Pd/(R)-BINAP-catalyzed asymmetric benzylic substitution of secondary benzyl carbonates with amides and amines proceeds to form the corresponding optically active benzylamines in good yields with a high enantiomeric ratio. The reaction occurs in a dynamic kinetic asymmetric transformation (DYKAT) manner. Additionally, the asymmetric Pd catalysis can also be applicable to phenol nucleophiles, thus delivering chiral ethers with acceptable yields and enantioselectivity.

  10. Fragrance material review on benzyl alcohol.

    Science.gov (United States)

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

    2012-09-01

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

  11. ROMP-derived Oligomeric Phosphates for Application in Facile Benzylation

    Science.gov (United States)

    Long, Toby R.; Maity, Pradip K.; Samarakoon, Thiwanka B.; Hanson, Paul R.

    2010-01-01

    The development of new ROMP-based oligomeric benzyl phosphates (OBPn) is reported for use as soluble, stable benzylating reagents. These oligomeric reagents are readily synthesized from commercially available materials and conveniently polymerized and purified in a one-pot process, affording bench stable, pure white, free-flowing solids on multi-gram scale. Utilization in benzylation reactions with a variety of nucleophiles is reported. PMID:20521800

  12. Conformational Studies on γ - Benzyl- L- Glutamate and L- Valine Containing Block Copolypeptides

    OpenAIRE

    Kumar, Ajay

    2010-01-01

    Conformational studies on γ - benzyl-L- glutamate and L- valine containing block copolypeptides are reported using IR and CD spectra. The block copolypeptides contain valine block in the center and on both sides of the valine are γ - benzyl- L- glutamate blocks. The changes in conformation with increase in chain length of γ - benzyl- L- glutamate blocks are observed. When the chain length of γ - benzyl-L- glutamate block is 13, the block copolypeptide crystallized into beta conformation. With...

  13. Enhanced catalytic properties of mesoporous mordenite for benzylation of benzene with benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

    Saxena, Sandeep K.; Viswanadham, Nagabhatla, E-mail: nagabhatla.viswanadham@gmail.com

    2017-01-15

    Graphical abstract: The nano size pores (∼10 nm) created in the microporous mordenite zeolite facilitated enhanced catalytic activity to produce as high as 97 wt.% yield of di-phenyl methane in the benzylation of benzene with benzyl alcohol at solvent-free liquid phase reaction conditions. - Highlights: • Nano pores of ∼10 nm size have been created in microporous mordenite. • Dealumination at optimized conditions resulted in enhanced properties of mordenite. • Hierarchically porous mordenite enhanced bulky catalytic reactions. • As high as 97% selectivity to Di-phenyl methane obtained. • Solvent-free, liquid phase alkylation catalyst with stable activity for reusability. - Abstract: Zeolite mordenite has been treated with nitric acid at different severities so as to facilitate the framework dealumination and optimization of the textural properties such as acidity and porosity. The samples obtained have been characterized by X-ray diffraction, FTIR, SEM, TEM, surface area, porosity by N{sub 2} adsorption and ammonia TPD. The resultant samples have been evaluated towards the bulky alkylation reaction of benzylation of benzene with benzyl alcohol. The studies indicated the improvement in the textural properties such as surface area, pore volume and acidity of the samples after the acid treatment. While, the phenomenon of enhancement in properties was exhibited by all the acid treated mordenite samples, the highest improvement in properties was observed at a particular condition of acid treatment (SM-2 sample). This particular sample also exhibited highest acidity and the presence of ∼10 nm size pores that resulted in the effective catalytic activity towards the bulky alkylation reaction of benzene with benzyl alcohol to produce high yields of di-phenyl methane.

  14. Highly Selective Liquid-Phase Benzylation of Anisole with Solid-Acid Zeolite Catalysts

    DEFF Research Database (Denmark)

    Poreddy, Raju; Shunmugavel, Saravanamurugan; Riisager, Anders

    2015-01-01

    Zeolites were evaluated as solid acid catalysts for the liquid-phase benzylation of anisole with benzyl alcohol, benzyl bromide, and benzyl chloride at 80 °C. Among the examined zeolites, H-mordenite-10 (H-MOR-10) demonstrated particular high activity (>99 %) and excellent selectivity (>96...... %) to the monobenzylated products, ortho/para benzyl anisole, using benzyl alcohol as reagent (anisole/alcohol molar ratio = 28). Analogous reactions with benzyl halides resulted in lower yields of the desired monobenzylated products. The conversion of benzyl alcohol was confirmed to be proportional to the amount of added...

  15. Synthesis and anticonvulsant studies of N-Benzyl-3-[(Chlorophenyl ...

    African Journals Online (AJOL)

    ... isomeric benzylated products were found to be far more potent than valproate in both the MES and the scPTZ tests with favourable therapeutic indices signifying their great potential for use against generalized seizures. Acute toxicity studies revealed that N-Benzyl-3-[(chlorophenyl)amino]propanamides are relatively safe.

  16. Selective oxidation of benzyl alcohol with tert-butylhydroperoxide ...

    Indian Academy of Sciences (India)

    butylhydroperoxide (TBHP) as an oxidant. The effects ... The order of reaction with respect to benzyl alcohol was determined to be pseudo-first order. The value of the ..... showing a pseudo-first-order dependence on the benzyl alcohol (figure 6b).

  17. Desulfurizing Difluorination Reaction of Benzyl Sulfides Using IF5

    OpenAIRE

    Fukuhara, Tadahito; Hara, Shoji

    2009-01-01

    A desulfurizing difluorination reaction of benzyl sulfides having a functional group such as an ester, a ketone, a nitrile, or an amide was performed by a reaction with IF5. Consequently, gem-difluoro compounds could be obtained selectively.

  18. Toxicity of benzyl alcohol in adult and neonatal mice.

    Science.gov (United States)

    McCloskey, S E; Gershanik, J J; Lertora, J J; White, L; George, W J

    1986-07-01

    Benzyl alcohol, a bacteriostatic agent found in many parenteral preparations, has been implicated as the agent responsible for precipitating "the gasping syndrome" in premature neonates. To investigate this toxicity, benzyl alcohol was administered intraperitoneally to adult (23-28 g) and neonatal (2-7 g) CD-1 male mice. Gross behavioral changes were monitored. Low doses (less than 800 mg/kg) produced minimal toxic effects within an initial 4-h observation period. At the end of this time, the LD50 was determined to be 1000 mg/kg for both age groups. When mortality in the adult group was observed after 7 d following a single treatment with benzyl alcohol, the LD50 on day 7 was determined to be 650 mg/kg. Rapid absorption and conversion of benzyl alcohol to its primary metabolite, benzaldehyde, occurred within both experimental groups; the plasma levels of each were comparable in both neonatal and mature animals when determined by GC. In an attempt to alter the toxicity of benzyl alcohol, pyrazole and disulfiram were used to inhibit the activities of alcohol dehydrogenase and aldehyde dehydrogenase, respectively. Treatment with pyrazole, before benzyl alcohol exposure, resulted in an increase in benzyl alcohol levels to 203% of control values and a marked increase in toxicity. Although pretreatment with disulfiram led to benzaldehyde levels which were 368% of control values, toxicity was unchanged. These data imply that the acute toxicity of benzyl alcohol, which includes sedation, dyspnea, and loss of motor function, is due to the alcohol itself and not to its metabolite, benzaldehyde.

  19. Palladium-Catalyzed α-Arylation of Benzylic Phosphine Oxides

    Science.gov (United States)

    Montel, Sonia; Jia, Tiezheng

    2014-01-01

    A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)2/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51–91%). PMID:24295336

  20. Toluene and benzyl decomposition mechanisms: elementary reactions and kinetic simulations.

    Science.gov (United States)

    Derudi, Marco; Polino, Daniela; Cavallotti, Carlo

    2011-12-28

    The high temperature decomposition kinetics of toluene and benzyl were investigated by combining a kinetic analysis with the ab initio/master equation study of new reaction channels. It was found that similarly to toluene, which decomposes to benzyl and phenyl losing atomic hydrogen and methyl, also benzyl decomposition proceeds through two channels with similar products. The first leads to the formation of fulvenallene and hydrogen and has already been investigated in detail in recent publications. In this work it is proposed that benzyl can decompose also through a second decomposition channel to form benzyne and methyl. The channel specific kinetic constants of benzyl decomposition were determined by integrating the RRKM/master equation over the C(7)H(7) potential energy surface. The energies of wells and saddle points were determined at the CCSD(T) level on B3LYP/6-31+G(d,p) structures. A kinetic mechanism was then formulated, which comprises the benzyl and toluene decomposition reactions together with a recently proposed fulvenallene decomposition mechanism, the decomposition kinetics of the fulvenallenyl radical, and some reactions describing the secondary chemistry originated by the decomposition products. The kinetic mechanism so obtained was used to simulate the production of H atoms measured in a wide pressure and temperature range using different experimental setups. The calculated and experimental data are in good agreement. Kinetic constants of the new reaction channels here examined are reported as a function of temperature at different pressures. The mechanism here proposed is not compatible with the assumption often used in literature kinetic mechanisms that benzyl decomposition can be effectively described through a lumped reaction whose products are the cyclopentadienyl radical and acetylene.

  1. A convenient procedure for the synthesis of allyl and benzyl ethers ...

    Indian Academy of Sciences (India)

    Unknown

    (scheme 1). Even though benzyl protection on a carbohydrate substrate was previously carried out with benzyl chloride in the presence of potassium hydroxide pellets 9, the scope of the reaction was not fully explored. While our work was in progress, Bogdal and coworkers recently reported 10 solvent-free allyl and benzyl ...

  2. short communication efficient and convenient oxidation of benzyl

    African Journals Online (AJOL)

    Preferred Customer

    ketones in good to high yields by phase transfer catalysis combined with sodium nitrate and acetic acid at reflux. As a result, a simple and high yield procedure has been developed. KEY WORDS. KEY WORDS: Oxidation, Benzyl halides, Phase ...

  3. Research note : Miscibility behaviour of binary mixtures of benzyl ...

    African Journals Online (AJOL)

    Miscibility of binary mixtures of benzyl benzoate and liquid paraffin as functions of temperature and composition has been determined using phase separation method. The binary mixtures demonstrated a critical (upper) solution temperature of 35 °C at 101325 Nm-2 with a mixing gap. A tie-line drawn at 28 °C across the ...

  4. catalysed selective oxidation of benzyl alcohols using TEMPO and ...

    Indian Academy of Sciences (India)

    A general scheme for the oxidation of benzyl alcohols catalyzed by silica functionalized copper (II) has been designed. TEMPO, a free radical, assists this oxidation that was initiated by molecular oxygen which converts it to a primary oxidant. This catalytic combination i.e. SiO2 -Cu(II) in presence of TEMPO and oxygen ...

  5. Efficient and convenient oxidation of benzyl halides to carbonyl ...

    African Journals Online (AJOL)

    ketones in good to high yields by phase transfer catalysis combined with sodium nitrate and acetic acid at reflux. As a result, a simple and high yield procedure has been developed. KEY WORDS: Oxidation, Benzyl halides, Phase transfer catalyst, ...

  6. Effect of different combinations of 6-benzyl amino purine and ...

    African Journals Online (AJOL)

    This study was conducted at the Amhara Region Agricultural Research Institute Tissue culture Laboratory, Ethiopia from April to June 2012 to investigate the effect of different concentrations of 6-benzyl amino purine (BAP) and naphthalene acetic acid (NAA) on virus free plant regeneration and shoot multiplication.

  7. Selective oxidation of benzyl alcohol in dense CO2

    DEFF Research Database (Denmark)

    Beier, Matthias Josef; Grunwaldt, Jan-Dierk; Tsivintzelis, Ioannis

    2012-01-01

    systems, based on the Cubic Plus Association (CPA) equation of state, is utilized in order to gain insight into the phase behavior during the palladium-catalyzed selective oxidation of benzyl alcohol to benzaldehyde. The catalytic reaction was studied in a tubular continuous reactor both under biphasic...

  8. Experimental and theoretical investigation of benzyl-N ...

    Indian Academy of Sciences (India)

    Experimental and theoretical investigation of benzyl-N-pyrrolylketene, one- step procedure for preparing of new β-lactams by [2+2] cycloaddition reaction. MASOUMEH BEHZADI, KAZEM SAIDI. ∗. , MOHAMMAD REZA ISLAMI and. HOJATOLLAH KHABAZZADEH. Department of Chemistry, Shahid Bahonar University of ...

  9. Benzyl alcohol–ammonia (1: 1) cluster structure investigated by ...

    Indian Academy of Sciences (India)

    Laser-induced fluorescence excitation and IR-UV double resonance spectroscopy have been used to determine the hydrogen-bonded structure of benzyl alcohol-ammonia (1:1) cluster in a jet-cooled molecular beam. In addition, ab initio quantum chemical calculations have been performed at HF/6-31G and HF/6-31G(d, ...

  10. 3-Benzyl-5-methyl-1,2-benzoxazole 2-oxide

    Directory of Open Access Journals (Sweden)

    G. Anuradha

    2012-10-01

    Full Text Available In the title compound, C15H13NO2, the isoxazole unit and the attached benzene ring are almost coplanar, making a dihedral angle of 1.42 (8°. The benzyl ring is inclined to the isoxazole ring by 74.19 (8° and is in a +sc conformation with respect to the benzisoxazole unit. In the crystal, C—H...O hydrogen bonds link the molecules, forming zigzag chains propagating along the b axis. There are also π–π interactions present involving the isoxazole and benzyl rings [centroid–centroid distance = 3.5209 (10 Å], and C—H...π interactions involving the benzene ring of the benzoisoxazole unit and the methylene bridging group.

  11. Friction behavior of 304 stainless steel of varying hardness lubricated with benzene and some benzyl structures

    Science.gov (United States)

    Buckley, D. H.

    1974-01-01

    The lubricating properties of some benzyl and benzene structures were determined by using 304 stainless steel surfaces strained to various hardness. Friction coefficients and wear track widths were measured with a Bowden-Leben type friction apparatus by using a pin-on-disk specimen configuration. Results obtained indicate that benzyl monosulfide, dibenzyl disulfide, and benzyl alcohol resulted in the lowest friction coefficients for 304 stainless steel, while benzyl ether provided the least surface protection and gave the highest friction. Strainhardening of the 304 stainless steel prior to sliding resulted in reduced friction in dry sliding. With benzyl monosulfide, dibenzyl disulfide, and benzyl alcohol changes in 304 stainless steel hardness had no effect upon friction behavior.

  12. Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates

    OpenAIRE

    Mei, Qinggang; Wang, Chun; Yuan, Weicheng; Zhang, Guolin

    2015-01-01

    A strategy for selective mono-, di- and tri-O-methylation of kaempferol, predominantly on the basis of selective benzylation and controllable deacetylation of kaempferol acetates, was developed. From the selective deacetylation and benzylation of kaempferol tetraacetate (1), 3,4′,5,-tri-O-acetylkaempferol (2) and 7-O-benzyl-3,4′5,-tri-O-acetylkaempferol (8) were obtained, respectively. By controllable deacetylation and followed selective or direct methylation of these two intermediates, eight...

  13. Effect of strain hardening on friction behavior of iron lubricated with benzyl structures

    Science.gov (United States)

    Buckley, D. H.; Brainard, W. A.

    1974-01-01

    Sliding friction experiments were conducted with iron, copper, and aluminum in contact with iron in various states of strain. The surfaces were examined in dry sliding and with various benzyl compounds applied as lubricants. Friction experiments were conducted with a hemispherical rider contacting a flat disk at loads of from 50 to 600 grams with a sliding speed of 0.15 cm/min. Results indicate that straining increases friction for dry sliding and for surfaces lubricated with certain benzyl structures such as dibenzyl disulfide. With other benzyl compounds (e.g., benzyl formate), friction coefficients are lower for strained than for annealed iron.

  14. 1-Benzyl-3-methylquinoxalin-2(1H-one

    Directory of Open Access Journals (Sweden)

    Youssef Ramli

    2018-03-01

    Full Text Available The asymmetric unit of the title compound, C16H14N2O, contains three independent molecules differing primarily in the orientations of the benzyl groups. Each independent molecule forms inversion related dimers via offset π-stacking interactions. For two of these dimers, stacks are formed approximately along the a-axis direction by a combinations of C—H...N and C—H...π(ring contacts, in addition to the offset π-stacking interactions. The third set of dimers are also stacked in the same direction but only by pairwise C—H...N hydrogen bonds.

  15. Synthesis of Benzyl 4-Hydroxy-5-iodo-2,3-dimethoxy-6-methylbenzoate: The Aromatic Unit of Calicheamicin g1

    Directory of Open Access Journals (Sweden)

    Alvarenga Elson Santiago de

    1999-01-01

    Full Text Available Orsellinic acid (6 was benzylated, and the benzyl 4-benzyloxy-2-hydroxy-6-methylbenzoate (7 was then elaborated into the title compound (2, which is the aromatic constituent of calicheamicin gamma1I.

  16. A convenient procedure for the synthesis of allyl and benzyl ethers ...

    Indian Academy of Sciences (India)

    Unknown

    Allyl and benzyl groups are commonly employed for the protection of alcohol and phenol moieties for ease of synthesis and convenient deprotection. Allyl and benzyl ethers are also intermediates in sigmatropic rearrangement reactions such as the Claisen and the. Cope rearrangements. Allyl ethers can be prepared from ...

  17. FTIR study of hydrogen bonding between substituted benzyl alcohols and acrylic esters

    Directory of Open Access Journals (Sweden)

    P. Sivagurunathan

    2016-11-01

    Full Text Available Hydrogen bonding between substituted benzyl alcohols (benzyl alcohol, o-aminobenzyl alcohol, o-chlorobenzyl alcohol and o-nitrobenzyl alcohol and acrylic esters (methyl methacrylate, ethyl methacrylate is studied in carbon tetrachloride by using the FTIR spectroscopic method. Utilizing the Nash method, the formation constant (K of the 1:1 complexes is calculated. Using the K value, the Gibbs free energy change (ΔG0 is also calculated. The calculated formation constant and Gibbs free energy change values vary with the substituent of benzyl alcohol and ester chain length, which suggests that the proton donating ability of substituted benzyl alcohols is in the order: o-aminobenzyl alcohol < benzyl alcohol < o-chlorobenzyl alcohol < o-nitrobenzyl alcohol, and proton accepting ability of acrylic esters is in the order: methyl methacrylate < ethyl methacrylate.

  18. Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

    Science.gov (United States)

    Balachandran, C.; Kumar, P. Saravana; Arun, Y.; Duraipandiyan, V.; Sundaram, R. Lakshmi; Vijayakumar, A.; Balakrishna, K.; Ignacimuthu, S.; Al-Dhabi, N. A.; Perumal, P. T.

    2015-02-01

    N-Benzyl-2,2,2-trifluoroacetamide was obtained by acylation of benzylamine with trifluoroacetic anhydride using Friedel-Crafts acylation method. The synthesised compound was confirmed by spectroscopic and crystallographic techniques. N-Benzyl-2,2,2 -trifluoroacetamide was assessed for its antimicrobial, antioxidant, cytotoxic and molecular docking properties. It showed good antifungal activity against tested fungi and moderate antibacterial activity. The minimum inhibitory concentration values of N-benzyl-2,2,2 -trifluoroacetamide against fungi were 15.62 μg/mL against A. flavus, 31.25 μg/mL against B. Cinerea and 62.5 μg/mL against T. mentagrophytes, Scopulariopsis sp., C. albicans and M. pachydermatis. N-Benzyl-2,2,2-trifluoroacetamide showed 78.97 ± 2.24 of antioxidant activity at 1,000 μg/mL. Cupric ion reducing antioxidant capacity of N-benzyl-2,2,2-trifluoroacetamide was dependent on the concentration. Ferric reducing antioxidant power assay of N-benzyl-2,2,2-trifluoroacetamide showed (1.352 ± 0.04 mM Fe(II)/g) twofold higher value compared to the standard. N-Benzyl-2,2,2-trifluoroacetamide showed 75.3 % cytotoxic activity at the dose of 200 μg/mL with IC50 (54.7 %) value of 100 μg/mL. N-Benzyl-2,2,2-trifluoroacetamide was subjected to molecular docking studies for the inhibition AmpC beta-lactamase, Glucosamine-6-Phosphate Synthase and lanosterol 14 alpha-demethylase (CYP51) enzymes which are targets for antibacterial and antifungal drugs. Docking studies of N-benzyl-2,2,2-trifluoroacetamide showed low docking energy. N-Benzyl-2,2,2-trifluoroacetamide can be evaluated further for drug development.

  19. Rate and Product Studies of Solvolyses of Benzyl Fluoroformate

    Directory of Open Access Journals (Sweden)

    Dennis N. Kevill

    2006-07-01

    Full Text Available The specific rates of solvolysis of benzyl fluoroformate have been measured inseveral hydroxylic solvents at 25.0 °C. For methanolysis, the solvent deuterium isotopeeffect and activation parameters were determined and activation parameters were alsodetermined for solvolyses in ethanol and 80% ethanol. For several of the binary hydroxylicsolvents, measurement of product ratios allowed selectivity values to be determined. Anextended Grunwald–Winstein treatment of the data led to sensitivities to changes in solventnucleophilicity and ionizing power. Comparison with previously determined specific ratesfor solvolysis of the chloroformate gave fluorine/chlorine rate ratios greater than unity. Allof the determinations made were consistent with an addition–elimination (association–dissociation mechanism, with addition rate-determining.

  20. Antiamoebic activity of benzyl glucosinolate from Lepidium virginicum.

    Science.gov (United States)

    Calzada, Fernando; Barbosa, Elizabeth; Cedillo-Rivera, Roberto

    2003-06-01

    In a continuation of our search for potential antiprotozoal agents from plants, we found that a crude extract from the roots of Lepidium virginicum exhibited antiprotozoal activity against Entamoeba histolytica trophozoites (IC(50) of 100.1 micro g/mL). Bioassay-guided fractionation resulted in the isolation of one known glucosinolate responsible for such activity. This compound was identified as benzyl glucosinolate. It showed in vitro activity against Entamoeba histolytica strain HM1-IMSS (IC(50) of 20.4 micro g/mL). The results support the anecdotal reports for the traditional use of L. virginicum roots in the control of diarrhoea and dysentery in the highlands of Chiapas, Mexico. Copyright 2003 John Wiley & Sons, Ltd.

  1. 1-Benzyl-5-bromoindoline-2,3-dione

    Directory of Open Access Journals (Sweden)

    Yassine Kharbach

    2016-04-01

    Full Text Available In the title compound, C15H10BrNO2, the indoline ring system, the two ketone O atoms and the Br atom lie in a common plane, with the largest deviation from the mean plane being 0.073 (1 Å for the Br atom. The fused-ring system is nearly perpendicular to the benzyl ring, as indicated by the dihedral angle between them of 74.58 (10°. In the crystal, molecules are linked by weak C—H...O hydrogen bonds and by π–π interactions [inter-centroid distance = 3.625 (2 Å], forming a two-dimensional structure.

  2. Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension.

    Science.gov (United States)

    Ohno, Osamu; Ye, Mao; Koyama, Tomoyuki; Yazawa, Kazunaga; Mura, Emi; Matsumoto, Hiroshi; Ichino, Takao; Yamada, Kaoru; Nakamura, Kazuhiko; Ohno, Tomohiro; Yamaguchi, Kohji; Ishida, Junji; Fukamizu, Akiyoshi; Uemura, Daisuke

    2008-08-15

    Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2'-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension.

  3. Structure and dynamics at the liquid surface of benzyl alcohol

    International Nuclear Information System (INIS)

    Dietter, J.; Morgner, H.

    1999-01-01

    A molecular dynamics simulation of a liquid layer of benzyl alcohol has been performed in order to compare the results with those obtained in experimental studies of our group. The main result of the experimental work was a strong orientational ordering of the benzyl alcohol molecules in the surface as well as an exceptionally large surface potential of ca. 0.6 V. According to the experiments the surface molecules orientate in such a way that the benzene ring points toward the vapor phase while the CH 2 group and the OH group are directed towards the bulk of the liquid. The simulation confirms this orientation of the surface molecules. The surface potential resulting from the simulation is 350 mV. The simulation reveals that the rather large surface potential can be understood as a consequence of the mean orientation of the molecular dipole moment in the surface region. The mean orientation of the molecules themselves in the surface is due to the tendency of the system to maintain the hydrogen bonding structure of the bulk in the surface region as well. The preferential orientation of the surface molecules causes a change of the dynamics of the individual components of the molecules when switching from bulk to surface which depends on the separation of these components from the polar group. This becomes most obvious in case of the reorientation dynamics of the molecular axes, e.g. the reorientation of the benzene ring is faster than the reorientation of the OH group. (Copyright (c) 1999 Elsevier Science B.V., Amsterdam. All rights reserved.)

  4. Anaphylaxis Triggered by Benzyl Benzoate in a Preparation of Depot Testosterone Undecanoate

    Directory of Open Access Journals (Sweden)

    Gregory S. Y. Ong

    2012-01-01

    Full Text Available We report the first case of an anaphylactic reaction to Reandron 1000 (depot testosterone undecanoate with a castor oil and benzyl benzoate vehicle. While considered to have a favourable safety profile, serious complications such as oil embolism and anaphylaxis can occur. In our patient, skin testing identified benzyl benzoate to be the trigger, with no reaction to castor oil or testosterone undecanoate components. As benzyl benzoate exists in multiple pharmaceuticals, foods, and cosmetics, individual components of pharmaceuticals should be tested when investigating drug allergies. Doctors should be alert to the potential for serious reactions to any of the components of Reandron 1000.

  5. 1D AND 2D NMR STUDIES OF BENZYL O–VANILLIN

    Directory of Open Access Journals (Sweden)

    Mohammed Hadi Al–Douh

    2010-06-01

    Full Text Available The reaction of o-vanillin A with benzyl bromide B2 in acetone as the solvent and K2CO3 as a base in the presence of tetra-n-butylammonium iodide (TBAI as catalyst formed benzyl o-vanillin, C. The complete assignments of C using PROTON, APT, DEPT-135, COSY, NOESY, HMQC and HMBC NMR in both CDCl3 and acetone-d6 are discussed, and the coupling constants J are reported in Hertz (Hz.     Keywords: 1H NMR; 13C NMR; 2D NMR; Benzyl o-Vanillin

  6. The retro Grignard addition reaction revisited: the reversible addition of benzyl reagents to ketones

    DEFF Research Database (Denmark)

    Christensen, Stig Holden; Holm, Torkil; Madsen, Robert

    2014-01-01

    The Grignard addition reaction is known to be a reversible process with allylic reagents, but so far the reversibility has not been demonstrated with other alkylmagnesium halides. By using crossover experiments it has been established that the benzyl addition reaction is also a reversible......, but in these two cases the Grignard addition reaction did not show any sign of a reverse transformation....... transformation. The retro benzyl reaction was shown by the addition of benzylmagnesium chloride to di-tert-butyl ketone followed by exchange of both the benzyl and the ketone moiety with another substrate. Similar experiments were performed with phenylmagnesium bromide and tert-butylmagnesium chloride...

  7. Study of selected benzyl azides by UV photoelectron spectroscopy and mass spectrometry

    Science.gov (United States)

    Pinto, R. M.; Olariu, R. I.; Lameiras, J.; Martins, F. T.; Dias, A. A.; Langley, G. J.; Rodrigues, P.; Maycock, C. D.; Santos, J. P.; Duarte, M. F.; Fernandez, M. T.; Costa, M. L.

    2010-09-01

    Benzyl azide and the three methylbenzyl azides were synthesized and characterized by mass spectrometry (MS) and ultraviolet photoelectron spectroscopy (UVPES). The electron ionization fragmentation mechanisms for benzyl azide and their methyl derivatives were studied by accurate mass measurements and linked scans at constant B/ E. For benzyl azide, in order to clarify the fragmentation mechanism, labelling experiments were performed. From the mass analysis of methylbenzyl azides isomers it was possible to differentiate the isomers ortho, meta and para. The abundance and nature of the ions resulting from the molecular ion fragmentation, for the three distinct isomers of substituted benzyl azides, were rationalized in terms of the electronic properties of the substituent. Concerning the para-isomer, IRC calculations were performed at UHF/6-31G(d) level. The photoionization study of benzyl azide, with He(I) radiation, revealed five bands in the 8-21 eV ionization energies region. From every photoelectron spectrum of methylbenzyl azides isomers it has been identified seven bands, on the same range as the benzyl azide. Interpretation of the photoelectron spectra was accomplished applying Koopmans' theorem to the SCF orbital energies obtained at HF/6-311++G(d, p) level.

  8. [Determination of benzyl glucosinolate in Lepidium meyenii from different regions by HPLC].

    Science.gov (United States)

    Tang, Lin; Yin, Hong-jun; Si, Cong-cong; Hu, Xiao-yan; Long, Zheng-hai

    2015-12-01

    The content of benzyl isothiocyanate (BITC) which as the enzymatic hydrolysis product of benzyl glucosinolate through thioglucosidase was determined by HPLC. The content of benzyl isothiocyanate (BITC) which as the enzymatic hydrolysis product of benzyl glucosinolate through thioglucosidase was determined by HPLC. The chromatography condition was as follows: Kaseisorb LC ODS 2000 (4.6 mm x 150 mm, 5 min) column with the mobile phase of acetonitrile(A)-water( B) under gradient elution (0-5 min, 3%-8% A; 5-9 min, 8%-48% A; 9-23 min, 48%-62% A; 23-28 min, 62%-99% A); the flow rate was 1.0 mL x min(-1) with 10 microL injection volume; detection wavelength was 246 nm and temperature of column was 40 degrees C. The content of benzyl glucosinolate was in the range of 10.76-17.91 g x L(-1). The method is simple, accurate and good reproducibility which can be used for the determination of benzyl glucosinolate in Lepidium meyenii, effectively.

  9. Kinetic Studies on the Selective Oxidation of Benzyl Alcohols in Organic Medium under Phase Transfer Catalysis

    Directory of Open Access Journals (Sweden)

    K. Bijudas

    2014-07-01

    Full Text Available Kinetic studies on the oxidation of benzyl alcohol and substituted benzyl alcohols in benzene as the reaction medium have been studied by using potassium dichromate under phase transfer catalysis (PTC. The phase transfer catalysts (PT catalysts used were tetrabutylammonium bromide (TBAB and tetrabutylphosphonium bromide (TBPB.  Benzyl alcohols were selectively oxidised to corresponding benzaldehydes in good yield (above 90%.  The order of reactivity among the studied benzyl alcohols is p - OCH3 > p - CH3 > - H > p - Cl.  Plots of log k2 versus Hammett's substituent constant (s has been found to be curve shaped and this suggests that there should be a continuous change in transition state with changes in substituent present in the substrate from electron donating to electron withdrawing. A suitable mechanism has been suggested in which the rate determining step involves both C - H bond cleavage and C - O bond formations in concerted manner. © 2014 BCREC UNDIP. All rights reserved.Received: 16th March 2014; Revised: 18th May 2014; Accepted: 18th May 2014[How to Cite: Bijudas, K., Bashpa, P., Nair, T.D.R. (2014. Kinetic Studies on the Selective Oxidation of Benzyl Alcohol and Substituted Benzyl Alcohols in Organic Medium under Phase Transfer Catalysis. Bulletin of Chemical Reaction Engineering & Catalysis, 9 (2: 142-147. (doi:10.9767/bcrec.9.2.6476.142-147][Permalink/DOI: http://dx.doi.org/10.9767/bcrec.9.2.6476.142-147] 

  10. Toxicity of benzyl alcohol in adult and neonatal mice

    International Nuclear Information System (INIS)

    McCloskey, S.E.

    1987-01-01

    Benzyl alcohol (BA) is an aromatic alcohol, which is used as a bacteriostat in a variety of parenteral preparations. In 1982, it was implicated as the agent responsible for precipitating The Gasping Syndrome in premature neonates. The investigate further this toxicity, BA was administered, intraperiotoneally, to adult and neonatal CD-1 male mice. Gross behavioral changes were monitored. Low doses produced minimal toxic effects within an initial 4 hour observation period. At the end of this time, the LD 50 was determined to be 1000 mg/kg for both age groups. Death was due to respiratory arrest in all cases. Rapid absorption and conversion of BA to its primary metabolite, benzaldehyde, was demonstrated by gas chromatographic analysis of plasma from both experimental groups. The conversion of BA to benzaldehyde was confirmed in in vitro by using both horse-liver and mouse liver ADH. The inhibition of alcohol dehydrogenase (ADH) by pyrazole was similarly demonstrated in both enzyme systems. 14 C-labelled BA was utilized to determine the distribution of BA and its metabolites in the body, and to possibly pinpoint a target organ of toxicity

  11. 3 Benzyl-6-chloropyrone: a suicide inhibitor of cholesterol esterase

    International Nuclear Information System (INIS)

    Saint, C.; Gallo, I.; Kantorow, M.; Bailey, J.M.

    1986-01-01

    Cholesterol, absorbed from the intestine, appears in lymph as the ester. Cholesterol esterase is essential for this process, since depletion of the enzyme blocks and repletion restores, absorption. Selective inhibitors of cholesterol esterase may thus prove useful in reducing cholesterol uptake. A series of potential suicide substrates were synthesized which, following cleavage by the enzyme, would attack the putative nucleophile in the active site. One of these, 3-benzyl-6-chloropyrone (3BCP), inhibited both synthesis and hydrolysis of 14 C-cholesteryl oleate with an I 50 of approximately 150 μM. The inactivation was time-dependent and characteristic of a suicide mechanism. The α pyrone structure (lactone analog) is cleaved by a serine-hydroxyl in the active site. This generates an enoyl chloride which inactivates the imidazole believed to play a part in the catalytic function of the enzyme. Inhibition by 3BCP is selective for cholesterol esterase. The activity of pancreatic lipase as not affected by concentrations up to 1 mM

  12. Synthesis and Anti-HIV-1 Activity of New MKC-442 Analogues with an Alkynyl-Substituted 6-Benzyl Group

    DEFF Research Database (Denmark)

    Aly, Youssef L.; Pedersen, Erik Bjerreg.; La Colla, Paolo

    2007-01-01

    Synthesis and antiviral activities are reported of a series of 6-(3-alkynyl benzyl)-substituted analogues of MKC-442 (6-benzyl-1-(ethoxymethyl)-5-isopropyluracil), a highly potent agent against HIV. The 3-alkynyl group is assumed to give a better stacking of the substituted benzyl group to reverse...... transcriptase (RT) and this was believed to improve antiviral activity against HIV-1. The bromo derivatives, 5-alkyl-6-(3-bromo-benzyl)-1-ethoxymethyl derivatives 7a, b and 5-alkyl-6-(3-bromobenzyl)-1-allyloxymethyl derivatives 9a, b, showed activity against HIV on the same level as their corresponding...

  13. Synthesis of Cycloveratrylene Macrocycles and Benzyl Oligomers Catalysed by Bentonite under Microwave/Infrared and Solvent-Free Conditions

    Directory of Open Access Journals (Sweden)

    Manuel Salmón

    2013-10-01

    Full Text Available Tonsil Actisil FF, which is a commercial bentonitic clay, promotes the formation of cycloveratrylene macrocycles and benzyl oligomers from the corresponding benzyl alcohols in good yields under microwave heating and infrared irradiation in the absence of solvent in both cases. The catalytic reaction is sensitive to the type of substituent on the aromatic ring. Thus, when benzyl alcohol was substituted with a methylenedioxy, two methoxy or three methoxy groups, a cyclooligomerisation process was induced. Unsubstituted, methyl and methoxy benzyl alcohols yielded linear oligomers. In addition, computational chemistry calculations were performed to establish a validated mechanistic pathway to explain the growth of the obtained linear oligomers.

  14. Solubilities of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures

    International Nuclear Information System (INIS)

    Wang, Hui; Wang, Qinbo; Xiong, Zhenhua; Chen, Chuxiong; Shen, Binwei

    2015-01-01

    Highlights: • Solubilities of benzoic acid in (benzyl alcohol + benzaldehyde) mixtures were measured at 1 atm. • The experimental temperature ranges at (298.35 to 355.65) K. • Effects of benzyl alcohol mass concentration at (0.00 to 1.00) on the solubilities of benzoic acid were studied. • The experimental data were correlated with NRTL model. • Thermodynamic functions of dissolution of benzoic acid in (benzyl alcohol + benzaldehyde) mixtures were discussed. - Abstract: The solubility of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures was measured at temperature from (298.35 to 355.65) K and atmospheric pressure. The measured solubility increases with the increasing temperature at constant solvent composition. The effects of mass fraction benzaldehyde in the solvent mixtures at (0.0 to 1.00) on the solubility were studied. The measured solubility decreases with the increasing mass fraction of benzaldehyde. The experimental results were correlated with the non-random two-liquid (NRTL) equations, and good agreement between the correlated and the experimental values was obtained. Thermodynamic functions for the solution of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures were calculated with the van’t Hoff plot. The apparent dissolution Gibbs free energy change was also calculated

  15. Radiolysis of benzyl alcohol in aqueous solution by external gamma-irradiation

    International Nuclear Information System (INIS)

    Ikebuchi, Hideharu; Kido, Yasumasa; Urakubo, Goro

    1977-01-01

    Radiolysis of 0.05% aqueous solution of benzyl alcohol with 60 Co γ-rays ranging from 1 x 10 4 to 7 x 10 5 rad was investigated, in order to presume the change of it contained in radiopharmaceuticals. For both O 2 free and oxygenated solutions, an approximately linear relationship holds between the retaining benzyl alcohol and dose in the range from 1 x 10 5 to 7 x 10 5 rads. The G(-M) values of benzyl alcohol calculated from the relation were 2.34 in the absence and 1.92 in presence of oxygen. In the presence of oxygen, a main product was benzaldehyde and its G value was 0.87. In the absence of oxygen, the main products of the radiolysis were dibenzyl, benzyl phenylcalbinol and hydrobenzoin, which were regarded as the radical-reaction products of PhCH 2 and PhCHOH, and the yield of benzaldehyde was negligible. Irrespective of the presence of oxygen, o- and p-hydroxylated products of benzyl alcohol were found only in small quantity. (auth.)

  16. Formation of nanocrystalline barium titanate in benzyl alcohol at room temperature.

    Science.gov (United States)

    Veldhuis, Sjoerd A; Vijselaar, Wouter J C; Stawski, Tomasz M; ten Elshof, Johan E

    2014-12-15

    Nanocrystalline barium titanate (8-10 nm crystallite size) was prepared at temperatures of 23-78 °C through reaction of a modified titanium alkoxide precursor in benzyl alcohol with barium hydroxide octahydrate. The room temperature formation of a perovskite phase from solution is associated with the use of benzyl alcohol as solvent medium. The formation mechanism was elucidated by studying the stability and interaction of each precursor with the solvent and with each other using various experimental characterization techniques. Density functional theory (DFT) computational models which agreed well with our experimental data could explain the formation of the solid phase. The stability of the Ti precursor was enhanced by steric hindrance exerted by phenylmethoxy ligands that originated from the benzyl alcohol solvent. Electron microscopy and X-ray diffraction indicated that the crystallite sizes were independent of the reaction temperature. Crystal growth was inhibited by the stabilizing phenylmethoxy groups present on the surface of the crystallites.

  17. Synthesis, Anticancer and Antibacterial Activity of Salinomycin N-Benzyl Amides

    Directory of Open Access Journals (Sweden)

    Michał Antoszczak

    2014-11-01

    Full Text Available A series of 12 novel monosubstituted N-benzyl amides of salinomycin (SAL was synthesized for the first time and characterized by NMR and FT-IR spectroscopic methods. Molecular structures of three salinomycin derivatives in the solid state were determined using single crystal X-ray method. All compounds obtained were screened for their antiproliferative activity against various human cancer cell lines as well as against the most problematic bacteria strains such as methicillin-resistant Staphylococcus aureus (MRSA and Staphylococcus epidermidis (MRSE, and Mycobacterium tuberculosis. Novel salinomycin derivatives exhibited potent anticancer activity against drug-resistant cell lines. Additionally, two N-benzyl amides of salinomycin revealed interesting antibacterial activity. The most active were N-benzyl amides of SAL substituted at -ortho position and the least anticancer active derivatives were those substituted at the -para position.

  18. t-3-Benzyl-r-2,c-6-diphenylpiperidin-4-one oxime

    Directory of Open Access Journals (Sweden)

    R. Arulraj

    2016-12-01

    Full Text Available In the title compound, C24H24N2O [systematic name: (E-3-benzyl-2,6-diphenylpiperidin-4-one oxime], the piperidine ring adopts a slightly distorted chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The oxime group makes a dihedral angle of 42.88 (12° with the piperidine ring. The dihedral angle between the phenyl rings is 71.96 (8°. The benzyl ring makes dihedral angles of 63.01 (8 and 59.35 (8° with the two phenyl rings. In the crystal, molecules are linked by O—H...N hydrogen bonds, forming C(7 chains along the c axis. The chains are linked by C—H...π interactions, forming slabs lying parallel to the bc plane.

  19. Benzyl alcohol increases voluntary ethanol drinking in rats.

    Science.gov (United States)

    Etelälahti, T J; Eriksson, C J P

    2014-09-01

    The anabolic steroid nandrolone decanoate has been reported to increase voluntary ethanol intake in Wistar rats. In recent experiments we received opposite results, with decreased voluntary ethanol intake in both high drinking AA and low drinking Wistar rats after nandrolone treatment. The difference between the two studies was that we used pure nandrolone decanoate in oil, whereas in the previous study the nandrolone product Deca-Durabolin containing benzyl alcohol (BA) was used. The aims of the present study were to clarify whether the BA treatment could promote ethanol drinking and to assess the role of the hypothalamic-pituitary-adrenal-gonadal axes (HPAGA) in the potential BA effect. Male AA and Wistar rats received subcutaneously BA or vehicle oil for 14 days. Hereafter followed a 1-week washout and consecutively a 3-week voluntary alcohol consumption period. The median (± median absolute deviation) voluntary ethanol consumption during the drinking period was higher in BA-treated than in control rats (4.94 ± 1.31 g/kg/day vs. 4.17 ± 0.31 g/kg/day, p = 0.07 and 1.01 ± 0.26 g/kg/day vs. 0.38 ± 0.27 g/kg/day, p = 0.05, for AA and Wistar rats, respectively; combined effect p < 0.01). The present results can explain the previous discrepancy between the two nandrolone studies. No significant BA effects on basal and ethanol-mediated serum testosterone and corticosterone levels were observed in blood samples taken at days 1, 8 and 22. However, 2h after ethanol administration significantly (p = 0.02) higher frequency of testosterone elevations was detected in high drinking AA rats compared to low drinking Wistars, which supports our previous hypotheses of a role of testosterone elevation in promoting ethanol drinking. Skin irritation and dermatitis were shown exclusively in the BA-treated animals. Altogether, the present results indicate that earlier findings obtained with Deca-Durabolin containing BA need to be re-evaluated. Copyright © 2014 Elsevier Inc. All

  20. Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

    NARCIS (Netherlands)

    Vliegenthart, J.F.G.; Kerékgyártó, J.; Ágoston, K.; Batta, G.; Kamerling, J.P.

    1998-01-01

    Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in

  1. t-3-Benzyl-r-2,c-6-bis(4-methoxyphenylpiperidin-4-one

    Directory of Open Access Journals (Sweden)

    A. Thangamani

    2008-07-01

    Full Text Available In the title compound, C26H27NO3, the piperidine ring adopts a chair conformation. The two methoxyphenyl groups attached to the piperidine ring at positions 2 and 6 have equatorial orientations and make a dihedral angle of 87.33 (8°. The benzyl group at position 3 has an equatorial orientation. The phenyl ring of the benzyl group makes dihedral angles of 75.60 (9 and 73.69 (9° with the two benzene rings. Molecules are linked by intermolecular N—H...O and C—H...O hydrogen bonds and by C—H...π interactions.

  2. [Growth-regulating activity of N-benzyl- and O-benzyl-containing compounds belonging to a new group of synthetic analogues of natural auxins].

    Science.gov (United States)

    Gafurov, R G; Makhmutova, A A

    2005-01-01

    We studied the effect of benzylamine, benzyl alcohol, and their derivatives (constituting a new group of synthetic analogues of natural auxins) on rooting of leaf and stem cuttings, rhizogenesis and growth of barley plantlets and tomato seedlings, and tomato plant productivity. These compounds promoted rooting of leaf and stem bean cuttings, increased rhizogenic activity, and stimulated the development of root systems in barley and tomato seeds. The activity of the compounds studied was similar to that of standard substances (3-indoleacetic acid potassium salt and 2-naphthylacetic acid). The benzyl group attached to the oxygen or nitrogen atom was shown to be the smallest molecular structure which provided auxin activity of the compounds. Derivatives of benzyl alcohol containing the quaternary ammonium fragment possessed auxin and anti-gibberellin (retardant) properties. They were selected by chemical synthesis of low-molecular-weight bioregulators with desired properties (a combination of chemical fragments with complementary physiological activity in the molecule). Auxin and anti-gibberellin (retardant) activities produced a synergistic effect. Germination of seeds treated with these compounds was accompanied by a more significant increase in the weight and length of roots (compared to standard auxins). The rate of seedling establishment reached 100%. The development of fruits and accumulation of reserve nutrient substances were synchronized and accelerated after spraying vegetating plants with solutions of studied compounds. The synergistic effect underlay a significant increase in the amount and quality of the crop (e.g., tomatoes).

  3. Homocoupling of benzyl halides catalyzed by POCOP-nickel pincer complexes

    KAUST Repository

    Chen, Tao

    2012-08-01

    Two types of POCOP-nickel(II) pincer complexes were prepared by mixing POCOP pincer ligands and NiX 2 in toluene at reflux. The resulting nickel complexes efficiently catalyze the homocoupling reactions of benzyl halides in the presence of zinc. The coupled products were obtained in excellent to quantitative yields. © 2012 Elsevier Ltd. All rights reserved.

  4. Effect of 6-benzyl aminopurine (BAP) on meristem culture for virus ...

    African Journals Online (AJOL)

    , Granula and Cardinal for meristem culture and four 6-benzyl aminopurine levels namely 0, 1.0, 1.5, 2.0 mg/l. As a whole, twenty treatments were allotted in complete randomized design with three replications. Resulted in vitro regenerated ...

  5. Design, synthesis and biological activity of novel peptidyl benzyl ketone FVIIa inhibitors

    DEFF Research Database (Denmark)

    Storgaard, Morten; Henriksen, Signe Teuber; Zaragoza, Florencio

    2011-01-01

    Herein is described the synthesis of a novel class of peptidyl FVIIa inhibitors having a C-terminal benzyl ketone group. This class is designed to be potentially suitable as stabilization agents of liquid formulations of rFVIIa, which is a serine protease used for the treatment of hemophilia...

  6. "Decarbonization" of an imino N-heterocyclic carbene via triple benzyl migration from hafnium

    Science.gov (United States)

    An imino N-heterocyclic carbene underwent three sequential benzyl migrations upon reaction with tetrabenzylhafnium, resulting in complete removal of the carbene carbon from the ligand. The resulting eneamido-amidinato hafnium complex showed alkene polymerization activity comparable to that of a prec...

  7. Preparation and characterization of N-benzyl-N,O-succinyl chitosan ...

    African Journals Online (AJOL)

    Purpose: To investigate the solubilization of poorly water-soluble non-steroidal anti-inflammatory drugs. (NSAIDs) in N-benzyl-N,O-succinyl chitosan (BSCS) polymeric micelles. Methods: BSCS was synthesized by reductive amination and succinylation, respectively. NSAIDs; meloxicam (MX), piroxicam (PRX), ketoprofen ...

  8. Benzyl alcohol–ammonia (1:1) cluster structure investigated by ...

    Indian Academy of Sciences (India)

    Unknown

    They found a large red-shift of the OH-stretching mode of the phenol and naphthol moieties in the clusters compared to the bare molecule which reflected a strong proton affinity of the amine group in the clusters. The molecule benzyl alcohol is of particular interest as it has a vast synthetic utility, found in the natural product, ...

  9. Effects of liquid nitrogen fertilizer and Benzyl Amino Purine (BAP) on ...

    African Journals Online (AJOL)

    The effects of combined treatment of liquid nitrogen fertilizer and benzyl amino purine (BAP) was studied on mineral elements (Magnesium, Phosphorus, Potassium, Calcium, sodium, iron and Manganese) and lipid content in relation to senescence. The experimental site for this study was situated at the botanical garden of ...

  10. Study of the antibacterial and antifungal activities of synthetic benzyl bromides, ketones, and corresponding chalcone derivatives.

    Science.gov (United States)

    Shakhatreh, Muhamad Ali K; Al-Smadi, Mousa L; Khabour, Omar F; Shuaibu, Fatima A; Hussein, Emad I; Alzoubi, Karem H

    2016-01-01

    Several applications of chalcones and their derivatives encouraged researchers to increase their synthesis as an alternative for the treatment of pathogenic bacterial and fungal infections. In the present study, chalcone derivatives were synthesized through cross aldol condensation reaction between 4-( N , N -dimethylamino)benzaldehyde and multiarm aromatic ketones. The multiarm aromatic ketones were synthesized through nucleophilic substitution reaction between 4-hydroxy acetophenone and benzyl bromides. The benzyl bromides, multiarm aromatic ketones, and corresponding chalcone derivatives were evaluated for their activities against eleven clinical pathogenic Gram-positive, Gram-negative bacteria, and three pathogenic fungi by the disk diffusion method. The minimum inhibitory concentration was determined by the microbroth dilution technique. The results of the present study demonstrated that benzyl bromide derivatives have strong antibacterial and antifungal properties as compared to synthetic chalcone derivatives and ketones. Benzyl bromides (1a and 1c) showed high ester activity against Gram-positive bacteria and fungi but moderate activity against Gram-negative bacteria. Therefore, these compounds may be considered as good antibacterial and antifungal drug discovery. However, substituted ketones (2a-b) as well as chalcone derivatives (3a-c) showed no activity against all the tested strains except for ketone (2c), which showed moderate activity against Candida albicans .

  11. Polycyclic aromatic hydrocarbon (PAH) formation from benzyl radicals: a reaction kinetics study.

    Science.gov (United States)

    Sinha, Sourab; Raj, Abhijeet

    2016-03-21

    The role of resonantly stabilized radicals such as propargyl, cyclopentadienyl and benzyl in the formation of aromatic hydrocarbons such as benzene and naphthalene in the high temperature environments has been long known. In this work, the possibility of benzyl recombination to form three-ring aromatics, phenanthrene and anthracene, is explored. A reaction mechanism for it is developed, where reaction energetics are calculated using density functional theory (B3LYP functional with 6-311++G(d,p) basis set) and CBS-QB3, while temperature-dependent reaction kinetics are evaluated using transition state theory. The mechanism begins with barrierless formation of bibenzyl from two benzyl radicals with the release of 283.2 kJ mol(-1) of reaction energy. The further reactions involve H-abstraction by a H atom, H-desorption, H-migration, and ring closure to gain aromaticity. Through mechanism and rate of production analyses, the important reactions leading to phenanthrene and anthracene formation are determined. Phenanthrene is found to be the major product at high temperatures. Premixed laminar flame simulations are carried out by including the proposed reactions for phenanthrene formation from benzyl radicals and compared to experimentally observed species profiles to understand their effects on species concentrations.

  12. 1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2 ,4 ...

    Indian Academy of Sciences (India)

    Mass spectra were recorded on LCQ FINNI-. GAN MAT (ESI), NIPER, Mohali. Thin layer chro- matography (TLC) plates were coated with silica gel-G suspended in methanol–chloroform. Elemental analy- sis was carried out using Elementar vario MICRO cube. CHN analyser. 2.2 General procedure for synthesis of N-benzyl.

  13. Effect of cotton pectin content and bioscouring on alkyl-dimethyl-benzyl-ammonium chloride adsorption

    Science.gov (United States)

    Our previous research has shown both the rate and the total amount of alkyl-dimethyl-benzyl-ammonium chloride (ADBAC) exhausted from a bulk solution of ADBAC are significantly greater for greige cotton nonwovens than cotton nonwovens that have been both scoured and bleached. The presence of pectin ...

  14. Investigation of comparative efficacy of eugenol and benzyl benzoate in therapy of sheep mange

    Directory of Open Access Journals (Sweden)

    Jezdimirović Milanka

    2010-01-01

    Full Text Available The acaricide efficacy, tolerance and safety of eugenol (10 and 20 % in the treatment of sarcoptic mange in sheep have been investigated. The results were compared with those corresponding for benzyl benzoate (25 %, which was applied to sheep in the same way. The treatment was applied on sheep three times in one-week intervals. Skin scrapings were sampled seven days after each treatment, as well as twenty-eight days following the third one. The changes on the skin were quantified and the mean recovery response (MRR was calculated. The clinical efficacy was assessed according to the MRR and the number of mites in the samples. Following the first treatment 10%eugenol was not significantly less efficacious in comparison with the higher concentration. Having been applied twice 20% eugenol was significantly more efficacious when compared to the lower concentration, which remained the same seven and twenty-eight days after the third application. The efficacy of 10% eugenol in the therapy of mange was significantly higher in comparison with benzyl benzoate following one, two or three administrations. The efficacy of benzyl benzoate four weeks after the third treatment was still significantly lower in comparison with 10% eugenol. The efficacy of 20% eugenol was significantly higher in comparison with its lower concentration as well as that of benzyl benzoate, following the second, and seven and twenty-eight days after the third one. No signs of local or systemic intolerance were observed in sheep treated with either 10 or 20% eugenol, or 25 % benzyl benzoate. .

  15. Asymmetric Synthesis of Diarylmethyl Sulfones by Palladium-Catalyzed Enantioselective Benzylic Substitution: A Remarkable Effect of Water.

    Science.gov (United States)

    Najib, Atifah; Hirano, Koji; Miura, Masahiro

    2018-03-25

    A Pd/(R)-BINAP-catalyzed enantioselective benzylic sulfonation of diarylmethyl carbonates with sodium sulfinates proceeds to deliver the corresponding chiral diarylmethyl sulfones in good yields with high enantioselectivity. The reaction occurs in a dynamic kinetic asymmetric transformation (DYKAT) manner and thus provides convergent access to optically active benzylic sulfones from racemic secondary benzylic carbonates. Additionally, the addition of H 2 O is found to be critical for high enantioselectivity. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Synthesis, physical-chemical and biological properties of 7-benzyl-3-methyl-8-thioxanthine derivatives

    Directory of Open Access Journals (Sweden)

    D. H. Ivanchenko

    2017-12-01

    Full Text Available Introduction . Interest to the problem of creating new effective antimicrobial agents among xanthine derivatives does not decrease. Primarily, this is due to the increasing of microbial resistance to conventional antimicrobial agents and the emergence of their new strains. In recent years interest to the therapeutic use of antioxidants in the treatment of diseases associated with oxidative stress has increased. The aim of this work is to elaborate simple laboratory methods of 7-benzyl-3-methyl-8-thioxanthine derivatives synthesis, unspecified in scientific papers earlier, and to study their physical, chemical and biological properties. Materials and methods. The melting point has been determined with the help of an open capillary method with PTP-M device. Elemental analysis has been performed with the help of the instrument Elementar Vario L cube, NMR-spectra have been taken on a spectrometer Bruker SF-400 (operating frequency of 400 MHz, solvent DMSO, internal standard – TMS. Study of antimicrobial and antifungal activity of synthesized compounds has been performed by two-fold serial dilution method. Standard test strains have been used for the study: Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Candida albicans ATCC 885-653. Dimethylsulfoxide was used as the solvent of the compounds. Results. Under short-time heating up of the initial 7-benzyl-3-methyl-8-thioxanthine with alkyl, alkenyl, benzyl halides or heteroalkylchlorides in a water-propanol-2 mixture in the presence of an equimolar amount of sodium hydroxide leads to the formation of 8-S-substituted of 7-benzyl-3-methylxanthines. Structure of synthesized compounds was definitely proved by NMR-spectroscopy. We conducted primary screening research of antimicrobial activity of 7-benzyl-3-methyl-8-thioxanthine derivatives, which revealed moderate and weak activity in concentrations 50-100 mcg/ml. Most of the obtained compounds showed a

  17. Solid-state conformation of copolymers of ß-benzyl-L-aspartate with L-alanine, L-leucine, L-valine, γ-benzyl-L-glutamate, or ε-carbobenzoxy-L-lysine

    NARCIS (Netherlands)

    Sederel, Willem L.; Bantjes, Adriaan; Feijen, Jan; Anderson, James M.

    1980-01-01

    The solid-state conformation of copolymers of ß-benzyl-L-aspartate [L-Asp(OBzl)] with L-leucine (L-Leu), L-alanine (L-Ala), L-valine (L-Val), γ-benzyl-L-glutamate [L-Glu(OBzl)], or ε-carbobenzoxy-L-lysine (Cbz-L-Lys) has been studied by ir spectroscopy and circular dichroism (CD). The ir spectra in

  18. Electrocatalytic activity of surface adsorbed ruthenium-alizarin complexone toward the oxidation of benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

    Marques, Aldalea Lopes Brandes; Li Weihua; Marques, Edmar Pereira; Zhang Jiujun

    2004-03-01

    The surface electrochemical behavior of an adsorbed alizarin complexone (abbreviated as AC) and its surface coordination with Ru(II) were studied in aqueous solution at a pH range of 0-6. The surface complex of ruthenium with AC displays strong electrocatalytic activities toward benzyl alcohol. Based on the rotating disk electrode measurement, it is believed that the electrocatalytic oxidation of benzyl alcohol is a two-electron and two-proton process with benzaldehyde as a major product. On the other hand, ruthenium-AC surface complex has also shown catalytic activities toward electro-oxidation of several small organic molecules such as methanol, formic acid, formaldehyde, ethanol, and acetaldehyde.

  19. Spectroscopic and structural studies of a new para-iodo-N-benzyl amide of salinomycin

    Science.gov (United States)

    Antoszczak, Michał; Janczak, Jan; Rutkowski, Jacek; Brzezinski, Bogumił; Huczyński, Adam

    2017-11-01

    A new para-iodo-N-benzyl amide of salinomycin was synthesized and characterized by NMR, FT-IR, DFT, single crystal X-ray diffraction and theoretical methods. The results obtained for the crystal, in solution and in gas phase provided evidence of pseudo-cyclic structure of this compound stabilized by intramolecular hydrogen bonds. It was shown that the compound studied forms stable 1:1 complexes with monovalent (Li+, Na+, K+, Rb+ and Cs+) and divalent (Mg2+, Ca2+, Sr2+ and Ba2+) cations demonstrating that the chemical modification of salinomycin carboxyl group considerably changes the ionophoretic properties of this antibiotic. For the first time, the ESI MS fragmentations of the complex of para-iodo-N-benzyl amide of salinomycin with Na+ are also discussed in details.

  20. Crystal structure of O-benzyl-l-tyrosine N-carboxy anhydride

    Directory of Open Access Journals (Sweden)

    Aya Inada

    2017-04-01

    Full Text Available In the title compound, C17H15NO4 (alternative name; O-benzyl-l-tyrosine N-carboxy anhydride, the oxazolidine ring is planer, with an r.m.s. deviation of 0.039 Å. The benzyloxy and benzyl rings are almost coplanar, making a dihedral angle of 0.078 (10°, and are inclined to the oxazolidine ring by 59.16 (11 and 58.42 (11°, respectively. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds, forming ribbons propagating along [010]. The ribbons are linked by C—H...π interactions, forming a three-dimensional supramolecular structure. The oxazolidine rings of adjacent ribbons are arranged into a layer parallel to the ab plane. This arrangement is favourable for the polymerization of the compound in the solid state.

  1. Crystal structure of β-benzyl dl-aspartate N-carboxyanhydride

    Directory of Open Access Journals (Sweden)

    Hitoshi Kanazawa

    2017-03-01

    Full Text Available In the title racemic compound, C12H11NO5 [systematic name: benzyl 2-(2,5-dioxooxazolidin-4-ylacetate], the oxazolidine ring is planar, with an r.m.s. deviation of 0.03 Å. The benzyl ring is almost normal to the oxazolidine ring, making a dihedral angle of 80.11 (12°. In the crystal, inversion dimers are formed between the l- and d-enantiomers via pairs of N—H...O hydrogen bonds. This arrangement is favourable for the polymerization of the compound in the solid state. The dimers are linked by C—H...O hydrogen bonds, forming layers parallel to the ab plane.

  2. t-3-Benzyl-r-2,c-6-bis(4-methoxyphenylpiperidin-4-one oxime

    Directory of Open Access Journals (Sweden)

    A. Thangamani

    2008-07-01

    Full Text Available In the title molecule, C26H28N2O3, the piperidine ring adopts a chair conformation. The two methoxyphenyl groups attached to the piperidine ring at positions 2 and 6 have equatorial orientations, and make a dihedral angle of 80.72 (15°. The benzyl group at position 3 has an equatorial orientation. The oxime group at position 4 has a bisectional orientation. The ring of the benzyl group makes dihedral angles of 64.71 (16 and 84.79 (17° with the two benzene rings. Molecules are linked by intermolecular N—H...O, O—H...N and C—H...O hydrogen bonds, and C—H...π interactions. There is also a C—H...O intramolecular interaction.

  3. Bis(1-benzyl-1H-benzimidazole-κN3dichloridozinc

    Directory of Open Access Journals (Sweden)

    Rachid Bouhfid

    2014-03-01

    Full Text Available In the title compound, [ZnCl2(C14H12N22], the ZnII atom exhibits a distorted tetrahedral coordination geometry involving two chloride anions and two N-atom donors from 1-benzyl-1H-benzimidazole ligands. In both ligands, the benzyl and benzimidazole rings are nearly perpendicular [dihedral angles = 81.7 (2 and 81.5 (2°]. The two benzimidazole systems are essentially planar [maximum deviations = 0.015 (3 and 0.020 (2 Å] and form a dihedral angle of 78.09 (8°. In the crystal, centrosymmetrically related molecules are linked by pairs of C—H...Cl hydrogen bonds into chains parallel to the a axis.

  4. Bimetallic Cu-Ni nanoparticles supported on activated carbon for catalytic oxidation of benzyl alcohol

    Science.gov (United States)

    Kimi, Melody; Jaidie, Mohd Muazmil Hadi; Pang, Suh Cem

    2018-01-01

    A series of bimetallic copper-nickel (CuNix, x = 0.1, 0.2, 0.5 and 1) nanoparticles supported on activated carbon (AC) were prepared by deposition-precipitation method for the oxidation of benzyl alcohol to benzaldehyde using hydrogen peroxide as oxidising agent. Analyses by means of X-ray Diffraction (XRD) and Scanning Electron Microscopy (SEM) confirmed that Cu and Ni was successfully added on the surface of activated carbon. CuNi1/AC showed the best catalytic activity for the oxidation of benzyl alcohols to the corresponding aldehyde within a short reaction period at 80 °C. The catalytic performance is significantly enhanced by the addition of equal amount of Ni as compared to the monometallic counterpart. This result indicates the synergistic effect between Ni and Cu particles in the catalytic oxidation reaction.

  5. Quantitative Structure-Activity Relationship of Insecticidal Activity of Benzyl Ether Diamidine Derivatives

    Science.gov (United States)

    Zhai, Mengting; Chen, Yan; Li, Jing; Zhou, Jun

    2017-12-01

    The molecular electrongativity distance vector (MEDV-13) was used to describe the molecular structure of benzyl ether diamidine derivatives in this paper, Based on MEDV-13, The three-parameter (M 3, M 15, M 47) QSAR model of insecticidal activity (pIC 50) for 60 benzyl ether diamidine derivatives was constructed by leaps-and-bounds regression (LBR) . The traditional correlation coefficient (R) and the cross-validation correlation coefficient (R CV ) were 0.975 and 0.971, respectively. The robustness of the regression model was validated by Jackknife method, the correlation coefficient R were between 0.971 and 0.983. Meanwhile, the independent variables in the model were tested to be no autocorrelation. The regression results indicate that the model has good robust and predictive capabilities. The research would provide theoretical guidance for the development of new generation of anti African trypanosomiasis drugs with efficiency and low toxicity.

  6. Influence of gamma irradiation and benzyl adenine on keeping quality of custard apple fruits during storage

    International Nuclear Information System (INIS)

    Chouksey, Swati; Singh, Alpana; Thakur, Rajendra Singh; Deshmukh, Reena

    2013-01-01

    The custard apple (Annona squamosa) fruits were procured from local market, irradiated with radiation doses 0, 0.25, 0.50, 0.75, 1.00, 1.25, 1.50, 1.75 kGy and then treated with benzyl adenine (50 and 100 part per million) and stored at ambient temperature (25±5 °C, Relative Humidity 90±2%) for 12 days. The treated fruits were evaluated for sensory (viz; flavour, texture, internal and external colour) and chemical constituents (viz; Total Soluble Solids, titrable acidity, ascorbic acid, free soluble sugar, reducing sugar, non reducing sugar, carbohydrate) during storage. The study concluded that radiation dose of 1.5 kilo Gray along with 50 ppm benzyl adenine enhanced in shelf-life of custard apple fruits by 6 days at ambient temperature with good pulp texture, flavour, colour and nutritional quality as compared to control. (author)

  7. Crystal structures of HIV-1 nonnucleoside reverse transcriptase inhibitors: N-benzyl-4-methyl-benzimidazoles

    Science.gov (United States)

    Ziółkowska, Natasza E.; Michejda, Christopher J.; Bujacz, Grzegorz D.

    2009-07-01

    HIV-1 nonnucleoside reverse transcriptase inhibitors are potentially specific and effective drugs in AIDS therapy. The presence of two aromatic systems with an angled orientation in the molecule of the inhibitor is crucial for interactions with HIV-1 RT. The inhibitor drives like a wedge into the cluster of aromatic residues of RT HIV-1 and restrains the enzyme in a conformation that blocks the chemical step of nucleotide incorporation. Structural studies provide useful information for designing new, more active inhibitors. The crystal structures of four NNRTIs are presented here. The investigated compounds are derivatives of N-benzyl-4-methyl-benzimidazole with various aliphatic and aromatic substituents at carbon 2 positions and a 2,6-dihalogeno-substituted N-benzyl moiety. Structural data reported here show that the conformation of the investigated compounds is relatively rigid. Such feature is important for the nonnucleoside inhibitor binding to HIV-1 reverse transcriptase.

  8. Alkylation of pyridines at their 4-positions with styrenes plus yttrium reagent or benzyl Grignard reagents.

    Science.gov (United States)

    Mizumori, Tomoya; Hata, Takeshi; Urabe, Hirokazu

    2015-01-02

    A new regioselective alkylation of pyridines at their 4-position was achieved with styrenes in the presence of yttrium trichloride, BuLi, and diisobutylaluminium hydride (DIBAL-H) in THF. Alternatively, similar products were more simply prepared from pyridines and benzyl Grignard reagents. These reactions are not only a useful preparation of 4-substituted pyridines but are also complementary to other relevant reactions usually giving 2-substituted pyridines. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  9. Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols

    Directory of Open Access Journals (Sweden)

    Anthony Fers-Lidou

    2016-09-01

    Full Text Available The Pd-catalyzed direct alkylation of H-phosphinic acids and hypophosphorous acid with allylic/benzylic alcohols has been described previously. Here, the extension of this methodology to H-phosphinate esters is presented. The new reaction appears general, although its scope is narrower than with the acids, and its mechanism is likely different. Various alcohols are examined in their reaction with phosphinylidene compounds R1R2P(OH.

  10. 1,3-Dipolar Cycloaddition Reactions of Substituted Benzyl Azides with Acetylenic Compounds

    Directory of Open Access Journals (Sweden)

    Sultan T. Abu-Orabi

    2002-02-01

    Full Text Available We review in this article some of our work which has been published over the last fifteen years in the area of 1,3-dipolar cycloaddition reactions of substituted benzyl azides with acetylenic compounds to form the corresponding 1,2-3-triazoles. Several triazole derivatives were transformed into triazolopyridazine and triazolo-1,3,4-oxadiazole derivatives upon their reactions with hydrazine.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2014-03-01

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

  12. Synthesis, Characterization, and Nonlinear Optical Properties of P-Substituted Poly Gamma-Benzyl

    Science.gov (United States)

    Choi, Dong-Hoon

    Poly gamma-benzyl-L-glutamate (PBLG), poly gamma-p-fluorobenzyl -L-glutamate (PGLU(pFB)), poly gamma -p-nitrobenzyl-L-glutamate (PGLU(pNB)), and poly gamma-p-trifluoromethylbenzyl-L-glutamate (PGLU(pTFMB)) have been synthesized. These PBLG polymers show variations in the side chain conformations in the solid state and solution state. In the solid state, the side chain orientation was assigned to a longitudinal or transverse direction by virtue of the polarized infrared spectrum of each PBLG analogue. The characteristics of the lyotropic liquid crystalline behavior could be observed. The optical waveguiding property of these polymers facilitated measurement of the refractive index and the thickness of each polymer film. Poling the polymer films and using the simple reflection technique, the electro -optic coefficients of the PBLG analogues could be determined. The effect of the para substitution on benzyl ester as it effected the electro-optic coefficient and the relation between the dielectric properties and the electro-optic effect of each polymer were investigated. These studies were able to demonstrate which conformation of the side chain in para substituted poly gamma-benzyl -L-glutamates is a more favorable conformation for enhancing the electro-optic behavior of these polymers.

  13. Atmospheric chemistry of benzyl alcohol: kinetics and mechanism of reaction with OH radicals.

    Science.gov (United States)

    Bernard, François; Magneron, Isabelle; Eyglunent, Grégory; Daële, Véronique; Wallington, Timothy J; Hurley, Michael D; Mellouki, Abdelwahid

    2013-04-02

    The atmospheric oxidation of benzyl alcohol has been investigated using smog chambers at ICARE, FORD, and EUPHORE. The rate coefficient for reaction with OH radicals was measured and an upper limit for the reaction with ozone was established; kOH = (2.8 ± 0.4) × 10(-11) at 297 ± 3 K (averaged value including results from Harrison and Wells) and kO(3) < 2 × 10(-19) cm(3) molecule(-1) s(-1) at 299 K. The products of the OH radical initiated oxidation of benzyl alcohol in the presence of NOX were studied. Benzaldehyde, originating from H-abstraction from the -CH(2)OH group, was identified using in situ FTIR spectroscopy, HPLC-UV/FID, and GC-PID and quantified in a yield of (24 ± 5) %. Ring retaining products originating from OH-addition to the aromatic ring such as o-hydroxybenzylalcohol and o-dihydroxybenzene as well as ring-cleavage products such as glyoxal were also identified and quantified with molar yields of (22 ± 2)%, (10 ± 3)%, and (2.7 ± 0.7)%, respectively. Formaldehyde was observed with a molar yield of (27 ± 10)%. The results are discussed with respect to previous studies and the atmospheric oxidation mechanism of benzyl alcohol.

  14. Oral amoxicillin versus benzyl penicillin for severe pneumonia among kenyan children: a pragmatic randomized controlled noninferiority trial.

    Science.gov (United States)

    Agweyu, Ambrose; Gathara, David; Oliwa, Jacquie; Muinga, Naomi; Edwards, Tansy; Allen, Elizabeth; Maleche-Obimbo, Elizabeth; English, Mike

    2015-04-15

    There are concerns that the evidence from studies showing noninferiority of oral amoxicillin to benzyl penicillin for severe pneumonia may not be generalizable to high-mortality settings. An open-label, multicenter, randomized controlled noninferiority trial was conducted at 6 Kenyan hospitals. Eligible children aged 2-59 months were randomized to receive amoxicillin or benzyl penicillin and followed up for the primary outcome of treatment failure at 48 hours. A noninferiority margin of risk difference between amoxicillin and benzyl penicillin groups was prespecified at 7%. We recruited 527 children, including 302 (57.3%) with comorbidity. Treatment failure was observed in 20 of 260 (7.7%) and 21 of 261 (8.0%) of patients in the amoxicillin and benzyl penicillin arms, respectively (risk difference, -0.3% [95% confidence interval, -5.0% to 4.3%]) in per-protocol analyses. These findings were supported by the results of intention-to-treat analyses. Treatment failure by day 5 postenrollment was 11.4% and 11.0% and rising to 13.5% and 16.8% by day 14 in the amoxicillin vs benzyl penicillin groups, respectively. The most frequent cause of cumulative treatment failure at day 14 was clinical deterioration within 48 hours of enrollment (33/59 [55.9%]). Four patients died (overall mortality 0.8%) during the study, 3 of whom were allocated to the benzyl penicillin group. The presence of wheeze was independently associated with less frequent treatment failure. Our findings confirm noninferiority of amoxicillin to benzyl penicillin, provide estimates of risk of treatment failure in Kenya, and offer important additional evidence for policy making in sub-Saharan Africa. NCT01399723. © The Author 2014. Published by Oxford University Press on behalf of the Infectious Diseases Society of America.

  15. Synthesis and antimicrobial activities of 1-(3-benzyl-4-oxo-3H-quinazolin-2-yl-4-(substitutedthiosemicarbazide derivatives

    Directory of Open Access Journals (Sweden)

    Alagarsamy Veerachamy

    2015-01-01

    Full Text Available A series of 1-(3-benzyl-4-oxo-3H-quinazolin-2-yl-4-(substituted thiosemicarbazides (AS1-AS10 were obtained by the reaction of 2-hydrazino- 3-benzyl quinazolin-4(3H-one (6 with different dithiocarbamic acid methyl ester derivatives. The key intermediate 3-benzyl-2-thioxo-2,3-dihydro-1Hquinazolin-4-one (4 was obtained by reacting benzyl amine (1 with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulfate to yield the dithiocarbamic acid methyl ester (2 and condensed with methyl anthranilate (3 in ethanol yielded the desired compound (4 via the thiourea intermediate. The SH group of compound (4 was methylated for the favorable nucleophilic displacement reaction with hydrazine hydrate, which afford 2-hydrazino-3- benzyl-3H-quinazolin-4-one (6. The IR, 1H, and 13C NMR spectrum of these compounds showed the presence of peaks due to thiosemicarbazides, carbonyl (C=O, NH and aryl groups. The quinazolin-4-one moiety molecular ion peaks (m/z 144 were observed all the mass spectrum of compounds (AS1-AS10. Elemental (C, H, N analysis satisfactorily confirmed purity of the synthesized compounds and elemental composition. All synthesized compounds were also screened for their antimicrobial activity against selective gram positive and gram negative by agar dilution method. In the present study compounds AS8 and AS9 were emerged as the most active compounds of the series.

  16. Comparison of Simulated Drift Rates of Common ALS-Inhibiting Rice Herbicides to Florpyrauxifen-Benzyl on Soybean

    Directory of Open Access Journals (Sweden)

    Lauren M. Schwartz-Lazaro

    2017-01-01

    Full Text Available Acetolactate synthase- (ALS- herbicides are among the most commonly used sites of action (SOA in rice production. Many herbicides used in rice can cause carryover to soybean, which is commonly grown near to or rotated with rice. Florpyrauxifen-benzyl (Rinskor™ Active brings an alternative SOA to rice production. The objective of this study was to compare the effects of simulated drift rates of florpyrauxifen-benzyl to commonly used ALS-inhibiting rice herbicides on soybean. A field study was conducted at two locations examining five ALS-inhibiting rice herbicides as well as florpyrauxifen-benzyl at a 1/20x and 1/80x simulated drift rate. Crop injury, height, and yield were evaluated at 14, 21, and 35 days after treatment (DAT. Florpyrauxifen-benzyl and bispyribac showed high injury levels at both drift rates. At 35 DAT florpyrauxifen-benzyl caused 76% and 17% visible damage to soybean whereas bispyribac caused 35 and 9% injury at 1/20x and 1/80x, respectively. These treatments resulted in a reduction in soybean height and yield. Although this alternative SOA herbicide in rice may be effective for weed control, our research demonstrates it to be injurious to soybean at both drift rates tested. Thus, proper precautions should be taken to avoid injury by ensuring that the label is followed.

  17. Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols

    KAUST Repository

    Veenboer, Richard M. P.

    2015-01-01

    © The Royal Society of Chemistry 2015. We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(i) complexes (NHC = N-heterocyclic carbene). Our progress in developing this reaction into a straightforward procedure is discussed in detail. The optimised methodology proceeds under mild reaction conditions and produces water as the sole by-product. The synthetic utility of this environmentally benign methodology is exemplified by the formation of a range of new ethers from readily available phenols bearing electron withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, we present experimental results to account for the chemoselectivity obtained in these reactions.

  18. Structure and properties of poly(benzyl acrylate) synthesized under microwave energy

    Energy Technology Data Exchange (ETDEWEB)

    Oberti, Tamara G. [Instituto de Investigaciones Fisicoquimicas Teoricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Universidad Nacional de La Plata-CONICET Casilla de Correo 16, Sucursal 4, 1900 La Plata (Argentina); Laboratorio de Estudio de Compuestos Organicos (LADECOR), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 1900 La Plata (Argentina); Schiavoni, M. Mercedes [Laboratorio de Estudio de Compuestos Organicos (LADECOR), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 1900 La Plata (Argentina); Cortizo, M. Susana [Instituto de Investigaciones Fisicoquimicas Teoricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Universidad Nacional de La Plata-CONICET Casilla de Correo 16, Sucursal 4, 1900 La Plata (Argentina)], E-mail: gcortizo@inifta.unlp.edu.ar

    2008-05-15

    Benzyl acrylate was polymerized under microwave irradiation using radical initiation (benzoyl peroxide, BP). The effect of the concentration of BP and power irradiation on the conversion, average molecular weights and the polydispersity index (M{sub w}/M{sub n}) were investigated. The {sup 1}H NMR and {sup 13}C NMR spectra analysis showed tendency to syndiotacticity and branched polymers were obtained at high conversion of reactions. A significant enhancement of the rates of polymerization and similar thermodynamic behavior, as compared with those obtained under thermal conditions was found.

  19. Pseudo-four component synthesis of mono- and di-benzylated-1,2,3-triazoles derived from aniline.

    Science.gov (United States)

    Mendoza-Espinosa, Daniel; Negron-Silva, Guillermo E; Lomas-Romero, Leticia; Gutierrez-Carrillo, Atilano; Santillán, Rosa

    2013-12-20

    The pseudo-four component click synthesis of dibenzylated 1,2,3-triazoles derived from aniline is reported. The cycloaddition of sodium azide to N-(prop-2-ynyl)-benzenamine (I) in the presence of equimolar amounts of p-substituted benzyl derivatives, yields a mixture of mono- and dibenzylated 1,2,3-triazoles. When two equivalents of the benzyl derivative are added to the multicomponent reaction, the selective preparation of the dibenzylated compounds is achieved. The reactivity of the aniline N-H bond in monobenzylated 1,2,3-triazoles was tested by treatment with one equivalent of a p-substituted benzyl chloride at 40 °C, rendering the dibenzylated derivatives quantitatively.

  20. Metal-free oxidative olefination of primary amines with benzylic C-H bonds through direct deamination and C-H bond activation.

    Science.gov (United States)

    Gong, Liang; Xing, Li-Juan; Xu, Tong; Zhu, Xue-Ping; Zhou, Wen; Kang, Ning; Wang, Bin

    2014-09-14

    An oxidative olefination reaction between aliphatic primary amines and benzylic sp(3) C-H bonds has been achieved using N-bromosuccinimide as catalyst and tert-butyl hydroperoxide as oxidant. The olefination proceeds under mild metal-free conditions through direct deamination and benzylic C-H bond activation, and provides easy access to biologically active 2-styrylquinolines with (E)-configuration.

  1. Modeling, Simulation, and Kinetic Studies of Solvent-Free Biosynthesis of Benzyl Acetate

    Directory of Open Access Journals (Sweden)

    Vijay Kumar Garlapati

    2013-01-01

    Full Text Available Solvent-free biosynthesis of benzyl acetate through immobilized lipase-mediated transesterification has been modeled and optimized through statistical integrated artificial intelligence approach. A nonlinear response surface model has been successfully developed based on central composite design with transesterification variables, namely, molarity of alcohol, reaction time, temperature, and immobilized lipase amount as input variables and molar conversion (% as an output variable. Statistical integrated genetic algorithm optimization approach results in an optimized molar conversion of 96.32% with the predicted transesterification variables of 0.47 M alcohol molarity in a reaction time of 13.1 h, at 37.5°C using 13.31 U of immobilized lipase. Immobilized lipase withstands more than 98% relative activity up to 6 recycles and maintains 50% relative activity until 12 recycles. The kinetic constants of benzyl acetate, namely, Km and Vmax were found to be 310 mM and 0.10 mmol h−1 g−1, respectively.

  2. Rate constants for some electrophilic reactions of benzyl, benzhydryl, and trityl cations in solution

    International Nuclear Information System (INIS)

    Ujdak, R.J.; Jones, R.L.; Dorfman, L.M.

    1976-01-01

    Absolute rate constants have been determined by the pulse radiolysis technique for several electrophilic reactions of the benzyl, the benzhydryl, and the trityl cation in 1,2-dichloroethane solution. The rate constants for the reactions of these carbonium ions with chloride ion, with bromide ion, and with iodide ion are all very nearly the same, namely 6 x 10 10 M -1 s -1 at 24 0 C. The values very likely represent the diffusion controlled limit for the ion combination reactions. The rate constants for the reactions with triethylamine, tri-n-propylamine, and tri-n-butylamine range from 2.0 x 10 9 to 7 x 10 6 M -1 s -1 at 24 0 C. With increasing phenyl substitution, the decreasing trend in the magnitude of the rate constant is consistent with the combined electronic and steric effects. With increasing size of the amine, the decrease in the value of the rate constant seems to indicate that the steric effect predominates. The values of the rate constants for reactions of benzyl and benzhydryl cation with methanol, ethanol, and 2-propanol indicate the following. The rate constant is higher for reaction with the alcohol dimer in solution than with alcohol monomer. The rate constants for reaction with alcohol monomer have values of 1 x 10 8 M -1 s -1 or lower

  3. Antioxidant activity of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate, from Petiveria alliacea L.

    Science.gov (United States)

    Okada, Youji; Tanaka, Kaoru; Sato, Eisuke; Okajima, Haruo

    2008-03-21

    The antioxidant effects of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate (BPT), against the oxidation of cumene and methyl linoleate (ML) in chlorobenzene were studied in detail using HPLC. The results showed that BPT provided effective inhibition with a well-defined induction period under these oxidation conditions, and it was found that the stoichiometric factor (n), the number of peroxyl radicals trapped by one antioxidant molecule, of BPT is about 2. We then undertook a thorough investigation aimed at elucidating the active structural site of BPT. Various model compounds, such as diphenyl disulfide, dibenzyl disulfide, S-phenyl benzenethiosulfinate and S-ethyl phenylmethanethiosulfinate, were used which provided evidence that the benzylic hydrogen of BPT is mainly associated with the peroxyl radical scavenging. Moreover, we measured the rate constant for the reaction of BPT with peroxyl radicals derived from cumene and ML in chlorobenzene, and based on these measurements, BPT reacts with these peroxyl radicals with a rate constant of k(inh) = 8.6 x 10(3) and 6.2 x 10(4) M(-1) s(-1), respectively.

  4. Developmental and testicular toxicity of butyl benzyl phthalate in the rat and the impact of study design

    NARCIS (Netherlands)

    Piersma AH; Verhoef A; Dormans JAMA; Elvers LH; Valk V de; Biesebeek JD te; Pieters MN; Slob W; LEO

    1999-01-01

    The developmental toxicity of butyl benzyl phthalate was investigated in the rat in an alternative study design using ten treatment groups. The effect of exposure period was studied, and a comparison of reaction to treatment in pregnant versus non-pregnant females was made. The classical data

  5. Sulfonamides as new hydrogen atom transfer (HAT) catalysts for photoredox allylic and benzylic C-H arylations.

    Science.gov (United States)

    Tanaka, Hirotaka; Sakai, Kentaro; Kawamura, Atsushi; Oisaki, Kounosuke; Kanai, Motomu

    2018-02-02

    A catalytic amount of a sterically and electronically tuned diarylsulfonamide promoted allylic and benzylic C-H arylations in cooperation with a visible light photoredox catalyst. This is the first example of the catalytic use of a sulfonamidyl radical to promote the hydrogen atom transfer process.

  6. 1-[(1-Benzyl-1H-1,2,3-triazol-4-ylmethyl]-1H-1,3-benzodiazole

    Directory of Open Access Journals (Sweden)

    Azzeddine Sahbi

    2017-06-01

    Full Text Available The title molecule, C17H15N5, adopts a Z-shaped conformation, with the benzyl and benzodiazole substituents disposed on opposite sides of the plane of the triazole ring. A three-dimensional network is generated in the crystal by a combination of C—H...N hydrogen bonds and C—H...π(ring interactions.

  7. Nuclear magnetic resonance of D(-)-{alpha}-amino-benzyl penicillin; Ressonancia magnetica nuclear da D(-)-{alpha}-amino-benzil penicilina

    Energy Technology Data Exchange (ETDEWEB)

    Aguiar, Monica R.M.P.; Gemal, Andre L.; San Gil, Rosane A.S. [Universidade Federal, Rio de Janeiro, RJ (Brazil). Inst. de Quimica; Menezes, Sonia M.C. [PETROBRAS, Rio de Janeiro, RJ (Brazil). Centro de Pesquisas

    1995-12-31

    The development of new drugs from penicillins has induced the study of this substances by nuclear magnetic resonance. Several samples of D(-)-{alpha}-amino-benzyl penicillin were analysed using {sup 13} C NMR techniques in aqueous solution and solid state. Spectral data of this compounds were shown and the results were presented and analysed 7 figs., 4 tabs.

  8. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists

    DEFF Research Database (Denmark)

    Hansen, Martin; Phonekeo, Karina; Paine, James S

    2014-01-01

    N-benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a se...

  9. 1,3-dipolar cyclo addition of benzyl aside to alpha-beta-unsaturated five-membered lactones

    Energy Technology Data Exchange (ETDEWEB)

    Alonso-Perarnau, D.; March, P. de; Figueredo, M.; Font, J. [Departamento de Quimica, Universidad Autonoma de Barcelona, Barcelona (Spain)

    1994-12-31

    The 1,3-dipolar cyclo addition reactions between benzyl azide and the alpha,beta-unsaturated lactones crotonolactone, alpha-methylenebutyrolactone and Beta-angelica lactone have been performed. The best yields of cycloadducts were obtained by working without solvent, at 60 degree centigree in a sealed tube under nitrogen atmosphere. (3aRS,6aSR)-1-Benzyl-3 a, 4,6,6a-tetrahydro-1H-furo[3,4-d]-1,2,3-triazol-4-one and 3-benzyl-7-oxa-1,2,3-triazaspiro[4.4] non-1-en-6-one have been isolated in 36% and 78% yield from the reactions of the two first lactones respectively. The second product is the first example of this heterocyclic system. The reaction with Beta-angelica lactone yielded the primary cycloadducts (3aR,S,6RS,6aSR)-and (3aRS,6SR,6aSR)-1-benzyl-3a,4,6,6a-tetrahydro-6-methyl-1H-furo[3,4-d]-1,1,3-triazol-4-one and the nitrogen elimination product 4-benzylamino-5-methyl 1-2(5H)-furanone in 44%, 11%, and 7% yield respectively. 26 refs.

  10. 3-Benzyl-3-hydroxy-2-phenyl-3H-indole 1-oxide

    Directory of Open Access Journals (Sweden)

    Corrado Rizzoli

    2010-08-01

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

  11. Neuroprotective benzyl benzoate glycosides from Disporum viridescens roots in HT22 hippocampal neuronal cells.

    Science.gov (United States)

    Cho, Namki; Yang, Heejung; Lee, Mina; Huh, Jungmoo; Kim, Hyeon-Woo; Kim, Hong-Pyo; Sung, Sang-Hyun

    2013-12-27

    Bioassay-guided fractionation of the EtOAc extract from Disporum viridescens roots led to the isolation of five new benzyl benzoate glycosides, BBGs (1-5). The neuroprotective activities of the BBGs were screened using neuronal HT22 hippocampal cells. BBG-D (4) significantly protected murine hippocampal HT22 cells against glutamate-induced neurotoxicity by maintaining the antioxidative defense systems such as superoxide dismutase, glutathione reductase, glutathione peroxidase, and the glutathione content. BBG-D, in a dose-and time-dependent manner, increased HO-1 expression through the selective activation of pERK signaling among the MAPK pathways. These results suggest that BBG-D could be a promising candidate for the treatment of neurodegenerative diseases related to glutamate-induced oxidative neuronal cytotoxicity.

  12. 17O NMR parameters of some substituted benzyl ethers components: Ab initio study

    Directory of Open Access Journals (Sweden)

    Mahdi Rezaei Sameti

    2016-09-01

    Full Text Available The 17O NMR chemical shielding tensors and chemical shift for a set of substituted benzyl ethers derivatives containing (methyl, ethyl, isopropyl, t-butyl, brome and lithium have been calculated. The molecular structures were fully optimized using B3LYP/6-31G(d,p. The calculation of the 17O shielding tensors employed the GAUSSIAN 98 implementation of the gauge-including atomic orbital (GIAO and continuous set of gauge transformations (CSGT by using 6-31G (d,p, 6-31++G(d,p and 6-311++G(d,p basis set methods at density functional levels of theories (DFT. The values determined using the GIAO and CSGT were found to give a good agreement with the experimental chemical shielding.

  13. 3,3'-Diaryl-BINOL phosphoric acids as enantioselective extractants of benzylic primary amines.

    Science.gov (United States)

    Verkuijl, Bastiaan J V; de Vries, Johannes G; Feringa, Ben L

    2011-01-01

    We report that 3,3'-diaryl-BINOL phosphoric acids are effective enantioselective extractants in chiral separation methods based on reactive liquid-liquid extraction. These new extractants are capable of separating racemic benzylic primary amine substrates. The effect of the nature of the substituents at the 3,3'-positions of the host were examined as well as the structure of the substrate, together with important parameters such as the organic solvent, the pH of the aqueous phase, and the host stoichiometry. Titration of the substrate with the host was monitored by FTIR, NMR, UV-Vis, and CD spectroscopy, which provided insight into the structure of the host-guest complex involved in extraction. Copyright © 2010 Wiley-Liss, Inc.

  14. Biologically active diorganotin(IV complexes of N-(2-hydroxy-3-isopropyl-6-methyl benzyl glycine

    Directory of Open Access Journals (Sweden)

    Robina Aman

    2015-09-01

    Full Text Available A new series of diorganotin(IV complexes of general formula [Ph2Sn(OPri(Hhbgl] (1, [Ph2Sn(Hhbgl2] (2, [Bu2Sn(OPri(Hhbgl] (3, [Bu2Sn(Hhbgl2] (4, [Me2Sn(OPri(Hhbgl] (5, and [Me2Sn(Hhbgl2] (6 [where H2hbgl = N-(2-hydroxy-3-isopropyl-6-methyl benzyl glycine] were synthesized by reacting diorganotin(IV chloride with the ligand, with the aid of sodium iso-propoxide in appropriate stoichiometric ratios (1:1 and 1:2. All the six complexes were tested in vitro for their antibacterial activity against Gram-positive bacteria namely, Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121 and two Gram-negative bacteria namely, Escherichia coli MTCC 1652 and Pseudomonas aeruginosa MTCC 741 and in vitro antifungal activity against three pathogenic fungal strains namely, Aspergillus niger, Aspergillus flavus and Penicillium sp.

  15. Tuning the Synthesis of Manganese Oxides Nanoparticles for Efficient Oxidation of Benzyl Alcohol

    Science.gov (United States)

    Fei, Jingyuan; Sun, Lixian; Zhou, Cuifeng; Ling, Huajuan; Yan, Feng; Zhong, Xia; Lu, Yuxiang; Shi, Jeffrey; Huang, Jun; Liu, Zongwen

    2017-01-01

    The liquid phase oxidation of benzyl alcohol is an important reaction for generating benzaldehyde and benzoic acid that are largely required in the perfumery and pharmaceutical industries. The current production systems suffer from either low conversion or over oxidation. From the viewpoint of economy efficiency and environmental demand, we are aiming to develop new high-performance and cost-effective catalysts based on manganese oxides that can allow the green aerobic oxidation of benzyl alcohol under mild conditions. It was found that the composition of the precursors has significant influence on the structure formation and surface property of the manganese oxide nanoparticles. In addition, the crystallinity of the resulting manganese nanoparticles was gradually improved upon increasing the calcination temperature; however, the specific surface area decreased obviously due to pore structure damage at higher calcination temperature. The sample calcined at the optimal temperature of 600 °C from the precursors without porogen was a Mn3O4-rich material with a small amount of Mn2O3, which could generate a significant amount of {O}_2- species on the surface that contributed to the high catalytic activity in the oxidation. Adding porogen with precursors during the synthesis, the obtained catalysts were mainly Mn2O3 crystalline, which showed relatively low activity in the oxidation. All prepared samples showed high selectivity for benzaldehyde and benzoic acid. The obtained catalysts are comparable to the commercial OMS-2 catalyst. The synthesis-structure-catalysis interaction has been addressed, which will help for the design of new high-performance selective oxidation catalysts.

  16. Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

    DEFF Research Database (Denmark)

    Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane

    2015-01-01

    N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine......-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines....

  17. ynthesis and Characterization of 1-Aryl-5-hepta-O-acetyl-β-D-maltosyl-2-S-benzyl-2,4-isodithiobiurets

    Directory of Open Access Journals (Sweden)

    R. D. Ghuge

    2012-01-01

    Full Text Available The facile synthesis of 1-aryl-5-hepta-o-acetyl-β-D-maltosyl-2-S-benzyl-2,4-isodithiobiurets (IIIa-g has been achieved by the interaction of 1-hepta-O-acetyl-β–D-maltosyl isothiocyanate (I with various1-aryl-S-benzyl isothiocarbamides (IIa-g. All the newly synthesized N-maltosylated compounds characterized by elemental analysis, IR, NMR and Mass spectral studies.

  18. Dimerization of the Benzyl Radical in a High-Temperature Pyrolysis Reactor, investigated by IR/UV ion dip spectroscopy.

    Science.gov (United States)

    Hirsch, Florian; Constantinidis, Philipp; Fischer, Ingo; Bakels, Sjors; Rijs, Anouk

    2018-03-12

    We investigate the self-reaction of benzyl, C7H7 in a high tempera-ture pyrolysis reactor. The work is motivated by the observation that resonance-stabilized benzyl radicals can accumulate in reactive environments and contribute to the formation of polycyclic aromatic hydrocarbons (PAH) and soot. Reaction products are detected by IR/UV ion dip spectroscopy, using infrared radiation from the free electron laser FELIX, and are identified by comparison with com-puted spectra. Among the reaction products identified by their IR absorption are several PAH linked to toluene combustion such as bibenzyl, phenanthrene, diphenylmethane and fluorene. The identi-fication of 9,10-dihydrophenanthrene provides evidence for a mechanism of phenanthrene formation from bibenzyl that proceeds via initial cyclization rather than an initial hydrogen loss to stilbene. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Molecular origin of the selectivity differences between palladium and gold-palladium in benzyl alcohol oxidation: Different oxygen adsorption properties

    Energy Technology Data Exchange (ETDEWEB)

    Savara, Aditya Ashi [Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Chan-Thaw, Carine E. [Univ. degli Studi di Milano, Milano (Italy); Sutton, Jonathan E. [Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Wang, Di [Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen (Germany); Prati, Laura [Univ. degli Studi di Milano, Milano (Italy); Villa, Alberto [Univ. degli Studi di Milano, Milano (Italy)

    2016-12-22

    The same mechanism and microkinetic model used for benzyl alcohol oxidation over Pd/C was shown to apply to benzyl alcohol oxidation over AuPd/C. Almost all of the selectivity differences could be explained by a decrease in oxygen adsorption on AuPd. After isolating oxygen adsorption as being the origin of the selectivity differences, density functional theory was used to investigate the oxygen adsorption properties of a pure Pd surface, a pure Au surface, and an alloyed AuPd surface. Finally, the calculations showed that Au–Pd alloying decreased the oxygen adsorption properties relative to pure Pd, which explained the selectivity differences, consistent with the microkinetic modeling.

  20. Study of the Chemical Mechanism Involved in the Formation of Tungstite in Benzyl Alcohol by the Advanced QEXAFS Technique

    DEFF Research Database (Denmark)

    Olliges‐Stadler, Inga; Stötzel, Jan; Koziej, Dorota

    2012-01-01

    Insight into the complex chemical mechanism for the formation of tungstite nanoparticles obtained by the reaction of tungsten hexachloride with benzyl alcohol is presented herein. The organic and inorganic species involved in the formation of the nanoparticles were studied by time‐dependent gas...... chromatography and X‐ray diffraction as well as by time‐resolved in situ X‐ray absorption near‐edge structure and extended X‐ray absorption fine structure spectroscopy. Principal component analysis revealed two intermediates, which were identified as WCl4 and WOCl4 by using linear combination analysis. Quick...... of the tungsten hexachloride in benzyl alcohol followed by the generation of intermediates with WO double bonds and finally the construction of the WOW network of the tungstite structure....

  1. Esterification of Benzyl Alcohol with Acetic Acid over Mesoporous H-ZSM-5

    Directory of Open Access Journals (Sweden)

    Desy Tri Kusumaningtyas

    2017-05-01

    Full Text Available In this study, the performance of mesoporous ZSM-5 has been studied on the esterification of acetic acid (AA with benzyl alcohol (BA. The mesoporous ZSM-5 catalyst has been synthesized with the variation of aging time i.e. 6, 12, and 24 hours at the same temperature, 70 °C. The cation exchange of Na-ZSM-5 to H-ZSM-5 was performed before the catalytic activity test. The acidity type and amount of solids were determined by FT-IR spectroscopy using pyridine as a probe molecule. The characterization by pyridine adsorption showed that at a higher mesoporous surface area, the number of Lewis acid was increased. The highest mesoporous surface area, Lewis, and Brönsted acid sites were obtained by sample which has the lowest crystallinity, i.e. 255.78 m2/g, 0.2732 mmol/g, and 0.20612 mmol/g, respectively. Influence of mesoporous volume was studied on the catalytic activity of the mesoporous ZSM-5 in the esterification reaction. Conversion of acetic acid in the esterification reaction for samples of    HZ-6, HZ-12, and HZ-24 were obtained by titration methods, i.e. 39.59, 36.39, and 32.90 %, respectively. Hence, the reaction temperature of 393 K, molar ratio 1:4 (AA:BA and catalyst loading 5 % were selected as an optimum reaction parameters. Copyright © 2017 BCREC Group. All rights reserved Received: 21st November 2016; Revised: 1st February 2017; Accepted: 18th February 2017 How to Cite: Kusumaningtyas, D.T., Prasetyoko, D., Suprapto, Triwahyono, S., Jalil, A.A., Rosidah, A. (2017. Esterification of Benzyl Alcohol with Acetic Acid over Mesoporous H-ZSM-5. Bulletin of Chemical Reaction Engineering & Catalysis, 12 (2: 243-250 (doi:10.9767/bcrec.12.2.806.243-250 Permalink/DOI: http://dx.doi.org/10.9767/bcrec.12.2.806.243-250

  2. Transition metal-free generation of N-unsubstituted imines from benzyl azides: synthesis of N-unsubstituted homoallylic amines.

    Science.gov (United States)

    Pramanik, Suman; Reddy, Reddy Rajasekhar; Ghorai, Prasanta

    2015-04-03

    An efficient transition metal-free approach for the generation of N-unsubstituted imines from azides followed by trapping with allyl nucleophile to provide N-unsubstituted homoallylic amines has been described. Although catalytic KO(t)Bu in DMSO is sufficient to allow imine generation, stoichiometric KO(t)Bu is essential in THF. Further, an enantio- and diastereoselective synthesis of homoallylic amines from benzyl azide has also been exemplified.

  3. Physico-chemical properties and degradability of non-woven hyaluronan benzylic esters as tissue engineering scaffolds.

    Science.gov (United States)

    Milella, E; Brescia, E; Massaro, C; Ramires, P A; Miglietta, M R; Fiori, V; Aversa, P

    2002-02-01

    The development of biocompatible materials which can be processed into three-dimensional scaffolds and the design of appropriate configurations in order to enable the cellular infiltration and proliferation is a major issue in the tissue engineering. The hyaluronan total benzyl ester (Hyaff 11) has been found to be suitable substrate to grow a variety of cell types. Since structural, physical, chemical and biological data can help for tailoring appropriate scaffold for tissue engineering, information on chemicophysical properties on degradability of hyaluronan total benzyl ester non-woven has been obtained. The thermal analysis, the evaluation of the surface chemical composition, the morphology, the mechanical behaviour and the swelling tests were carried out on these materials. The hyaluronan total benzyl ester non-woven showed a thermal stability up to 220 degrees C and the surface composition differed from that of the bulk for C-O and C-C contribution. No contaminant were detected. The non-woven swelled in culture medium. Moreover the mechanical tests showed that when submitted to a press treatment, the samples have best mechanical properties. The pressed Hyaff 11 non-woven undergoes degradation when exposed to DMEM. The frying and breaking of the fibres, a decrease of the mechanical properties and a molecular weight loss have been observed. First, the ester bond of the Hyaff 11 non-woven is hydrolysed and the benzylic alcohol is released and the low molecular weight values indicate that a cleavage of the polymer is promoted by the components of the culture medium. After 11 days, some fragments, constituted by hyaluronic acid with a molecular weight of 23,000 Da became soluble in the medium. No oligomer was detected.

  4. Gold & silver nanoparticles supported on manganese oxide: Synthesis, characterization and catalytic studies for selective oxidation of benzyl alcohol

    OpenAIRE

    Alabbad, Saad; Adil, S.F.; Assal, M.E.; Khan, Mujeeb; Alwarthan, Abdulrahman; Siddiqui, M. Rafiq H.

    2014-01-01

    Nano-gold and silver particles supported on manganese oxide were synthesized by the co-precipitation method. The catalytic properties of these materials were investigated for the oxidation of benzyl alcohol using molecular oxygen as a source of oxygen. The catalyst was calcined at 300, 400 and 500 °C. They were characterized by electron microscopy, powder X-ray diffraction (XRD) and surface area. It was observed that the calcination temperature affects the size of the nanoparticle, which play...

  5. Effects of molecule stabilization energies on radical reactions: G3 and G3(MP2) model chemistries applied to benzylic systems.

    Science.gov (United States)

    Rogers, Donald W; Zavitsas, Andreas A; Matsunaga, Nikita

    2009-11-05

    We have carried out G3 and G3(MP2) calculations of the molecule stabilization energies (MSEs) brought about by 11 common substituent groups in the meta and para positions of benzyl fluoride. We find that MSE is a function of the tendency of the substituent to donate or to withdraw electrons, such that a classic Hammett plot can be drawn. We propose that, in general, the direction of the benzylic Z-X dipole of YC6H4ZX is the major factor controlling the sign of the slope of Hammett plots of benzylic atom abstractions by radicals. When the Z-X dipole is pointed away from the substituted ring, electron withdrawing substituents destabilize the molecule, contributing to a decrease of the Z-X bond dissociation energy, and electron donating substituents stabilize it. The reverse is true when the dipole is reversed. This proposal is supported by 13C NMR results and by a survey of relevant benzylic and quasi-benzylic hydrogen or halogen atom abstractions studied experimentally. Calculations at the G3 level of theory demonstrate an increase in the bond dissociation energy of p-YC6H4CH2-H with increasing electron withdrawing ability of Y, contrary to results of previous lower level calculations. MSE values of substituted benzyl fluorides (p-YC6H4CH2F) correlate well with allylic MSE (trans-YCH=CHCH2F) and quantify the relative efficacy of transmission of electronic effects by vinylogy.

  6. Optimization of Microencapsulation Composition of Menthol, Vanillin, and Benzyl Acetate inside Polyvinyl Alcohol with Coacervation Method for Application in Perfumery

    Science.gov (United States)

    Sahlan, Muhamad; Raihani Rahman, Mohammad

    2017-07-01

    One of many applications of essential oils is as fragrance in perfumery. Menthol, benzyl acetate, and vanillin, each represents olfactive characteristic of peppermint leaves, jasmine flowers, and vanilla beans, are commonly used in perfumery. These components are highly volatile, hence the fragrance components will quickly evaporate resulting in short-lasting scent and low shelf life. In this research, said components have been successfully encapsulated simultaneously inside Polyvinyl Alcohol (PVA) using simple coacervation method to increase its shelf life. Optimization has been done using Central Composite Diagram with 4 independent variables, i.e. composition of menthol, benzyl acetate, vanillin, and tergitol 15-S-9 (as emulsifier). Encapsulation efficiency, loading capacity, and microcapsule size have been measured. In optimized composition of menthol (13.98 %w/w), benzyl acetate (14.75 %w/w), vanillin (17.84 %w/w), and tergitol 15-S-9 (13.4 %w/w) encapsulation efficiency of 97,34% and loading capacity of 46,46% have been achieved. Mean diameter of microcapsule is 20,24 μm and within range of 2,011-36,24 μm. Final product was achieved in the form of cross linked polyvinyl alcohol with hydrogel consistency and orange to yellow in color.

  7. Cationic Poly(benzyl ether)s as Self-Immolative Antimicrobial Polymers.

    Science.gov (United States)

    Ergene, Cansu; Palermo, Edmund F

    2017-10-09

    Self-immolative polymers (SIMPs) are macromolecules that spontaneously undergo depolymerization into small molecules when triggered by specific external stimuli. We report here the first examples of antimicrobial SIMPs with potent, rapid, and broad-spectrum bactericidal activity. Their antibacterial and hemolytic activities were examined as a function of cationic functionality. Polymers bearing primary ammonium cationic groups showed more potent bactericidal activity against Escherichia coli, relative to tertiary and quaternary ammonium counterparts, whereas the quaternary ammonium polymers showed the lowest hemolytic toxicity. These antibacterial polycations undergo end-to-end depolymerization when triggered by an externally applied stimulus. Specifically, poly(benzyl ether)s end-capped with a silyl ether group and bearing pendant allyl side chains were converted to polycations by photoinitiated thiol-ene radical addition using cysteamine HCl. The intact polycations are stable in solution, but they spontaneously unzip into their component monomers upon exposure to fluoride ions, with excellent sensitivity and selectivity. Upon triggered depolymerization, the antibacterial potency was largely retained but the hemolytic toxicity was substantially reduced. Thus, we reveal the first example of a self-immolative antibacterial polymer platform that will enable antibacterial materials to spontaneously unzip into biologically active small molecules upon the introduction of a specifically designed stimulus.

  8. Glucuronoyl Esterase Screening and Characterization Assays Utilizing Commercially Available Benzyl Glucuronic Acid Ester

    Directory of Open Access Journals (Sweden)

    Hampus Sunner

    2015-09-01

    Full Text Available Research on glucuronoyl esterases (GEs has been hampered by the lack of enzyme assays based on easily obtainable substrates. While benzyl d-glucuronic acid ester (BnGlcA is a commercially available substrate that can be used for GE assays, several considerations regarding substrate instability, limited solubility and low apparent affinities should be made. In this work we discuss the factors that are important when using BnGlcA for assaying GE activity and show how these can be applied when designing BnGlcA-based GE assays for different applications: a thin-layer chromatography assay for qualitative activity detection, a coupled-enzyme spectrophotometric assay that can be used for high-throughput screening or general activity determinations and a HPLC-based detection method allowing kinetic determinations. The three-level experimental procedure not merely facilitates routine, fast and simple biochemical characterizations but it can also give rise to the discovery of different GEs through an extensive screening of heterologous Genomic and Metagenomic expression libraries.

  9. Pertumbuhan Plantlet Anggrek Cattleya sp. dengan Perlakuan Benzyl Amino Purine pada Media Dasar Pupuk Daun Modifikasi

    Directory of Open Access Journals (Sweden)

    HESTIN YUSWANTI

    2015-09-01

    Full Text Available Growth of Plantlets of Cattleya Orchid on The Fooliar Fertilizer-Based Medium added with Benzyl Amino Purine. The aim of the current research was to investigate the appropriate concentrationof plant growth regulator BAP on the growth of Cattleya plantlet. The experiment was utilized a Randomized Completely Design with five treatments and six replications. The basal medium used was modification of foliar fertilizer of Growmore (trade mark with addition of fish emulsion, Vitamin B1 and active charcoal. BAP concentration used as treatment were 0 ppm, 0.5 ppm, 1.0 ppm, 1.5 ppm and 2.0 ppm. Variables observed were height, leaf number, root number, root length, fresh weight and dry weight of plantlets. The result showed that concentration of 1 ppm BAP resulted in the highest value for plantlet height (5.67 cm, leaf number (4.67, root length (2.07 cm, fresh weight (0.36 g and dry weight (0.043 g.

  10. The effect of alkali promoters on Cu-Na-ZSM-5 catalysts in the oxidation of benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

    Hayashibara, Hirofuni; Nishiyama, Satoru; Tsuruya, Shigeru [Kobe Univ. (Japan)] [and others

    1995-05-01

    The oxidation activities of alkali-added Cu-Na-ZSM-5 zeolites in the gas-phase catalytic oxidation of benzyl alcohol were studied. The main products were benzaldehyde and carbon oxides (carbon dioxide and carbon monoxide). The partial oxidation activity was found to markedly increase when an alkali-metal-added Cu-Na-ZSM-5 was used, in comparison with that obtained when the Cu-Na-ZSM-5 zeolite itself was used. On the other hand, the increase in yield of deep oxidation products (CO{sub 2} + CO) catalyzed by the alkali-added Cu-Na-ZSM-5 was rather low. The alkali added to the Cu-Na-ZSM-5 zeolite was thus found to selectively promote catalytic activity for the partial oxidation of benzyl alcohol. Certain types of alkali salts were used as the additive with the results that Na{sup +}, K{sup +}, and Rb{sup +}, but not Li{sup +}, had similar behavior for benzyl alcohol oxidation. An alkali oxide such as Na;{sub 2}O, rather than the alkali salt itself, was suggested to substantially function as an active promoter for the oxidation of benzyl alcohol as judged from the pretreatment condition of the alkali-added Cu-Na-ZSM-5 zeolite and its similar catalytic activity in the oxidation of alkali salts with the same alkali cation but different counteranions. The added alkali was found to act more effectively as a promoter for oxidation when alkali and Cu ions were accessible to each other; therefore the alkali was suggested to interact directly with the Cu ion to promote the oxidation of benzyl alcohol, rather than this promotion being a separate function of the alkali itself. One of the roles of the alkali added to the Cu-Na-ZSM-5 zeolite was promoting the dissociation of the oxygen molecule, as evidenced by the results of the exchange reaction of the oxygen molecule. The alkali was also suggested to neutralize the acid sites in the Cu-Na-ZSM-5 zeolite and prevent its deactivation by retarding the formation of coke-like material on the zeolite. 30 refs., 12 figs., 5 tabs.

  11. Butyl benzyl phthalate suppresses the ATP-induced cell proliferation in human osteosarcoma HOS cells

    International Nuclear Information System (INIS)

    Liu, P.-S.; Chen, C.-Y.

    2010-01-01

    Butyl benzyl phthalate (BBP), an endocrine disruptor present in the environment, exerts its genomic effects via intracellular steroid receptors and elicits non-genomic effects by interfering with membrane ion-channel receptors. We previously found that BBP blocks the calcium signaling coupled with P2X receptors in PC12 cells (Liu and Chen, 2006). Osteoblast P2X receptors were recently reported to play a role in cell proliferation and bone remodeling. In this present study, the effects of BBP on ATP-induced responses were investigated in human osteosarcoma HOS cells. These receptors mRNA had been detected, named P2X4, P2X7, P2Y2, P2Y4, P2Y5, P2Y9, and P2Y11, in human osteosarcoma HOS cells by RT-PCR. The enhancement of cell proliferation and the decrease of cytoviability had both been shown to be coupled to stimulation via different concentrations of ATP. BBP suppressed the ATP-induced calcium influx (mainly coupled with P2X) and cell proliferation but not the ATP-induced intracellular calcium release (mainly coupled with P2Y) and cytotoxicity in human osteosarcoma HOS cells. Suramin, a common P2 receptor's antagonist, blocked the ATP-induced calcium signaling, cell proliferation, and cytotoxicity. We suggest that P2X is mainly responsible for cell proliferation, and P2Y might be partially responsible for the observed cytotoxicity. BBP suppressed the calcium signaling coupled with P2X, suppressing cell proliferation. Since the importance of P2X receptors during bone metastasis has recently become apparent, the possible toxic risk of environmental BBP during bone remodeling is a public problem of concern.

  12. Improving quality indices of Rosa ‘Yellow Finesse’ using methyl jasmonate and benzyl adenine

    Directory of Open Access Journals (Sweden)

    Omid Askari-Khorasgani

    2016-06-01

    Full Text Available Plant growth regulators (PGRs play a key role in regulating physiological and morphological development of plant species. Application of these PGRs can improve pre- and post-harvest quality and quantity of ornamental flowers and lessen the harmful effects of injury incurred at harvesting time. The objective of this study was to determine the appropriate spraying solution for improving pre- and postharvest quality indices of Rosa hybrida L. cv. ‘Yellow Finesse’. So, the effect of methyl jasmonate (MeJA at 0, 50, 100, or 150 mg*l-1 alone or in combination with benzyl adenine (BA at 0, 10, or 20 mg*l-1 was investigated. Plants were sprayed at a 15-day interval for two months and then harvested at a mature bud stage. The results showed that flower head diameter and leaf chlorophyll content were improved by applying 100 mg*l-1 MeJA + 20 mg*l-1 BA. The application of 100 mg*l-1 MeJA + 10 mg*l-1 BA or 10 mg*l-1 BA resulted in improving its petal carotenoid content. The plants treated with 150 mg*l-1 MeJA had the longest shelf life. The findings demonstrated that while 100 mg*l-1 MeJA + 20 mg*l-1 BA and 100 mg*l-1 MeJA + 10 mg*l-1 BA were the best preharvest spraying solutions due to the highest carotenoid content and largest flower head diameter. Particularly, 150 mg*l-1 MeJA was the best spraying solution for extending cut flower shelf life and had the potential to function as a postharvest treatment.

  13. Curcumin inhibits adipogenesis induced by benzyl butyl phthalate in 3T3-L1 cells.

    Science.gov (United States)

    Sakuma, Satoru; Sumida, Maki; Endoh, Yukiko; Kurita, Ayaka; Yamaguchi, Ayana; Watanabe, Tomoki; Kohda, Tetsuya; Tsukiyama, Yui; Fujimoto, Yohko

    2017-08-15

    Phthalates are a group of endocrine disrupting chemicals and may have contributed to the recent global obesity health crisis. Increased adipogenesis via the peroxisome proliferator-activated receptor γ (PPARγ)-CCAAT-enhancer binding protein α (C/EBPα) pathway could be one critical mechanism responsible for phthalate-induced weight gain. On the other hand, curcumin has been shown to inhibit adipogenesis in cells and animal models. The present study was undertaken to evaluate, for the first time, whether curcumin could reduce adipogenesis induced by benzyl butyl phthalate (BBP) via downregulation of the PPARγ-C/EBPα pathway. 3T3-L1 preadipocytes were differentiated by treating them with insulin, dexamethasone, and 3-isobutyl-1-methylxanthine in the presence of BBP, with or without curcumin. Cells that were grown in the presence of BBP alone showed a significant increase in triacylglycerol (TG) levels. In addition, the number of Oil Red O-stained cells and the mRNA expression levels of PPARγ, C/EBPα, adiponectin, and tumor necrosis factor-α (TNFα) were significantly increased. However, treatment with BBP in combination with curcumin resulted in major reductions in TG levels, the numbers of Oil Red O-stained cells, and the mRNA expression levels of the four proteins. These results suggest that curcumin might be an inhibitor of BBP-induced weight gain and inflammation via stimulation of adipocyte differentiation and TNFα generation. Curcumin may, therefore, be a potential medication for preventing the harmful effects of phthalates. Copyright © 2017 Elsevier Inc. All rights reserved.

  14. Molecular structure and conformation of N-2-[3'-(methoxysalicylideneimino)benzyl]-3″-methoxysalicylideneimine

    Science.gov (United States)

    Dey, D. K.; Dey, S. P.; Elmali, A.; Elerman, Y.

    2001-05-01

    The Schiff base, N-2-[3'-(methoxysalicylideneimino)benzyl]-3″-methoxysalicylidene-imine, 1,2-C 6H 4[NCHC 6H 3(OMe-3')OH-2']CH 2NCHC 6H 3(OMe-3″)OH-2″, has been prepared by the reaction of 2-amino-1-benzylamine and 3-methoxysalicylaldehyde ( o-vanillin) in ethanol. The molecular structure has been confirmed by single crystal X-ray crystallography. The crystal is in the monoclinic space group P2 1/ n with a=16.179(5), b=6.715(5), c=18.780(6) Å, β=100.56(3)°, Dcalc=1.293 mg cm -3, V=2006(2) Å 3 and R=0.0357 for 3929 independent reflections. The 1H and 13C NMR spectra in CDCl 3 solution indicate the retention of solid state structure in solution. The title compound is not planar. Intramolecular hydrogen bonds occur between O(1) and N(1) [2.614(2) Å] and between O(2) and N(2) [2.585(2) Å] atoms, the hydrogen atom essentially being bonded to the oxygen atom. Minimum energy conformations from AM1 were calculated as a function of five torsion angles θ1 (C6-C7-N1-C8), θ2 (C14-N2-C15-C16), θ3 (C9-C8-N1-C7), θ4 (C13-C14-N2-C15) and θ5 (C10-C9-C8-N1), varied every 5°. The optimized geometry of the crystal structure corresponding to the non-planar conformation is the most stable conformation in all calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded hydrogen-hydrogen repulsions.

  15. On the role of resonantly stabilized radicals in polycyclic aromatic hydrocarbon (PAH) formation: pyrene and fluoranthene formation from benzyl-indenyl addition.

    Science.gov (United States)

    Sinha, Sourab; Rahman, Ramees K; Raj, Abhijeet

    2017-07-26

    Resonantly stabilized radicals, such as propargyl, cyclopentadienyl, benzyl, and indenyl, play a vital role in the formation and growth of polycyclic aromatic hydrocarbons (PAHs) that are soot precursors in engines and flames. Pyrene is considered to be an important PAH, as it is thought to nucleate soot particles, but its formation pathways are not well known. This paper presents a reaction mechanism for the formation of four-ring aromatics, pyrene and fluoranthene, through the combination of benzyl and indenyl radicals. The intermediate species and transition structures involved in the elementary reactions of the mechanism were studied using density functional theory, and the reaction kinetics were evaluated using transition state theory. The barrierless addition of benzyl and indenyl to form the adduct, 1-benzyl-1H-indene, was found to be exothermic with a reaction energy of 204.2 kJ mol -1 . The decomposition of this adduct through H-abstraction and H 2 -loss was studied to determine the possible products. The rate-of-production analysis was conducted to determine the most favourable reactions for pyrene and fluoranthene formation. The premixed laminar flames of toluene, ethylbenzene, and benzene were simulated using a well-validated hydrocarbon fuel mechanism with detailed PAH chemistry after adding the proposed reactions to it. The computed and experimentally observed species profiles were compared to determine the effect of the new reactions for pyrene and fluoranthene formation on their concentration profiles. The role of benzyl and indenyl combination in PAH formation and growth is highlighted.

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

    Science.gov (United States)

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

    2015-12-01

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

  17. Benzyl isothiocyanate, a major component from the roots of Salvadora persica is highly active against Gram-negative bacteria.

    Directory of Open Access Journals (Sweden)

    Abier Sofrata

    Full Text Available Plants produce a number of antimicrobial substances and the roots of the shrub Salvadora persica have been demonstrated to possess antimicrobial activity. Sticks from the roots of S. persica, Miswak sticks, have been used for centuries as a traditional method of cleaning teeth. Diverging reports on the chemical nature and antimicrobial repertoire of the chewing sticks from S. persica led us to explore its antibacterial properties against a panel of pathogenic or commensal bacteria and to identify the antibacterial component/s by methodical chemical characterization. S. persica root essential oil was prepared by steam distillation and solid-phase microextraction was used to sample volatiles released from fresh root. The active compound was identified by gas chromatography-mass spectrometry and antibacterial assays. The antibacterial compound was isolated using medium-pressure liquid chromatography. Transmission electron microscopy was used to visualize the effect on bacterial cells. The main antibacterial component of both S. persica root extracts and volatiles was benzyl isothiocyanate. Root extracts as well as commercial synthetic benzyl isothiocyanate exhibited rapid and strong bactericidal effect against oral pathogens involved in periodontal disease as well as against other Gram-negative bacteria, while Gram-positive bacteria mainly displayed growth inhibition or remained unaffected. The short exposure needed to obtain bactericidal effect implies that the chewing sticks and the essential oil may have a specific role in treatment of periodontal disease in reducing Gram-negative periodontal pathogens. Our results indicate the need for further investigation into the mechanism of the specific killing of Gram-negative bacteria by S. persica root stick extracts and its active component benzyl isothiocyanate.

  18. Vibronic Spectroscopy of Hetero Dihalo-Benzyl Radicals Generated by Corona Discharge : Jet-Cooled Chlorofluorobenzyl Radicals

    Science.gov (United States)

    Yoon, Young; Lee, Sang

    2015-06-01

    The technique of corona excited supersonic jet expansion coupled with a pinhole-type glass nozzle was applied to vibronic spectroscopy of jet-cooled chlorofluorobenzyl radicals for the vibronic assignments and measurements of electronic energies of the D_1 → D_0 transition. The vibronic emission spectra were recorded with a long-path monochromator in the visible region. The 2,3-, 2,4-, and 2.5-chlorofluorobenzyl radicals were generated by corona discharge of corresponding precursor molecules, chlorofluorotoluenes seeded in a large amount of helium carrier gas. The emission spectra show the vibronic bands originating from two benzyl-type radicals, chlorofluorobenzyl and fluorobenzyl benzyl radicals, in which fluorobenzyl radicals were obtained by displacement of Cl by H atom produced by the dissociation of methyl C-H bond. From an analysis of the spectra observed, we could determine the electronic energies in D_1 → D_0 transition and vibrational mode frequencies at the D_0 state of chlorofluorobenzyl radicals which show the origin band of the electronic transition to be shifted to red region, comparing with the parental benzyl radical. The red-shift is highly sensitive to the number, position, and kind of substituents in chlorofluorobenzyl radicals. From the quantitative analysis of the red-shift, it has been found that the additivity rule, discovered recently by Lee group predicts the observation very well. In addition, the negligible contribution of the substituent at the 4-position, the nodal point of the Hückel's molecular orbital theory, can be well describes by the disconnection of substituent from molecular plane of the benzene ring available for delocalized π electrons. In this presentation, I will discuss the spectroscopic observation of new chlorofluorobenzyl radicals and substituent effect on electronic transition energy which is useful for identification of isomeric substituted benzyl radicals. C.~S.~Huh, Y.~W.~Yoon, and S.~K.~Lee, J. Chem

  19. Anchoring Tri(8-QuinolinolatoIron Onto Sba-15 for Partial Oxidation of Benzyl Alcohol Using Water as the Solvent

    Directory of Open Access Journals (Sweden)

    Yang Xiaoyuan

    2014-09-01

    Full Text Available Tri(8-quinolinolatoiron complex immobilized onto SBA-15 catalyst has been synthesized through a stepwise procedure. The characterization results indicated that the BET surface area, total pore volume and average pore width decrease after stepwise modification of SBA-15, while the structure keeps intact. Catalytic tests showed that FeQ3-SBA-15 catalyzes the oxidation reaction well with 34.8% conversion of benzyl alcohol and 74.7% selectivity to benzaldehyde when water is used as the solvent after 1 h reaction. In addition, homogeneous catalyst tri(8-quinolinolatoiron exhibits very bad catalytic behavior using water as the solvent.

  20. Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives

    Directory of Open Access Journals (Sweden)

    E. K. Mikhalchenko

    2017-04-01

    Full Text Available Introduction. Heterocyclic compounds play an important role in the metabolic processes of human organism. Structures of vitamins, nucleotides, chromoproteins are based on Nitrogen-containing heterocycles (purine, pyrimidine, thiazole etc. Thus, it was obvious to use these organic substances as basic molecules for synthetic research of biologically active compounds which could be used for treatment of different pathological processes. In their research, some scientist pay special attention to xanthine derivatives that are well-known low toxic natural compounds with wide spectrum of pronounced pharmacological properties (antioxidant, diuretic, antibacterial, anti-inflammatory etc. Insertion of carboxyl group in the structure of xanthine molecule is a prospective ability of its synthetic potential increasing. Aim of our research was the development of method of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives synthesis and studying their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M. 1Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian», USA solvent – (DMSO-d6, internal standard – ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Results and discussion. We selected 3-benzyl-8-propyl xanthine as initial compound for our study. By its interaction with chloroacetic acid, chloroacetamide or propyl chloroacetate in DMF in the presence of calculated amount of NaHCO3 we synthesized 3-benzyl-8-propylxanthinyl-7-acetic acid its ester and amide. At the same time we found that obtaining of xanthinyl-7-acetic acid by hydrolysis of its ester produced with higher yield. On the next stage of our research we synthesized a number of water-soluble salts of 3-benzyl-8-propylxanthinyl-7-acetic acid by reaction of acid with different primary and secondary amines. The structures of all obtained compounds were

  1. Synthesis and physical-chemical properties of functional derivatives of 3-benzyl-8-propylxanthinyl-7-acetic acid

    Directory of Open Access Journals (Sweden)

    E. K. Mikhal’chenko

    2017-08-01

    Full Text Available Introduction. Synthetic research of new biologically active compounds occupies an important place in modern pharmaceutical science.Thus it is important to develop techniques for the biologically active substances functionalization. Esters and amides take special place among the variety of functional derivatives of organic acids,. These fragments are well-known pharmacophores and could be found in a wide range of drugs. Thus, the nootropic agent pyracetam is 2-oxo-1-pyrolidineacetamide, and is the selective antagonist of β-adrenoreceptores; atenolol is a derivative of benzeneacetamide. Substituted acetamide and ester fragments are also present in the structures of aprofen, spasmolitin, acetylidine and β-lactam cephalosporins and penicillins antibiotics.Aim of our research was the synthetic method development for functional derivatives of 3-benzyl-8-propylxanthinyl-7-acetic acid and the study of their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M. 1Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian» – USA solvent – (DMSO-d6, internal standard – ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Chemical shifts were reported in ppm (parts per million values. Infrared (IR spectra were measured on a Bruker Alpha instrument using a potassium bromide (KBr disk, scanning from 400 to 4000 cm-1. Results and discussion. We selected 3-benzyl-8-propylxanthinyl-7-acetic acid as initial compound for our study. For synthesis of hexyl, heptyl, octyl, nonyl, decyl and benzyl esters of 3-benzyl-8-propylxanthinyl-7-acetic acid we used alternative method, that included alkylation of sodium salts of acids with alkyl halogens. Reaction was made at DMF medium by reflux of reagents. Next stage of our research was the synthesis of amides of 3-beznyl-8-propylxanthinyl-7-acetic acid by the reaction of ethyl or propyl esters

  2. (4Z-1-Benzyl-4-(2-oxopropylidene-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

    Directory of Open Access Journals (Sweden)

    Mohamed Samba

    2016-09-01

    Full Text Available The title compound, C19H18N2O2, crystallizes with two independent molecules in the asymmetric unit which differ in conformation. The seven-membered ring adopts a `bowl' conformation with the benzyl group oriented away from the open face in one molecule, while the benzyl group is oriented towards the open face in the other. The benzyl group of one independent molecule is disordered over two sets of sites with refined site-occupancy factors of 0.454 (8 and 0.546 (8. The two molecules are linked via C—H...O hydrogen bonds and centrosymmetrically related pairs of molecules form dimers through C—H...O hydrogen bonds, packing in rows parallel to the c axis.

  3. 1-O-Acetyl-3,4,6-tri-O-benzyl-2-C-bromomethyl-2-deoxy-α-d-glucopyranose

    Directory of Open Access Journals (Sweden)

    Henok H. Kinfe

    2013-01-01

    Full Text Available In the title compound, C30H33BrO6, the pyranose ring adopts a chair conformation. Two of the O-benzyl phenyl rings lie almost perpendicular to C/C/C/O plane formed by the ring atoms not attached to these O-benzyl phenyl rings, and form dihedral angles of 85.1 (2 and 64.6 (2°, while the third O-benzyl phenyl ring is twisted so that it makes a dihedral angle 34.9 (2° to this C/C/C/O plane. This twist is ascribed to the formation of an S(8 loop stabilized by a weak intramolecular C—H...O hydrogen bond.

  4. A novel serotonin transporter ligand: (5-Iodo-2-(2-dimethylaminomethylphenoxy)-benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

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

    2000-02-01

    The serotonin transporters (SERT) are the primary binding sites for selective serotonin reuptake inhibitors, commonly used antidepressants such as fluoxetine, sertraline, and paroxetine. Imaging of SERT with positron emission tomography and single photon emission computed tomography in humans would provide a useful tool for understanding how alterations of this system are related to depressive illnesses and other psychiatric disorders. In this article the synthesis and characterization of [{sup 125}I]ODAM [(5-iodo-2-(2-dimethylaminomethylphenoxy)-benzyl alcohol, 9)] as an imaging agent in the evaluation of central nervous system SERT are reported. A new reaction scheme was developed for the preparation of compound 9, ODAM, and the corresponding tri-n-butyltin derivative 10. Upon reacting 10 with hydrogen peroxide and sodium[{sup 125}I]iodide, the radiolabeled [{sup 125}I]9 was obtained in good yield (94% yield, radiochemical purity >95%). In an initial binding study using cortical membrane homogenates of rat brain, ODAM displayed a good binding affinity with a value of K{sub i}=2.8{+-}0.88 nM. Using LLC-PK{sub 1} cells specifically expressing the individual transporter (i.e. dopamine [DAT], norepinephrine [NET], and SERT, respectively), ODAM showed a strong inhibition on SERT (K{sub i}=0.12{+-}0.02 nM). Inhibition constants for the other two transporters were lower (K{sub i}=3.9{+-}0.7 {mu}M and 20.0 {+-} 1.9 nM for DAT and NET, respectively). Initial biodistribution study in rats after an intravenous (IV) injection of [{sup 125}I]ODAM showed a rapid brain uptake and washout (2.03, 1.49, 0.79, 0.27, and 0.07% dose/organ at 2, 30, 60, 120, and 240 min, respectively). The hypothalamus region where the serotonin neurons are located exhibited a high specific uptake. Ratios of hypothalamus-cerebellum/cerebellum based on percent dose per gram of these two regions showed values of 0.35, 0.86, 0.86, 0.63, and 0.34 at 2, 30, 60, 120, and 240 min, post-IV injection

  5. A novel mesoporous sulfated zirconium solid acid catalyst for Friedel-Crafts benzylation reaction

    Energy Technology Data Exchange (ETDEWEB)

    Miao, Zhichao; Zhou, Jin; Zhao, Jinping; Liu, Dandan; Bi, Xu [School of Chemical Engineering, Shandong University of Technology, Zibo, 255049 (China); Chou, Lingjun, E-mail: ljchou@licp.cas.cn [State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (China); Zhuo, Shuping, E-mail: zhuosp_academic@yahoo.com [School of Chemical Engineering, Shandong University of Technology, Zibo, 255049 (China)

    2017-07-31

    Highlights: • A novel mesoporous ZrO{sub 2}/SO{sub 4}{sup 2−} has been prepared via a facile one-pot EISA strategy. • The M-ZrO{sub 2}/SO{sub 4}{sup 2−} exhibited excellent textural and acidic properties. • The introduced S species were homogeneously dispersed in mesoporous skeleton. • The M-ZrO{sub 2}/SO{sub 4}{sup 2−} exhibited excellent catalytic performance and reusability. - Abstract: In this paper, a novel mesoporous sulfated zirconium (M-ZrO{sub 2}/SO{sub 4}{sup 2−}) has been gotten by one-pot evaporation-induced self-assembly (one-pot EISA) strategy. The SXRD, N{sub 2}-physisorption and TEM characterization techniques indicated that M-ZrO{sub 2}/SO{sub 4}{sup 2−} possessed distinct mesostructure with big specific surface area (133.5 m{sup 2} g{sup −1}), large pore volume (0.18 cm{sup 3} g{sup −1}) and narrow pore size distribution (4.90 nm). Moreover, the existing states and the influence in mesostructure of introduced S species were detailedly investigated by the XRD, N{sub 2}-physisorption, TEM, TG-DSC, FT-IR and XPS techniques and the results showed that the S species, which existed as the type of SO{sub 4}{sup 2−}, improved the textural properties of prepared materials. In addition, the NH{sub 3}-TPD and IR spectra of adsorbed pyridine indicated the existence of strong Brønsted and Lewis acid sites in M-ZrO{sub 2}/SO{sub 4}{sup 2−} even evacuated at 400 °C. Furthermore, the M-ZrO{sub 2}/SO{sub 4}{sup 2−} was used as a promise solid acid catalyst and displayed excellent catalytic performance and reusability in Friedel-Crafts benzylation reaction.

  6. Benzyl isothiocyanate causes FoxO1-mediated autophagic death in human breast cancer cells.

    Directory of Open Access Journals (Sweden)

    Dong Xiao

    Full Text Available Benzyl isothiocyanate (BITC, a constituent of edible cruciferous vegetables, inhibits growth of breast cancer cells but the mechanisms underlying growth inhibitory effect of BITC are not fully understood. Here, we demonstrate that BITC treatment causes FoxO1-mediated autophagic death in cultured human breast cancer cells. The BITC-treated breast cancer cells (MDA-MB-231, MCF-7, MDA-MB-468, BT-474, and BRI-JM04 and MDA-MB-231 xenografts from BITC-treated mice exhibited several features characteristic of autophagy, including appearance of double-membrane vacuoles (transmission electron microscopy and acidic vesicular organelles (acridine orange staining, cleavage of microtubule-associated protein 1 light chain 3 (LC3, and/or suppression of p62 (p62/SQSTM1 or sequestosome 1 expression. On the other hand, a normal human mammary epithelial cell line (MCF-10A was resistant to BITC-induced autophagy. BITC-mediated inhibition of MDA-MB-231 and MCF-7 cell viability was partially but statistically significantly attenuated in the presence of autophagy inhibitors 3-methyl adenine and bafilomycin A1. Stable overexpression of Mn-superoxide dismutase, which was fully protective against apoptosis, conferred only partial protection against BITC-induced autophagy. BITC treatment decreased phosphorylation of mTOR and its downstream targets (P70s6k and 4E-BP1 in cultured MDA-MB-231 and MCF-7 cells and MDA-MB-231 xenografts, but activation of mTOR by transient overexpression of its positive regulator Rheb failed to confer protection against BITC-induced autophagy. Autophagy induction by BITC was associated with increased expression and acetylation of FoxO1. Furthermore, autophagy induction and cell growth inhibition resulting from BITC exposure were significantly attenuated by small interfering RNA knockdown of FoxO1. In conclusion, the present study provides novel insights into the molecular circuitry of BITC-induced cell death involving FoxO1-mediated autophagy.

  7. The Synthesis and Characterization of Hydroxyapatite-β-Alanine Modified by Grafting Polymerization of γ-Benzyl-L-glutamate-N-carboxyanhydride

    OpenAIRE

    Shan, Yukai; Qin, Yuyue; Chuan, Yongming; Li, Hongli; Yuan, Minglong

    2013-01-01

    In this study, hydroxyapatite (HAP) was surface-modified by the addition of β-alanine (β-Ala), and the ring-opening polymerization of γ-benzyl-L-glutamate-N-carboxy-anhydride (BLG-NCA) was subsequently initiated. HAP containing surface poly-γ-benzyl-L-glutamates (PBLG) was successfully prepared in this way. With the increase of PBLG content in HAP-PBLG, the solubility of HAP-PBLG increased gradually and it was ultimately soluble in chloroform. HAP-PLGA with surface carboxyl groups was obtaine...

  8. AlCl3catalyzed coupling of N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage.

    Science.gov (United States)

    Hu, Chen; Hong, Gang; Qian, Xiaofei; Kim, Kwang Rim; Zhu, Xiaoyan; Wang, Limin

    2017-06-14

    A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl 3 , a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.

  9. The influence of the substrate structure in the telluro-cyclo-functionalization reaction of {gamma}, {delta}-unsaturated carboxylic acids and their corresponding benzyl esters

    Energy Technology Data Exchange (ETDEWEB)

    Moraes, Denilson N.; Santos, Rute A.; Comasseto, Joao V. [Sao Paulo Univ., SP (Brazil). Inst. de Quimica

    1998-07-01

    {gamma},{delta}-Unsaturated carboxylic acids containing mono substituted double bonds react with aryl tellurium trichlorides to give the expected telluro lactone. Reaction of the corresponding benzyl esters gives the addition product of the aryl tellurium trichlorides to the double bond {gamma}, {delta}-Unsaturated carboxylic acids containing 1,1-disubstituted double bonds lead to a mixture of the expected telluro lactone and the product of hydrochloric acid addition to the double bond; the corresponding benzyl ester gives the telluro lactone as the only product. The stereoselectivity of the reaction is low; mixtures of the two possible diastereomeric lactones are formed in approximately 1:1 ratios. (author)

  10. Effects of sucrose and benzyl alcohol on GCSF conformational dynamics revealed by hydrogen deuterium exchange mass spectrometry.

    Science.gov (United States)

    Zhang, Jun; Banks, Douglas D; He, Feng; Treuheit, Michael J; Becker, Gerald W

    2015-05-01

    Protein stability, one of the major concerns for therapeutic protein development, can be optimized during process development by evaluating multiple formulation conditions. This can be a costly and lengthy procedure where different excipients and storage conditions are tested for their impact on protein stability. A better understanding of the effects of different formulation conditions at the molecular level will provide information on the local interactions within the protein leading to a more rational design of stable and efficacious formulations. In this study, we examined the roles of the excipients, sucrose and benzyl alcohol, on the conformational dynamics of recombinant human granulocyte colony stimulating factor using hydrogen/deuterium exchange coupled with mass spectrometry (HDX-MS). Under physiological pH and temperature, sucrose globally protects the whole molecule from deuterium uptake, whereas benzyl alcohol induces increased deuterium uptake of the regions within the α-helical bundle, with even larger extent. The HDX experiments described were incorporated a set of internal peptides (Zhang et al., 2012. Anal Chem 84:4942-4949) to monitor the differences in intrinsic exchange rates in different formulations. In addition, we discussed the feasibility of implementing HDX-MS with these peptide probes in protein formulation development. © 2015 Wiley Periodicals, Inc. and the American Pharmacists Association.

  11. Synthesis and Structure–Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists

    Science.gov (United States)

    2014-01-01

    N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2C receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with 1b being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with 1b being more than 400-fold selective for the 5-HT2A receptor. PMID:24397362

  12. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists.

    Science.gov (United States)

    Hansen, Martin; Phonekeo, Karina; Paine, James S; Leth-Petersen, Sebastian; Begtrup, Mikael; Bräuner-Osborne, Hans; Kristensen, Jesper L

    2014-03-19

    N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2C receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with 1b being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with 1b being more than 400-fold selective for the 5-HT2A receptor.

  13. Synergistic effect in the oxidation of benzyl alcohol using citrate-stabilized gold bimetallic nanoparticles supported on alumina

    Science.gov (United States)

    Gómez-Villarraga, Fernando; Radnik, Jörg; Martin, Andreas; Köckritz, Angela

    2016-06-01

    Bimetallic nanoparticles (NPs) containing gold and various second metals ( M = Pd, Pt, Cu, and Ag) supported on alumina (AuM/Alumina) were prepared using sodium citrate as stabilizer. In addition, supported monometallic Au/Alumina and Pd/Alumina were synthesized and tested to reveal synergistic effects in the catalytic evaluation of the bimetallic catalysts. The monometallic and bimetallic NPs revealed average sizes below 10 nm. The oxidation of benzyl alcohol with molecular oxygen as oxidant at mild conditions in liquid phase in the absence and presence (toluene or NaOH aqueous solution, 0.2 M) of a solvent was selected as test reaction to evaluate the catalytic properties of the above-mentioned solids. AuPd/Alumina exhibited the best catalytic activity among all bimetallic catalysts using toluene as solvent and under solvent-free conditions, respectively. In comparison to the monometallic catalysts, a synergistic effect with AuPd/Alumina was only evident in the solvent-free reaction. The AuPd/Alumina catalyst was able to oxidize benzyl alcohol selectively depending on the reaction medium into benzaldehyde (toluene or solvent-free) or benzoic acid (NaOH aqueous solution, 0.2 M). However, the catalyst deactivated due to particle growth of the bimetallic AuPd NPs by Ostwald ripening and leaching was not observed in the oxidation using toluene as solvent. The size of the catalytically active NPs, the metal composition of the particles, and the reaction conditions greatly influenced the catalytic oxidation results.

  14. Synthesis, growth and characterization of organic nonlinear optical material: N-benzyl-2-methyl-4-nitroaniline (BNA)

    Science.gov (United States)

    Kalaivanan, R.; Srinivasan, K.

    2017-05-01

    Synthesis of the organic nonlinear optical compound N-benzyl-2-methyl-4-nitroaniline (BNA) was carried out in a newer chemical environment using the mixture of benzyl chloride and 2-methl-4-nitroaniline by a preferred laboratory synthesis process. The synthesized BNA compound was separated by column chromatography (CC) with low pressure silica gell using petrollium benzine and purity of the separated resultant product was confirmed by thin layer chromatography (TLC). Further, the material was recrystallized atleast four times in methanol and the highly purified BNA was used for the growth of single crystals from solutions with selected solvents by slow evaporation method at room temperature. Single crystals having natural growth morphology were harvested and their different growth faces were identified by optical goniometry. The grown crystals were subjected to different characterization techniques such as powder x-ray diffraction (PXRD), fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC) and UV-vis-Near IR spectroscopy. Further, the second harmonic generation (SHG) efficiency of the grown BNA crystal was studied by Kurtz and Perry powder technique using Nd:YAG laser as fundamental source and found to be twice that of inorganic standard KDP.

  15. Effect of polyester blends in hydroentangled raw and bleached cotton nonwoven fabrics on the adsorption of alkyl-dimethyl-benzyl-ammonium chloride

    Science.gov (United States)

    The adsorption kinetics and isotherms of alkyl-dimethyl-benzyl-ammonium chloride (ADBAC), a cationic surfactant commonly employed as an antimicrobial agent, on hydroentangled nonwoven fabrics (applicable for wipes) including raw cotton, bleached cotton, and their blends with polyester (PES) were stu...

  16. Efficient and convenient oxidation of benzyl halides to carbonyl compounds with sodium nitrate and acetic acid by phase transfer catalysis in aqueous media

    Directory of Open Access Journals (Sweden)

    Yu Lin Hu

    2010-08-01

    Full Text Available A variety of benzyl halides were converted to the corresponding aldehydes/ketones in good to high yields by phase transfer catalysis combined with sodium nitrate and acetic acid at reflux. As a result, a simple and high yield procedure has been developed.

  17. The Synthesis of "N"-Benzyl-2-Azanorbornene via Aqueous Hetero Diels-Alder Reaction: An Undergraduate Project in Organic Synthesis and Structural Analysis

    Science.gov (United States)

    Sauvage, Xavier; Delaude, Lionel

    2008-01-01

    The synthesis of "N"-benzyl-2-azanorbornene via aqueous hetero Diels-Alder reaction of cyclopentadiene and benzyliminium chloride formed in situ from benzylamine hydrochloride and formaldehyde is described. Characterization of the product was achieved by IR and NMR spectroscopies. The spectral data acquired are thoroughly discussed. Numerous…

  18. Grafting of benzylic amide macrocycles onto acid-terminated self-assembled monolayers studied by XPS, RAIRS, and contact angle measurements

    NARCIS (Netherlands)

    Cecchet, F; Pilling, M; Hevesi, L; Schergna, S; Wong, JKY; Clarkson, GJ; Leigh, DA; Rudolf, P; Wong, Jenny K.Y.; Clarkson, Guy J.

    2003-01-01

    The grafting of benzylic amide macrocycles, the basic units of more complex mechanically interlocked architectures such as catenanes and rotaxanes, was performed via the functionalization of an acid-terminated self-assembled monolayer (SAM) of 11-mercaptoundecanoic acid (11-MUA). Both chemical and

  19. Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A2: Synthesis, spectroscopic and computational studies

    Science.gov (United States)

    Henao Castañeda, I. C.; Pereañez, J. A.; Jios, J. L.

    2012-11-01

    4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculations were performed with Gaussian 09 to calculate the geometric parameters and vibrational spectra. Phospholipase A2 (PLA2) was purified from Crotalus durissus cumanensis venom by molecular exclusion chromatography, followed by reverse phase-high performance liquid chromatography. Two studies of the inhibition of phospholipase A2 activity were performed using phosphatidilcholine and 4-nitro-3-octanoyloxybenzoic acid as substrates, in both cases compound II showed the best inhibitory ability, with 74.89% and 69.91% of inhibition, respectively. Average percentage of inhibition was 52.49%. Molecular docking was carried out with Autodock Vina using as ligands the minimized structures of compounds (I-IV) and as protein PLA2 (PDB code 2QOG). The results suggest that compounds I-IV could interact with His48 at the active site of PLA2. In addition, all compounds showed Van der Waals interactions with residues from hydrophobic channel of the enzyme. This interaction would impede normal catalysis cycle of the PLA2.

  20. General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

    Science.gov (United States)

    Wiȩcław, Michał; Bobin, Mariusz; Kwast, Andrzej; Bujok, Robert; Wróbel, Zbigniew; Wojciechowski, Krzysztof

    2015-11-01

    Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.

  1. Adsorption of alkyl-dimethyl-benzyl-ammonium chloride on low-weight greige and bleached cotton nonwovens in different aqueous environments

    Science.gov (United States)

    Previous research has shown the adsorption of alkyl-dimethyl-benzyl-ammonium chloride (ADBAC) on cotton nonwovens is dependent on pretreatment of the substrate, more specifically whether it is greige or bleached fabric. In this work we examine the effect of varying the chemical and physical propert...

  2. Antidepressent Effect of Two New Benzyl Derivatives from Wild Strawberry Fragaria vesca var. nubicola Lindl. ex Hook.f.

    Science.gov (United States)

    Naz, Sadia; Farooq, Umar; Khan, Ajmal; Khan, Haroon; Karim, Nasiara; Sarwar, Rizwana; Hussain, Javid; Rauf, Abdur

    2017-01-01

    Two new benzyl derivatives were isolated from ethyl acetate fraction of wild strawberry, Fragaria vesca var. nubicola Lindl. ex Hook.f. The structures of these compounds were elucidated to be 5-(4-hydroxy-3-methoxyphenethyl)-7-methoxy-2H-chromen-3-ol (1) and 5-(4-hydroxy-3-methoxyphenethyl)-4,7-dimethoxy-2H-chromen-3-ol (2) based on spectroscopic data through IR, UV, 1H-NMR, 13C-NMR along with two dimensional (2D) techniques HMBC, HMQC, and COSY. Both compounds 1 and 2 were studied in tail suspension and forced swim tests for antidepressant like effects. A significant dose dependent antidepressant like effect was observed by causing spontaneous anti-immobility at various test doses upon intraperitoneal administration. PMID:28790915

  3. 4-Benzyl-1-(4-nitrophenyl-1H-1,2,3-triazole: crystal structure and Hirshfeld analysis

    Directory of Open Access Journals (Sweden)

    Julio Zukerman-Schpector

    2017-11-01

    Full Text Available The molecule in the title compound, C15H12N4O2, has a twisted L-shape with the dihedral angle between the aromatic rings of the N-bound benzene and C-bound benzyl groups being 70.60 (9°. The nitro group is co-planar with the benzene ring to which it is connected [C—C—N—O torsion angle = 0.4 (3°]. The three-dimensional packing is stabilized by a combination of methylene-C—H...O(nitro, methylene-C—H...π(phenyl, phenyl-C—H...π(triazolyl and nitro-O...π(nitrobenzene interactions, along with weak π(triazolyl–π(nitrobenzene contacts [inter-centroid distance = 3.8386 (10 Å]. The importance of the specified intermolecular contacts has been verified by an analysis of the calculated Hirshfeld surface.

  4. Gold & silver nanoparticles supported on manganese oxide: Synthesis, characterization and catalytic studies for selective oxidation of benzyl alcohol

    Directory of Open Access Journals (Sweden)

    Saad Alabbad

    2014-12-01

    Full Text Available Nano-gold and silver particles supported on manganese oxide were synthesized by the co-precipitation method. The catalytic properties of these materials were investigated for the oxidation of benzyl alcohol using molecular oxygen as a source of oxygen. The catalyst was calcined at 300, 400 and 500 °C. They were characterized by electron microscopy, powder X-ray diffraction (XRD and surface area. It was observed that the calcination temperature affects the size of the nanoparticle, which plays a significant role in the catalytic process. The catalyst calcined at 400 °C, gave a 100% conversion and >99% selectivity, whereas catalysts calcined at 300 and 500 °C gave a conversion of 69.51% and 19.90% respectively, although the selectivity remains >99%.

  5. 1-Benzyl-2-Phenylbenzimidazole (BPB, a Benzimidazole Derivative, Induces Cell Apoptosis in Human Chondrosarcoma through Intrinsic and Extrinsic Pathways

    Directory of Open Access Journals (Sweden)

    Ju-Fang Liu

    2012-12-01

    Full Text Available In this study, we investigated the anticancer effects of a new benzimidazole derivative, 1-benzyl-2-phenyl -benzimidazole (BPB, in human chondrosarcoma cells. BPB-mediated apoptosis was assessed by the MTT assay and flow cytometry analysis. The in vivo efficacy was examined in a JJ012 xenograft model. Here we found that BPB induced apoptosis in human chondrosarcoma cell lines (JJ012 and SW1353 but not in primary chondrocytes. BPB induced upregulation of Bax, Bad and Bak, downregulation of Bcl-2, Bid and Bcl-XL and dysfunction of mitochondria in chondrosarcoma. In addition, BPB also promoted cytosolic releases AIF and Endo G. Furthermore, it triggered extrinsic death receptor-dependent pathway, which was characterized by activating Fas, FADD and caspase-8. Most importantly, animal studies revealed a dramatic 40% reduction in tumor volume after 21 days of treatment. Thus, BPB may be a novel anticancer agent for the treatment of chondrosarcoma.

  6. Structure of HIV-1 nonnucleoside reverse transcriptase inhibitors derivatives of N-benzyl-benzimidazole with different substituents in position 4

    Science.gov (United States)

    Ziółkowska, Natasza E.; Michejda, Christopher J.; Bujacz, Grzegorz D.

    2010-01-01

    The constant development of new drugs against HIV-1 is necessary due to global expansion of AIDS and HIV-1 drug resistance. Nonnucleoside reverse transcriptase inhibitors of HIV-1 (NNRTIs) are potentially effective and nontoxic drugs in AIDS therapy. The crystal structures of six nonnucleoside inhibitors of HIV-1 reverse transcriptase (RT) derivatives of N-benzyl-benzimidazole are reported here. The investigated compounds belong to the group of so called "butterfly like" inhibitors with characteristic two π-electron moieties with an angled orientation. The structural data show the influence of the substituents of the benzimidazole ring on the geometry of the molecule and correlation between the structure of the inhibitor and its biological activity.

  7. Synergistic effect in the oxidation of benzyl alcohol using citrate-stabilized gold bimetallic nanoparticles supported on alumina

    Energy Technology Data Exchange (ETDEWEB)

    Gómez-Villarraga, Fernando, E-mail: ferchogomezv@gmail.com; Radnik, Jörg; Martin, Andreas; Köckritz, Angela [Leibniz-Institut für Katalyse e.V. an der Universität Rostock (Germany)

    2016-06-15

    Bimetallic nanoparticles (NPs) containing gold and various second metals (M = Pd, Pt, Cu, and Ag) supported on alumina (AuM/Alumina) were prepared using sodium citrate as stabilizer. In addition, supported monometallic Au/Alumina and Pd/Alumina were synthesized and tested to reveal synergistic effects in the catalytic evaluation of the bimetallic catalysts. The monometallic and bimetallic NPs revealed average sizes below 10 nm. The oxidation of benzyl alcohol with molecular oxygen as oxidant at mild conditions in liquid phase in the absence and presence (toluene or NaOH aqueous solution, 0.2 M) of a solvent was selected as test reaction to evaluate the catalytic properties of the above-mentioned solids. AuPd/Alumina exhibited the best catalytic activity among all bimetallic catalysts using toluene as solvent and under solvent-free conditions, respectively. In comparison to the monometallic catalysts, a synergistic effect with AuPd/Alumina was only evident in the solvent-free reaction. The AuPd/Alumina catalyst was able to oxidize benzyl alcohol selectively depending on the reaction medium into benzaldehyde (toluene or solvent-free) or benzoic acid (NaOH aqueous solution, 0.2 M). However, the catalyst deactivated due to particle growth of the bimetallic AuPd NPs by Ostwald ripening and leaching was not observed in the oxidation using toluene as solvent. The size of the catalytically active NPs, the metal composition of the particles, and the reaction conditions greatly influenced the catalytic oxidation results.Graphical Abstract.

  8. Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs.

    Science.gov (United States)

    Zuba, Dariusz; Sekuła, Karolina

    2013-08-01

    This publication reports analytical properties of three new hallucinogenic substances identified in blotter papers seized from the drug market, namely 25D-NBOMe [2-(2,5-dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethanamine], 25E-NBOMe [2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine] and 25G-NBOMe [2-(2,5-dimethoxy-3,4-dimethylphenyl)-N-(2-methoxybenzyl)ethanamine]. These substances are N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. The applied procedure covered a variety of analytical methods, including gas chromatography with electron impact mass spectrometry (GC-EI-MS; without derivatization and after derivatization with trifluoroacetic anhydride (TFAA)), liquid chromatography-electrospray ionization-quadrupole time of flight mass spectrometry (LC-ESI-QTOF-MS), Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR), which made it possible to identify the active components unequivocally. The GC-MS spectra of analyzed compounds were very similar, with dominant ions observed at m/z = 150, 121, and 91. The remaining ions were analogous to those observed for parent substances, namely 2C-D, 2C-E, 2C-G, but their intensities were low. Derivatization allowed determination of molecular masses of the investigated substances. Their exact masses and chemical formulas were confirmed by LC-QTOF-MS experiments and the fragmentation patterns of these compounds following ESI were determined. The tandem mass spectrometry (MS/MS) experiments confirmed that the studied substances were N-(2-methoxy)benzyl derivatives of the 2C-series compounds. Final elucidation of the structures was performed by NMR spectroscopy. The substances were also characterized by FTIR spectroscopy to corroborate the identity of the compounds. Copyright © 2012 John Wiley & Sons, Ltd.

  9. 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.

  10. Promoting effects of thoria on the nickel-manganese mixed oxide catalysts for the aerobic oxidation of benzyl alcohol

    Directory of Open Access Journals (Sweden)

    S.S.P. Sultana

    2017-05-01

    Full Text Available Due to the recent advancement in the development of various characterization techniques, mixed metal oxide (MMO based catalysts have gained tremendous attention in the field of catalysis. In this study, we demonstrated the synthesis of a series of novel MMO based catalysts by a facile co-precipitation method. The detailed structure and composition of thoria promoted NiMnO catalysts was investigated using various microscopic and spectroscopic techniques such as, SEM, EDAX, XRD, TGA, BET and TPR. In order to study the effect of the content of thorium oxide on the catalytic activity of the as-prepared material various samples were prepared by the addition of low quantities of thorium oxide with 1%, 3% and 5% on NiMnO. The catalytic performances of the as-prepared catalysts were evaluated towards the aerobic oxidation of benzyl alcohol using molecular oxygen as oxidant. Furthermore, in order to investigate the effect of the calcination temperatures on the catalytic activities of the as-prepared materials, the samples were calcined at three different temperatures at 300 °C, 400 °C and 500 °C. The catalysts displayed significant enhancement in catalytic activity towards the catalytic conversion of benzyl alcohol (C6H5CH2OH to benzaldehyde (C6H5CHO. Detailed kinetic studies of the reactions using gas chromatography have revealed that the variation of calcination temperature and the percentage of thoria had significant effect on the catalytic performances of the materials. Among all synthesized catalysts ThO2-(5%-NiMnO catalyst calcined at 400 °C exhibited the highest catalytic performance and stability for the selective oxidation of alcohols.

  11. Experimental density, viscosity, interfacial tension and water solubility of ethyl benzene-α-methyl benzyl alcohol–water system

    International Nuclear Information System (INIS)

    Barega, Esayas W.; Zondervan, Edwin; Haan, André B. de

    2013-01-01

    Highlights: • Properties were measured for MBA (methyl benzyl alcohol)-EB (ethyl benzene)-water. • MBA concentration was found to influence all the properties strongly. • The water solubility, density, and viscosity increased at high MBA concentration. • The interfacial tension decreased sharply at high MBA concentration. • MBA dictates the phase separation and mass transfer of the ternary system. -- Abstract: Density, viscosity, interfacial tension, and water solubility were measured for the (α-methyl benzyl alcohol (MBA) + Ethyl benzene (EB)) system at different concentrations of MBA in contact with water and sodium hydroxide solution (0.01 mol · kg −1 ) as aqueous phases. The properties were measured to identify the component which plays a governing role in changing the physical properties relevant to mass transfer and phase separation of the ternary system. The concentration of MBA was found to be the major factor influencing all the properties. The water solubility, the density, and the viscosity increased notably at higher concentrations of MBA; while, the interfacial tension decreased strongly. The use of 0.01 mol · kg −1 NaOH as an aqueous phase resulted in a decrease of the interfacial tension and a minor decrease in the water solubility. The density data were correlated using a quadratic mixing rule to describe the influence of concentration at any temperature. The viscosity data are correlated using the Nissan and Grunberg and Katti-Chaudhri equations. The Szyzkowski’s equation was used to correlate the interfacial tension data. The water solubility data were described using an exponential relationship. All the correlations described the experimental physical property data adequately

  12. An Optimized Synthesis, Molecular Structure and Characterization of Benzylic Derivatives of 1,2,4-Triazin-3,5(2H,4H-dione

    Directory of Open Access Journals (Sweden)

    Long-Chih Hwang

    2017-11-01

    Full Text Available 4-Benzyl-1,2,4-triazin-3,5(2H,4H-dione (3-benzyl-6-azauracil, 2, and 2,4-dibenzyl-1,2,4-triazin-3,5(2H,4H-dione (1,3-dibenzyl-6-azauracil, 3 were synthesized by the reaction of 1,2,4-triazin-3,5(2H,4H-dione (6-azauracil, 1 with benzyl bromide and potassium carbonate in dry acetone via the 18-crown-6-ether catalysis. In these reaction methods, we developed more convenient and efficient methodologies to afford compounds 2 and 3 in good yields. These compounds were characterized by 1H- and 13C-NMR, MS spectrum, IR spectroscopy and elemental analysis. The structure of 2 was verified by 2D-NMR measurements, including gHSQC and gHMBC measurements. A single-crystal X-ray diffraction experiment indicated that compound 3, with the molecular formula C17H15N3O2, crystallized from a CH3OH/CH2Cl2 diffusion solvent system in a monoclinic space group P21/c with a = 13.7844(13, b = 8.5691(8, c = 13.0527(12 Å, β = 105.961(2°, V = 1482.3(2 Å3, Z = 4, resulting in a density Dcalc of 1.314 g/cm3. The crystal structure of compound 3 is tightly stabilized by contact with five other molecules from the six short contacts formed by intermolecular C−O···H−Car, C−H···Car, and weakly π···π stacking interactions. The dihedral angle 31.90° is formed by the mean planes of the benzene rings of the N-2 and N-4 benzyl groups.

  13. Single-step functionalization of vertically aligned MWCNTs with Cu and Ni by chemical reduction of copper and nickel acetyl acetonate in benzyl alcohol

    OpenAIRE

    Ilari Gabriele et al.

    2014-01-01

    We report a one-step functionalization reaction of forests of vertically aligned multi-walled carbon nanotubes (MWCNTs) with Cu or Ni nanoparticles. The benzyl alcohol assisted deposition reaction reduces copper or nickel acetyl acetonate to metallic homogeneously distributed nanoparticles and a 1 mu m thick metallic capping layer normal to the MWCNT forests. Scanning electron microscopy and transmission electron microscopy images reveal a trimodal diameter regime for the Cu nanoparticles and...

  14. Transition metal-free oxidation of benzylic alcohols to carbonyl compounds by hydrogen peroxide in the presence of acidic silica gel

    Directory of Open Access Journals (Sweden)

    Hossein Ghafuri

    2015-01-01

    Full Text Available Oxidation of alcohols to carbonyl compounds has become an important issue in the process industry as well as many other applications. In this method, various benzylic alcohols were successfully converted to corresponding aldehydes and ketones under transition metal-free condition using hydrogen peroxide in the presence of some amount of catalytic acidic silica gel. Silica gel is inexpensive and available. One of the most important features of this method is its short reaction time.

  15. Synthesis, characterization, computational studies and biological evaluation of S-benzyl-β-N-[3-(4-hydroxy-3-methoxy-phenylallylidene)]dithiocarbazate

    Science.gov (United States)

    Bhat, Rayees A.; Kumar, D.; Malla, Manzoor A.; Bhat, Sami U.; Khan, Md Shahzad; Manzoor, Ovais; Srivastava, Anurag; Naikoo, Rawoof A.; Mohsin, Mohd; Mir, Muzzaffar A.

    2018-03-01

    S-Benzyl-β-N-[3-(4-hydroxy-3-methoxy-phenylallylidene)]dithiocarbazate (HL1), Schiff base of S-benzyl dithiocarbazate, was synthesized by 1:1 condensation between S-benzyl dithiocarbazate and 4-hydroxy-3-methoxy cinnamaldehyde. The nitrogen-sulfur Schiff base (HL1) was characterized by Mass, FT-IR, H1-NMR, Raman, and UV-VIS spectroscopic techniques. Theoretical quantum chemical calculations were performed using DFT in combination with B3LYP exchange correlation functional and 6-311++ G (d, p) basis sets level. The calculated values of chemical potential (μ), HOMO-LUMO energy gap, chemical hardness, softness (S), ionization energy (IE), electron affinity (EA), dipole moment (D) and relative stabilization energy of the compound were 0.14881 eV, 0.12542 eV, 0.06271 eV, 3.37299 eV, -0.21152 eV, -0.08610 eV, 4.4090 Debye and -1753.350 eV respectively. Theoretically calculated parameters like H1-NMR, FT-IR, UV-VIS, Raman, electrostatic potential and HOMO-LUMO energy gap are in good agreement with experimental results. Also, in-vitro cytotoxicity studies were done against two habitually infection causing bacteria strains including gram-positive (S. aureus) and gram-negative (E. coli) for antibacterial activity. The results showed appreciable biological activity and the activity increased with increase in dose.

  16. Direct determination of rate constants for coupling between aromatic radical anions and alkyl and benzyl radicals by laser-flash photolysis

    DEFF Research Database (Denmark)

    Lund, T.; Christensen, P.; Wilbrandt, Robert Walter

    2003-01-01

    generated by a photoinduced electron transfer reaction between the aromatic compound A and the alkyl or benzyl triphenylborate anion RB(Ph)(3)(-). For the first time the rate constants of the coupling reaction between methyl and benzyl radicals with aromatic radical anions have been obtained. For all...... the measured coupling rate constants an average value of k(1) = 1.9 x 10(9) M-1 s(-1) was found with a relatively small variation in the coupling rates (0.8-2.9 x 10(9) M-1 s(-1)). The results demonstrate that the coupling rate k(1) is insensitive to changes in the steric and electronic properties......Coupling rates between the radicals methyl, n-, sec-, tert-butyl and benzyl (R-.) and the aromatic radical anions of 1,4-dicyanonaphthalene, 9,10-dicyanoanthracene and fluorenone (A(-.)) have been obtained using a new laser-flash photolysis method. The radicals R-. and the radical anions A(-.) were...

  17. Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases

    Science.gov (United States)

    Min, Tongpil; Kasahara, Hiroyuki; Bedgar, Diana L.; Youn, Buhyun; Lawrence, Paulraj K.; Gang, David R.; Halls, Steven C.; Park, HaJeung; Hilsenbeck, Jacqueline L.; Davin, Laurence B.; hide

    2003-01-01

    Despite the importance of plant lignans and isoflavonoids in human health protection (e.g. for both treatment and prevention of onset of various cancers) as well as in plant biology (e.g. in defense functions and in heartwood development), systematic studies on the enzymes involved in their biosynthesis have only recently begun. In this investigation, three NADPH-dependent aromatic alcohol reductases were comprehensively studied, namely pinoresinol-lariciresinol reductase (PLR), phenylcoumaran benzylic ether reductase (PCBER), and isoflavone reductase (IFR), which are involved in central steps to the various important bioactive lignans and isoflavonoids. Of particular interest was in determining how differing regio- and enantiospecificities are achieved with the different enzymes, despite each apparently going through similar enone intermediates. Initially, the three-dimensional x-ray crystal structures of both PLR_Tp1 and PCBER_Pt1 were solved and refined to 2.5 and 2.2 A resolutions, respectively. Not only do they share high gene sequence similarity, but their structures are similar, having a continuous alpha/beta NADPH-binding domain and a smaller substrate-binding domain. IFR (whose crystal structure is not yet obtained) was also compared (modeled) with PLR and PCBER and was deduced to have the same overall basic structure. The basis for the distinct enantio-specific and regio-specific reactions of PCBER, PLR, and IFR, as well as the reaction mechanism and participating residues involved (as identified by site-directed mutagenesis), are discussed.

  18. Catalytic Performance of Co3O4 on Different Activated Carbon Supports in the Benzyl Alcohol Oxidation

    Directory of Open Access Journals (Sweden)

    Misael Cordoba

    2017-12-01

    Full Text Available Co3O4 particles were supported on a series of activated carbons (G60, CNR, RX3, and RB3. Incipient wetness method was used to prepare these catalysts. The effect of the structural and surface properties of the carbonaceous supports during oxidation of benzyl alcohol was evaluated. The synthetized catalysts were characterized via IR, TEM, TGA/MS, XRD, TPR, AAS, XPS, and N2 adsorption/desorption isotherm techniques. Co3O4/G60 and Co3O4/RX3 catalysts have high activity and selectivity on the oxidation reaction reaching conversions above 90% after 6 h, without the presence of promoters. Catalytic performances show that differences in chemistry of support surface play an important role in activity and suggest that the presence of different ratios of species of cobalt and oxygenated groups on surface in Co3O4/G60 and Co3O4/RX3 catalysts, offered a larger effect synergic between both active phase and support increasing their catalytic activity when compared to the other tested catalysts.

  19. Photosensized Controlling Benzyl Methacrylate-Based Matrix Enhanced Eu3+ Narrow-Band Emission for Fluorescence Applications

    Directory of Open Access Journals (Sweden)

    Mei-Hsiang Lin

    2012-03-01

    Full Text Available This study synthesized a europium (Eu3+ complex Eu(DBM3Cl-MIP (DBM = dibenzoyl methane; Cl-MIP = 2-(2-chlorophenyl-1-methyl-1H-imidazo[4,5-f][1,10]phenanthroline dispersed in a benzyl methacrylate (BMA monomer and treated with ultraviolet (UV light for polymerization. Spectral results showed that the europium complex containing an antenna, Cl-MIP, which had higher triplet energy into the Eu3+ energy level, was an energetically enhanced europium emission. Typical stacking behaviors of π–π interactions between the ligands and the Eu3+-ion were analyzed using single crystal X-ray diffraction. Regarding the luminescence performance of this europium composite, the ligand/defect emission was suppressed by dispersion in a poly-BMA (PBMA matrix. The underlying mechanism of the effective enhancement of the pure Eu3+ emission was attributed to the combined effects of structural modifications, defect emissions, and carrier charge transfer. Fluorescence spectra were compared to the composite of optimized Eu3+ emission where they were subsequently chelated to four metal ions via carboxylate groups on the BMA unit. The optical enhanced europium composite clearly demonstrated highly efficient optical responses and is, therefore a promising application as an optical detection material.

  20. Substitution Effects and Linear Free Energy Relationships During Reduction of 4- Benzoyl-n-(4-substituted Benzyl)pyridinium Cations

    Science.gov (United States)

    Leventis, Nicholas; Zhang, Guo-Hui; Rawashdeh, Abdel-Monem M.; Sotiriou-Leventis, Chariklia; Gray, Hugh R. (Technical Monitor)

    2003-01-01

    In analogy to 4-(para-substituted benzoyl)-N-methylpyridinium cations (1-X's), the title species (2-X's, -X = -OCH3, -CH3, -H, -Br, -COCH3, -NO2) undergo two reversible, well-separated (E(sub 1/2) greater than or equal to 650 mV) one-electron reductions. The effect of substitution on the reduction potentials of 2-X's is much weaker than the effect of the same substituents on 1-X's: the Hammett rho-values are 0.80 and 0.93 for the 1st- and 2nd-e reduction of 2-X's vs. 2.3 and 3.3 for the same reductions of 1-X's, respectively. Importantly, the nitro group of 2-NO2 undergoes reduction before the 2nd-e reduction of the 4-benzoylpyridinium system. These results suggest that the redox potentials of the 4-benzoylpyridinium system can be course-tuned via p-benzoyl substitution and fine-tuned via para-benzyl substitution. Introducing the recently derived substituent constant of the -NO2(sup)- group (sigma para-NO2(sup)- = -0.97) yields an excellent correlation for the 3rd-e reduction of 2- NO2 (corresponding to the reduction of the carbonyl group) with the 2nd-e reduction of the other 2-X's, and confirms the electron donating properties of -NO2(sup)-.

  1. The Mechanism by Which Dodecyl Dimethyl Benzyl Ammonium Chloride Increased the Toxicity of Chlorpyrifos to Spodoptera exigua

    Directory of Open Access Journals (Sweden)

    Li Cui

    2017-07-01

    Full Text Available Beet armyworm, Spodoptera exigua (Hübner is one of the most destructive pests that causes significant losses in crops. Unfortunately, S. exigua have developed resistance toward the majority of insecticides. Synergists may provide an important choice to deal with the resistance problems. Dodecyl dimethyl benzyl ammonium chloride (DDBAC is a cationic surfactant, which displayed enhancement effect when combined with chlorpyrifos against S. exigua, giving enhancement factors of 1.50 and 1.57 at the concentrations of 90 and 810 mg L−1. In order to clarify the possible mechanisms, we investigate the effects of DDBAC on detoxification enzymes. However, DDBAC showed no inhibition on these enzymes activities. Meanwhile, scanning electron microscope images indicated DDBAC did not affect the cuticle super micro structure of S. exigua. The alterations in cuticular penetration rate have also been observed; indeed, it has been suggested that synergism is obtained by an acceleration of insecticide penetration through the cuticle. The chlorpyrifos penetration increased sharply when combined with 90 and 810 mg L−1 DDBAC, with only 12.6 and 8.5% of the initial chlorpyrifos recovered by external rinsing after 8 h. In contrast, when there was no DDBAC, more than 23.3% of the initial dose was recovered after 8 h.

  2. Demonstration of Improved Charge Transfer in Graphene/Au Nanorods Plasmonic Hybrids Stabilized by Benzyl Thiol Linkers

    Directory of Open Access Journals (Sweden)

    Giuseppe Valerio Bianco

    2016-01-01

    Full Text Available Hybrids based on graphene decorated with plasmonic gold (Au nanostructures are being investigated as possible materials combination to add to graphene functionalities of tunable plasmon resonance and enhanced absorption at selected wavelength in the visible-near-infrared region of the spectrum. Here, we report a solution drop-casting approach for fabricating stable hybrids based on chemical vapor deposition (CVD graphene and Au nanorods, which are able to activate effective charge transfer from graphene. We demonstrate that CVD graphene functionalization by benzyl thiol (BZT provides the linker to strong anchoring, via S-Au bonds, Au nanorods to graphene. Optical measurements by spectroscopic ellipsometry give evidence of the introduction of plasmon resonances at 1.85 and 2.25 eV in the Au nanorods/BZT/graphene hybrids, which enable surface enhanced Raman scattering (SERS detection. Furthermore, an effective electron transfer from graphene to Au nanorods, resulting in an enhancement of p-type doping of graphene with a consequent decrease of its sheet resistance, is probed by Raman spectroscopy and corroborated by electrical measurements.

  3. Seed priming with sorghum extracts and benzyl aminopurine improves the tolerance against salt stress in wheat (Triticum aestivumL.).

    Science.gov (United States)

    Bajwa, Ali Ahsan; Farooq, Muhammad; Nawaz, Ahmad

    2018-03-01

    Salt stress impedes the productivity of wheat ( Triticum aestivum L.) in many parts of the world. This study evaluated the potential role of benzyl aminopurine (BAP) and sorghum water extract (SWE) in improving the wheat performance under saline conditions. Seeds were primed with BAP (5 mg L -1 ), SWE (5% v/v), BAP + SWE, and distilled water (hydropriming). Soil filled pots maintained at the soil salinity levels of 4 and 10 dS m -1 were used for the sowing of primed and non-primed seeds. Salt stress suppressed the wheat growth; seed priming treatments significantly improved the wheat growth under optimal and suboptimal conditions. Total phenolics, total soluble sugars and proteins, α-amylase activity, chlorophyll contents, and tissue potassium ion (K + ) contents were increased by seed priming under salt stress; while, tissue sodium ion (Na + ) contents were decreased. Seed priming with SWE + BAP was the most effective in this regard. Under salt stress, the tissue Na + contents were reduced by 5.78, 28.3, 32.2, 36.7% by hydropriming, seed priming with SWE, seed priming with BAP, and seed priming with SWE + BAP, respectively over the non-primed control. Effectiveness of seed priming techniques followed the order SWE + BAP > BAP > SWE > Hydropriming. In conclusion, seed priming with SWE + BAP may be opted to improve the tolerance against salt stress in wheat.

  4. The plasticizer butyl benzyl phthalate induces genomic changes in rat mammary gland after neonatal/prepubertal exposure

    Directory of Open Access Journals (Sweden)

    Lamartiniere Coral A

    2007-12-01

    Full Text Available Abstract Background Phthalate esters like n-butyl benzyl phthalate (BBP are widely used plasticizers. BBP has shown endocrine-disrupting properties, thus having a potential effect on hormone-sensitive tissues. The aim of this study is to determine the effect of neonatal/prepubertal exposure (post-natal days 2–20 to BBP on maturation parameters and on the morphology, proliferative index and genomic signature of the rat mammary gland at different ages of development (21, 35, 50 and 100 days. Results Here we show that exposure to BBP increased the uterine weight/body weight ratio at 21 days and decreased the body weight at time of vaginal opening. BBP did not induce significant changes on the morphology of the mammary gland, but increased proliferative index in terminal end buds at 35 days and in lobules 1 at several ages. Moreover, BBP had an effect on the genomic profile of the mammary gland mainly at the end of the exposure (21 days, becoming less prominent thereafter. By this age a significant number of genes related to proliferation and differentiation, communication and signal transduction were up-regulated in the glands of the exposed animals. Conclusion These results suggest that BBP has an effect in the gene expression profile of the mammary gland.

  5. 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione.

    Science.gov (United States)

    Karczmarzyk, Zbigniew; Pitucha, Monika; Wysocki, Waldemar; Pachuta-Stec, Anna; Stańczuk, Andrzej

    2013-02-01

    The title compound, C(11)H(13)N(3)S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intra-molecular C-H⋯S contact. In the crystal, pairs of N-H⋯S hydrogen bonds link mol-ecules into inversion dimers. π-π inter-actions are observed between the triazole and benzene rings, with centroid-centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively.

  6. 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H-thione

    Directory of Open Access Journals (Sweden)

    Zbigniew Karczmarzyk

    2013-02-01

    Full Text Available The title compound, C11H13N3S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2:0.23 (2 for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3 Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18 and 86.56 (49° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15° and this conformation is stabilized by an intramolecular C—H...S contact. In the crystal, pairs of N—H...S hydrogen bonds link molecules into inversion dimers. π–π interactions are observed between the triazole and benzene rings, with centroid–centroid separations of 3.547 (4 and 3.544 (12 Å for components A and B, and slippages of 0.49 (6 and 0.58 (15 Å, respectively.

  7. [{sup 14}C]Benzyl acetate is a potential radiotracer for the measurement of glial metabolism in the rat brain

    Energy Technology Data Exchange (ETDEWEB)

    Momosaki, Sotaro [Division of Health Sciences, Graduate School of Medicine, Osaka University, Osaka 565-0871 (Japan)], E-mail: momosaki@sahs.med.osaka-u.ac.jp; Hosoi, Rie; Sanuki, Tomoya [Division of Health Sciences, Graduate School of Medicine, Osaka University, Osaka 565-0871 (Japan); Todoroki, Kenichiro; Yamaguchi, Masatoshi [Faculty of Pharmaceutical Sciences, Fukuoka University, Nanakuma, Johnan-ku, Fukuoka 814-0180 (Japan); Gee, Antony [GlaxoSmithkline, Clinical Research Unit, ACCI, CB2 2GC Cambridge (United Kingdom); Department of Chemistry, Imperial College of London, SW7 2AZ London (United Kingdom); Inoue, Osamu [Division of Health Sciences, Graduate School of Medicine, Osaka University, Osaka 565-0871 (Japan)

    2007-11-15

    In order to develop a suitable radiotracer for the measurement of glial metabolism, we synthesized four different types of ester derivatives of [{sup 14}C]acetate, namely, [{sup 14}C]phenyl acetate, [{sup 14}C]para-nitrophenyl acetate, [{sup 14}C]2,4-dinitrophenyl acetate and [{sup 14}C]benzyl acetate ([{sup 14}C]BA), and evaluated their potencies in rats. Among the derivatives, the highest brain uptake at 30 s postinjection was observed for [{sup 14}C]BA, which was more than 23 times higher than that of [{sup 14}C]acetate itself. A long-term retention of [{sup 14}C]BA radioactivity in the brain was observed, whereas rapid clearance of radioactivity was seen in the heart. [{sup 14}C]BA was rapidly hydrolyzed in the intact rat brain, and less than 5% of radiolabeled parent was observed 1 min after the injection. Radiochemical analysis using thin-layer chromatography revealed that [{sup 14}C]BA was rapidly converted to [{sup 14}C]glutamine and [{sup 14}C]glutamate in the cortex within 10 min after injection. Furthermore, the uptake of [{sup 14}C]BA was significantly decreased following microinjection of fluorocitrate, a selective glial toxin. These results strongly suggest that [{sup 14}C]BA may be a useful radiotracer for the measurement of glial metabolism in the intact rat brain.

  8. Quantitative Analysis of Benzyl Isothiocyanate inSalvadora persicaExtract and Dental Care Herbal Formulations Using Reversed Phase C18 High-Performance Liquid Chromatography Method.

    Science.gov (United States)

    Abdel-Kader, Maged Saad; Kamal, Y T; Alam, Prawez; Alqarni, Mohammed Hamed; Foudah, Ahmed Ibrahim

    2017-10-01

    Benzyl isothiocyanate is the active antimicrobial agent in Salvadora persica (siwak) widely used in Islamic countries for oral hygiene. Quantification of benzyl isothiocyanate in the ethanol extract of S. persica and some dental care herbal formulations labeled to contain siwak. Simple and sensitive high-performance liquid chromatography method was designed. Separation was achieved on reverse phase C 18 (250 mm × 4.6 mm, 5 μ) column with a mobile phase comprising acetonitrile and water (1:1). The detection was carried out at 190 nm using ultra violet-visible detector. The flow rate was kept at 1 mL/min. A sharp and well-defined peak was obtained at the retention time of 9.322 ± 0.3 min. Linear regression analysis data for the calibration plot showed a good linear relationship between response and concentration in the range of 0.5-500 μg/mL with a regression coefficient ( r 2 ) of 0.9977. The method was validated for accuracy, precision, robustness, and sensitivity. All the parameters examined met the current recommendations for the International Conference on Harmonization guidelines for method validation. The method was applied for the quantification of benzyl isothiocyanate in siwak extract, dental care powder, mouth wash, and toothpaste claimed to contain siwak. The developed method was found specific, simple, selective, and reliable for routine use in quality control analysis of different commercially available herbal care products. A simple, accurate and precise method was developed for the analysis of the antimicrobial agent benzyl isothiocyanate in Salvadora persica (Siwak) extract and selected dental care herbal formulations using RP18 HPLCAmount of benzyl isothiocyanate will indicate the efficacy of Siwak productsThe method subject to ICH validation guidelines. Abbreviations used: RP18: Reversed phase C18, HPLC: High performance liquid chromatography, UV: Ultra violet, r 2 : regression coefficient, ICH: international conference on harmonization, TLC

  9. Selective liquid phase oxidation of benzyl alcohol to benzaldehyde by tert-butyl hydroperoxide over γ-Al2O3 supported copper and gold nanoparticles

    International Nuclear Information System (INIS)

    Ndolomingo, Matumuene Joe; Meijboom, Reinout

    2017-01-01

    Highlights: • Cu and Au on γ-Al 2 O 3 catalysts were prepared and characterized. • Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide in the absence of any solvent using the prepared catalysts. • The as prepared catalysts exhibited good performance in terms of conversion and selectivity towards benzaldehyde. • The kinetics of the reaction was investigated; k app was proportional to the amount of nano catalyst and oxidant present in the system. • The catalysts was recycled and reused with neither significant loss of activity nor selectivity. - Abstract: Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide (TBHP) in the absence of any solvent using γ-Al 2 O 3 supported copper and gold nanoparticles. Li 2 O and ionic liquids were used as additive and stabilizers for the synthesis of the catalysts. The physico-chemical properties of the catalysts were characterized by atomic absorption spectroscopy (AAS), X-ray diffraction spectroscopy (XRD), N 2 absorption/desorption (BET), transmission electron microscopy (TEM), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and temperature programmed reduction (TPR), whereas, the oxidation reaction was followed by gas chromatography with a flame ionization detector (GC-FID). The as prepared catalysts exhibited good catalytic performance in terms of conversion and selectivity towards benzaldehyde. The performance of the Au-based catalysts is significantly higher than that of the Cu-based catalysts. For both Cu and Au catalysts, the conversion of benzyl alcohol increased as the reaction proceeds, while the selectivity for benzaldehyde decreased. Moreover, the catalysts can be easily recycled and reused with neither significant loss of activity nor selectivity. A kinetic study for the Cu and Au-catalyzed oxidation of benzyl alcohol to benzyldehyde is reported. The rate at which the oxidation of benzyl alcohol is occurring as a function of

  10. Synthesis and evaluation of radioiodinated (S,S)-2-({alpha}-(2-iodophenoxy)benzyl)morpholine for imaging brain norepinephrine transporter

    Energy Technology Data Exchange (ETDEWEB)

    Kanegawa, Naoki; Kimura, Hiroyuki; Sugita, Taku; Kajiyama, Satomi; Kuge, Yuji; Saji, Hideo [Kyoto University, Department of Patho-Functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Sakyo-ku, Kyoto (Japan); Kiyono, Yasushi [Kyoto University, Radioisotopes Research Laboratory, Kyoto University Hospital, Faculty of Medicine, Sakyo-ku, Kyoto (Japan); Kawashima, Hidekazu [Kyoto University, Department of Nuclear Medicine and Diagnostic Imaging, Graduate School of Medicine, Sakyo-ku, Kyoto (Japan); Ueda, Masashi [Kyoto Prefectural University of Medicine, Radioisotope Laboratory, Sakyo-ku, Kyoto (Japan)

    2006-06-15

    Abnormality of the brain norepinephrine transporter (NET) has been reported in several psychiatric and neuronal disorders. Since NET is an important target for the diagnosis of these diseases, the development of radiopharmaceuticals for imaging of brain NET has been eagerly awaited. In this study, we synthesized (S,S)-2-({alpha}-(2-iodophenoxy)benzyl)morpholine [(S,S)-IPBM], a derivative of reboxetine iodinated at position 2 of the phenoxy ring, and evaluated its potential as a radiopharmaceutical for imaging brain NET using SPECT. (S,S)-{sup 123/125}I-IPBM was synthesized in a halogen exchange reaction. The affinity and selectivity of (S,S)-IPBM for NET was measured by assaying the displacement of {sup 3}H-nisoxetine and (S,S)-{sup 125}I-IPBM from the binding site in rat brain membrane, respectively. The biodistribution of (S,S)-{sup 125}I-IPBM was also determined in rats. Furthermore, SPECT studies with (S,S)-{sup 123}I-IPBM were carried out in the common marmoset. (S,S)-{sup 125}I-IPBM was prepared with high radiochemical yields (65%) and high radiochemical purity (>98%). (S,S)-IPBM showed high affinity and selectivity for NET in the binding assay experiments. In biodistribution experiments, (S,S)-{sup 125}I-IPBM showed rapid uptake in the brain, and the regional cerebral distribution was consistent with the density of NET. The administration of nisoxetine, a selective NET-binding agent, decreased the accumulation of (S,S)-{sup 125}I-IPBM in the brain, but the administration of selective serotonin transporter and dopamine transporter binding agents caused no significant changes in the accumulation. Moreover, (S,S)-{sup 123}I-IPBM allowed brain NET imaging in the common marmoset with SPECT. These results suggest that (S,S)-{sup 123}I-IPBM is a potential SPECT radiopharmaceutical for imaging brain NET. (orig.)

  11. Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives

    Directory of Open Access Journals (Sweden)

    Mohammed Mahbubul Matin

    2016-08-01

    Full Text Available Benzyl α-l-rhamnopyranoside 4, obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound 5 which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside 7 in reasonable yield. Di-O-acetyl derivative of benzoate 7 was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR of the designed compounds was performed along with the prediction of activity spectra for substances (PASS training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides 5 and 6 exhibited slight distortion from regular 1C4 conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides 4–8 were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives 4–8 were 0.49 < Pa < 0.60 (where Pa is probability ‘to be active’ as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives 4–8 were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures 4–8 have not been reported with antimicrobial activity, making it a possible valuable lead compound.

  12. Muscarinic receptors in the prenatal mouse embryo. Comparison of M35-immunohistochemistry with [3H]quinuclidinyl benzylate autoradiography.

    Science.gov (United States)

    Lammerding-Köppel, M; Greiner-Schröder, A; Drews, U

    1995-04-01

    Muscarinic cholinergic receptors are widespread in nervous tissue and smooth muscle or paracrine epithelial cells of various organs. In the embryo, muscarinic receptors are transitorily expressed in the early blastoderm and later on in blastemic tissues during morphogenesis. Recently, a monoclonal antibody (M35) against muscarinic receptor from calf brain became available. In the present study the use of M35-immunohistochemistry is compared to autoradiographic localization of muscarinic binding sites in the mouse embryo. The aim of the study is to test the suitability of the antibody for localization of muscarinic receptors in embryonic tissues. For autoradiography whole-body sagittal cryostat sections of the 17- and 18-day mouse embryo were covered with LKB-Ultrofilm after incubation with the radioactive ligand [3H] quinuclidinyl benzylate (QNB). For immunohistochemistry cryostat sections of formalin fixed tissues were used. In general, all tissues exhibiting ligand binding were also recognized by the antibody. M35-immunohistochemistry resulted in higher spatial resolution of receptor localization than [3H]QNB autoradiography. Definitive muscarinic receptors were observed in smooth muscle and the epithelial lining of the vasuclar, intestinal, respiratory and urinary system, in the brain, spinal cord and peripheral nerves. The embryonic type of the muscarinic receptor was detected in the mesothelium of lung and liver, in the nephrogenic blastema of the metanephros, and in lung mesenchyme. A large amount of embryonic muscarinic receptors was found in the remnants of the notochord and in the nucleus pulposus of the developing vertebral column. A function in morphogenesis is discussed of the embryonic muscarinic receptor.

  13. The Synthesis and Characterization of Hydroxyapatite-β-Alanine Modified by Grafting Polymerization of γ-Benzyl-L-glutamate-N-carboxyanhydride

    Directory of Open Access Journals (Sweden)

    Yukai Shan

    2013-11-01

    Full Text Available In this study, hydroxyapatite (HAP was surface-modified by the addition of β-alanine (β-Ala, and the ring-opening polymerization of γ-benzyl-L-glutamate-N-carboxy-anhydride (BLG-NCA was subsequently initiated. HAP containing surface poly-γ-benzyl-L-glutamates (PBLG was successfully prepared in this way. With the increase of PBLG content in HAP-PBLG, the solubility of HAP-PBLG increased gradually and it was ultimately soluble in chloroform. HAP-PLGA with surface carboxyl groups was obtained by the catalytic hydrogenation of HAP-PBLG. In the process of HAP modification, the morphology changes from rod to sheet and from flake to needle. The effect of BLG-NCA concentration on the character of hydroxyapatite-β-alanine-poly(γ-benzyl-L-glutamate (HAP-PBLG was investigated. The existence of amino acids on the HAP surfaces was confirmed in the resulting Fourier transform infrared (FTIR spectra. The resulting powder X-ray diffraction patterns indicated that the crystallinity of HAP decreased when the ratio of BLG-NCA/HAP-NH2 increased to 20/1. Transmission electron microscopy (TEM indicated that the particle size of HAP-PBLG decreased significantly and that the resulting particles appeared less agglomerated relative to that of the HAP-NH2 crystals. Furthermore, 1H-NMR spectra and FTIR spectra revealed that hydroxyapatite-β-alanine-poly (L-glutamic acid (HAP-PLGA was able to successfully bear carboxylic acid groups on its side chains.

  14. The synthesis and characterization of hydroxyapatite-β-alanine modified by grafting polymerization of γ-benzyl-L-glutamate-N-carboxyanhydride.

    Science.gov (United States)

    Shan, Yukai; Qin, Yuyue; Chuan, Yongming; Li, Hongli; Yuan, Minglong

    2013-11-13

    In this study, hydroxyapatite (HAP) was surface-modified by the addition of β-alanine (β-Ala), and the ring-opening polymerization of γ-benzyl-L-glutamate-N-carboxy-anhydride (BLG-NCA) was subsequently initiated. HAP containing surface poly-γ-benzyl-L-glutamates (PBLG) was successfully prepared in this way. With the increase of PBLG content in HAP-PBLG, the solubility of HAP-PBLG increased gradually and it was ultimately soluble in chloroform. HAP-PLGA with surface carboxyl groups was obtained by the catalytic hydrogenation of HAP-PBLG. In the process of HAP modification, the morphology changes from rod to sheet and from flake to needle. The effect of BLG-NCA concentration on the character of hydroxyapatite-β-alanine-poly(γ-benzyl-L-glutamate) (HAP-PBLG) was investigated. The existence of amino acids on the HAP surfaces was confirmed in the resulting Fourier transform infrared (FTIR) spectra. The resulting powder X-ray diffraction patterns indicated that the crystallinity of HAP decreased when the ratio of BLG-NCA/HAP-NH2 increased to 20/1. Transmission electron microscopy (TEM) indicated that the particle size of HAP-PBLG decreased significantly and that the resulting particles appeared less agglomerated relative to that of the HAP-NH₂ crystals. Furthermore, ¹H-NMR spectra and FTIR spectra revealed that hydroxyapatite-β-alanine-poly (L-glutamic acid) (HAP-PLGA) was able to successfully bear carboxylic acid groups on its side chains.

  15. Investigation of the mode of binding of a novel series of N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamides to the hepatitis C virus polymerase

    Energy Technology Data Exchange (ETDEWEB)

    Gentles, Robert G.; Sheriff, Steven; Beno, Brett R.; Wan, Changhong; Kish, Kevin; Ding, Min; Zheng, Xiaofan; Chupak, Louis; Poss, Michael A.; Witmer, Mark R.; Morin, Paul; Wang, Ying-Kai; Rigat, Karen; Lemm, Julie; Voss, Stacey; Liu, Mengping; Pelosi, Lenore; Roberts, Susan B.; Gao, Min; Kadow, John F. (BMS)

    2013-11-20

    Structure based rationales for the activities of potent N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamide inhibitors of the hepatitis C viral polymerase are described herein. These compounds bind to the hepatitis C virus non-structural protein 5B (NS5B), and co-crystal structures of select examples from this series with NS5B are reported. Comparison of co-crystal structures of a potent analog with both NS5B genotype 1a and genotype 1b provides a possible explanation for the genotype-selectivity observed with this compound class and suggests opportunities for the further optimization of the series.

  16. Silica functionalized Cu(II) acetylacetonate Schiff base complex: An efficient catalyst for the oxidative condensation reaction of benzyl alcohol with amines

    Science.gov (United States)

    Anbarasu, G.; Malathy, M.; Karthikeyan, P.; Rajavel, R.

    2017-09-01

    Silica functionalized Cu(II) acetylacetonate Schiff base complex via the one pot reaction of silica functionalized 3-aminopropyltriethoxysilane with acetyl acetone and copper acetate has been reported. The synthesized material was well characterized by analytical techniques such as FT-IR, UV-DRS, XRD, SEM-EDX, HR-TEM, EPR, ICP-AES and BET analysis. The characterization results confirmed the grafting of Cu(II) Schiff base complex on the silica surface. The catalytic activity of synthesized silica functionalized Cu(II) acetylacetonate Schiff base complex was evaluated through the oxidative condensation reaction of benzyl alcohol to imine.

  17. Practical metal-free C(sp(3))-H functionalization: construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates.

    Science.gov (United States)

    Xie, Zhiyu; Liu, Lei; Chen, Wenfang; Zheng, Hongbo; Xu, Qingqing; Yuan, Huiqing; Lou, Hongxiang

    2014-04-07

    Described is a practical and universal CH functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3 CClO4 . The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and CH compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. The reduction of nitrate, nitrite and hydroxylamine to ammonia by enzymes from Cucurbita pepo L. in the presence of reduced benzyl viologen as electron donor

    Science.gov (United States)

    Cresswell, C. F.; Hageman, R. H.; Hewitt, E. J.; Hucklesby, D. P.

    1965-01-01

    1. Enzyme systems from Cucurbita pepo have been shown to catalyse the reduction of nitrite and hydroxylamine to ammonia in yields about 90–100%. 2. Reduced benzyl viologen serves as an efficient electron donor for both systems. Activity of the nitrite-reductase system is directly related to degree of dye reduction when expressed in terms of the function for oxidation–reduction potentials, but appears to decrease to negligible activity below about 9% dye reduction. 3. NADH and NADPH alone produce negligible nitrite loss, but NADPH can be linked to an endogenous diaphorase system to reduce nitrite to ammonia in the presence of catalytic amounts of benzyl viologen. 4. The NADH– or NADPH–nitrate-reductase system that is also present can accept electrons from reduced benzyl viologen, but shows relationships opposite to that for the nitrite-reductase system with regard to effect of degree of dye reduction on activity. The product of nitrate reduction may be nitrite alone, or nitrite and ammonia, or ammonia alone, according only to the degree of dye reduction. 5. The relative activities of nitrite-reductase and hydroxylamine-reductase systems show different relationships with degree of dye reduction and may become reversed in magnitude when effects of degree of dye reduction are tested over a suitable range. 6. Nitrite severely inhibits the rate of reduction of hydroxylamine without affecting the yield of ammonia as a percentage of total substrate loss, but hydroxylamine has a negligible effect on the activity of the nitrite-reductase system. 7. The apparent Km for nitrite (1 μm) is substantially less than that for hydroxylamine, for which variable values between 0·05 and 0·9mm (mean 0·51 mm) have been observed. 8. The apparent Km values for reduced benzyl viologen differ for the nitrite-reductase and hydroxylamine-reductase systems: 60 and 7·5 μm respectively. 9. It is concluded that free hydroxylamine may not be an intermediate in the reduction of nitrite

  19. N3S-ligated Copper(II) Complex Catalyzed Selective Oxidation of Benzylic Alcohols to Aldehydes under Mild Reaction Conditions

    Energy Technology Data Exchange (ETDEWEB)

    Dharmalingam, Sivanesan; Yoon, Sungho; Park, Gyoosoon [Kookmin Univ., Seoul (Korea, Republic of); Koo, Eunhae [Korea Institute of Ceramic Engineering and Technology, Seoul (Korea, Republic of)

    2014-03-15

    A Cu(II) complex with an three nitrogens and one sulfur coordination environment was synthesized and characterized. Its redox potential was observed at 0.483 V vs. NHE, very similar to that of a Cu-containing fungal enzyme, galactose oxidase, which catalyzes the oxidation of alcohols to corresponding aldehydes with the concomitant reduction of molecular oxygen to water. The Cu(II) complex selectively oxidizes the benzylic alcohols using TEMPO/O{sub 2} under mild reaction conditions to corresponding aldehydes without forming any over-oxidation product. Moreover, the catalyst can be recovered and reused multiple times for further oxidation reactions, thus minimizing the waste generation.

  20. Zeolite-encapsulated Co(II), Mn(II), Cu(II) and Cr(III) salen complexes as catalysts for efficient selective oxidation of benzyl alcohol

    Science.gov (United States)

    Li, F. H.; Bi, H.; Huang, D. X.; Zhang, M.; Song, Y. B.

    2018-01-01

    Co(II), Mn(II), Cu(II) and Cr(III) salen type complexes were synthesized in situ in Y zeolite by the reaction of ion-exchanged metal ions with the flexible ligand molecules that had diffused into the cavities. Data of characterization indicates the formation of metal salen complexes in the pores without affecting the zeolite framework structure, the absence of any extraneous species and the geometry of encapsulated complexes. The catalytic activity results show that Cosalcyen Y exhibited higher catalytic activity in the water phase selective oxidation of benzyl alcohol, which could be attributed to their geometry and the steric environment of the metal actives sites.

  1. Data on the kinetics of the deactivation of a 10% Cu/0. 5% Cr/sub 2/O/sub 3//asbestos catalyst for benzyl alcohol dehydrogenation

    Energy Technology Data Exchange (ETDEWEB)

    Corella, J.; Asua, J.M.

    1980-01-01

    Data on the kinetics of the deactivation of a 10 % Cu/0.5 % Cr/sub 2/O/sub 3//asbestos catalyst for benzyl alcohol dehydrogenation were obtained in a differential reactor fed with 10-100% alcohol at 1 atm, spatial time of 1.0 g-hr/mole, linear gas velocity of 5.2 cm/sec, and catalyst particle size of -2.0 + 1.25 mm, and in an integral reactor fed with 100% alcohol at the same conditions but different temperatures and spatial time.

  2. Synthesis of 2-(2-R1-Hydrazino-5-(R2-benzyl-2-thiazolines on the Basis of Meerweins Arylation Products of Allyl Isothiocyanate

    Directory of Open Access Journals (Sweden)

    Mykola I. Ganushchak

    2003-02-01

    Full Text Available 3-Aryl-2-chloropropylisothiocyanates (1 are formed by interaction of arenediazonium chlorides with allyl isothiocyanate. Adducts 1 react with monoacylhydrazines to form 1-acyl-4-(3-aryl-2-chloropropylthiosemicarbazides (2a–d. Thiosemicarbazides 2a–d in the presence of bases selectively transform into 2-(2-R1-hydrazino-5-(R2-benzyl-2-thiazolines (3a–d.

  3. Introduction of 2-O-benzyl abasic nucleosides to the 3'-overhang regions of siRNAs greatly improves nuclease resistance.

    Science.gov (United States)

    Nagaya, Yuki; Kitamura, Yoshiaki; Shibata, Aya; Ikeda, Masato; Akao, Yukihiro; Kitade, Yukio

    2017-12-15

    Chemically modified siRNAs containing 2-O-benzyl-1-deoxy-d-ribofuranose (R H OBn ) in their 3'-overhang region were significantly more resistant towards serum nucleases than siRNAs possessing the natural nucleoside in this region. The knockdown efficacies and binding affinities of these modified siRNAs to the recombinant human Argonaute protein 2 (hAgo2) PAZ domain were comparable with that of siRNA with a thymidine dimer at the 3'-end. Copyright © 2017 Elsevier Ltd. All rights reserved.

  4. The preparation of benzyl esters using stoichiometric niobium (V) chloride versus niobium grafted SiO2 catalyst: A comparison study

    OpenAIRE

    Sandro L. Barbosa; Camila D. Lima; Melina A.R. Almeida; Larissa S. Mourão; Myrlene Ottone; David L. Nelson; Stanlei I. Klein; Lucas D. Zanatta; Giuliano C. Clososki; Franco J. Caires; Eduardo J. Nassar; Gabriela R. Hurtado

    2018-01-01

    Two solvent free methods of a one-to-one alcohol/acid mol ratio synthesis of benzyl esters of the formic, acetic, benzoic, salicylic, nicotinic, and oxalic acids are described. The stoichiometric reactions used 1.5 mol ratio solid NbCl5 as the reagent and required from two to three hours for completion at room temperature; for the catalytic processes, NbCl5 was grafted directly, at room temperature, onto a silica gel of specific area of 507 m2g−1, produced from construction sand and sodium ca...

  5. 5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile.

    Science.gov (United States)

    Nawrozkij, Maxim B; Rotili, Dante; Tarantino, Domenico; Botta, Giorgia; Eremiychuk, Alexandre S; Musmuca, Ira; Ragno, Rino; Samuele, Alberta; Zanoli, Samantha; Armand-Ugón, Mercedes; Clotet-Codina, Imma; Novakov, Ivan A; Orlinson, Boris S; Maga, Giovanni; Esté, José A; Artico, Marino; Mai, Antonello

    2008-08-14

    A series of dihydro-alkylthio-benzyl-oxopyrimidines (S-DABOs) bearing a 2-aryl-2-oxoethylsulfanyl chain at pyrimidine C2, an alkyl group at C5, and a 2,6-dichloro-, 2-chloro-6-fluoro-, and 2,6-difluoro-benzyl substitution at C6 (oxophenethyl- S-DABOs, 6-8) is here described. The new compounds showed low micromolar to low nanomolar (in one case subnanomolar) inhibitory activity against wt HIV-1. Against clinically relevant HIV-1 mutants (K103N, Y181C, and Y188L) as well as in enzyme (wt and K103N, Y181I, and L100I mutated RTs) assays, compounds carrying an ethyl/ iso-propyl group at C5 and a 2,6-dichloro-/2-chloro-6-fluoro-benzyl moiety at C6 were the most potent derivatives, also characterized by low fold resistance ratio. Interestingly, the structure-activity relationship (SAR) data drawn from this DABO series are more related to HEPT than to DABO derivatives. These findings were at least in part rationalized by the description of a fair superimposition between the 6-8 and TNK-651 (a HEPT analogue) binding modes in both WT and Y181C RTs.

  6. Critical role of p53 upregulated modulator of apoptosis in benzyl isothiocyanate-induced apoptotic cell death.

    Directory of Open Access Journals (Sweden)

    Marie Lue Antony

    Full Text Available Benzyl isothiocyanate (BITC, a constituent of edible cruciferous vegetables, decreases viability of cancer cells by causing apoptosis but the mechanism of cell death is not fully understood. The present study was undertaken to determine the role of Bcl-2 family proteins in BITC-induced apoptosis using MDA-MB-231 (breast, MCF-7 (breast, and HCT-116 (colon human cancer cells. The B-cell lymphoma 2 interacting mediator of cell death (Bim protein was dispensable for proapoptotic response to BITC in MCF-7 and MDA-MB-231 cells as judged by RNA interference studies. Instead, the BITC-treated MCF-7 and MDA-MB-231 cells exhibited upregulation of p53 upregulated modulator of apoptosis (PUMA protein. The BITC-mediated induction of PUMA was relatively more pronounced in MCF-7 cells due to the presence of wild-type p53 compared with MDA-MB-231 with mutant p53. The BITC-induced apoptosis was partially but significantly attenuated by RNA interference of PUMA in MCF-7 cells. The PUMA knockout variant of HCT-116 cells exhibited significant resistance towards BITC-induced apoptosis compared with wild-type HCT-116 cells. Attenuation of BITC-induced apoptosis in PUMA knockout HCT-116 cells was accompanied by enhanced G2/M phase cell cycle arrest due to induction of p21 and down regulation of cyclin-dependent kinase 1 protein. The BITC treatment caused a decrease in protein levels of Bcl-xL (MCF-7 and MDA-MB-231 cells and Bcl-2 (MCF-7 cells. Ectopic expression of Bcl-xL in MCF-7 and MDA-MB-231 cells and that of Bcl-2 in MCF-7 cells conferred protection against proapoptotic response to BITC. Interestingly, the BITC-treated MDA-MB-231 cells exhibited induction of Bcl-2 protein expression, and RNA interference of Bcl-2 in this cell line resulted in augmentation of BITC-induced apoptosis. The BITC-mediated inhibition of MDA-MB-231 xenograft growth in vivo was associated with the induction of PUMA protein in the tumor. In conclusion, the results of the present study

  7. Metal ion recognition via 'selective detuning'. The interaction of selected transition and post-transition metal ions with a mono-N-benzylated O2N3-donor macrocycle and its xylyl-bridged ring analogue.

    Science.gov (United States)

    Fainerman-Melnikova, Marina; Nezhadali, Azizollah; Rounaghi, Gholamhossin; McMurtrie, John C; Kim, Jeong; Gloe, Karsten; Langer, Matthias; Lee, Shim Sung; Lindoy, Leonard F; Nishimura, Tomoko; Park, Ki-Min; Seo, Joobeom

    2004-01-07

    The interaction of cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II) with symmetrical mono-N-benzylated and xylyl-linked macrocyclic ligands derived from the O2N3-macrocycle, 1,12,15-triaza-3,4:9,10-dibenzo-5,8-dioxacycloheptadecane, has been investigated. The log K values for the respective 1 : 1 complexes in 95% methanol (I= 0.1; Et4NClO4, 25 degrees C) of the mono-benzylated derivative have been determined potentiometrically and the results compared with the values obtained previously for the parent (non-benzylated) ring system as well as for related di- and tri-benzylated macrocyclic species. Mono-benzylation results in slightly enhanced stability for the 1 : 1 silver(I) complex while the values for the corresponding complexes of the other six ions are in each case decreased even though the highest stability is still maintained for the 1 : 1 copper(II) complex. The log K results are in accord with a previous proposal that N-benzylation of amine-containing macrocyclic rings of the present type will normally have only a minor (positive or negative) influence on the affinity towards silver(I) while the corresponding binding strengths towards the remaining six metal ions are significantly reduced-behaviour we term 'selective detuning'. Competitive seven-metal transport experiments across a bulk chloroform membrane have been performed using both ligand systems as ionophores. In parallel to the log K results, transport selectivity for copper(II) was exhibited by both systems, with similar transport efficiencies being evident when compared on a 'per macrocyclic cavity' basis.

  8. Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water.

    Science.gov (United States)

    Ramakrishna, V; Dastagiri Reddy, N

    2017-07-04

    N-(3-Chloro-2-quinoxalinyl)-N'-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N'-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh 3 ) 4 and Pd 2 (dba) 3 /PPh 3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh 3 )Cl 2 ] (I) and [Pd(HL2)(PPh 3 )Cl 2 ] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K 2 CO 3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K 2 CO 3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.

  9. A simple spectrophotometric method for the determination of trace levels of molybdenum using N,N‧-bis(2-hydroxy-5-bromo-benzyl)1,2 diaminopropane

    Science.gov (United States)

    Kara, Derya; Karadaş, Cennet

    2015-08-01

    The present work describes a selective, rapid and economical spectrophotometric method for the determination of molybdenum using N,N‧-bis(2-hydroxy-5-bromo-benzyl)1,2 diaminopropane. Molybdenum(VI) reacts with N,N‧-bis(2-hydroxy-5-bromo-benzyl)1,2 diaminopropane to form a stable 1:1 yellow complex with an absorption maximum at 342 nm. The reaction is completed within 10 min and the absorbance of the molybdenum complex remains stable for at least 1 week at room temperature. The effective molar absorption coefficient at 342 nm was 9.6 × 103 L mol-1 cm-1. Under optimal conditions, the complex obeys Beer's law from 0 to 9.9 μg mL-1. The relative standard deviation was 0.08% (for 11 samples, each containing 6 μg mL-1 molybdenum). Under the optimum conditions, the detection limit (3σ) was 17.7 μg L-1 for molybdenum without any preconcentration. The precision was determined from 30 results obtained for 4.80 μg mL-1 Mo(VI); the mean value of a molybdenum(VI) was 4.83 μg ml-1 with a standard derivation of 0.002 μg ml-1 molybdenum(VI).

  10. Reaction of 11 C-benzoyl chlorides with metalloid reagents: 11 C-labeling of benzyl alcohols, benzaldehydes, and phenyl ketones from [11 C]CO.

    Science.gov (United States)

    Roslin, Sara; Dahl, Kenneth; Nordeman, Patrik

    2018-01-26

    In this article, we describe the carbon-11 ( 11 C, t 1/2  = 20.4 minutes) labeling of benzyl alcohols, benzaldehydes, and ketones using an efficient 2-step synthesis in which 11 C-carbon monoxide is used in an initial palladium-mediated reaction to produce 11 C-benzoyl chloride as a key intermediate. In the second step, the obtained 11 C-benzoyl chloride is further treated with a metalloid reagent to furnish the final 11 C-labeled product. Benzyl alcohols were obtained in moderated to high non-isolated radiochemical yields (RCY, 35%-90%) with lithium aluminum hydride or lithium aluminum deuteride as metalloid reagent. Changing the metalloid reagent to either tributyltin hydride or sodium borohydride, allowed for the reliable syntheses of 11 C-benzaldehydes in RCYs ranging from 58% to 95%. Finally, sodium tetraphenylborate were utilized to obtain 11 C-phenyl ketones in high RCYs (77%-95%). The developed method provides a new and efficient route to 3 different classes of compounds starting from aryl iodides or aryl bromides. Copyright © 2018 John Wiley & Sons, Ltd.

  11. Synthesis of solketalacetin as a green fuel additive via ketalization of monoacetin with acetone using silica benzyl sulfonic acid as catalyst

    Directory of Open Access Journals (Sweden)

    Hassan S. Ghaziaskar

    2018-03-01

    Full Text Available Silica benzyl sulfonic acid (SBSA was prepared as a catalyst for reacting monoacetin with acetone to synthesize solketalacetin as a green fuel additive. To synthesize SBSA, commercially available silica gel was functionalized with benzyl alcohol in the presence of sulfuric acid as catalyst and was then sulfonated with chlorosulfonic acid. The catalyst was characterized by FT-IR, XRD, and TGA. The catalytic activity of SBSA was compared with those of Amberlyst 36 and Purolite PD 206 as two sulfonated acidic catalysts, in a continuous flow system. The effect of different operation conditions such as acetone to monoacetin molar ratio, reaction temperature, and feed flow rate were investigated. Increasing acetone to monoacetin molar ratio increased the solketalacetin yield for the three catalysts but SBSA demonstrated the highest solketalacetin yield. Solketalacetin yield was reduced with temperature increase for all the catalysts and the maximum solketalacetin yields were recorded with Amberlyst 36 and SBSA catalyst at 20 °C and 40 °C, respectively. The catalytic activity was examined by keeping the catalysts on–stream for 25 h while the reusability tests were performed in four consecutive runs and showed that SBSA was stable up to 25 h and had the highest stability in 4 runs.

  12. Determination of parabens and benzophenone-type UV filters in human placenta. First description of the existence of benzyl paraben and benzophenone-4.

    Science.gov (United States)

    Valle-Sistac, Jennifer; Molins-Delgado, Daniel; Díaz, Marta; Ibáñez, Lourdes; Barceló, Damià; Silvia Díaz-Cruz, M

    2016-03-01

    UV filters and parabens (PBs) are chemicals used in daily personal care and hygiene products to protect materials and humans from the adverse effects of UV radiation and to preserve the integrity of the formulation, respectively. Several studies highlight their widespread environmental occurrence and endocrine disrupting effects. However, little is known about human exposure to these compounds. The objective of this study was to investigate the exposure of human embryos and foetuses to endocrine disrupting UV filters and PBs. Placentas from volunteer mothers in Barcelona were collected at delivery after informed, written consent by the pregnant women. UV filters and parabens were analysed by liquid chromatography-tandem mass spectrometry. The excellent performance of the method allowed measuring the target compounds in human placental tissue at low ng/g fresh weight level. The detection frequency of the selected compounds was in the range 17-100%. Benzophenone-1, methyl paraben, butyl paraben and benzyl paraben were detected in all samples. The highest measured concentration corresponded to methyl paraben, 11.77ng/g fresh weight. Reported concentrations of benzophenone-4 and benzyl paraben constitute the first evidence about their accumulation in placenta. The results obtained corroborate that foetuses are exposed to a wide diversity of UV filters and PBs via the placenta. Copyright © 2015 Elsevier Ltd. All rights reserved.

  13. Crystal Structure and Molecular Mechanics Modelling of 2-(4-Amino-3-benzyl-2-thioxo-2,3-dihydrothiazol-5-ylbenzoxazole

    Directory of Open Access Journals (Sweden)

    Ahmed F. Mabied

    2014-01-01

    Full Text Available The crystal structure of the title compound, 2-(4-amino-3-benzyl-2-thioxo-2,3-dihydrothiazol-5-ylbenzoxazole, was determined. The crystal has P1 space group and triclinic system with unit cell parameters a = 5.174(3 Å, b = 6.411(6 Å, c = 12.369(10 Å, α = 86.021(4°, β = 84.384(5°, and γ = 77.191(5°. The structure consists of benzoxazole group connected with benzyl via thiazole (attached with amino and thione. Benzoxazole and thiazole rings are almost planar (maximum deviation at C1, −0.013(3 Å, and C10, 0.0041(3 Å, resp.. The phenyl ring is nearly perpendicular to both thiazole and benzoxazole rings. A network of intermolecular hydrogen bonds and intermolecular interactions stabilizes the structure, forming parallel layers. The molecular geometry obtained using single crystal analysis is discussed along with results of the molecular mechanics modeling (MM, and the results showed the same cis conformation between benzoxazole nitrogen atom and the amino group.

  14. Administration of 4-(α-L-Rhamnosyloxy-benzyl Isothiocyanate Delays Disease Phenotype in SOD1G93A Rats: A Transgenic Model of Amyotrophic Lateral Sclerosis

    Directory of Open Access Journals (Sweden)

    Maria Galuppo

    2015-01-01

    Full Text Available 4-(α-L-Rhamnosyloxy-benzyl glucosinolate (glucomoringin, GMG is a compound found in Moringa oleifera seeds. Myrosinase-catalyzed hydrolysis at neutral pH of GMG releases the biologically active compound 4-(α-L-rhamnosyloxy-benzyl isothiocyanate (GMG-ITC. The present study was designed to test the potential therapeutic effectiveness of GMG-ITC to counteract the amyotrophic lateral sclerosis (ALS using SOD1tg rats, which physiologically develops SOD1G93A at about 16 weeks of life, and can be considered a genetic model of disease. Rats were treated once a day with GMG (10 mg/Kg bioactivated with myrosinase (20 µL/rat via intraperitoneal (i.p. injection for two weeks before disease onset and the treatment was prolonged for further two weeks before the sacrifice. Immune-inflammatory markers as well as apoptotic pathway were investigated to establish whether GMG-ITC could represent a new promising tool in clinical practice to prevent ALS. Achieved data display clear differences in molecular and biological profiles between treated and untreated SOD1tg rats leading to guessing that GMG-ITC can interfere with the pathophysiological mechanisms at the basis of ALS development. Therefore, GMG-ITC produced from myrosinase-catalyzed hydrolysis of pure GMG could be a candidate for further studies aimed to assess its possible use in clinical practice for the prevention or to slow down this disease.

  15. Benzyl and Methyl Fatty Hydroxamic Acids Based on Palm Kernel Oil as Chelating Agent for Liquid-Liquid Iron(III Extraction

    Directory of Open Access Journals (Sweden)

    Jamileh Amin

    2012-02-01

    Full Text Available Liquid-liquid iron(III extraction was investigated using benzyl fatty hydroxamic acids (BFHAs and methyl fatty hydroxamic acids (MFHAs as chelating agents through the formation of iron(III methyl fatty hydroxamate (Fe-MFHs or iron(III benzyl fatty hydroxamate (Fe-BFHs in the organic phase. The results obtained under optimized conditions, showed that the chelating agents in hexane extract iron(III at pH 1.9 were realized effectively with a high percentage of extraction (97.2% and 98.1% for MFHAs and BFHAs, respectively. The presence of a large amount of Mg(II, Ni(II, Al(III, Mn(II and Co(II ions did affect the iron(III extraction. Finally stripping studies for recovering iron(III from organic phase (Fe-MFHs or Fe-BFHs dissolved in hexane were carried out at various concentrations of HCl, HNO3 and H2SO4. The results showed that the desired acid for recovery of iron(III was 5 M HCl and quantitative recovery of iron(III was achieved from Fe(III-MFHs and Fe(III-BFHs solutions in hexane containing 5 mg/L of Fe(III.

  16. Valyl benzyl ester chloride

    Directory of Open Access Journals (Sweden)

    Grzegorz Dutkiewicz

    2010-02-01

    Full Text Available In the title compound (systematic name: 1-benzyloxy-3-methyl-1-oxobutan-2-aminium chloride, C12H18NO2+·Cl−, the ester group is approximately planar, with a maximum deviation of 0.040 (2 Å from the least-squares plane, and makes a dihedral angle of 28.92 (16° with the phenyl ring. The crystal structure is organized by N—H...Cl hydrogen bonds which join the two components into a chain along the b axis. Pairs of chains arranged antiparallel are interconnected by further N—H...Cl hydrogen bonds, forming eight-membered rings. Similar packing modes have been observed in a number of amino acid ester halides with a short unit-cell parameter of ca 5.5 Å along the direction in which the chains run.

  17. One-pot deposition of gold on hybrid TiO{sub 2} nanoparticles and catalytic application in the selective oxidation of benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

    Mehri, Afef [University Tunis El-Manar, Laboratoire de Chimie des Matériaux et Catalyse, Tunis (Tunisia); Kochkar, Hafedh, E-mail: h_kochkar@yahoo.fr [University Tunis El-Manar, Laboratoire de Chimie des Matériaux et Catalyse, Tunis (Tunisia); Laboratoire de Valorisation des Matériaux Utiles, Centre National de Recherches en Sciences des Matériaux, Technopôle de Borj-Cedria, 2050 Hammam-Lif (Tunisia); Berhault, Gilles [Institut de Recherches sur la Catalyse et de l' Environnement de Lyon, CNRS-Université Lyon I, 69100 Villeurbanne (France); Cómbita Merchán, Diego Fernando; Blasco, Teresa [Instituto de Tecnología Química (UPV-CSIC), Universidad Politécnica de Valencia-Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos, s/n, Valencia (Spain)

    2015-01-15

    One-pot deposition of Au onto TiO{sub 2} has been achieved through directly contacting gold (III) salt with nanosized functionalized TiO{sub 2} support initially obtained by sol–gel process using titanium isopropoxide and citric acid. Citrate groups act as functional moieties able to directly reduce the Au salt avoiding any further reducing treatment. Various gold salts (NaAuCl{sub 4}·2H{sub 2}O or HAuCl{sub 4}·3H{sub 2}O) and titanium to citrate (Ti/Cit) molar ratios (20, 50 and 100) were used in order to study the effect of the nature of the precursor and of the citrate content on the final Au particle size and catalytic properties of the as-obtained Au/TiO{sub 2} materials. Au/(TiO{sub 2}){sub x}(Cit){sub 1} catalysts characterization was performed using N{sub 2} adsorption–desorption, ICP-AES, X-ray diffraction and TEM. The effect of the Ti/Cit molar ratio and of the gold precursor was evaluated. The selective oxidation of benzyl alcohol (BzOH) to benzaldehyde (BzH) was studied as a model reaction. Kinetic analysis showed that the catalytic reaction rate was pseudo first-order and the values of activation energy have been reported. Results showed that the functionalization of TiO{sub 2} by citrate allows tuning the size of the Au nanoparticles deposited onto TiO{sub 2} as well as their morphology. Citrate also strongly enhances the benzyl alcohol oxidation through the control of the size and morphology of gold nanoparticles. - Highlights: • One-pot deposition of Au onto TiO{sub 2} has been achieved. • Citrates act as active sites for selective deposition and reduction of gold. • The presence of citrates influences the size and the morphology of gold NPs. • Au NPs with well-defined morphologies were obtained for Cit/Ti molar ratio of 100. • The selective oxidation of benzyl alcohol was studied as a model reaction.

  18. The Antimalarial Activities of Methylene Blue and the 1,4-Naphthoquinone 3-[4-(Trifluoromethyl)Benzyl]-Menadione Are Not Due to Inhibition of the Mitochondrial Electron Transport Chain

    Science.gov (United States)

    Ehrhardt, Katharina; Ke, Hangjun; Vaidya, Akhil B.; Lanzer, Michael

    2013-01-01

    Methylene blue and a series of recently developed 1,4-naphthoquinones, including 3-[4-(substituted)benzyl]-menadiones, are potent antimalarial agents in vitro and in vivo. The activity of these structurally diverse compounds against the human malaria parasite Plasmodium falciparum might involve their peculiar redox properties. According to the current theory, redox-active methylene blue and 3-[4-(trifluoromethyl)benzyl]-menadione are “subversive substrates.” These agents are thought to shuttle electrons from reduced flavoproteins to acceptors such as hemoglobin-associated or free Fe(III)-protoporphyrin IX. The reduction of Fe(III)-protoporphyrin IX could subsequently prevent essential hemoglobin digestion and heme detoxification in the parasite. Alternatively, owing to their structures and redox properties, methylene blue and 1,4-naphthoquinones might also affect the mitochondrial electron transport chain. Here, we tested the latter hypothesis using an established system of transgenic P. falciparum cell lines and the antimalarial agents atovaquone and chloroquine as controls. In contrast to atovaquone, methylene blue and 3-[4-(trifluoromethyl)benzyl]-menadione do not inhibit the mitochondrial electron transport chain. A systematic comparison of the morphologies of drug-treated parasites furthermore suggests that the three drugs do not share a mechanism of action. Our findings support the idea that methylene blue and 3-[4-(trifluoromethyl)benzyl]-menadione exert their antimalarial activity as redox-active subversive substrates. PMID:23439633

  19. Radioiodination and biodistribution of NBNPQD ( 2-benzyl-1-oxo-1-2-dihydropyrido (4,3-b) quinoxaline 5,10- dioxide) in tumor bearing mice

    International Nuclear Information System (INIS)

    Ibrahim, I. T.; Habib, S. A.; Wally, H. A.; El-Shishtawy, M. M.

    2012-12-01

    NBNPQD (2-benzyl-1-oxo-1,2 dihydropyrido (quinoxaline 5,10-dioxide) is a new synthesized quinoxaline derivative. It could be labeled with Auger emitter iodine-125 successfully with yield about 90%. The labeled product was evaluated by electrophoresis and studied. 1 23I - NBNPQD was stable up to 48 h post labeling. Biodistribution study of 1 23I - NBNPQD in normal and tumor bearing mice was also conducted. The biodistribution data revealed that 1 23I -NBNPQD diffused rapidly to tumor sites in to both ascites and solid tumor bearing mice. 1 23I -NBNPQD was decline rapidly from most of organs but slowly from tumor sites. In-vitro radiotoxicity of 1 23I - NBNPQD increased with the increase of its radioactivity. This study encourages the possible use of 1 23I - NBNPQD in tumor imaging and treatment. It also encourages further studies on the chemotherapeutic activity of NBNPQD hoping to get a new potent antitumor agent. (Author)

  20. Meyer-Overton reforged: The origins of alcohol and anesthetic potency in membranes as determined by a new NMR partitioning probe, benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

    Janes, N.; Ma, L.; Hsu, J.W.; Rubin, E.; Taraschi, T.F. (Thomas Jefferson Univ., Philadelphia, PA (United States))

    1992-01-01

    The Meyer-Overton hypothesis--that anesthesia arises from the nonspecific action of solutes on membrane lipids--is reformulated using colligative thermodynamics. Configurational entropy, the randomness imparted by the solute through the partitioning process, is implicated as the energetic driving force that pertubs cooperative membrane equilibria. A proton NMR partitioning approach based on the anesthetic benzyl alcohol is developed to assess the reformulation. Ring resonances from the partitioned drug are shielded by 0.2 ppm and resolved from the free, aqueous drug. Free alcohol is quantitated in dilute lipid dispersions using an acetate internal standard. Cooperative equilibria in model dipalmitoyl lecithin membranes are examined with changes in temperature and alcohol concentration. The L[sub [beta][prime

  1. OSU-6: A Highly Efficient, Metal-Free, Heterogeneous Catalyst for the Click Synthesis of 5-Benzyl and 5-Aryl-1H-tetrazoles

    Directory of Open Access Journals (Sweden)

    Baskar Nammalwar

    2015-12-01

    Full Text Available OSU-6, an MCM-41 type hexagonal mesoporous silica with mild Brönsted acid properties, has been used as an efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles from nitriles in DMF at 90 °C. This catalyst offers advantages including ease of operation, milder conditions, high yields, and reusability. Studies are presented that demonstrate the robust nature of the catalyst under the optimized reaction conditions. OSU-6 promotes the 1,3-dipolar addition of azides to nitriles without significant degradation or clogging of the nanoporous structure. The catalyst can be reused up to five times without a significant reduction in yield, and it does not require treatment with acid between reactions.

  2. Chirality and helicity of poly-benzyl-L-glutamate in liquid crystals and a wave structure that mimics collagen helicity in crimp

    Directory of Open Access Journals (Sweden)

    Vidal Benedicto de Campos

    2001-01-01

    Full Text Available Ideal biocompatible polymers must show a mimetic superstructure with biological supra-organization. Collagen-rich structures like tendons and ligaments are materials with various levels of order, from molecules to bundles of fibers, which affect their biomechanical properties and cellular interactions. Poly-benzyl-L-glutamate (PBLG displaying helicity was used here to test the development of wave-like structures as those occurring in collagen fibers. Birefringence of PBLG under various crystallization conditions was studied with a lambda/4 compensator according to Sénarmont. Qualitative observations were plainly sufficient to conclude that the PBLG fibrils were supra-organized helically as a chiral object. During crystallization stretched PBLG formed a helical superstructure with characteristic striation resembling waves (crimp. Supported by optical anisotropy findings, a twisted grain boundary liquid crystal type is proposed as a transition phase in the formation of the PBLG chiral object. A similarity with the wavy organization (crimp of collagen bundles is proposed.

  3. Unusual C-C bond cleavage in the formation of amine-bis(phenoxy) group 4 benzyl complexes: Mechanism of formation and application to stereospecific polymerization

    KAUST Repository

    Gowda, Ravikumar R.

    2014-08-11

    Group 4 tetrabenzyl compounds MBn4 (M = Zr, Ti), upon protonolysis with an equimolar amount of the tetradentate amine-tris(phenol) ligand N[(2,4-tBu2C6H2(CH 2)OH]3 in toluene from -30 to 25 °C, unexpectedly lead to amine-bis(phenoxy) dibenzyl complexes, BnCH2N[(2,4- tBu2C6H2(CH2)O] 2MBn2 (M = Zr (1), Ti (2)) in 80% (1) and 75% (2) yields. This reaction involves an apparent cleavage of the >NCH2-ArOH bond (loss of the phenol in the ligand) and formation of the >NCH 2-CH2Bn bond (gain of the benzyl group in the ligand). Structural characterization of 1 by X-ray diffraction analysis confirms that the complex formed is a bis(benzyl) complex of Zr coordinated by a newly derived tridentate amine-bis(phenoxy) ligand arranged in a mer configuration in the solid state. The abstractive activation of 1 and 2 with B(C6F 5)3·THF in CD2Cl2 at room temperature generates the corresponding benzyl cations {BnCH2N[(2,4- tBu2C6H2(CH2)O] 2MBn(THF)}+[BnB(C6F5) 3]- (M = Zr (3), Ti, (4)). These cationic complexes, along with their analogues derived from (imino)phenoxy tri- and dibenzyl complexes, [(2,6-iPr2C6H3)N=C(3,5- tBu2C6H2)O]ZrBn3 (5) and [2,4-Br2C6H2(O)(6-CH2(NC 5H9))CH2N=CH(2-adamantyl-4-MeC 6H2O)]ZrBn2 (6), have been found to effectively polymerize the biomass-derived renewable β-methyl-α-methylene- γ-butyrolactone (βMMBL) at room temperature into the highly stereoregular polymer PβMMBL with an isotacticity up to 99% mm. A combined experimental and DFT study has yielded a mechanistic pathway for the observed unusual C-C bond cleavage in the present protonolysis reaction between ZrBn4 and N[(2,4-tBu2C 6H2(CH2)OH]3 for the formation of complex 1, which involves the benzyl radical and the Zr(III) species, resulting from thermal and photochemical decomposition of ZrBn4, followed by a series of reaction sequences consisting of protonolysis, tautomerization, H-transfer, oxidation, elimination, and radical coupling. © 2014 American Chemical Society.

  4. Extraction and Chromatographic Determination of Shikimic Acid in Chinese Conifer Needles with 1-Benzyl-3-methylimidazolium Bromide Ionic Liquid Aqueous Solutions

    Science.gov (United States)

    Chen, Fengli; Hou, Kexin; Li, Shuangyang; Zu, Yuangang; Yang, Lei

    2014-01-01

    An ionic liquids-based ultrasound-assisted extraction (ILUAE) method was successfully developed for extracting shikimic acid from conifer needles. Eleven 1-alkyl-3-methylimidazolium ionic liquids with different cations and anions were investigated and 1-benzyl-3-methylimidazolium bromide solution was selected as the solvent. The conditions for ILUAE, including the ionic liquid concentration, ultrasound power, ultrasound time, and liquid-solid ratio, were optimized. The proposed method had good recovery (99.37%–100.11%) and reproducibility (RSD, n = 6; 3.6%). ILUAE was an efficient, rapid, and simple sample preparation technique that showed high reproducibility. Based on the results, a number of plant species, namely, Picea koraiensis, Picea meyeri, Pinus elliottii, and Pinus banksiana, were identified as among the best resources of shikimic acid. PMID:24782942

  5. Facile green synthesis of Pd/N-doped carbon nanotubes catalysts and their application in Heck reaction and oxidation of benzyl alcohol

    Science.gov (United States)

    Wang, Ling-ling; Zhu, Lu-ping; Bing, Nai-ci; Wang, Li-jun

    2017-08-01

    Evenly dispersed Pd nanoparticles are facilely and successfully deposited on N-doped carbon nanotubes (Pd/N-CNTs) by employing sodium dodecyl sulfate (SDS) as a salt and polyvinylpyrrolidone (PVP) as both a surface modifier and a stabilizing agent. The presence of SDS and the amount of PVP have significant influences on the formation of evenly dispersed Pd/N-CNTs catalyst. No additional functionalization steps, reducing agents and stabilizers are required as usual to achieve the uniform deposition of Pd NPs over the N-CNTs surfaces. The as-synthesized Pd/N-CNTs catalyst is proved to be very active in the Heck reaction and can be reused at least for 5 times without significant loss of catalytic activity in the aerobic oxidation of benzyl alcohol.

  6. One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R-(−-N-Benzyl-3-(benzylaminobutanamide: The Effect of Solvent Polarity on Enantioselectivity

    Directory of Open Access Journals (Sweden)

    Marina A. Ortega-Rojas

    2017-12-01

    Full Text Available The use of the solvent engineering has been applied for controlling the resolution of lipase-catalyzed synthesis of β-aminoacids via Michael addition reactions. The strategy consisted of the thermodynamic control of products at equilibrium using the lipase CalB as a catalyst. The enzymatic chemo- and enantioselective synthesis of (R-(−-N-benzyl-3-(benzylaminobutanamide is reported, showing the influence of the solvent on the chemoselectivity of the aza-Michael addition and the subsequent kinetic resolution of the Michael adduct; both processes are catalyzed by CalB and both are influenced by the nature of the solvent medium. This approach allowed us to propose a novel one-pot strategy for the enzymatic synthesis of enantiomerically enriched β-aminoesters and β-aminoacids.

  7. Use of Quantitative Structure-Activity Relationship (QSAR) and ADMET prediction studies as screening methods for design of benzyl urea derivatives for anti-cancer activity.

    Science.gov (United States)

    Lokwani, Deepak; Bhandari, Shashikant; Pujari, Radha; Shastri, Padma; Shelke, Ganesh; Pawar, Vidya

    2011-06-01

    2D and 3D quantitative structure-activity relationship studies have been carried out for establishing a correlation between the structural properties of benzyl urea derivatives and their anti-tumour activities. From this correlation, the new chemical entities were designed, and their activity and absorption, distribution, metabolism, excretion, and toxicity properties were also predicted. Finally, the most promising compounds from these screening were synthesized and biologically evaluated for their anti-cancer properties. Compound 1-(2, 4-dimethylphenyl)-3, 3-dimethyl-1-(2-nitrobenzyl) urea (7d) showed significant anti-proliferative activity (at 100 µg/mL) in human cancer cell lines-T-cell leukemia (Jurkat J6), myelogenous leukemia (K562), and breast cancer (MCF-7) compared to reference standard 5-flurouracil.

  8. Determination of neodymium(III) ions in soil and sediment samples by a novel neodymium(III) sensor based on benzyl bisthiosemicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Behmadi, Hossein [Department of Applied Chemistry, Mashhad Branch, Islamic Azad University, Mashhad (Iran, Islamic Republic of); Zamani, Hassan Ali [Department of Chemistry, Quchan Branch, Islamic Azad University, Quchan (Iran, Islamic Republic of)], E-mail: haszamani@yahoo.com; Ganjali, Mohammad Reza; Norouzi, Parviz [Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehran (Iran, Islamic Republic of); Endocrine and Metabolism Research Center, Tehran University of Medical Sciences, Tehran (Iran, Islamic Republic of)

    2007-12-31

    The PVC membrane, containing benzyl bisthiosemicarbazone (BTC) as a suitable ionophore, exhibited a Nernstian response for the Nd{sup 3+} ions over a wide concentration range between 1.0 x 10{sup -2} and 1 x 10{sup -6} M, with a detection limit of 6.2 x 10{sup -7} M in the pH range of 3.7-8.3. It demonstrated a fast response time (<10 s) and it could be used for at least 7 weeks without any major potential deviation. Furthermore, the electrode revealed high selectivity with respect to all the common alkali, alkaline earth, transition and heavy metal ions, including the members of the lanthanide family other than Nd{sup 3+}. Concerning its applications, it was effectively employed for the determination of neodymium ions in soil and sediment samples and its validation with CRM.

  9. 1-Benzyl-2-phenyl-1H-benzimidazole–4,4′-(cyclohexane-1,1-diyldiphenol (1/1

    Directory of Open Access Journals (Sweden)

    Chunhua Ge

    2011-07-01

    Full Text Available The asymmetric unit of the title co-crystal, C20H16N2·C18H20O2, contains one molecule of 4,4′-(cyclohexane-1,1-diyldiphenol (in which the cyclohexane ring adopts a chair conformation and one molecule of 1-benzyl-2-phenyl-1H-benzimidazole, which are paired through an O—H...N hydrogen bond. These pairs are further linked by intermolecular O—H...O hydrogen bonds into chains along [010]. Weak intermolecular C—H...O and C—H...π interactions further consolidate the crystal packing. The dihedral angles between the pendant phenyl rings and the benzimidazole ring are 86.9 (2 and 43.1 (2°.

  10. Bis(2-amino-5-benzyl-3-ethoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium bis(4-methoxyphenyldiphosphonate

    Directory of Open Access Journals (Sweden)

    Mehmet Akkurt

    2014-03-01

    Full Text Available The asymmetric unit of the title salt, 2C17H21N2O2S+·C14H14O7P22−, contains half of a centrosymmetric bis(4-methoxyphenyldiphosphonate anion and one 2-amino-5-benzyl-3-ethoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium cation. In the anion, the O atoms of the diphosphonate group are disordered over two positions with equal occupancies. In the cation, the ethyl group is disordered over two orientations with a refined occupancy ratio of 0.753 (5:0.247 (5, and the tetrahydropyridinium ring adopts a distorted half-chair conformation. In the crystal, the ions are linked by C—H...O, N—H...O and C—H...S hydrogen bonds into a three-dimensional network.

  11. (2E,5E)-2,5-Bis(4-hy-droxy-3-meth-oxy-benzyl-idene)cyclo-penta-none ethanol monosolvate.

    Science.gov (United States)

    Da'i, Muhammad; Yanuar, Arry; Meiyanto, Edy; Jenie, Umar Anggara; Supardjan, Amir Margono

    2013-04-01

    In the title structure, C21H20O5·C2H5OH, the curcumine-type mol-ecule has a double E conformation for the two benzyl-idene double bonds [C=C = 1.342 (4) and 1.349 (4) Å] and is nearly planar with respect to the non-H atoms (r.m.s. deviation from planarity = 0.069 Å). The two phenolic OH groups form bifurcated hydrogen bonds with intra-molecular branches to adjacent meth-oxy O atoms and inter-molecular branches to either a neighbouring mol-ecule or an ethanol solvent mol-ecule. The ethanol O atom donates a hydrogen bond to the keto O atom. These hydrogen bonds link the constituents into layers parallel to (101) in the crystal structure.

  12. Synthesis, spectral (IR, UV-Vis and variable temperature NMR) characterization and crystal structure of (N-benzyl-N-furfuryldithicarbamato-S,S‧)(thiocyanato-N)(triphenylphosphine)nickel(II)

    Science.gov (United States)

    Valarmathi, P.; Thirumaran, S.; Sarmal, Lovely; Kant, Rajni

    2014-08-01

    Planar (N-benzyl-N-furfuryldithiocarbamato-S,S‧)(thiocyanato-N)(triphenylphospine)nickel(II), [Ni(bfdtc)(NCS)(PPh3)], (1) was prepared from bis(N-benzyl-N-furfuryldithiocarbamato-S,S‧)nickel(II), [Ni(bfdtc)2], (2) and characterized by elemental analysis, cyclic voltammetry, electronic, IR and variable temperature 1H and 13C NMR spectra. For complex 1, the thioureide vCsbnd N value is shifted to higher wavenumber compared to 2 and N13CS2 carbon signal observed for 1 is additionally shielded compared to the parent complex 2, suggesting increased strength of the thioureide bond due to the presence of the π-accepting phosphine. In the room temperature 13C NMR spectrum of 1, two pseudo doublets are observed in the aliphatic region. Variable temperature 13C NMR spectral studies suggest that the fast thiocyanate exchange appears to be responsible for the appearance of pseudo doublets. Single crystal X-ray structural analysis of 1 and 2 confirm the presence of four coordinated nickel in a distorted square planar arrangement with the NiS2PN and NiS4 chromophores, respectively. The Nisbnd S bonds are symmetric in 2 (2.1914(14) and 2.2073(13) Å). But significant asymmetry in Nisbnd S bond distances was observed in 1 (2.2202(8) Å and 2.1841 Å). This observation clearly supports the less effective trans effect of SCN- over PPh3. Cyclic voltammetric studies revealed easier reduction of nickel(II) to nickel(I) in complex 1 compared to 2.

  13. Benzylic rearrangement stable isotope labeling for quantitation of guanidino and ureido compounds in thyroid tissues by liquid chromatography-electrospray ionization mass spectrometry

    Energy Technology Data Exchange (ETDEWEB)

    Fan, Ruo-Jing [State Key Laboratory of Organmetallic Chemistry and National Center for Organic Mass Spectrometry in Shanghai, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China); Guan, Qing [Department of Head and Neck Surgery, Fudan University Shanghai Cancer Center, Shanghai, 200032 (China); Department of Oncology, Shanghai Medical College, Fudan University, Shanghai, 200032 (China); Zhang, Fang, E-mail: fzhang@sioc.ac.cn [State Key Laboratory of Organmetallic Chemistry and National Center for Organic Mass Spectrometry in Shanghai, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China); Leng, Jia-Peng [State Key Laboratory of Organmetallic Chemistry and National Center for Organic Mass Spectrometry in Shanghai, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China); Sun, Tuan-Qi, E-mail: tuanqisun@163.com [Department of Head and Neck Surgery, Fudan University Shanghai Cancer Center, Shanghai, 200032 (China); Department of Oncology, Shanghai Medical College, Fudan University, Shanghai, 200032 (China); Guo, Yin-Long, E-mail: ylguo@sioc.ac.cn [State Key Laboratory of Organmetallic Chemistry and National Center for Organic Mass Spectrometry in Shanghai, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)

    2016-02-18

    Benzylic rearrangement stable isotope labeling (BRSIL) was explored to quantify the guanidino and ureido compounds (GCs and UCs). This method employed a common reagent, benzil, to label the guanidino and ureido groups through nucleophilic attacking then benzylic migrating. The use of BRSIL was investigated in the analysis of five GCs (creatine, L-arginine, homoarginine, 4-guanidinobutyric acid, and methylguanidine) and two UCs (urea and citrulline). The labeling was found simple and specific. The introduction of bi-phenyl group and the generation of nitrogen heterocyclic ring in the benzil-d0/d5 labeled GCs and UCs improved the retention behaviors in liquid chromatography (LC) and increased the sensitivity of electrospray ionization mass spectrometry (ESI MS) detection. The fragment ion pairs of m/z 182/187 and m/z 210/215 from the benzil-d0/d5 tags facilitated the discovery of potential GCs and UCs candidates residing in biological matrices. The use of BRSIL combined with LC-ESI MS was applied for simultaneously quantitation of GCs and UCs in thyroid tissues. It was demonstrated that nine GCs and UCs were detected, six of which were further quantified based on corresponding standards. It was concluded that five GCs and UCs (L-arginine, homoarginine, 4-guanidinobutyric acid, methylguanidine, and citrulline) were statistically significantly different (p < 0.05) between the para-carcinoma and carcinoma thyroid tissue samples. - Highlights: • A common reagent, benzil-d0/d5 was employed to label the GCs and UCs through BRSIL. • The benzil-d0/d5 labeling improved the retention behavior in RPLC and increased the sensitivity by ESI MS detection. • BRSIL coupled with LC-ESI MS was applied to the qualitation and quantitation of GCs and UCs in thyroid tissues.

  14. Environmentally friendly synthesis of CeO2 nanoparticles for the catalytic oxidation of benzyl alcohol to benzaldehyde and selective detection of nitrite

    Science.gov (United States)

    Tamizhdurai, P.; Sakthinathan, Subramanian; Chen, Shen-Ming; Shanthi, K.; Sivasanker, S.; Sangeetha, P.

    2017-04-01

    Cerium oxide nanoparticles (CeO2 NPs) are favorable in nanotechnology based on some remarkable properties. In this study, the crystalline CeO2 NPs are successfully prepared by an efficient microwave combustion (MCM) and conventional route sol-gel (CRSGM) methods. The structural morphology of the as-prepared CeO2 NPs was investigated by various spectroscopic and analytical techniques. Moreover, the XRD pattern confirmed the formation of CeO2 NPs as a face centered cubic structure. The magnetometer studies indicated the low saturation magnetization (23.96 emu/g) of CeO2 NPs for weak paramagnetic and high saturation magnetization (32.13 emu/g) of CeO2 NPs for super paramagnetic. After that, the oxidation effect of benzyl alcohol was investigated which reveals good conversion and selectivity. Besides, the CeO2 NPs modified glassy carbon electrode (GCE) used for the detection of nitrite with linear concentration range (0.02-1200 μM), low limit of detection (0.21 μM) and higher sensitivity (1.7238 μAμM-1 cm-2). However, the CeO2 NPs modified electrode has the fast response, high sensitivity and good selectivity. In addition, the fabricated electrode is applied for the determination of nitrite in various water samples. Eventually, the CeO2 NPs can be regarded as an effective way to enhance the catalytic activity towards the benzyl alcohol and nitrite.

  15. Environmentally friendly synthesis of CeO2 nanoparticles for the catalytic oxidation of benzyl alcohol to benzaldehyde and selective detection of nitrite.

    Science.gov (United States)

    Tamizhdurai, P; Sakthinathan, Subramanian; Chen, Shen-Ming; Shanthi, K; Sivasanker, S; Sangeetha, P

    2017-04-13

    Cerium oxide nanoparticles (CeO 2 NPs) are favorable in nanotechnology based on some remarkable properties. In this study, the crystalline CeO 2 NPs are successfully prepared by an efficient microwave combustion (MCM) and conventional route sol-gel (CRSGM) methods. The structural morphology of the as-prepared CeO 2 NPs was investigated by various spectroscopic and analytical techniques. Moreover, the XRD pattern confirmed the formation of CeO 2 NPs as a face centered cubic structure. The magnetometer studies indicated the low saturation magnetization (23.96 emu/g) of CeO 2 NPs for weak paramagnetic and high saturation magnetization (32.13 emu/g) of CeO 2 NPs for super paramagnetic. After that, the oxidation effect of benzyl alcohol was investigated which reveals good conversion and selectivity. Besides, the CeO 2 NPs modified glassy carbon electrode (GCE) used for the detection of nitrite with linear concentration range (0.02-1200 μM), low limit of detection (0.21 μM) and higher sensitivity (1.7238 μAμM -1 cm -2 ). However, the CeO 2 NPs modified electrode has the fast response, high sensitivity and good selectivity. In addition, the fabricated electrode is applied for the determination of nitrite in various water samples. Eventually, the CeO 2 NPs can be regarded as an effective way to enhance the catalytic activity towards the benzyl alcohol and nitrite.

  16. NTP Toxicology and Carcinogenesis Studies of Benzyl Acetate (CAS No. 140-11-4) in F344/N Rats and B6C3F1 Mice (Gavage Studies).

    Science.gov (United States)

    1986-08-01

    Benzyl acetate, a water-white liquid with a pear-like odor, is a natural constituent of several essential oils and flower absolutes extracted from jasmine, hyacinth, gardenia, tuberose, ylang-ylang, cananga, and neroli. Commercial benzyl acetate, a liquid prepared synthetically from benzyl chloride, acetic acid, and triethylamine is used primarily as a component of perfumes for soaps and as a flavoring ingredient. This compound is practically insoluble in water but is miscible in alcohol and ether and soluble in benzene and chloroform. Toxicology and carcinogenesis studies of benzyl acetate (>99% pure) were conducted by administering benzyl acetate in corn oil gavage to groups of 50 male and 50 female F344/N rats at doses of 0, 250, or 500 mg/kg body weight and to groups of 50 male and 50 female B6C3F1 mice at doses of 0, 500, or 1,000 mg/kg once daily five days per week for 103 weeks. Dose selection for the 2-year study was based on mean body weight gain depression and decreased survival observed at higher doses in 13 week studies. The absence of any observable adverse effect of benzyl acetate on the survival or mean body weight gains of the rats or mice in the 2-year studies suggests that both the rats and the mice of each sex could have tolerated higher doses. An infection in the genital tract was probably responsible for the deaths of 26/35 control, 14/32 low-dose, and 8/20 high-dose female mice before the end of the study. Acinar-cell adenomas in the pancreas of male rats occurred with a positive trend (P<0.01), and the incidence in the high-dose group (37/49, 76%) was significantly (P<0.01) higher than in the vehicle controls (22/50, 40%). The incidence of these tumors in the low-dose group (27/50, 54%) was comparable to that in the gavage controls. Acinar-cell hyperplasia of the pancreas was observed in 37/50 control, 34/50 low-dose, and 36/49 high-dose male rats. No acinar-cell hyperplasia or adenoma of the pancreas was observed in female rats. The

  17. Synthesis of Novel 5-(N-Boc-N-Benzyl-2-aminoethyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carboxamides and Their Inhibition of Cathepsins B and K.

    Science.gov (United States)

    Lukić, Branislav; Grošelj, Uroš; Novinec, Marko; Svete, Jurij

    2017-12-01

    Eight novel 5-(N-Boc-N-benzyl-2-aminoethyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carboxamides were prepared in three steps from methyl 3-amino-1H-pyrazole-4-carboxylate and methyl 5-(benzyl(tert-butoxycarbonyl)amino)-3-oxopentanoate. The synthetic procedure comprises cyclocondensation of the above starting compounds, hydrolysis of the ester, and bis(pentafluorophenyl) carbonate (BPC)-mediated amidation. Title carboxamides were tested for inhibition of cathepsins K and B. The N-butylcarboxamide 5a exhibited appreciable inhibition of cathepsin K (IC50 ~ 25 μM), while the strongest inhibition of cathepsin B was achieved with N-(2-picolyl)carboxamide 5c (IC50 ~ 45 μM).

  18. RuO2 supported NaY zeolite catalysts: Effect of preparation methods on catalytic performance during aerobic oxidation of benzyl alcohol

    Science.gov (United States)

    Jung, Dasom; Lee, Sunwoo; Na, Kyungsu

    2017-10-01

    The effects of preparation method for RuO2 supported zeolite catalysts on the catalytic consequences during the aerobic oxidation of benzyl alcohol to benzaldehyde were investigated. Three preparation methods, i.e., (i) simultaneous crystallization of the zeolite framework in the presence of RuCl3 (Ru(SC)/NaY), (ii) post ion-exchange with RuCl3 on the zeolite framework (Ru(IE)/NaY), and (iii) post support of preformed Ru metal nanoparticles on the zeolite surface (Ru(PS)/NaY), were used to construct three different RuO2 supported NaY zeolite catalysts. The catalyst performance was investigated as functions of the reaction time and temperature, in correlation with the structural changes of the catalysts, as analyzed by X-ray diffraction (XRD). The results revealed that the catalytic consequences were dramatically affected by the preparation methods. Although similar conversion was achieved with all three catalysts, the turnover frequency (TOF) differed. The Ru(PS)/NaY catalyst exhibited the highest TOF (33-48 h-1), whereas the other catalysts produced much lower TOFs (9-12 h-1). The Ru(PS)/NaY catalyst also had the highest activation energy (Ea) of 48.39 kJ mol-1, whereas the Ru(SC)/NaY and Ru(IE)/NaY catalysts had Ea values of 18.58 and 24.11 kJ mol-1, respectively. Notably, the Ru(PS)/NaY catalyst yielded a significantly higher pre-exponential factor of 5.22 × 105 h-1, which is about 5 orders of magnitude larger than that of the Ru(SC)/NaY catalyst (7.15 × 100 h-1). This suggests that collision between benzyl alcohol and molecular oxygen was very intensive on the Ru(PS)/NaY catalyst, which explains the higher TOF of the Ru(PS)/NaY catalyst relative to the others in spite of the higher Ea value of the former. In terms of recyclability, the pristine crystallinity of the zeolite framework was maintained in the Ru(SC)/NaY catalyst and the RuO2 phase exhibited an insignificant loss of the initial activity up to three catalytic cycles, whereas Ru(PS)/NaY showed slight

  19. Uniting polypeptides with sequence-designed peptides: synthesis and assembly of poly(gamma-benzyl L-glutamate)-b-coiled-coil peptide copolymers.

    Science.gov (United States)

    Marsden, Hana Robson; Handgraaf, Jan-Willem; Nudelman, Fabio; Sommerdijk, Nico A J M; Kros, Alexander

    2010-02-24

    A new class of peptide has been created, polypeptide-b-designed peptides, which unites the useful qualities of the two constituent peptide types. We demonstrate the synthesis and self-assembly possibilities of this class of peptide chimera with a series of amphiphilic polypeptide-b-designed peptides in which the hydrophobic block is poly(gamma-benzyl l-glutamate) (PBLG) and the hydrophilic block is a coiled-coil forming peptide (denoted E). The synthetic approach was to synthesize the coiled-coil forming peptide on the solid phase, followed by the ring-opening polymerization of gamma-benzyl l-glutamate N-carboxyanhydride, initiated from the N-terminal amine of the peptide E on the solid support. The polypeptide-b-peptide was then cleaved from the resin, requiring no further purification. Peptide E contains 22 amino acids, while the average length of the PBLG block ranged from 36 to 250 residues. This new class of peptide was applied to create a modular system, which relied on juxtaposing the properties of the component peptide types, namely the broad size range and structure-inducing characteristics of the polypeptide PBLG blocks, and the complex functionality of the sequence-designed peptide. Specifically, the different PBLG block lengths could be connected noncovalently with various hydrophilic blocks via the specific coiled-coil folding of E with K or K-poly(ethylene glycol), where K is a peptide of complementary amino acid sequence to E. In this way, nanostructures could be formed in water at neutral pH over the entire compositional range, which has not been demonstrated previously with such large PBLG blocks. It was found that the size, morphology (polymersomes or bicelles), and surface functionality could be specified by combining the appropriate modular building blocks. The self-assembled structures were characterized by dynamic light scattering, circular dichroism, scanning electron microscopy, cryogenic-transmission electron microscopy, fluorescence

  20. Measurement and correlation of the solubility of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol in water and alcohols at temperatures from 292.15 K to 310.15 K

    Energy Technology Data Exchange (ETDEWEB)

    Liang, Shuqin [School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou, Henan 450001 (China); Li, Huiying [China Certification & Inspection (Group) Henan Co., Ltd., Zhengzhou, Henan 450000 (China); Shen, Le; Li, Huanxin; Mao, Zhendong [School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou, Henan 450001 (China); Li, Huiping, E-mail: huipingli@zzu.edu.cn [School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou, Henan 450001 (China)

    2016-04-20

    Highlights: • The (1-benzyl-1H-1,2,3-triazole-4-yl) methanol was successfully synthesized and characterized by IR and NMR. • The solubilities of (1-benzyl-1H-1,2,3-triazole-4-yl) methanol in water and alcohols were measured. • The experimental solubility data were correlated with the Van’t Hoff equation, modified Apelblat equation and λh equation model. • The dissolution enthalpy of (1-benzyl-1H-1,2,3-triazole-4-yl) methanol was calculated by using the modified Apelblat equation. • The solubility data, correlation models, and the thermodynamic parameters were discussed in detail. - Abstract: The solubilities of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol (BTZM) in water, methanol, ethanol, n-propanol, isopropanol, and n-butanol were measured at temperatures ranging from 292.15 K to 310.15 K by a dynamic method under normal atmospheric pressure. The results showed that it increased with the increasing temperature and the order of solvents was: order: methanol > ethanol > n-propanol > n-butanol > isopropanol > water except three points. The solubility data were correlated with the Van’t Hoff equation, modified Apelblat equation, and λh equation. The average relative deviations (ARD) were 1.87%, 1.53%, and 1.71%, and the root-mean-square-deviations (RMSD) were 2.37 × 10{sup −2}, 1.51 × 10{sup −2}, and 2.12 × 10{sup −2}, respectively. It was found that the modified Apelblat equation gave the best correlation results. Furthermore, the dissolution enthalpy of BTZM was calculated by the modified Apelblat equation.

  1. Clean and efficient benzylic C-H oxidation in water using a hypervalent iodine reagent: activation of polymeric iodosobenzene with KBr in the presence of montmorillonite-K10.

    Science.gov (United States)

    Dohi, Toshifumi; Takenaga, Naoko; Goto, Akihiro; Fujioka, Hiromichi; Kita, Yasuyuki

    2008-09-19

    We have found that unreactive and insoluble polymeric iodosobenzene [PhIO] n induced aqueous benzylic C-H oxidation to effectively give arylketones, in the presence of KBr and montmorillonite-K10 (M-K10) clay. Water-soluble and reactive species 1 having the unique I(III)-Br bond, in situ generated from [PhIO]n and KBr, was considered to be the key radical initiator during the reactions.

  2. Measurement and correlation of the solubility of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol in water and alcohols at temperatures from 292.15 K to 310.15 K

    International Nuclear Information System (INIS)

    Liang, Shuqin; Li, Huiying; Shen, Le; Li, Huanxin; Mao, Zhendong; Li, Huiping

    2016-01-01

    Highlights: • The (1-benzyl-1H-1,2,3-triazole-4-yl) methanol was successfully synthesized and characterized by IR and NMR. • The solubilities of (1-benzyl-1H-1,2,3-triazole-4-yl) methanol in water and alcohols were measured. • The experimental solubility data were correlated with the Van’t Hoff equation, modified Apelblat equation and λh equation model. • The dissolution enthalpy of (1-benzyl-1H-1,2,3-triazole-4-yl) methanol was calculated by using the modified Apelblat equation. • The solubility data, correlation models, and the thermodynamic parameters were discussed in detail. - Abstract: The solubilities of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol (BTZM) in water, methanol, ethanol, n-propanol, isopropanol, and n-butanol were measured at temperatures ranging from 292.15 K to 310.15 K by a dynamic method under normal atmospheric pressure. The results showed that it increased with the increasing temperature and the order of solvents was: order: methanol > ethanol > n-propanol > n-butanol > isopropanol > water except three points. The solubility data were correlated with the Van’t Hoff equation, modified Apelblat equation, and λh equation. The average relative deviations (ARD) were 1.87%, 1.53%, and 1.71%, and the root-mean-square-deviations (RMSD) were 2.37 × 10 −2 , 1.51 × 10 −2 , and 2.12 × 10 −2 , respectively. It was found that the modified Apelblat equation gave the best correlation results. Furthermore, the dissolution enthalpy of BTZM was calculated by the modified Apelblat equation.

  3. Reappraising the structures and distribution of metabolites from black aspergilli containing uncommon 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one systems.

    Science.gov (United States)

    Henrikson, Jon C; Ellis, Trevor K; King, Jarrod B; Cichewicz, Robert H

    2011-09-23

    To date, natural products containing 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one substructures have been encountered in relatively few fungi outside of the black aspergilli clade. While exploring the occurrence of these compounds among Aspergillus spp., it was determined that the structures of the unusual furopyrrols tensidols A and B (5 and 6) and JBIR-86 and JBIR-87 (9 and 10) were incorrect and should be reassigned as 2-benzyl-4H-pyran-4-ones (7, 8, 11e, and 12, respectively). The origin of the unique N-phenyl groups in the 2-benzylpyridin-4(1H)-ones nygerones A and B (1 and 2) were also examined, and it was established that N-phenylamides added to the culture medium were suitable substrates for generating these metabolites; however, this phenomenon remained limited to a single fungus in our collection (Aspergillus niger ATCC 1015). A variety of 2-benzyl-4H-pyran-4-ones and 2-benzylpyridin-4(1H)-ones were detected among the black aspergilli, but only pestalamide B (13) was found in all 11 of the tested strains. These metabolites, as well as a group of synthetic analogues, demonstrated weak antifungal activity against several Candida strains, Aspergillus flavus, and Aspergillus fumigatus.

  4. Evaluation of the efficiency of Pd/H2 -catalyzed benzylic H/D exchange of dehydroabietinal with D(2) O and synthesis of a tritium-labeled analogue.

    Science.gov (United States)

    Petros, Robby A; Shah, Jyoti

    2014-01-01

    Dehydroabietinal (DA) has been identified as an important signaling molecule in systemic acquired resistance in plants. Deuterium and tritium-labeled DA were synthesized to confirm its role in signaling and to further elucidate the mechanism by which DA induces systemic acquired resistance. Pd/H2 -catalyzed exchange of benzylic hydrogen atoms of DA with (2) H-H2 O or (3) H-H2 O was conducted with >97% label incorporation for (2) H-DA and a specific activity of 12.6 mCi/mmol for (3) H-DA synthesized from 90 mCi/mmol (3) H-H2 O. The extent of deuterium labeling at each benzylic position was determined via an inverse-gated (13) C NMR experiment. C7 and C15 were 87% and 81% labeled, respectively. Isotope-induced chemical shift changes at C6 were used to approximate the amount of singly (66%) and doubly (17%) labeled (2) H-DA at C7. Results also indicated that two of the three benzylic protons in DA underwent facile exchange. Exchange at the remaining position was likely hampered by steric interactions of nearby methyl groups at the surface of the Pd catalyst. Copyright © 2013 John Wiley & Sons, Ltd.

  5. Molecular structure (monomeric and dimeric) and hydrogen bonds in 5-benzyl 2-thiohydantoin studied by FT-IR and FT-Raman spectroscopy and DFT calculations.

    Science.gov (United States)

    Deval, Vipin; Kumar, Amit; Gupta, Vineet; Sharma, Anamika; Gupta, Archana; Tandon, Poonam; Kunimoto, Ko-Ki

    2014-11-11

    In the present work the structural and spectral characteristics of 5-benzyl-2-thiohydantoin (5-BTH) have been studied by methods of infrared, Raman spectroscopy and quantum chemistry. Electrostatic potential surface, optimized geometry, harmonic vibrational frequencies, infrared intensities and activities of Raman scattering were calculated by density functional theory (DFT) employing B3LYP with complete relaxation in the potential energy surface using 6-311G++(d,p) basis set. Our results support the hydrogen bonding pattern proposed by reported crystalline structure. Stability of the molecule arising from hyperconjugative interactions, charge delocalization have been analyzed using natural bond orbital (NBO) analysis. The 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule are calculated by the gauge independent atomic orbital (GIAO) method and compared with experimental results. UV-vis spectrum of the compound was recorded in methanol solvent. The TD-DFT calculations have been performed to explore the influence of electronic absorption spectra in the gas phase, as well as in solution environment using PCM and 6-311++G(d,p) basis set. In addition, the thermodynamic properties of the compound were calculated at different temperatures and corresponding relations between the properties and temperature were also studied. Copyright © 2014 Elsevier B.V. All rights reserved.

  6. Quantum chemical studies on molecular structure, spectroscopic (IR, Raman, UV-Vis), NBO and HOMO-LUMO analysis of 1-benzyl-3-(2-furoyl) thiourea.

    Science.gov (United States)

    Gil, Diego M; Defonsi Lestard, M E; Estévez-Hernández, O; Duque, J; Reguera, E

    2015-06-15

    Vibrational and electronic spectra for 1-benzyl-3-(2-furoyl) thiourea were calculated by using density functional method (B3LYP) with different basis sets. The complete assignment of all vibrational modes was performed on basis of the calculated frequencies and comparing with the reported IR and Raman spectra for that thiourea derivative. UV-visible absorption spectra of the compound dissolved in methanol were recorded and analyzed using time dependent density functional theory (TD-DFT). The calculated values for the geometrical parameters of the title compound are consistent with the ones reported from XRD studies. The stability of the molecule, related to hyper-conjugative interactions, and electron delocalization were evaluated using natural bond orbital (NBO) analysis. Intra-molecular interactions were studied by AIM approach. The HOMO and LUMO analysis are used to determine the charge transfer within the molecule. Molecular electrostatic potential map was performed by the DFT method. Copyright © 2015 Elsevier B.V. All rights reserved.

  7. Arborescent Unimolecular Micelles: Poly(γ-Benzyl l-Glutamate Core Grafted with a Hydrophilic Shell by Copper(I-Catalyzed Azide–Alkyne Cycloaddition Coupling

    Directory of Open Access Journals (Sweden)

    Mario Gauthier

    2017-10-01

    Full Text Available Amphiphilic copolymers were obtained by grafting azide-terminated polyglycidol, poly(ethylene oxide, or poly(2-hydroxyethyl acrylate chain segments onto alkyne-functionalized arborescent poly(γ-benzyl l-glutamate (PBG cores of generations G1–G3 via copper(I-catalyzed azide–alkyne Huisgen cycloaddition (CuAAC coupling. The alkyne functional groups on the arborescent PBG substrates were either distributed randomly or located exclusively at the end of the chains added in the last grafting cycle of the core synthesis. The location of these coupling sites influenced the ability of the arborescent copolymers to form unimolecular micelles in aqueous environments: The chain end grafting approach provided enhanced dispersibility in aqueous media and favored the formation of unimolecular micelles in comparison to random grafting. This is attributed to a better defined core-shell morphology for the copolymers with end-grafted shell segments. Aqueous solubility also depended on the type of material used for the shell chains. Coupling by CuAAC opens up possibilities for grafting a broad range of polymers on the arborescent substrates under mild conditions.

  8. Benzyl butyl phthalate decreases myogenic differentiation of endometrial mesenchymal stem/stromal cells through miR-137-mediated regulation of PITX2.

    Science.gov (United States)

    Chen, Hung-Sheng; Hsu, Chia-Yi; Chang, Yu-Chia; Chuang, Hui-Yu; Long, Cheng-Yu; Hsieh, Tsung-Hua; Tsai, Eing-Mei

    2017-03-15

    Phthalate, an environmental toxin, has been considered as an endocrine-disrupting chemical. Growing evidence has demonstrated links between endocrine-disrupting chemicals, tissue development, and reproductive physiology, but the mechanisms of gene expression regulation by environmental factors that affect cell differentiation are unclear. Herein, we investigated the effects of butyl benzyl phthalate (BBP) on human endometrial mesenchymal stem/stromal cell (EN-MSC) differentiation and identified a novel signaling pathway. Differentiation of endometrial mesenchymal stem/stromal cells decreased after administration of BBP. We analyzed BBP regulation of gene expression in EN-MSC using cDNA microarrays and Ingenuity Pathway Analysis software to identify affected target genes and their biological functions. PITX2 emerged as a common gene hit from separate screens targeting skeletal and muscular disorders, cell morphology, and tissue development. BBP decreased transcription of PITX2 and elevated expression of the microRNA miR-137, the predicted upstream negative regulator of PITX2. These data indicated that BBP affects PITX2 expression through miR-137 targeting of the 3' untranslated region of PITX2 mRNA. PITX2 down-regulation also decreased MyoD transcript levels in EN-MSC. Our results demonstrate that BBP decreases EN-MSC myogenic differentiation through up-regulation of miR-137, contribute to our understanding of EN-MSC differentiation, and underline the hazardous potential of environmental hormones.

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

    Science.gov (United States)

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

    2017-09-21

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

  10. Benzyl Isothiocyanate Inhibits Prostate Cancer Development in the Transgenic Adenocarcinoma Mouse Prostate (TRAMP Model, Which Is Associated with the Induction of Cell Cycle G1 Arrest

    Directory of Open Access Journals (Sweden)

    Han Jin Cho

    2016-02-01

    Full Text Available Benzyl isothiocyanate (BITC is a hydrolysis product of glucotropaeolin, a compound found in cruciferous vegetables, and has been shown to have anti-tumor properties. In the present study, we investigated whether BITC inhibits the development of prostate cancer in the transgenic adenocarcinoma mouse prostate (TRAMP mice. Five-week old, male TRAMP mice and their nontransgenic littermates were gavage-fed with 0, 5, or 10 mg/kg of BITC every day for 19 weeks. The weight of the genitourinary tract increased markedly in TRAMP mice and this increase was suppressed significantly by BITC feeding. H and E staining of the dorsolateral lobes of the prostate demonstrated that well-differentiated carcinoma (WDC was a predominant feature in the TRAMP mice. The number of lobes with WDC was reduced by BITC feeding while that of lobes with prostatic intraepithelial neoplasia was increased. BITC feeding reduced the number of cells expressing Ki67 (a proliferation marker, cyclin A, cyclin D1, and cyclin-dependent kinase (CDK2 in the prostatic tissue. In vitro cell culture results revealed that BITC decreased DNA synthesis, as well as CDK2 and CDK4 activity in TRAMP-C2 mouse prostate cancer cells. These results indicate that inhibition of cell cycle progression contributes to the inhibition of prostate cancer development in TRAMP mice treated with BITC.

  11. Subcutaneous Construction of Engineered Adipose Tissue with Fat Lobule-Like Structure Using Injectable Poly-Benzyl-L-Glutamate Microspheres Loaded with Adipose-Derived Stem Cells.

    Directory of Open Access Journals (Sweden)

    Wentao Sun

    Full Text Available Porous microcarriers were fabricated from synthesized poly(γ-benzyl-L-glutamate (PBLG polymer to engineer adipose tissue with lobule-like structure via the injectable approach. The adipogenic differentiation of human adipose-derived stem cells (hASCs seeded on porous PBLG microcarriers was determined by adipogenic gene expression and glycerol-3-phosphate dehydrogenase enzyme activity. In vitro adipogenic cultivation was performed for 7 days, and induced hASC/PBLG complex (Adi-ASC/PBLG group was subcutaneously injected into nude mice. Injections of PBLG microcarriers alone (PBLG group and non-induced hASC/PBLG complex (ASC/PBLG group served as controls. Newly formed tissues were harvested after 4 and 8 weeks. Generation of subcutaneous adipose tissue with typical lobule-like structure separated by fibrous septa was observed upon injection of adipogenic-induced hASC/microsphere complex. Adipogenesis significantly increased in the Adi-ASC/PBLG group compared with the control groups. The angiogenesis in the engineered adipose tissue was comparable to that in normal tissue as determined by capillary density and luminal diameter. Cell tracking assay demonstrated that labeled hASCs remained detectable in the neo-generated tissues 8 weeks post-injection using green fluorescence protein-labeled hASCs. These results indicate that adipose tissue with typical lobule-like structure could be engineered using injectable porous PBLG microspheres loaded with adipogenic-induced hASCs.

  12. Study of the radiolysis of tetracycline hydrochloride in powder form, in aqueous solutions and in benzyl alcohol, at 77K, by electron paramagnetic resonance spectroscopy

    International Nuclear Information System (INIS)

    Guedes, S.M.L.

    1984-01-01

    The radiolysis of tetracycline hydrochloride in powder form, dissolved in benzyl alcohol and in acid, neutral and alkaline aerated aqueous solutions at 77K is studied by electron paramagnetic resonance spectroscopy. Mechanisms of reactions that occur in the radiolysis of these systems are proposed and some aspects of the reactions that occurs with electrons and with hydrogen atoms at 77K are investigated, since tetracycline hydrochloride captures both paramagnetic species. Also discussed is the influence of some factors in the migration of these species at 77K, such as: the position of solutes, the crystalline structure of the solvent, the kinetic energy of the species and the angle of incidence in the channeling. The rate constants for the reaction between the electron and physical and chemical traps which are present in the alkaline aerated aqueous solutions, at 77k, are calculated. The values found are, respectively: k=9.6 x 10 15 1 mol -1 s -1 and k= 1.8 x 10 10 1 mol -1 s -1 . (Author) [pt

  13. H-Abstraction reactions by OH, HO2, O, O2 and benzyl radical addition to O2 and their implications for kinetic modelling of toluene oxidation.

    Science.gov (United States)

    Pelucchi, M; Cavallotti, C; Faravelli, T; Klippenstein, S J

    2018-02-01

    Alkylated aromatics constitute a significant fraction of the components commonly found in commercial fuels. Toluene is typically considered as a reference fuel. Together with n-heptane and iso-octane, it allows for realistic emulations of the behavior of real fuels by the means of surrogate mixture formulations. Moreover, it is a key precursor for the formation of poly-aromatic hydrocarbons, which are of relevance to understanding soot growth and oxidation mechanisms. In this study the POLIMI kinetic model is first updated based on the literature and on recent kinetic modelling studies of toluene pyrolysis and oxidation. Then, important reaction pathways are investigated by means of high-level theoretical methods, thereby advancing the present knowledge on toluene oxidation. H-Abstraction reactions by OH, HO 2 , O and O 2 , and the reactivity on the multi well benzyl-oxygen (C 6 H 5 CH 2 + O 2 ) potential energy surface (PES) were investigated using electronic structure calculations, transition state theory in its conventional, variational, and variable reaction coordinate forms (VRC-TST), and master equation calculations. Exploration of the effect on POLIMI model performance of literature rate constants and of the present calculations provides valuable guidelines for implementation of the new rate parameters in existing toluene kinetic models.

  14. Mechanism of alpha-amino acids decomposition in the gas phase. experimental and theoretical study of the elimination kinetics of N-benzyl glycine ethyl ester.

    Science.gov (United States)

    Tosta, Maria; Oliveros, Jhenny C; Mora, Jose R; Córdova, Tania; Chuchani, Gabriel

    2010-02-25

    The gas-phase elimination kinetics of N-benzylglycine ethyl ester was examined in a static system, seasoned with allyl bromide, and in the presence of the free chain radical suppressor toluene. The working temperature and pressure range were 386.4-426.7 degrees C and 16.7-40.0 torr, respectively. The reaction showed to be homogeneous, unimolecular, and obeys a first-order rate law. The elimination products are benzylglycine and ethylene. However, the intermediate benzylglycine is unstable under the reaction conditions decomposing into benzyl methylamine and CO(2) gas. The variation of the rate coefficients with temperature is expressed by the following Arrhenius equation: log k(1) (s(-1)) = (11.83 +/- 0.52) - (190.3 +/- 6.9) kJ mol(-1) (2.303RT)(-1). The theoretical calculation of the kinetic parameters and mechanism of elimination of this ester were performed at B3LYP/6-31G*, B3LYP/6-31+G**, MPW1PW91/6-31G*, and MPW1PW91/6-31+G** levels of theory. The calculation results suggest a molecular mechanism of a concerted nonsynchronous six-membered cyclic transition state process. The analysis of bond order and natural bond orbital charges implies that the bond polarization of C(=O)O-C, in the sense of C(=O)O(delta-)...C(delta+), is rate determining. The experimental and theoretical parameters have been found to be in reasonable agreement.

  15. Subcutaneous Construction of Engineered Adipose Tissue with Fat Lobule-Like Structure Using Injectable Poly-Benzyl-L-Glutamate Microspheres Loaded with Adipose-Derived Stem Cells.

    Science.gov (United States)

    Sun, Wentao; Fang, Jianjun; Yong, Qi; Li, Sufang; Xie, Qingping; Yin, Jingbo; Cui, Lei

    2015-01-01

    Porous microcarriers were fabricated from synthesized poly(γ-benzyl-L-glutamate) (PBLG) polymer to engineer adipose tissue with lobule-like structure via the injectable approach. The adipogenic differentiation of human adipose-derived stem cells (hASCs) seeded on porous PBLG microcarriers was determined by adipogenic gene expression and glycerol-3-phosphate dehydrogenase enzyme activity. In vitro adipogenic cultivation was performed for 7 days, and induced hASC/PBLG complex (Adi-ASC/PBLG group) was subcutaneously injected into nude mice. Injections of PBLG microcarriers alone (PBLG group) and non-induced hASC/PBLG complex (ASC/PBLG group) served as controls. Newly formed tissues were harvested after 4 and 8 weeks. Generation of subcutaneous adipose tissue with typical lobule-like structure separated by fibrous septa was observed upon injection of adipogenic-induced hASC/microsphere complex. Adipogenesis significantly increased in the Adi-ASC/PBLG group compared with the control groups. The angiogenesis in the engineered adipose tissue was comparable to that in normal tissue as determined by capillary density and luminal diameter. Cell tracking assay demonstrated that labeled hASCs remained detectable in the neo-generated tissues 8 weeks post-injection using green fluorescence protein-labeled hASCs. These results indicate that adipose tissue with typical lobule-like structure could be engineered using injectable porous PBLG microspheres loaded with adipogenic-induced hASCs.

  16. The preparation of benzyl esters using stoichiometric niobium (V chloride versus niobium grafted SiO2 catalyst: A comparison study

    Directory of Open Access Journals (Sweden)

    Sandro L. Barbosa

    2018-03-01

    Full Text Available Two solvent free methods of a one-to-one alcohol/acid mol ratio synthesis of benzyl esters of the formic, acetic, benzoic, salicylic, nicotinic, and oxalic acids are described. The stoichiometric reactions used 1.5 mol ratio solid NbCl5 as the reagent and required from two to three hours for completion at room temperature; for the catalytic processes, NbCl5 was grafted directly, at room temperature, onto a silica gel of specific area of 507 m2g−1, produced from construction sand and sodium carbonate, forming a 5.4% Nb w/w SiO2-Nb gel with a specific area of 412 m2g−1. At 10% w/w catalyst/alcohol ratio, this SiO2-Nb catalyst gave similarly very good yields but required from 6 to 9 hours at the reflux temperature of the slurry. The catalyst could be re-used three times. Keyword: Organic chemistry

  17. Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling.

    Science.gov (United States)

    Lapinsky, David J; Velagaleti, Ranganadh; Yarravarapu, Nageswari; Liu, Yi; Huang, Yurong; Surratt, Christopher K; Lever, John R; Foster, James D; Acharya, Rejwi; Vaughan, Roxanne A; Deutsch, Howard M

    2011-01-01

    In contrast to tropane-based compounds such as benztropine and cocaine, non-tropane-based photoaffinity ligands for the dopamine transporter (DAT) are relatively unexplored. Towards addressing this knowledge gap, ligands were synthesized in which the piperidine nitrogen of 3- and 4-iodomethylphenidate was substituted with a benzyl group bearing a photoreactive azide. Analog (±)-3a demonstrated modest DAT affinity and a radioiodinated version was shown to bind covalently to rat striatal DAT and hDAT expressed in cultured cells. Co-incubation of (±)-3a with nonradioactive d-(+)-methylphenidate or (-)-2-β-carbomethoxy-3-β-(4-fluorophenyl)tropane (β-CFT, WIN-35,428, a cocaine analog) blocked DAT labeling. Compound (±)-3a represents the first successful example of a DAT photoaffinity ligand based on the methylphenidate scaffold. Such ligands are expected to assist in mapping non-tropane ligand-binding pockets within plasma membrane monoamine transporters. Copyright © 2010 Elsevier Ltd. All rights reserved.

  18. Fabrication of reduced graphene oxide-BiOCl hybrid material via a novel benzyl alcohol route and its enhanced photocatalytic activity

    Energy Technology Data Exchange (ETDEWEB)

    Tian, Lihong; Liu, Jinyan; Gong, Chuqing; Ye, Liqun; Zan, Ling, E-mail: irlab@whu.edu.cn [Wuhan University, College of Chemistry and Molecular Sciences (China)

    2013-09-15

    Reduced graphene oxide (RGO)-BiOCl hybrid materials were prepared by a novel benzyl alcohol route. The formation of uniform RGO-BiOCl hybrids was attributed to the interaction of introduced graphene oxide and BiOCl, which resulted in a selective growth of BiOCl along (110) orientation. The RGO-BiOCl hybrids showed both enhanced visible-light and ultraviolet light photocatalytic activities compared to nano-BiOCl with similar particle size. In particular, the first-order kinetic constant (k) of Rhodamine B on the optimal RGO (0.73 %)-BiOCl hybrid was 2.5 times that on bare nano-BiOCl under visible-light irradiation. For RGO-BiOCl hybrids, RGO probably acted as a photosensitizer in photocatalytic reaction and resulted in the improved visible-light photocatalytic performance. However, RGO was an excellent electron transfer and inhibited the recombination of electron-hole pairs on BiOCl under ultraviolet light.

  19. Effects of a myosin-II inhibitor (N-benzyl-p-toluene sulphonamide, BTS) on contractile characteristics of intact fast-twitch mammalian muscle fibres.

    Science.gov (United States)

    Pinniger, G J; Bruton, J D; Westerblad, H; Ranatunga, K W

    2005-01-01

    We have examined the effects of N-benzyl-p-toluene sulphonamide (BTS), a potent and specific inhibitor of fast muscle myosin-II, using small bundles of intact fibres or single fibres from rat foot muscle. BTS decreased tetanic tension reversibly in a concentration-dependent manner with half-maximal inhibition at approximately approximately 2 microM at 20 degrees C. The inhibition of tension with 10 microM BTS was marked at the three temperatures examined (10, 20 and 30 degrees C), but greatest at 10 degrees C. BTS decreased active muscle stiffness to a lesser extent than tetanic tension indicating that not all of the tension inhibition was due to a reduced number of attached cross-bridges. BTS-induced inhibition of active tension was not accompanied by any change in the free myoplasmic Ca2+ transients. The potency and specificity of BTS make it a very suitable myosin inhibitor for intact mammalian fast muscle and should be a useful tool for the examination of outstanding questions in muscle contraction.

  20. Effects of BTS (N-benzyl-p-toluene sulphonamide), an inhibitor for myosin-actin interaction, on myofibrillogenesis in skeletal muscle cells in culture.

    Science.gov (United States)

    Kagawa, Maiko; Sato, Naruki; Obinata, Takashi

    2006-11-01

    Actin filaments align around myosin filaments in the correct polarity and in a hexagonal arrangement to form cross-striated structures. It has been postulated that this myosin-actin interaction is important in the initial phase of myofibrillogenesis. It was previously demonstrated that an inhibitor of actin-myosin interaction, BDM (2,3-butanedione monoxime), suppresses myofibril formation in muscle cells in culture. However, further study showed that BDM also exerts several additional effects on living cells. In this study, we further examined the role of actin-myosin interaction in myofibril assembly in primary cultures of chick embryonic skeletal muscle by applying a more specific inhibitor, BTS (N-benzyl-p-toluene sulphonamide), of myosin ATPase and actin-myosin interaction. The assembly of sarcomeric structures from myofibrillar proteins was examined by immunocytochemical methods with the application of BTS to myotubes just after fusion. Addition of BTS (10-50 microM) significantly suppressed the organization of actin and myosin into cross-striated structures. BTS also interfered in the organization of alpha-actinin, C-protein (or MyBP-C), and connectin (or titin) into ordered striated structures, though the sensitivity was less. Moreover, when myotubes cultured in the presence of BTS were transferred to a control medium, sarcomeric structures were formed in 2-3 days, indicating that the inhibitory effect of BTS on myotubes is reversible. These results show that actin-myosin interaction plays a critical role in the process of myofibrillogenesis.

  1. Study of the Activity of 3-benzyl-5-(4-chloro-arylazo-4-thioxo-imidazolidin-2-one against Schistosomiasis Mansoni in Mice

    Directory of Open Access Journals (Sweden)

    Andréa Cristina Apolinário da Silva

    2012-01-01

    Full Text Available Previous studies conducted with the imidazolidinic derivative 3-benzyl-5-(4-chloro-arylazo-4-thioxo-imidazolidin-2-one (LPSF-PT05 show outstanding activity against adult Schistosoma mansoni worms in vitro. In the first phase of this study, S. mansoni-infected mice were treated, orally, with 100 mg/Kg of the LPSF-PT05 in three formulations: Tween 80 and saline solution, oil/water (70 : 30 emulsion, and solid dispersion with polyethylene glycol (PEG. In the second phase, three other doses of the LPSF-PT05 in PEG were tested: 3, 10, 30 mg/kg. These treatment regimens significantly reduced the number of recovered worms due to increases in the solubility of the compound in this formulation; the greatest reduction (70.5% was observed at the dose of 100 mg/kg. There was no changes in the pattern of mature egg compared to immature eggs; however there was a significant increase in the number of dead eggs. Histopathological analysis of liver tissue showed changes in morphological aspects of the hepatic parenchyma with decrease exudative-productive hepatic granuloma stages, although we found no significant differences in IFN-γ, IL-4, IL-10, or NO production in response to the specific antigen SEA. The results show the derivative LPSF-PT05 to be a potential candidate in the etiological treatment of schistosomiasis with a possible dampening effect of the granulomatous process.

  2. Selective liquid phase oxidation of benzyl alcohol to benzaldehyde by tert-butyl hydroperoxide over γ-Al{sub 2}O{sub 3} supported copper and gold nanoparticles

    Energy Technology Data Exchange (ETDEWEB)

    Ndolomingo, Matumuene Joe; Meijboom, Reinout, E-mail: rmeijboom@uj.ac.za

    2017-03-15

    Highlights: • Cu and Au on γ-Al{sub 2}O{sub 3} catalysts were prepared and characterized. • Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide in the absence of any solvent using the prepared catalysts. • The as prepared catalysts exhibited good performance in terms of conversion and selectivity towards benzaldehyde. • The kinetics of the reaction was investigated; k{sub app} was proportional to the amount of nano catalyst and oxidant present in the system. • The catalysts was recycled and reused with neither significant loss of activity nor selectivity. - Abstract: Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide (TBHP) in the absence of any solvent using γ-Al{sub 2}O{sub 3} supported copper and gold nanoparticles. Li{sub 2}O and ionic liquids were used as additive and stabilizers for the synthesis of the catalysts. The physico-chemical properties of the catalysts were characterized by atomic absorption spectroscopy (AAS), X-ray diffraction spectroscopy (XRD), N{sub 2} absorption/desorption (BET), transmission electron microscopy (TEM), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and temperature programmed reduction (TPR), whereas, the oxidation reaction was followed by gas chromatography with a flame ionization detector (GC-FID). The as prepared catalysts exhibited good catalytic performance in terms of conversion and selectivity towards benzaldehyde. The performance of the Au-based catalysts is significantly higher than that of the Cu-based catalysts. For both Cu and Au catalysts, the conversion of benzyl alcohol increased as the reaction proceeds, while the selectivity for benzaldehyde decreased. Moreover, the catalysts can be easily recycled and reused with neither significant loss of activity nor selectivity. A kinetic study for the Cu and Au-catalyzed oxidation of benzyl alcohol to benzyldehyde is reported. The rate at which the oxidation of benzyl alcohol

  3. Determination of Benzyl-hexadecyldimethylammonium 1,4-Bis(2-ethylhexyl)sulfosuccinate Vesicle Permeability by Using Square Wave Voltammetry and an Enzymatic Reaction.

    Science.gov (United States)

    Cobo Solis, Airam K; Correa, N Mariano; Molina, Patricia G

    2017-10-31

    This report describes the studies performed to determine the permeability coefficient value (P) of 1-naphthyl phosphate (1-NP) through the benzyl-hexadecyldimethylammonium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT-BHD) vesicle bilayer. 1-NP was added in the external phase and must cross the bilayer of the vesicle to react with the encapsulated enzyme (alkaline phosphatase) to yield 1-naphtholate (NPh - ), the product of the enzymatic hydrolysis. This product is electrochemically detected, at basic pH value, by a square wave voltammetry technique, which can be a good alternative over the spectroscopic one, to measure the vesicle solutions because scattering (due to its turbidity) does not make any influence in the electrochemical signal. The experimental data allow us to propose a mathematical model, and a value of P = (1.00 ± 0.15) × 10 -9 cm s -1 was obtained. Also, a value of P = (2.0 ± 0.5) × 10 -9 cm s -1 was found by using an independent technique, ultraviolet-visible spectroscopy, for comparison. It is evident that the P values obtained from both the techniques are comparable (within the experimental error of both techniques) under the same experimental conditions. This study constitutes the first report of the 1-NP permeability determination in this new vesicle. We want to highlight the importance of the introduction of a new method and the electrochemical response of the product generated through an enzymatic reaction that occurs in the inner aqueous phase of the vesicle, where the enzyme is placed.

  4. The Novel SCN''- Ion-selective Electrode Based on the 1-Benzyl-3-(4-nitrophenyl) thio-urea Ionophore

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Kyung Mi; Kang, Dong Hyeon; Choe, Ju Eun; You, Jung Min; Go, Min Jeong; Lee, Jung Seong; Jeon, Seung Won [Chungnam National University, Daejeon (Korea, Republic of)

    2014-09-15

    A potentiometric sensor based on the 1-benzyl-3-(4-nitrophenyl) thio-urea was synthesized and tested as an ionophore in PVC based membrane sensor towards SCN - ions. This membrane exhibits a linear stable response over a wide concentration range (1.0 × 10''-5 to 1.0 × 10''-2 M) with a slope of -59.2 mV/dec., a detection limit of log[SCN''- ] = -5.05, and a selectivity coefficient for thiocyanate against perchlorate anion of logK{sub s}cn''pot = -0.133. The selectivity series of the membrane is as follows: SCN''- > ClO{sub 4}''- > I''- >NO{sub 3}''- >HSO{sub 3}''- > Cl''-HSO{sub '}'-''4 > F''- > CH{sub 3}COO''- > HCO''-''3 > Br''- > H{sub 2}PO{sub 4}''- > SO{sub 3}''-''2 > SO{sub 4}''-''2 > CO{sub 3}''-''2. The proposed electrode showed good selectivity and a good response for the SCN''- ion over a wide variety of other anions in pH 6.0 buffer solutions and has a fast response time of about < 5s.. The influences of the membrane by pH, ionophore, and plasticizer were studied.

  5. Antimicrobial, free radical scavenging activities and catalytic oxidation of benzyl alcohol by nano-silver synthesized from the leaf extract of Aristolochia indica L.: a promenade towards sustainability

    Science.gov (United States)

    Shanmugam, C.; Sivasubramanian, G.; Parthasarathi, Bera; Baskaran, K.; Balachander, R.; Parameswaran, V. R.

    2016-06-01

    Silver nanoparticles (Ag-NPs) were synthesized from aqueous silver nitrate through a simple route using the leaf extract of Aristolochia indica L. (LAIL) which acted as a reducing as well as capping agent. X-ray diffraction confirmed that the synthesized silver particles have a face centred cubic structure. EDS predicted the presence of elemental silver. The SEM images showed the synthesis of spherically mono-dispersed particles, with nano dimensions accounted by the TEM images. Infra-red spectrum adopted to the different organic functionalities present at the surface of the particles. TGA indicated an overall 11 % weight loss up to 1000 °C, suggesting desorption of biomolecules from the surface. X-ray photoelectron spectroscopy (XPS) analysis revealed the presence of metallic silver nanoparticles. The prepared material was utilized as catalyst in the oxidation of benzyl alcohol with molecular oxygen as the oxidant in methanol, under ambient conditions of temperature and pressure. Also Ag-NPs showed good to moderate anti-microbial activity employing the Agar disc diffusion method against various strains using Ciprofloxacin and Fluconazole as standard. Free radical scavenging activity of the nanoparticles were observed by modified 1,1-diphynyl-2-picrylhydrazyl, DPPH and 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), ABTS in vitro assays. The work presented here demonstrates the adaptability of the synthesized Ag-NPs in participating as a disinfectant agent, free radical scavenger and an effective oxidation catalyst. The basic premise of attaining sustainability through the green synthesis of smart multifaceted materials has been consciously addressed.

  6. Hindered rotor tunneling splittings: an application of the two-dimensional non-separable method to benzyl alcohol and two of its fluorine derivatives.

    Science.gov (United States)

    Alves, Tiago Vinicius; Simón-Carballido, Luis; Ornellas, Fernando Rei; Fernández-Ramos, Antonio

    2016-04-07

    In this work we present a novel application of the two-dimensional non-separable (2D-NS) method to the calculation of torsional tunneling splittings in systems with two hindered internal rotors. This method could be considered an extension of one-dimensional methods for the case of compounds with two tops. The 2D-NS method includes coupling between torsions in the kinetic and potential energy. Specifically, it has been applied to benzyl alcohol (BA) and two of its fluorine derivatives: 3-fluorobenzyl alcohol (3FBA) and 4-fluorobenzyl alcohol (4FBA). These molecules present two torsions, i.e., about the -CH2OH (ϕ1) and -OH (ϕ2) groups. The electronic structure calculations to build the two-dimensional torsional potential energy surface were performed at the DF-LMP2-F12//DF-LMP2/cc-pVQZ level of theory. For BA and 4FBA the calculated ground-state vibrational level splittings are 429 and 453 MHz, respectively, in good agreement with the experimental values of 337.10 and 492.82 MHz, respectively. In these two cases there are four equivalent wells and the tunneling splitting is the result of transitions between the two closer minima along ϕ1. The analysis of the wavefunctions, as well as the previous experimental work on the system, supports this conclusion. For 3FBA the observed ground-state splitting is 0.82 MHz, whereas in this case the calculated value amounts only to 0.02 MHz. The 2D-NS method, through the analysis of the wavefunctions, shows that this tiny tunneling splitting occurs between the two most stable minima of the potential energy surface. Additionally, we predict that the first vibrationally excited tunneling splitting will also be small and exclusively due to the interconversion between the second lowest minima.

  7. DETERMINATION OF DIBUTYL PHTHALATE (DBP, BENZYL BUTYL PHTHALATE (BBP AND BIS (2-ETHYLHEXYL PHTHALATE (DEHP IN SOFT PLASTIC TOYS AND THE FIRST SURVEY OF THE BULGARIAN MARKET

    Directory of Open Access Journals (Sweden)

    Valentina CHRISTOVA-BAGDASSARIAN

    2017-12-01

    Full Text Available Phthalates are a large group of compounds with similar chemical structure widely used as plasticizers for plastics. They can easily be released from the polymer during usage and in this way enter the human body. Their adverse effect on health is known as "phthalate syndrome" and can impact children and adults alike. For children in particular, there is an additional potential risk of exposure to phthalates via toys intended for oral use. The Regulation (EC No 1907/2006 (REACH prohibits the use of bis (2-ethylhexyl phthalate (DEHP, di butyl phthalate (DBP and benzyl butyl phthalate (BBP as a substance or constituent of preparations at concentrations higher than 0.1 % in the plasticized material meant to toys and childcare items. The aim of this article is to quantify the content of DEHP, DBP and BBP in soft toys intended for children up to 3 years of age, including toys designed to be placed in the mouth. A method consisting of an extraction procedure of phthalates from polymers, purification of the extract, followed by GC/MS identification and quantification was validated. Three different techniques for phthalates’ extraction (Soxhlet, ultrasonic and vibrator were compared and the most effective one was chosen.This method was applied to the analysis of DEHP, DBP and BBP in soft toys from the Bulgarian market to establish their compliance with REACH requirements. All the tested toys contained at least one phthalate. Exceedence of the permitted content for DEHP, DBP and BBP (as sume, mainly due to the high levels of DEHP, was observed in several toys from retail.

  8. Effect of addition of butyl benzyl phthalate plasticizer and zinc oxide nanoparticles on mechanical properties of cellulose acetate butyrate/organoclay biocomposite

    Science.gov (United States)

    Putra, B. A. P.; Juwono, A. L.; Rochman, N. T.

    2017-07-01

    Plastics as packaging materials and coatings undergo increasing demands globally each year. This pose a serious problem to the environment due to its difficulty to degrade. One solution to addressing the problem of plastic wastes is the use of bioplastics. According to the European Organization Bioplastic, one of the biodegradable plastics is derivative of cellulose. To improve mechanical properties of bioplastic, biocomposites are made with the addition of certain additives and fillers. The aim of this study is to investigate the effect of butyl benzyl phthalate plasticizer (BBP) and ZnO nanoparticles addition on mechanical properties of cellulose acetate butyrate (CAB) / organoclay biocomposite. ZnO nanoparticles synthesized from commercial ZnO precursor by using sol-gel size reduction method. ZnO was dissolved in a solution of citric acid in the ratio 1:1 to 1:5 to form zinc citrate. Zinc citrate then decomposed by calcination at temperature of 600oC. ZnO nanoparticles with an average size of 44.4 nm is obtained at a ratio of 1: 2. The addition of ZnO nanoparticles and BBP plasticizer was varied to determine the effect on the mechanical properties of biocomposite. The addition of 10 - 15 %wt ZnO nanoparticles and 30 - 40 %wt BBP plasticizer was studied to determine the effect on the tensile strength, elongation, and modulus elasticity of the biocomposites. Biocomposite films were made by using solution casting method with acetone as solvent. The addition of plasticizer BBP and ZnO nanoparticles by 30% and 10% made biocomposite has a tensile strength of 2.223 MPa.

  9. Dietary agent, benzyl isothiocyanate inhibits signal transducer and activator of transcription 3 phosphorylation and collaborates with sulforaphane in the growth suppression of PANC-1 cancer cells

    Directory of Open Access Journals (Sweden)

    Deangelis Stephanie

    2009-08-01

    Full Text Available Abstract The Signal Transducer and Activator of Transcription (STAT proteins comprise a family of latent transcription factors with diverse functions. STAT3 has well established roles in cell proliferation, growth and survival, and its persistent activation has been detected with high frequency in many human cancers. As constitutive activation of STAT3 appears to be vital for the continued survival of these cancerous cells, it has emerged as an attractive target for chemotherapeutics. We examined whether the inhibitory activities of bioactive compounds from cruciferous vegetables, such as Benzyl isothiocyanate (BITC and sulforaphane, extended to STAT3 activation in PANC-1 human pancreatic cancer cells. BITC and sulforaphane were both capable of inhibiting cell viability and inducing apoptosis in PANC-1. Sulforaphane had minimal effect on the direct inhibition of STAT3 tyrosine phosphorylation, however, suggesting its inhibitory activities are most likely STAT3-independent. Conversely, BITC was shown to inhibit the tyrosine phosphorylation of STAT3, but not the phosphorylation of ERK1/2, MAPK and p70S6 kinase. These results suggest that STAT3 may be one of the targets of BITC-mediated inhibition of cell viability in PANC-1 cancer cells. In addition, we show that BITC can prevent the induction of STAT3 activation by Interleukin-6 in MDA-MB-453 breast cancer cells. Furthermore, combinations of BITC and sulforaphane inhibited cell viability and STAT3 phosphorylation more dramatically than either agent alone. These findings suggest that the combination of the dietary agents BITC and sulforaphane has potent inhibitory activity in pancreatic cancer cells and that they may have translational potential as chemopreventative or therapeutic agents.

  10. Benzyl isothiocyanate suppresses pancreatic tumor angiogenesis and invasion by inhibiting HIF-α/VEGF/Rho-GTPases: pivotal role of STAT-3.

    Directory of Open Access Journals (Sweden)

    Srinivas Reddy Boreddy

    Full Text Available Our previous studies have shown that benzyl isothiocyanate (BITC suppresses pancreatic tumor growth by inhibiting STAT-3; however, the exact mechanism of tumor growth suppression was not clear. Here we evaluated the effects and mechanism of BITC on pancreatic tumor angiogenesis. Our results reveal that BITC significantly inhibits neovasularization on rat aorta and Chicken-Chorioallantoic membrane. Furthermore, BITC blocks the migration and invasion of BxPC-3 and PanC-1 pancreatic cancer cells in a dose dependant manner. Moreover, secretion of VEGF and MMP-2 in normoxic and hypoxic BxPC-3 and PanC-1 cells was significantly suppressed by BITC. Both VEGF and MMP-2 play a critical role in angiogenesis and metastasis. Our results reveal that BITC significantly suppresses the phosphorylation of VEGFR-2 (Tyr-1175, and expression of HIF-α. Rho-GTPases, which are regulated by VEGF play a crucial role in pancreatic cancer progression. BITC treatment reduced the expression of RhoC whereas up-regulated the expression of tumor suppressor RhoB. STAT-3 over-expression or IL-6 treatment significantly induced HIF-1α and VEGF expression; however, BITC substantially suppressed STAT-3 as well as STAT-3-induced HIF-1α and VEGF expression. Finally, in vivo tumor growth and matrigel-plug assay show reduced tumor growth and substantial reduction of hemoglobin content in the matrigel plugs and tumors of mice treated orally with 12 µmol BITC, indicating reduced tumor angiogenesis. Immunoblotting of BITC treated tumors show reduced expression of STAT-3 phosphorylation (Tyr-705, HIF-α, VEGFR-2, VEGF, MMP-2, CD31 and RhoC. Taken together, our results suggest that BITC suppresses pancreatic tumor growth by inhibiting tumor angiogenesis through STAT-3-dependant pathway.

  11. Unexpected side products in the conjugation of an amine-derivatized morpholino oligomer with p-isothiocyanate benzyl DTPA and their removal

    Energy Technology Data Exchange (ETDEWEB)

    Liu Guozheng, E-mail: guozheng.liu@umassmed.ed [Department of Radiology, University of Massachusetts Medical School, Worcester, MA 01655 (United States); Dou Shuping; Liu Yuxia; Liang Minmin; Chen Ling; Cheng Dengfeng [Department of Radiology, University of Massachusetts Medical School, Worcester, MA 01655 (United States); Greiner, Dale [Department of Medicine, University of Massachusetts Medical School, Worcester, MA 01655 (United States); Rusckowski, Mary; Hnatowich, Donald J. [Department of Radiology, University of Massachusetts Medical School, Worcester, MA 01655 (United States)

    2011-02-15

    In connection with pretargeting, an amine-derivatized morpholino phosphorodiamidate oligomer (NH{sub 2}-cMORF) was conjugated conventionally with p-isothiocyanate benzyl-DTPA (p-SCN-Bn-DTPA). However, after {sup 111}In radiolabeling, unexpected label instability was observed. To understand this instability, the NH{sub 2}-cMORF and, as control, the native cMORF without the amine were conjugated in the conventional manner. Surprisingly, the {sup 111}In labeling of the native cMORF conjugate was equally effective as that of the NH{sub 2}-cMORF conjugate (>95%) despite the absence of the amine group. Furthermore, heating the radiolabeled NH{sub 2}-cMORF and native cMORF conjugates resulted in a 35% loss and a complete loss of the label, respectively. Since the {sup 111}In labeled DTPA is known to be stable, the instability in both cases must be due to some unstable association of DTPA to the cMORF, presumably unstable association to some endogenous sites in cMORF. Based on this assumption, a postconjugation-prepurification heating step was introduced, and labeling efficiency and stability were again investigated. By introducing the heating step, the side products were dissociated, and after purification and labeling, the NH{sub 2}-cMORF conjugate provided a stable label and high labeling efficiency with no need for postlabeling purification. The biodistribution of this radiolabeled conjugate in normal mice showed significantly lower backgrounds compared with the labeled unstable native cMORF conjugate. In conclusion, the conventional conjugation procedure to attach the p-SCN-Bn-DTPA to NH{sub 2}-cMORF resulted in side product(s) that were responsible for the {sup 111}In label instability. Adding a postconjugation-prepurification heating step dissociated the side products, improved the label stability and lowered tissue backgrounds in mice.

  12. Cytotoxicity, Antioxidant and Apoptosis Studies of Quercetin-3-O Glucoside and 4-(β-D-Glucopyranosyl-1→4-α-L-Rhamnopyranosyloxy)-Benzyl Isothiocyanate from Moringa oleifera.

    Science.gov (United States)

    Maiyo, Fiona C; Moodley, Roshila; Singh, Moganavelli

    2016-01-01

    Moringa oleifera, from the family Moringaceae, is used as a source of vegetable and herbal medicine and in the treatment of various cancers in many African countries, including Kenya. The present study involved the phytochemical analyses of the crude extracts of M.oleifera and biological activities (antioxidant, cytotoxicity and induction of apoptosis in-vitro) of selected isolated compounds. The compounds isolated from the leaves and seeds of the plant were quercetin-3-O-glucoside (1), 4-(β-D-glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)-benzyl isothiocyanate (2), lutein (3), and sitosterol (4). Antioxidant activity of compound 1 was significant when compared to that of the control, while compound 2 showed moderate activity. The cytotoxicity of compounds 1 and 2 were tested in three cell lines, viz. liver hepatocellular carcinoma (HepG2), colon carcinoma (Caco-2) and a non-cancer cell line Human Embryonic Kidney (HEK293), using the MTT cell viability assay and compared against a standard anticancer drug, 5-fluorouracil. Apoptosis studies were carried out using the acridine orange/ethidium bromide dual staining method. The isolated compounds showed selective in vitro cytotoxic and apoptotic activity against human cancer and non-cancer cell lines, respectively. Compound 1 showed significant cytotoxicity against the Caco-2 cell line with an IC50 of 79 μg mL(-1) and moderate cytotoxicity against the HepG2 cell line with an IC50 of 150 μg mL(-1), while compound 2 showed significant cytotoxicity against the Caco- 2 and HepG2 cell lines with an IC50 of 45 μg mL(-1) and 60 μg mL(-1), respectively. Comparatively both compounds showed much lower cytotoxicity against the HEK293 cell line with IC50 values of 186 μg mL(-1) and 224 μg mL(-1), respectively.

  13. Neutral and stereospecific Tc-99m complexes: [99mTc]N-benzyl-3,4-di-(N-2-mercaptoethyl)-amino-pyrrolidines (P-BAT)

    International Nuclear Information System (INIS)

    Zhuang Zhiping; Ploessl, Karl; Kung Meiping; Mu Mu; Kung, Hank F.

    1999-01-01

    Technetium-99m-labeled radiopharmaceuticals are currently the most commonly used agents in nuclear medicine. To prepare binding site-specific small molecules containing a Tc-99m complexing core, it is important to consider a ligand system, which selectively forms only one stereoisomer. A novel series of bisaminoethanethiol (BAT) derivatives as a model system were prepared. Stereoisomers of N-benzyl-3,4-di-(N-2-mercaptoethyl)-amino pyrrolidines (P-BAT): (3R,4R)-P-BAT (R,R-4) and (3,4)meso-P-BAT (8), the trans and meso isomer, respectively, as a chelating group were prepared successfully. The desired Tc-99m P-BAT complexes were obtained by using Sn(II)/glucoheptonate as the reducing agent for [ 99m Tc]pertechnetate. As predicted, after complexation with [ 99m Tc]Tc v O, the trans isomer, (3R,4R)-P-BAT (R,R-4), showed only one isomer; whereas the corresponding meso isomer, (3,4)meso-P-BAT (8), produced two distinctive complexes isolated readily by high performance liquid chromatography (HPLC). The [ 99m Tc](R,S)meso-P-BAT (8) isomers showed a different lipophilicity (partition coefficient [P.C.]=54.3 and 55.4 for peak A and peak B, respectively), as compared with that of the corresponding [ 99m Tc](3R,4R)-P-BAT (R,R-4), trans isomer ( P.C.=163). Results of the biodistribution study in rats of these isomers show different heart and brain uptake, suggesting that the intrinsic differences in biodistribution are due to structural and stereospecific factors. Examples in this report confirm that it is possible to design stereospecific Tc-99m complexes based on the bisaminoethanethiol (N 2 S 2 , BAT) ligand system. Consideration on stereoselectivity of site-specific agents labeled with Tc-99m is likely an essential requirement on developing binding-site specific radiopharmaceuticals

  14. Evaluation of radioiodinated (2S,{alpha}S)-2-({alpha}-(2-iodophenoxy)benzyl)morpholine as a radioligand for imaging of norepinephrine transporter in the heart

    Energy Technology Data Exchange (ETDEWEB)

    Kiyono, Yasushi [Biomedical Imaging Research Center, University of Fukui, Fukui 910-1193 (Japan); Radioisotopes Research Laboratory, Kyoto University Hospital, Faculty of Medicine, Kyoto University, Kyoto 606-8507 (Japan)], E-mail: ykiyono@u-fukui.ac.jp; Sugita, Taku [Department of Pathofunctional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan); Ueda, Masashi [Radioisotopes Research Laboratory, Kyoto University Hospital, Faculty of Medicine, Kyoto University, Kyoto 606-8507 (Japan); Kawashima, Hidekazu [Department of Nuclear Medicine and Diagnostic Imaging, Graduate School of Medicine, Kyoto University, Kyoto 606-8507 (Japan); Kanegawa, Naoki; Kuge, Yuji [Department of Pathofunctional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan); Fujibayashi, Yasuhisa [Biomedical Imaging Research Center, University of Fukui, Fukui 910-1193 (Japan); Saji, Hideo [Department of Pathofunctional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan)

    2008-02-15

    Introduction: The norepinephrine transporter (NET) is located presynaptically on noradrenergic nerve terminals and plays a critical role in the regulation of the synaptic norepinephrine (NE) concentration via the reuptake of NE. Changes in NET have been recently reported in several cardiac failures. Therefore, a NET-specific radioligand is useful for in vivo assessment of changes in NET density in various cardiac disorders. Recently, we developed a radioiodinated reboxetine analogue, (2S,{alpha}S)-2-({alpha}-(2-iodophenoxy)benzyl)morpholine ((S,S)-IPBM), for NET imaging. In the current study, we assessed the applicability of radioiodinated (S,S)-IPBM to NET imaging in the heart. Methods: The NET affinity and selectivity were measured from the ability to displace specific [{sup 3}H]nisoxetine and (S,S)-[{sup 125}I]IPBM binding to rat heart membrane, respectively. To evaluate the distribution of (S,S)-[{sup 125}I]IPBM in vivo, biodistribution experiment was performed in rats. With the use of several monoamine transporter binding agents, pharmacological blocking experiments were performed in rats. Results: In vitro binding assays showed that the affinity of (S,S)-IPBM to NET was similar to those of the well-known NET-specific binding agents, nisoxetine and desipramine. Furthermore, (S,S)-[{sup 125}I]IPBM binding was inhibited by nisoxetine and desipramine, but not by dopamine or serotonin transporter binding agents. These data indicated that (S,S)-IPBM had high affinity and selectivity for NET in vitro. Biodistribution studies in rats showed rapid and high uptake of (S,S)-[{sup 125}I]IPBM by the heart and rapid clearance from the blood. The heart-to-blood ratio was 31.9 at 180 min after the injection. The administration of nisoxetine and desipramine decreased (S,S)-[{sup 125}I]IPBM accumulation in the heart, but injection of fluoxetine and GBR12909 had little influence. Conclusions: Radioiodinated (S,S)-IPBM is a potential radioligand for NET imaging in the heart.

  15. Potential of N-aryl(benzyl,heteryl-2-(tetrazolo[1,5-c]quinazolin-5-ylthioacetamides as anticancer and antimicrobial agents

    Directory of Open Access Journals (Sweden)

    Oleksii M. Antypenko

    2016-11-01

    Full Text Available The death rate from cancer and infectious diseases is still very high, therefore research in this area is extremely important and promising as in medical, so in economic point of view. Thus, potassium salt of tetrazolo[1,5-c]quinazolin-5-thion was modified per alkylation by N-aryl(benzyl,heterylacetamides with proper confirmation of newly synthesized compounds’ structures by FT-IR, LC–MS, 1H NMR and elemental analysis data. The substances were tested for bioluminescence inhibition against Photobacterium leiognathi Sh1 (5–50 μg/mL to check their cytotoxicity. Then they were screened for antibacterial and antifungal activities (100 μg against Escherichia coli, Staphylococcus aureus, Enterobacter aerogenes and Enterococcus faecalis, Pseudomonas aeruginosa, Klebsiella pneumoniae and Candida albicans. It was found that compounds 1.1, 1.5, 1.10, 1.31, 1.33 possessed light activity against K. pneumonia. The US National Cancer Institute (NCI has chosen 19 compounds and screened them for ability to inhibit in 10 μM concentration 60 different human tumor cell lines. The LOX IMVI cell line of melanoma appeared to be the most sensitive one, and N-(6-methylbenzo[d]thiazol-2-yl-2-(tetrazolo[1,5-c]quinazolin-5-ylthioacetamide (1.31 and N-(3-fluorobenzyl-2-(tetrazolo[1,5-c]quinazolin-5-ylthioacetamide (1.19 exhibited high growth inhibition rate, and N-(6-methoxybenzo[d]thiazol-2-yl-2-(tetrazolo[1,5-c]quinazolin-5-ylthioacetamide (1.32 showed lethal antitumor activity against it. The latter compound 1.32 showed the best anticancer results, also inhibiting growth of leukemia SR cell line, NCI-H460 of non-small cell lung cancer, KM12 of colon cancer and SF-295 of CNS cancer. The in silico molecular docking studies have predicted the affinity of the synthesized substances to the epidermal growth factor receptor (EGFR.

  16. Fractionated therapy of HER2-expressing breast and ovarian cancer xenografts in mice with targeted alpha emitting 227Th-DOTA-p-benzyl-trastuzumab.

    Directory of Open Access Journals (Sweden)

    Helen Heyerdahl

    Full Text Available BACKGROUND: The aim of this study was to investigate therapeutic efficacy and normal tissue toxicity of single dosage and fractionated targeted alpha therapy (TAT in mice with HER2-expressing breast and ovarian cancer xenografts using the low dose rate radioimmunoconjugate (227Th-DOTA-p-benzyl-trastuzumab. METHODOLOGY/PRINCIPAL FINDINGS: Nude mice carrying HER2-overexpressing subcutaneous SKOV-3 or SKBR-3 xenografts were treated with 1000 kBq/kg (227Th-trastuzumab as single injection or four injections of 250 kBq/kg with intervals of 4-5 days, 2 weeks, or 4 weeks. Control animals were treated with normal saline or unlabeled trastuzumab. In SKOV-3 xenografts tumor growth to 10-fold size was delayed (p<0.01 and survival with tumor diameter less than 16 mm was prolonged (p<0.05 in all TAT groups compared to the control groups. No statistically significant differences were seen among the treated groups. In SKBR-3 xenografts tumor growth to 10-fold size was delayed in the single injection and 4-5 days interval groups (p<0.001 and all except the 4 weeks interval TAT group showed improved survival to the control groups (p<0.05. Toxicity was assessed by blood cell counts, clinical chemistry measurements and body weight. Transient reduction in white blood cells was seen for the single injection and 4-5 days interval groups (p<0.05. No significant changes were seen in red blood cells, platelets or clinical chemistry parameters. Survival without life threatening loss of body weight was significantly prolonged in 4 weeks interval group compared to single injection group (p<0.05 for SKOV-3 animals and in 2 weeks interval group compared with the 4-5 days interval groups (p<0.05 for SKBR-3 animals. CONCLUSIONS/SIGNIFICANCE: The same concentration of radioactivity split into several fractions may improve toxicity of (227Th-radioimmunotherapy while the therapeutic effect is maintained. Thus, it might be possible to increase the cumulative absorbed radiation dose

  17. Synthesis, crystal structure analysis, spectral investigations, DFT computations and molecular dynamics and docking study of 4-benzyl-5-oxomorpholine-3-carbamide, a potential bioactive agent

    Science.gov (United States)

    Murthy, P. Krishna; Sheena Mary, Y.; Shyma Mary, Y.; Panicker, C. Yohannan; Suneetha, V.; Armaković, Stevan; Armaković, Sanja J.; Van Alsenoy, C.; Suchetan, P. A.

    2017-04-01

    4-benzyl-5-oxomorpholine-3-carbamide has been synthesized; single crystals were grown by slow evaporation solution growth technique at room temperature and characterized by single crystal X-ray diffraction, FT-IR, FT-Raman and 1H-NMR. The compound crystallizes in the monoclinic space group P21/n. The molecular geometry of the compound was optimized by using Density Functional Theory (DFT/B3LYP) method with 6-311++G(d,p) basis set in the ground state and geometric parameters are in agreement with the X-ray analysis results of the structure. The experimental vibrational spectra were compared with the calculated spectra and each vibrational wave number was assigned on the basis of potential energy distribution (PED). The electronic and charge transfer properties have been explained on the basis of highest occupied molecular orbital's (HOMOs) and lowest unoccupied molecular orbital's (LUMOs). Besides molecular electrostatic potential (MEP), frontier molecular orbital's (FMOs), some global reactivity descriptors, thermodynamic properties, non-linear optical (NLO) behavior and Mullikan charge analysis of the title compound were computed with the same method in gas phase, theoretically. Potential reactive sites of the title compound have been identified by average local ionization energy and Fukui functions, both mapped to the electron density surface. Bond dissociation energies for all single acyclic bonds have been calculated in order to investigate autoxidation and degradation properties of the title compound. Atoms with pronounced interactions with water molecules have been detected by calculations of radial distribution functions after molecular dynamics simulations. The experimental results are compared with the theoretical calculations using DFT methods for the fortification of the paper. Further the docking studies revealed that the title compound as a docked ligand forms a stable complex with pyrrole inhibitor with a binding affinity value of -7.5 kcal/mol. This

  18. Benzyl 3-(2-methylphenyldithiocarbazate

    Directory of Open Access Journals (Sweden)

    Mohamed Ibrahim Mohamed Tahir

    2012-05-01

    Full Text Available In the title compound, C15H16N2S2, the central C2N2S2 unit is essentially planar (r.m.s. deviation = 0.047 Å and forms dihedral angles of 68.26 (4 and 65.99 (4° with the phenyl and benzene rings, respectively, indicating a twisted molecule. Supramolecular chains with a step topology and propagating along [100] feature in the crystal packing, mediated through N—H...S hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H...π interactions.

  19. COMPLEXES CONTAINING HYDRAZINE AND BENZYL ...

    African Journals Online (AJOL)

    Preferred Customer

    ABSTRACT. The reaction of the polymeric species [{RuCl2(COD)}x] (1 ; x > 2; COD = cyclo-octa-1,5-diene) and hydrazine hydrate in methanol under reflux gave a pale pink solution from which the salt. [Ru(COD)(N2H4)4][BPh4]2.CH3OH (2) was isolated on addition of NaBPh4. Treatment of 2 in refluxing acetone.

  20. 9-Benzyl-10-methylacridinium trifluoromethanesulfonate

    Directory of Open Access Journals (Sweden)

    Damian Trzybiński

    2010-07-01

    Full Text Available In the crystal structure of the title compound, C21H18N+·CF3OS3−, the cations form inversion dimers through π–π interactions between the acridine ring systems. These dimers are further linked by C—H...π interactions. The cations and anions are connected by C—H...O, C—F...π and S—O...π interactions. The acridine and benzene ring systems are oriented at a dihedral angle of 76.8 (1°with respect to each other. The acridine moieties are either parallel or inclined at an angle of 62.4 (1° in the crystal structure.

  1. Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity.

    Science.gov (United States)

    Jiménez-Díaz, I; Molina-Molina, J M; Zafra-Gómez, A; Ballesteros, O; Navalón, A; Real, M; Sáenz, J M; Fernández, M F; Olea, N

    2013-10-01

    UV-filters are widely used in many personal care products and cosmetics. Recent studies indicate that some organic UV-filters can accumulate in biota and act as endocrine disruptors, but there are few studies on the occurrence and fate of these compounds in humans. In the present work, a new liquid chromatography-tandem mass spectrometry (LC-MS/MS) method to assess the presence of six UV-filters in current use (benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor, and 3-benzylidene camphor) in human placental tissue is proposed. The method involves the extraction of the analytes from the samples using ethyl acetate, followed by a clean-up step using centrifugation prior to their quantification by LC-MS/MS using an atmospheric pressure chemical ionization (APCI) interface. Bisphenol A-d16 was used as surrogate for the determination of benzyl salicylate, phenyl salicylate, octyl salicylate and homosalate in negative mode and benzophenone-d10, was used as surrogate for the determination of 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in positive mode. The found limits of detection ranged from 0.4 to 0.6ngg(-1) and the limits of quantification ranged from 1.3 to 2.0ngg(-1), while variability was under 13.7%. Recovery rates for spiked samples ranged from 97% to 104%. Moreover, the interactions of these compounds with the human estrogen receptor alpha (hERα) and androgen receptor (hAR), using two in vitro bioassays based on reporter gene expression and cell proliferation assessment, were also investigated. All tested compounds, except benzyl salicylate and octyl salicylate, showed estrogenic activity in the E-Screen bioassay whereas only homosalate and 3-(4-methylbenzylidene) camphor were potent hAR antagonists. Although free salicylate derivatives and free camphor derivatives were not detected in the human placenta samples analyzed, the observed estrogenic and anti-androgenic activities of some of these

  2. Homolytic bond dissociation energies for C-H bonds adjacent to sulfur and aromatic moieties: The effects of substituents of C-H bond strengths of the benzylic positions in coal model compounds

    Energy Technology Data Exchange (ETDEWEB)

    Alnajjar, M.S.; Franz, J.A. [Pacific Northwest Lab., Richland, WA (United States); Gleicher, G.J.; Truksa, S. [Oregon State Univ., Corvallis, OR (United States). Dept. of Chemistry; Bordwell, F.; Zhang, Xian-Man [Northwestern Univ., Evanston, IL (United States). Dept. of Chemistry

    1993-09-01

    Sulfur-containing compounds are precursors for thiyl radicals at coal liquefaction temperatures due to the weakness of The and S-S bonds. Thiyl radicals play important roles in hydrogen atom shuttling between benzylic positions and catalyze the cleavage and the formation of strong C-C bonds. Although many reactions of thiyl and other sulfur-containing radicals are qualitatively understood, the homolytic bond dissociation energies (EDE`s) and the thermochemistry associated with many key high molecular weight hydrocarbon and sulfur-containing organic structures important to coal is lacking because they are inappropriate for gas-phase techniques. The measurement of BDE`s has been proven to be difficult even in the simplest of molecules.

  3. Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E)-1-(2-benzyl?idene-1-methyl?hydrazin?yl)-3-hy?droxy-1-oxopropan-2-yl]carbamates

    OpenAIRE

    Noguiera, Thais C. M.; Pinheiro, Alessandra C.; Wardell, James L.; de Souza, Marcus V. N.; Abberley, Jordan P.; Harrison, William T. A.

    2015-01-01

    The crystal structures of three methyl?ated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopro?pan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tert-butyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopro?pan-2-yl]carbamate, C16H23N3O4. One of them shows...

  4. Synthesis, physicochemical and anticonvulsant properties of N-benzyl and N-aminophenyl derivatives of 2-azaspiro[4.4]nonane and [4.5]decane-1,3-dione. Part I.

    Science.gov (United States)

    Obniska, Jolanta; Dzierzawska-Majewska, Agnieszka; Zagorska, Agnieszka; Zajdel, Pawel; Karolak-Wojciechowska, Janina

    2005-01-01

    To continue our systematic SAR studies, two series of N-benzyl- (X=CH2) and N-aminophenyl- (X=NH) derivatives of 2-azaspiro[4.4]nonane (1a-1j) and 2-azaspiro[4.5]decane-1,3-dione (2a-2j) were synthesized, and evaluated in maximum electroshock seizure (MES), subcutaneous pentylenetetrazole (sc.MET) and rotorod (TOX) tests for their anticonvulsant activity. Among those derivatives, the most potent N-aminophenyl-2-azaspiro[4.4]nonane-1,3-dione 1j had ED50=76.27 mg kg-1. X-ray structures for two pairs of derivatives with a different linker were solved. Then 3-D data for the active 1j versus less active 2j, both having an imine linker (X=NH), and the respective parent of compounds with a methylene linker (X=CH2) (1a and 2a) were discussed.

  5. Determinação de isotiocianato de benzila em Carica papaya utilizando cromatografia gasosa com detectores seletivos Determination of benzyl isothiocyanate in Carica papaya using gas chromatography with selectives detectors

    Directory of Open Access Journals (Sweden)

    Izabela Miranda de Castro

    2008-01-01

    Full Text Available In the present work, a method was developed and validated for the quantification of benzyl isothiocyanate (BITC in the fruits of Carica papaya. The quantification of this compound was carried out by gas chromatography (GC with selective detectors - nitrogen phosphorus detector (NPD and flame photometric detector (FPD. The performance of these detectors showed a higher sensitivity of the NPD with a broader linear range of detection. The LOD/LOQ were 0.038/0.100 µg/mL for NPD and 5.78/19.29 µg/mL for FPD. The recovery of the method for BITC was 90,64%. An average value of BITC concentration in all the analyzed samples was 16,23 µg BITC/g.

  6. (2E,5E)-2,5-Bis(4-hy­droxy-3-meth­oxy­benzyl­idene)cyclo­penta­none ethanol monosolvate

    Science.gov (United States)

    Da’i, Muhammad; Yanuar, Arry; Meiyanto, Edy; Jenie, Umar Anggara; Supardjan, Amir Margono

    2013-01-01

    In the title structure, C21H20O5·C2H5OH, the curcumine-type mol­ecule has a double E conformation for the two benzyl­idene double bonds [C=C = 1.342 (4) and 1.349 (4) Å] and is nearly planar with respect to the non-H atoms (r.m.s. deviation from planarity = 0.069 Å). The two phenolic OH groups form bifurcated hydrogen bonds with intra­molecular branches to adjacent meth­oxy O atoms and inter­molecular branches to either a neighbouring mol­ecule or an ethanol solvent mol­ecule. The ethanol O atom donates a hydrogen bond to the keto O atom. These hydrogen bonds link the constituents into layers parallel to (101) in the crystal structure. PMID:23634071

  7. Synthesis of /sup 14/C- and /sup 2/H-labeled (3S)-1-benzyl-3-pyrrolidinyl methyl (4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride (YM-09730-5), a potent calcium antagonist

    Energy Technology Data Exchange (ETDEWEB)

    Arima, Hideki; Tamazawa, Kazuharu; Takeuchi, Makoto

    1988-02-01

    A potent and long acting calcium antagonist YM-09730-5, (3S)-1-benzyl-3-pyrrolidinyl methyl (4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride, was labeled with carbon-14 and deuterium. The labeled materials were prepared by either the cyclizing Michael addition of 3-aminocrotonate to benzylidene acetoacetate or the modified Hantzsch reaction using m-nitrobenzaldehyde, aminocrotonate and acetoacetate. The /sup 14/C-labeled material was synthesized from methyl (3-/sup 14/C)acetoacetate in a 32.0% radiochemical yield, at a specific activity of 60.9 mCimmol. The deuterium labeled material was synthesized from 1-benzyl-3-hydroxy-pyrrolidine-d/sub 4/ which was obtained by the reduction of succinimide with LiAlD/sub 4/.

  8. Synthesis and Antimicrobial Activity of 2-[2-(2,6-dichloro phenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H)ones.

    Science.gov (United States)

    Patel, Nb; Patel, Jc; Barat, Gg

    2010-04-01

    A series of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H) ones 6a-m have been synthesized by the reaction of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-substituted phenylacrylamido-6,8-dibromoquinazolin-4(3H) ones 5a-m with hydrazine hydrate in the presence of glacial acetic acid. The chalcones 5a-m were prepared by the condensation of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-acetamido-6,8-dibromoquinazolin-4(3H)one 4 with different substituted aromatic aldehyde. The benzoxazinone 2 was synthesized from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetyl chloride 1 on treatment with 3,5-dibromoanthranilic acid in pyridine, which on reaction with hydrazine hydrate and then on acetylation reaction yielded 4. The structures of these compounds have been elucidated by elemental analyses, IR, and NMR spectral data. The title compounds pyrazolyl-quinazolin-4(3H)ones 6a-m were evaluated for their antibacterial and antifungal activities in vitro.

  9. Distribution and metabolism of cis- and trans-resmethrin (5-benzyl-3-furyl-methyl-2,2-dimethyl 3-(2-methyl-propenyl)cyclopropanecarboxylate in laying hens

    Energy Technology Data Exchange (ETDEWEB)

    Christopher, R.J.

    1986-01-01

    The cis and trans isomers of the synthetic pyrethroid, resmethrin (5-benzyl-3-furylmethyl-(IRS)-chrysanthemate), labeled with radiocarbon in either the alcohol or acid moiety, were individually administered orally to White Leghorn laying hens at a dosage of 10 mg/kg. With each isomer and label position, greater than 90% of the radiocarbon was eliminated in the excreta within 24 hours posttreatment. Radiocarbon residues in the egg white and yolk fractions were low, with peak levels observed at 1-2 and 4-5 days post-treatment in white and yolk, respectively. Residues were considerably lower in egg whites than in yolks. In birds killed 12 hours post-treatment, radiocarbon residues in tissues were low with peak levels in liver and kidney. Unmetabolized cis- or trans-resmethrin was detected in all tissues analyzed from birds killed at 12 hours post-treatment and represented the major metabolite in fat. The majority of the tissues from hens 14 days post-treatment contained no detectable levels of radiocarbon and would appear not to be indicative of appreciable residue retention. Numerous metabolites were isolated and were present in both the free and conjugated form. The metabolic routes for both resmethrin isomers arise from ester hydrolysis and oxidation of the hydrolytic products. Certain of these metabolites are further conjugated with glucuronic acid, sulfate or other unidentified compounds before excretion.

  10. Simultaneous Preconcentration of Copper and Cadmium by Dispersive Liquid-Liquid Microextraction Using N,N'-Bis (2-Hydroxy-5-Bromo-Benzyl)1,2 Diaminopropane and Their Determination by Flame Atomic Absorption Spectrometry.

    Science.gov (United States)

    Arslan, Osman; Karadaş, Cennet; Kara, Derya

    2016-09-01

    In the present study, the simultaneous preconcentration of copper and cadmium based on dispersive liquid-liquid microextraction as a prior step to their determination using flame atomic absorption spectrometry was developed. Carbon tetrachloride and N,N'-bis(2-hydroxy-5-bromo-benzyl)1,2 diaminopropane were used as the extraction solvent and chelating ligand, respectively. Some parameters that influence the extraction efficiency-e.g., sample pH, volume of extraction solvent (carbon tetrachloride), concentration of the chelating ligand, effect of salt addition, and sample volume-were investigated and optimized. With a preconcentration factor of 10, the LODs (3σ) for Cd and Cu were 0.69 and 1.98 μg/L, respectively. The accuracy of the developed method was evaluated by analyzing SLRS-5 river water and SRM 1573a tomato leaves certified reference materials. Results obtained were in good agreement with the certified values. The proposed method was successfully applied to river water, seawater, and black tea samples. Good spike recoveries, varying within the range of 97.5 to 116.9%, confirmed the good performance of the method in real sample analysis.

  11. Microwave assisted synthesis and antimicrobial activity of novel 1-[1/2-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-naphthalen-2/1-yl]-3-(1-phenyl-3-aryl-1H-pyrazol-4-yl-propenones

    Directory of Open Access Journals (Sweden)

    Dongamanti Ashok

    2015-06-01

    Full Text Available A series of novel 1-[1/2-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-naphthalen-2/1-yl]-3-(1-phenyl-3-aryl-1H-pyrazol-4-yl-propenones were design and synthesized by Click reaction followed by Claisen-Schmidt condensation under microwave irradiation and conventional heating methods. The structures of newly synthesized compounds have been established on the basis of elemental analysis, IR, 1H & 13C NMR and mass spectral data. All the compounds were screened for their antimicrobial activity.

  12. RNAi-mediated silencing of the HD-Zip gene HD20 in Nicotiana attenuata affects benzyl acetone emission from corollas via ABA levels and the expression of metabolic genes

    Science.gov (United States)

    2012-01-01

    Background The N. attenuata HD20 gene belongs to the homeodomain-leucine zipper (HD-Zip) type I family of transcription factors and it has been previously associated with the regulation of ABA accumulation in leaves and the emission of benzyl acetone (BA; 4-phenyl-2-butanone) from night flowers. In this study, N. attenuata plants stably reduced in the expression of HD20 (ir-hd20) were generated to investigate the mechanisms controlling the emission of BA from night flowers. Results The expression of HD20 in corollas of ir-hd20 plants was reduced by 85 to 90% compared to wild-type plants (WT) without affecting flower morphology and development. Total BA emitted from flowers of ir-hd20 plants was reduced on average by 60%. This reduction occurred mainly at the late phase of BA emission and it was correlated with 2-fold higher levels of ABA in the corollas of ir-hd20 plants. When a 2-fold decline in ABA corolla levels of these plants was induced by salt stress, BA emissions recovered to WT levels. Supplying ABA to WT flowers either through the cuticle or by pedicle feeding reduced the total BA emissions by 25 to 50%; this reduction occurred primarily at the late phase of emission (similar to the reduction observed in corollas of ir-hd20 plants). Gene expression profiling of corollas collected at 12 pm (six hours before the start of BA emission) revealed that 274 genes changed expression levels significantly in ir-hd20 plants compared to WT. Among these genes, more than 35% were associated with metabolism and the most prominent group was associated with the metabolism of aromatic compounds and phenylpropanoid derivatives. Conclusions The results indicated that regulation of ABA levels in corollas is associated with the late phase of BA emission in N. attenuata plants and that HD20 affects this latter process by mediating changes in both ABA levels and metabolic gene expression. PMID:22548747

  13. Comparative effects of butyl benzyl phthalate (BBP) and di(2-ethylhexyl) phthalate (DEHP) on the aquatic larvae of Chironomus riparius based on gene expression assays related to the endocrine system, the stress response and ribosomes.

    Science.gov (United States)

    Planelló, Rosario; Herrero, Oscar; Martínez-Guitarte, José Luis; Morcillo, Gloria

    2011-09-01

    In this work, the effects of butyl benzyl phthalate (BBP) and di(2-ethylhexyl) phthalate (DEHP), two of the most extensively used phthalates, were studied in Chironomus riparius under acute short-term treatments, to compare their relative toxicities and identify genes sensitive to exposure. The ecotoxicity of these phthalates was assessed by analysis of the alterations in gene expression profiles of selected inducible and constitutive genes related to the endocrine system, the cellular stress response and the ribosomal machinery. Fourth instar larvae, a model system in aquatic toxicology, were experimentally exposed to five increasing concentrations (0.01, 0.1, 1, 10, and 100mg/L) of DEHP and BBP for 24h. Gene expression was analysed by the changes in levels of transcripts, using RT-PCR techniques with specific gene probes. The exposures to DEHP or BBP were able to rapidly induce the hsp70 gene in a concentration-dependent manner, whereas the cognate form hsc70 was not altered by either of these chemicals. Transcription of ribosomal RNA as a measure of cell viability, quantified by the levels of ITS2, was not affected by DEHP, but was slightly, yet significantly, downregulated by BBP at the highest concentrations tested. Finally, as these phthalates are classified as endocrine disruptor chemicals (EDCs), their potential effect on the ecdysone endocrine system was studied by analysing the two genes, EcR and usp, of the heterodimeric ecdysone receptor complex. It was found that BBP provoked the overexpression of the EcR gene, with significant increases from exposures of 0.1mg/L and above, while DEHP significantly decreased the activity of this gene at the highest concentration. These data are relevant as they show for the first time the ability of phthalates to interfere with endocrine marker genes in invertebrates, demonstrating their potential capacity to alter the ecdysone signalling pathway. Overall, the study clearly shows a differential gene-toxin interaction

  14. Design, synthesis and biological evaluation of new hybrid anticonvulsants derived from N-benzyl-2-(2,5-dioxopyrrolidin-1-yl)propanamide and 2-(2,5-dioxopyrrolidin-1-yl)butanamide derivatives.

    Science.gov (United States)

    Kamiński, Krzysztof; Rapacz, Anna; Łuszczki, Jarogniew J; Latacz, Gniewomir; Obniska, Jolanta; Kieć-Kononowicz, Katarzyna; Filipek, Barbara

    2015-05-15

    The purpose of this study was to synthesize the library of 33 new N-benzyl-2-(2,5-dioxopyrrolidin-1-yl)propanamides, 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)propanamides, and 2-(2,5-dioxopyrrolidin-1-yl)butanamides as potential new hybrid anticonvulsant agents. These hybrid molecules join the chemical fragments of well-known antiepileptic drugs (AEDs) such as ethosuximide, levetiracetam, and lacosamide. The coupling reaction of the 2-(2,5-dioxopyrrolidin-1-yl)propanoic acid, 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)propanoic acid, or 2-(2,5-dioxopyrrolidin-1-yl)butanoic acid with the appropriately substituted benzylamines in the presence of the coupling reagent, N,N-carbonyldiimidazole (CDI) generated the final compounds 4-36. Spectral data acquired via (1)H NMR, (13)C NMR, and LC-MS confirmed the chemical structures of the newly prepared compounds. The initial anticonvulsant screening was performed in mice intraperitoneally (ip), using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests. The rotarod test determined the acute neurological toxicity (NT). The results of preliminary pharmacological screening revealed that 25 compounds showed protection in half or more of the animals tested in the MES and/or scPTZ seizure models at the fixed dose of 100mg/kg. The broad spectra of activity across the preclinical seizure models displayed compounds 4, 7, 8, 13, 15-18, 24, and 26. The quantitative pharmacological studies in mice demonstrated the highest protection for compounds 4 (ED50 MES=67.65 mg/kg, ED50scPTZ=42.83 mg/kg); 8 (ED50 MES=54.90 mg/kg, ED50scPTZ=50.29 mg/kg); and 20 (ED50scPTZ=47.39 mg/kg). These compounds were distinctly more potent and provided better safety profiles in the rotarod test compared to valproic acid or ethosuximide, which were used as model AEDs. Compound 8 underwent only a slight metabolic change by the human liver microsomes (HLMs), and also did not affect the activity of human cytochrome P450 isoform

  15. A versatile synthesis of cyclic dipeptides using the stepwise construction of the piperazine-2,5-dione ring from simple precursors: synthetic sequence and the structure of a representative product, (3RS)-4-(2-allyl-3,5-dimethylphenyl)-1-benzyl-3-phenylpiperazine-2,5-dione.

    Science.gov (United States)

    Acosta Quintero, Lina M; Palma, Alirio; Cobo, Justo; Glidewell, Christopher

    2018-02-01

    A versatile synthesis of multiply substituted cyclic dipeptides has been designed, based on the stepwise construction of the piperazine-2,5-dione ring using molecular fragments from four different precursor molecules. Starting from substituted 2-allylanilines, reaction with methyl 2-bromo-2-phenylacetate yields the corresponding methyl 2-(2-allylanilino)-2-phenylacetates, which react with haloacetyl chlorides to give methyl 2-[N-(2-allylphenyl)-2-haloacetamido]-2-phenylacetates, which then undergo ring closure with benzylamine to yield the corresponding cyclic dipeptides of type 4-(2-allylphenyl)-1-benzyl-3-phenylpiperazine-2,5-dione. (3RS)-4-(2-Allyl-3,5-dimethylphenyl)-1-benzyl-3-phenylpiperazine-2,5-dione, C 28 H 28 N 2 O 2 , (IIId), crystallizes with Z' = 2 in the space group P2 1 /c; the allyl groups in the two independent molecules adopt different conformations and, in one of them, the allyl group is disordered over two sets of atomic sites having occupancies of 0.534 (4) and 0.466 (4). In both molecules, the piperazine-2,5-dione ring adopts a boat conformation, with the 3-phenyl ring in a quasi-axial site. The molecules of (IIId) are linked into a three-dimensional framework structure by a combination of three C-H...O hydrogen bonds and three C-H...π(arene) hydrogen bonds. Comparisons are made with some related structures.

  16. Optimized Formation of Benzyl Isothiocyanate by Endogenous ...

    African Journals Online (AJOL)

    has been reported have anthelmintic properties. [5], antimicrobial activity [6], antifungal activity. [7], inhibition of cell proliferation [8], the potential to reduce the risk .... capillary column (30 m × 0.32 mm i.d, 0.25 μm film thickness). The injection port was kept at 250. oC, and a ramp temperature program was run at. 50 oC (initial ...

  17. 4-Benzyl-4-ethylmorpholin-1-ium hexafluorophosphate

    Directory of Open Access Journals (Sweden)

    Yuanlin Ren

    2012-03-01

    Full Text Available The asymmetric unit of the title compound, C13H20NO+·PF6−, contains two cations, one complete anion and two half hexafluorophosphate anions having crystallographically imposed twofold rotation symmetry. In the cations, the morpholine rings are in a chair conformation. In the crystal, ions are linked by weak C—H...F hydrogen bonds into a three-dimensional network.

  18. Holograms preparation using commercial fluorescent benzyl

    Energy Technology Data Exchange (ETDEWEB)

    Dorantes-GarcIa, V; Olivares-Perez, A; Ordonez-Padilla, M J; Mejias-Brizuela, N Y, E-mail: valdoga@Hotmail.com, E-mail: olivares@inaoep.mx [Instituto Nacional de Astrofisica, Optica y Electronica (INAOE), Coordinacion de Optica, Calle Luis Enrique Erro N0 1, Santa Maria Tonantzintla, Puebla (Mexico)

    2011-01-01

    We have been able to make holograms with substances such as fluorescence thought of light blue laser to make transmissions holograms, using ammonium dichromate as photo-sensitizer and polyvinyl alcohol (PVA) as matrix. Ammonium dichromate inhibit the fluorescence properties of inks, both mixed in a (PVA) matrix, but we avoid this chemical reaction and we show the results to use the method of painting hologram with fluorescents ink and we describe how the diffraction efficiency parameter changes as a function of the ink absorbed by the emulsion recorded with the gratings, we got good results, making holographic gratings with a blue light from laser diode 470 nm. And we later were painting with fluorescent ink, integrating fluorescence characteristics to the hologram.

  19. (pt-BUTYL(BENZYL/BENZYLIDEN)AMINO)

    African Journals Online (AJOL)

    Preferred Customer

    standardized by titration against primary standard sodium carbonate (Merck). Solutions of standard bases containing 0.10 M NaCl were prepared as 50% (v/v) aqueous ethanol-water was potentiometrically standardized against hydrochloric acid solutions by use of Gran's plot techniques, allowing determination of dissolved ...

  20. Syntheses, structures, and stabilities of [PPh(4)][WS(3)(SR)](R=(i)Bu,(i)Pr,(i)Bu, benzyl, allyl) and [PPh(4)][MoS(3)(S(t)Bu)].

    Science.gov (United States)

    Kruhlak, N L; Wang, M; Boorman, P M; Parvez, M; McDonald, R

    2001-06-18

    Intermediates in the condensation process of [MS(4)](2)(-) (M = Mo, W) to polythiometalates, in the presence of alkyl halides, had not been reported prior to our communication of [PPh(4)][WS(3)(SEt)] (Boorman, P. M.; Wang, M.; Parvez, M. J. Chem. Soc., Chem. Commun. 1995, 999-1000). We now report the isolation of a range of related compounds, with 1 degrees, 2 degrees, and 3 degrees alkyl thiolate ligands, including one Mo example. [PPh(4)][WS(3)(SR)] (R = (i)Bu (1), (i)Pr (2), (t)Bu (3), benzyl (5), allyl (6)) and [PPh(4)][MoS(3)(S(t)Bu)] (4) have been isolated in fair to good yields from the reaction of [PPh(4)](2)[MS(4)] with the appropriate alkyl halide in acetonitrile and subjected to analysis by X-ray crystallography. Crystal data are as follows: for 1, triclinic space group P1 (No. 2), a = 11.0377(6) A, b = 11.1307(5) A, c = 13.6286(7) A, alpha = 82.941(1) degrees, beta = 84.877(1) degrees, gamma = 60.826(1) degrees, Z = 2; for 2, monoclinic space group P2(1)/c (No. 14), a = 9.499(6) A, b = 15.913(5) A, c = 18.582(6) A, beta = 99.29(4) degrees, Z = 4; for 3, monoclinic space group P2(1)/n (No. 14), a = 10.667(2) A, b = 17.578(2) A, c = 16.117(3) A, beta = 101.67(1) degrees, Z = 4; for 4, monoclinic space group P2(1)/n (No. 14), a = 10.558(3) A, b = 17.477(3) A, c = 15.954(3) A, beta = 101.18(2) degrees, Z = 4; for 5, monoclinic space group P2(1)/n (No. 14), a = 16.2111(9) A, b = 11.0080(6) A, c = 18.1339(10) A, beta = 111.722(1) degrees, Z = 4; for 6, triclinic space group P1 (No. 2), a = 9.4716(9) A, b = 10.4336(10) A, c = 14.4186(14) A, alpha = 100.183(2) degrees, beta = 90.457(2) degrees, gamma = 91.747(2) degrees, Z = 2. Structures 3 and 4 are isomorphous, and 1 exhibits disorder about the tertiary carbon. 6 has been shown to exhibit fluxionality in solution by variable-temperature (1)H NMR studies, and an allyl migration mechanism is implicated in this process. The kinetics for the reaction of [WS(4)](2)(-) and EtBr were measured and suggest an

  1. The Influence of the 1-(3-Trifluoromethyl-Benzyl-1H-Pyrazole-4-yl Moiety on the Adenosine Receptors Affinity Profile of Pyrazolo[4,3-e][1,2,4]Triazolo[1,5-c]Pyrimidine Derivatives.

    Directory of Open Access Journals (Sweden)

    Stephanie Federico

    Full Text Available A new series of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine (PTP derivatives has been developed in order to explore their affinity and selectivity profile at the four adenosine receptor subtypes. In particular, the PTP scaffold was conjugated at the C2 position with the 1-(3-trifluoromethyl-benzyl-1H-pyrazole, a group believed to confer potency and selectivity toward the human (h A2B adenosine receptor (AR to the xanthine ligand 8-(1-(3-(trifluoromethylbenzyl-1H-pyrazol-4-yl-1,3-dimethyl-1H-purine-2,6(3H,7H-dione (CVT 6975. Interestingly, the synthesized compounds turned out to be inactive at the hA2B AR but they displayed affinity at the hA3 AR in the nanomolar range. The best compound of the series (6 shows both high affinity (hA3 AR Ki = 11 nM and selectivity (A1/A3 and A2A/A3 > 9090; A2B/A3 > 909 at the hA3 AR. To better rationalize these results, a molecular docking study on the four AR subtypes was performed for all the synthesized compounds. In addition, CTV 6975 and two close analogues have been subjected to the same molecular docking protocol to investigate the role of the 1-(3-trifluoromethyl-benzyl-1H-pyrazole on the binding at the four ARs.

  2. 9-Benzyl-6-benzyl-sulfanyl-9H-purin-2-amine.

    Science.gov (United States)

    Hariono, Maywan; Wahab, Habibah A; Tan, Mei Lan; Rosli, Mohd Mustaqim; Razak, Ibrahim Abdul

    2014-03-01

    In the title compound, C19H17N5S, the dihedral angles between the purine ring system (r.m.s. deviation = 0.009 Å) and the S-bound and methyl-ene-bound phenyl rings are 74.67 (8) and 71.28 (7)°, respectively. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R 2 (2)(8) loops. C-H⋯N inter-actions link the dimers into (100) sheets.

  3. Conformation of the nootropic agents 1-(4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid (CI-933) and 4-hydroxymethyl-1-benzyl-pyrrolidin-2-one (WEB-1868): X-ray crystal structures, theoretical MO calculations (AM-1) and 600 MHZ 1H NMR spectra

    Science.gov (United States)

    Amato, Maria E.; Bandoli, Giuliano; Djedaïni, Florence; Dolmella, Alessandro; Grassi, Antonio; Pappalardo, Giuseppe C.

    1990-05-01

    The crystal and molecular structures of the cognition activators 1-(4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid (CI-933) ( 1) and 4-hydroxymethyl-1-benzyl-pyrrolidin-2-one (WEB-1868) ( 2) have been determined by X-ray analysis. The conformations of the isolated molecules 1 and 2 have been deduced from AM1-type theoretical calculations. Whilst in 1 there are no hydrogen bonds, in 2 stabilization of the crystal occurs through effective inter- and intramolecular ? bonds. The five-membered ring in both 1 and 2 adopts an envelope conformation in the solid with C(3) at the flap displaced from the C(1), C(2), C(4), N(5) mean plane. Bond distances and angles are normal and comparable with previously known similar structures. In the crystal, the torsion angles C(1)-N(5)-C(6)-C(7) and N(5)-C(6)-C(7)-C(8) in 1 are 43.1° and 44.8°, respectively; the same torsion angles in 2 are -101° and 42°, respectively. Results of theoretical calculations correlate well with the conformation of 1 in the solid, whilst in the case of 2 these indicate that the conformation in the crystal should not be retained by the isolated molecule. The complete analysis of the very high field (600 MHz) 1H NMR spectra of both compounds in CDCl 3, gives results well in line with the above established conformational features.

  4. Imaging of peripheral-type benzodiazepine receptor in tumor: in vitro binding and in vivo biodistribution of N-benzyl-N-[(11)C]methyl-2-(7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide.

    Science.gov (United States)

    Yamasaki, Tomoteru; Kumata, Katsushi; Yanamoto, Kazuhiko; Hatori, Akiko; Takei, Makoto; Nakamura, Yukio; Koike, Sachiko; Ando, Koichi; Suzuki, Kazutoshi; Zhang, Ming-Rong

    2009-10-01

    The aim of this study was to evaluate N-benzyl-N-[(11)C]methyl-2-(7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide ([(11)C]DAC) as a novel peripheral-type benzodiazepine receptor (PBR) ligand for tumor imaging. [(11)C]DAC was synthesized by the reaction of a desmethyl precursor with [(11)C]CH(3)I. In vitro uptake of [(11)C]DAC was examined in PBR-expressing C6 glioma and intact murine fibrosarcoma (NFSa) cells. In vivo distribution of [(11)C]DAC was determined using NFSa-bearing mice and small-animal positron emission tomography (PET). [(11)C]DAC showed specific binding to PBR in C6 glioma cells, a standard cell line with high PBR expression. Specific binding of [(11)C]DAC was also confirmed in NFSa cells, a target tumor cell line in this study. Results of PET experiments using NFSa-bearing mice, showed that [(11)C]DAC was taken up specifically into the tumor, and pretreatment with PK11195 abolished the uptake. [(11)C]DAC was taken up into PBR-expressing NFSa. [(11)C]DAC is a promising PET ligand that can be used for imaging PBR in tumor-bearing mice.

  5. 4,5-Dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxy-benzyl)-phenyl]-amine (RO1138452) is a selective, pseudo-irreversible orthosteric antagonist at the prostacyclin (IP)-receptor expressed by human airway epithelial cells: IP-receptor-mediated inhibition of CXCL9 and CXCL10 release.

    Science.gov (United States)

    Ayer, Linda M; Wilson, Sylvia M; Traves, Suzanne L; Proud, David; Giembycz, Mark A

    2008-02-01

    The extent to which the prostacyclin (IP) receptor regulates the release of two proinflammatory chemokines from human airway epithelial cells was investigated using the novel and competitive IP-receptor antagonist 4,5-dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxy-benzyl)-phenyl]-amine (RO1138452). In BEAS-2B human airway epithelial cells, taprostene, a selective IP-receptor agonist, suppressed interferon-gamma-induced CXCL9 and CXCL10 release in a concentration-dependent manner. These effects were mimicked by 8-bromo-cAMP, and they were abolished in cells infected with an adenovirus vector encoding a highly selective inhibitor of cAMP-dependent protein kinase (PKA). RO1138452 blocked the inhibitory effect of taprostene on chemokine output in a manner inconsistent with surmountable competitive antagonism. Comparable results were obtained using primary cultures of human airway epithelial cells. The basis of the antagonism imposed by RO1138452 was studied further using BEAS-2B cells stably transfected with a cAMP-response element (CRE) luciferase reporter. On this output, RO1138452 also behaved insurmountably. Mechanistically, this could not be attributed to covalent receptor inactivation, allosterism, or a state of hemiequilibrium. Other studies established that the degree by which RO1138452 antagonized taprostene-induced CRE-dependent transcription was not reversed over a 20-h "washout" period. This pharmacological profile is consistent with the behavior of a pseudo-irreversible antagonist where dissociation from its cognate receptor is so slow that re-equilibration is not achieved at the time the response is measured. Collectively, these data provide compelling evidence that human airway epithelial cells express inhibitory IP-receptors linked to the activation of PKA. Moreover, contrary to existing literature, RO1138452 behaved pseudoirreversibly, emphasizing the need, in drug discovery, to screen potential new medicines in the target tissue(s) of interest.

  6. Evaluation of N-benzyl-N-[11C]methyl-2- (7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide ([11C]DAC) as a novel translocator protein (18 kDa) radioligand in kainic acid-lesioned rat.

    Science.gov (United States)

    Yanamoto, Kazuhiko; Yamasaki, Tomoteru; Kumata, Katsushi; Yui, Joji; Odawara, Chika; Kawamura, Kazunori; Hatori, Akiko; Inoue, Osamu; Yamaguchi, Masatoshi; Suzuki, Kazutoshi; Zhang, Ming-Rong

    2009-11-01

    The aim of this study was to evaluate N-benzyl-N-[11C]methyl-2-(7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide ([11C]DAC) as a new translocator protein (18 kDa) [TSPO, formerly known as the peripheral-type benzodiazepine receptor (PBR)] positron emission tomography (PET) ligand in normal mice and unilateral kainic acid (KA)-lesioned rats. DAC is a derivative of AC-5216, which is a potent and selective PET ligand for the clinical investigation of TSPO. The binding affinity and selectivity of DAC for TSPO were similar to those of AC-5216, and DAC was less lipophilic than AC-5216. The distribution pattern of [11C]DAC was in agreement with TSPO distribution in rodents. No radioactive metabolite of [11C]DAC was found in the mouse brain, although it was metabolized rapidly in mouse plasma. Using small-animal PET, we examined the in vivo binding of [11C]DAC for TSPO in KA-lesioned rats. [11C]DAC and [11C]AC-5216 exhibited similar brain uptake in the lesioned and nonlesioned striatum, respectively. The binding of [11C]DAC to TSPO was increased significantly in the lesioned striatum, and [(11)C]DAC showed good contrast between the lesioned and nonlesioned striatum (the maximum ratio was about threefold). In displacement experiments, the uptake of [11C]DAC in the lesioned striatum was eventually blocked using an excess of either unlabeled DAC or PK11195 injected. [11C]DAC had high in vivo specific binding to TSPO in the injured rat brain. Therefore, [11C]DAC is a useful PET ligand for TSPO imaging, and its specific binding to TSPO is suitable as a new biomarker for brain injury.

  7. Benzyl-tributyl-ammonium 7-hydroxy-naphthalene-1-sulfonate.

    Science.gov (United States)

    Sato, Yohei; Uta, Kazuya; Mizuguchi, Jin

    2009-01-17

    The title compound, C(19)H(34)N(+)·C(10)H(7)O(4)S(-), is a charge-control agent used for toners in electrophotography. The anions form one-dimensional chains by O-H⋯O hydrogen bonds in a zigzag fashion along the c axis between the OH group of one anion and the sulfonate O atom of a neighboring anion. One of the n-butyl chains of the cation is disordered over two sites in a 0.77:0.23 ratio.

  8. Benzyl-tributyl-ammonium 6-hydroxy-naphthalene-2-sulfonate.

    Science.gov (United States)

    Uta, Kazuya; Sato, Yohei; Mizuguchi, Jin

    2009-01-17

    The title compound, C(19)H(34)N(+)·C(10)H(7)O(4)S(-), is a charge-control agent for toners used in electrophotography. Inter-moleclar O-H⋯O hydrogen bonding between the OH group of one anion and the sulfonate O atom of a neighboring anion leads to the formation of one-dimensional chains along the b axis. In addition, C-H⋯O hydrogen bonds are observed. One of the n-butyl chains of the cation is disordered over two sites in a 0.88:0.12 ratio.

  9. Benzyl-tributyl-ammonium 4-hydroxy-naphthalene-2-sulfonate.

    Science.gov (United States)

    Uta, Kazuya; Mizuguchi, Jin

    2009-01-17

    The title compound, C(19)H(34)N(+)·C(10)H(7)O(4)S(-), is a charge-control agent used for toners in electrophotography. In the crystal structure, centrosymmetric anions associate through O-H⋯O hydrogen bonds formed between the O-H group of one anion and the sulfonate O atom of a neighbor. The components of the dimer are offset with respect to each other so that the separation between the two parallel naphthalene skeletons is about 1.6 Å. The ethyl residues of two of the butyl groups are disordered and were modelled over two postions (site occupancies = 0.33/0.67 and 0.34/0.66).

  10. Selective oxidation of benzyl alcohol with tert-butylhydroperoxide ...

    Indian Academy of Sciences (India)

    butylhydroperoxide (TBHP) as an oxidant. The effects of Mn2+ loading and various solvents on the conversion and selectivity were studied. A second order function for the variation in catalytic activity with respect to the loading of Mn2+ ions in dif-.

  11. Silica functionalized Cu(II) catalysed selective oxidation of benzyl ...

    Indian Academy of Sciences (India)

    times, oxidation of alcohols has been carried out using stoichiometric amounts of chromium (VI) and manga- nese (VII)3,4 but these methodologies require costly and toxicsolvents.5 andproducedlargeamountofheavymetal wastes6 thus making these methods highly undesirable. In this regard, non-waste producing oxidants ...

  12. an efficient polymeric reagent for selective preparation of benzyl bro

    African Journals Online (AJOL)

    Preferred Customer

    The application of polymer supports as reagent and catalyst has received special attention in the past decades, due to the easy work up of reaction products and unique selectivity which are undoubtly attractive features of this methodology. In addition, most of the polymer supported reagents can be recycled after use [12, ...

  13. SYNTHESIS AND ANTICONVULSANT STUDIES OF N-BENZYL-3 ...

    African Journals Online (AJOL)

    USER

    generalized seizures (Lopes Lima, 2000; Prucca,. 2002; Berk et al., 2001; Duncan, 2002 and Eadie,. 2001). Hence, there is an urgent need to develop new ... (temperature 25±30C; humidity 45 – 60% and 12 hours light/dark cycle) and were allowed free access to both food (Vital feeds mixed with fish and groundnut.

  14. catalysed selective oxidation of benzyl alcohols using TEMPO and ...

    Indian Academy of Sciences (India)

    are also important moieties in plastic additives; process- ing of perfume and flavouring compounds and for the pre- paration of aniline dyes in the textile industry.2 In ... finally the product was obtained after the removal of solvent under reduced pressure followed by passing through column of silica and elution with EtOAc: pet.

  15. SYNTHESIS AND ANTICONVULSANT STUDIES OF N-BENZYL-3 ...

    African Journals Online (AJOL)

    USER

    INTRODUCTION. Epilepsy is a common neurological condition, affecting. 0.5 to 1 % (45-100 million people) of the population worldwide (Bell and Sander, 2002). Conventional antiepileptic drugs (AEDs) phenobarbital, primidone, phenytoin, carbamazepine, ethosuximide and benzodiazepine, are widely used but exhibit an.

  16. Effect of different combinations of 6-benzyl amino purine and ...

    African Journals Online (AJOL)

    SNAP CUSTOMER

    2013-02-13

    Feb 13, 2013 ... All sorts of varieties (dessert, cooking, brewing) are grown throughout Ethiopia. These materials are not ... the use of in vitro tissue culture technique. Through meristem micro propagation, pathogen ..... Micro propagation techniques were developed during the past two decades and are now well established ...

  17. 9-Benzyl-6-benzylsulfanyl-9H-purin-2-amine

    Directory of Open Access Journals (Sweden)

    Maywan Hariono

    2014-03-01

    Full Text Available In the title compound, C19H17N5S, the dihedral angles between the purine ring system (r.m.s. deviation = 0.009 Å and the S-bound and methylene-bound phenyl rings are 74.67 (8 and 71.28 (7°, respectively. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R22(8 loops. C—H...N interactions link the dimers into (100 sheets.

  18. Solvent effects in the reaction between piperazine and benzyl bromide

    Indian Academy of Sciences (India)

    WINTEC

    analysis indicates that the transition state is more solvated than the reactants due to hydrogen bond dona- tion and polarizability of the solvent while the reactant is more solvated than the transition state due to electrophilicity of the solvent. Study of ... and benzonitrile were all analytical grade and of. Merck or Sd-fine make.

  19. Rapid field multiplication of plantains using benzyl adenine or ...

    African Journals Online (AJOL)

    Up to 1,000 suckers can be generated from one Apantu sucker in a year, and 3,375 suckers from one Asamienu sucker in 18 months with the coconut water treatment. The cost of 25 ml coconut water required to treat one sucker is insignificant compared with the multiplication ratios derived from the treated suckers.

  20. Redetermination of 1-benzyl-3-furoyl-1-phenylthiourea

    Directory of Open Access Journals (Sweden)

    2009-03-01

    Full Text Available The title compound, C19H16N2O2S, was synthesized from furoyl isothiocyanate and N-benzylaniline in dry acetone and the structure redetermined. The structure [Otazo-Sánchez et al. (2001. J. Chem. Soc. Perkin Trans. 2, pp. 2211–2218] has been re-determined in order to establish the intramolecular and intermolecular interactions. The thiourea group is in the thioamide form. The thiourea group makes a dihedral angle of 29.2 (6° with the furoyl group. In the crystal structure, molecules are linked by intermolecular C—H...O interactions, forming one-dimensional chains along the a axis. An intramolecular N—H...O hydrogen bond is also present.

  1. Benzilaminopurina e ácido naftaleno acético na indução e multiplicação in vitro de gemas de abacaxizeiro da cultivar 'IAC Gomo-de-mel' In vitro bud induction and multiplication of cv. 'IAC Gomo-de-mel' pineapple fruit with benzyl amino purine and n aphthalene acetic acid

    Directory of Open Access Journals (Sweden)

    Chrystiane Borges Fráguas

    2009-09-01

    Full Text Available O objetivo deste trabalho foi avaliar os efeitos de BAP (6-benzilaminopurina e NAA (ácido naftaleno acético na indução, na multiplicação in vitro de gemas, nas brotações de Ananas comosus da cultivar 'IAC Gomo-de-mel' e a correlação desses efeitos com a atividade de peroxidase e o teor de proteína solúvel total. Foram utilizadas gemas axilares retiradas da coroa de frutos sadios, inoculadas em tubo de ensaio contendo meio de cultura MS solidificado com ágar a 5%, pH ajustado para 5,7, contendo os tratamentos que incluíam diferentes concentrações e combinações de BAP (0, 0,5, 1,0 e 1,5mg L-1 e NAA (0, 0,5 e 1,0mg L-1. Nessa fase, aos 65 dias, ocorreu a formação de 2,24 brotações, utilizando-se 1mg L-1 de BAP. Após o desenvolvimento, as gemas foram inoculadas em meio MS líquido associado a dois tratamentos (1,0mg L-1 BAP + 0,5mg L-1 NAA e 1,0mg L-1 BAP + 1,0mg L-1 NAA e, aos 95 dias, o meio de cultura mais adequado foi aquele que continha 1,0mg L-1 BAP + 0,5mg L-1 NAA, proporcionando 7,42 brotações, menor porcentagem de hiper-hidricidade, maior número de brotações e indução de gemas. As proteínas solúveis apresentaram relação negativa com hiper-hidricidade e comprimento de brotações. A atividade da peroxidase foi maior em plantas com maior número de brotos e com maior porcentagem de hiper-hidricidade.The objective of this research was to evaluate the effects of BAP (6-benzyl amino purine and NAA (naphthalene acetic acid on in vitro buds induction and multiplication on Ananas comosus cv. 'IAC Gomo-de-mel' shoots and its correlation with the peroxidase activity and soluble protein content. Axillary buds were excised from the healthy fruits crown and inoculated in MS solidified with agar at 5 % and pH adjusted to 5.7 with the treatments that included different concentrations and combinations of BAP (0, 0.5, 1.0 and 1.5mg L-1 and NAA (0, 0.5 and 1.0mg L-1. At, 65 days stage, 2.24 shoots were formatted using BAP 1

  2. Sequential meta-C-H olefination of synthetically versatile benzyl silanes: effective synthesis of meta-olefinated toluene, benzaldehyde and benzyl alcohols.

    Science.gov (United States)

    Patra, Tuhin; Watile, Rahul; Agasti, Soumitra; Naveen, Togati; Maiti, Debabrata

    2016-02-04

    Tremendous progress has been made towards ortho-selective C-H functionalization in the last three decades. However, the activation of distal C-H bonds and their functionalization has remained fairly underdeveloped. Herein, we report sequential meta-C-H functionalization by performing selective mono-olefination and bis-olefination with late stage modification of the C-Si as well as Si-O bonds. Temporary silyl connection was found to be advantageous due to its easy installation, easy removal and wide synthetic diversification.

  3. Crystal structure of [2-({2-[(2-azanidyl-benzyl-idene)amino]-benzyl-idene}amino)-4-chloro-phenol-ato]nickel(II).

    Science.gov (United States)

    Kobayashi, Fumiya; Koga, Atsushi; Ohtani, Ryo; Hayami, Shinya; Nakamura, Masaaki

    2017-04-01

    The title complex, [Ni(C 20 H 14 ClN 3 O)], with an asymmetrically chloride-appended Schiff base ligand has been synthesized and structurally characterized at 100 K. In the compound, the central nickel(II) ion has a square-planar coordination geometry with N 3 O donors of the π-conjugated tetra-dentate Schiff base ligand. In the crystal, the complexes are connected into an inversion dimer via an Ni⋯Ni inter-action [3.1753 (5) Å] and a pair of π-π inter-actions [centroid-centroid distance = 3.8416 (16) Å]. The dimers are linked via a C-H⋯Cl hydrogen bond, forming a chain along the c -axis direction. The dimer chains inter-act with each other through π-π inter-actions [centroid-centroid distance = 3.8736 (16) Å], forming a layer expanding parallel to the ac plane.

  4. Structural and Luminescent Properties of [N-benzyl-N-(2-pyridyl) methylamine]dichlorozinc(II): Dual Fluorescence of N-benzyl- N-(2-pyridyl)methylamine

    Energy Technology Data Exchange (ETDEWEB)

    Song, Young-Kwang; Kim, Young-Inn [Department of Chemistry Education and BK21 Plus Team for Advanced Chemical Materials, Seoul (Korea, Republic of); Kang, Sung Kwon [Pusan National University, Busan (Korea, Republic of)

    2015-01-15

    According to the TICT model, a molecule with an electron donor and acceptor group connected by a single bond may exist as a twisted structure and exhibit an ICT state upon excitation. Such molecules transform from the exited state to the twisted structure via a radiationless process, in which the donor group is perpendicular to the rest of the molecular frame generating a complete decoupling state. Such molecules generally exhibit dual emission, which is observed as two well-separated emission bands. Furthermore, the ratio of the intensities of these two bands is not dependent on its concentration. We designed and synthesized a novel dual fluorescent bpma molecule and its Zn(II) chloride complex Zn(bpma)Cl{sub 2}. The dual fluorescence exhibited by bpma was attributed to the formation of a TICT state in a polar medium. Furthermore, Zn(bpma)Cl{sub 2} was found to quench the emission from the TICT state, resulting in a single emission attributed to the LE state in the blue region. These findings indicate that Zn(bpma)Cl{sub 2} is a possible candidate for blue emissive photoactive material and Zn(II) recognition sensor.

  5. Benzyl­tributyl­ammonium 4-hydroxy­naphthalene-2-sulfonate

    Science.gov (United States)

    Uta, Kazuya; Mizuguchi, Jin

    2009-01-01

    The title compound, C19H34N+·C10H7O4S−, is a charge-control agent used for toners in electrophotography. In the crystal structure, centrosymmetric anions associate through O—H⋯O hydrogen bonds formed between the O—H group of one anion and the sulfonate O atom of a neighbor. The components of the dimer are offset with respect to each other so that the separation between the two parallel naphthalene skeletons is about 1.6 Å. The ethyl residues of two of the butyl groups are disordered and were modelled over two postions (site occupancies = 0.33/0.67 and 0.34/0.66). PMID:21581925

  6. Benzyl­tributyl­ammonium 4,6-dihydroxy­naphthalene-2-sulfonate

    Science.gov (United States)

    Uta, Kazuya; Mizuguchi, Jin

    2009-01-01

    The title mol­ecular salt, C19H34N+·C10H7O5S−, is a charge-control agent used for toners in electrophotography with a high melting point of 508 K. In the crystal structure, the anions form inversion dimers, linked by pairs of O—H⋯O hydrogen bonds. Further O—H⋯O links between dimers generate anionic sheets propagating in (010). One of the n-butyl chains of the cation is disordered over two sets of sites in a 0.53:0.47 ratio. PMID:21581927

  7. Benzyl­tributyl­ammonium 6,7-dihydroxy­naphthalene-2-sulfonate

    Science.gov (United States)

    Uta, Kazuya; Mizuguchi, Jin

    2009-01-01

    The title mol­ecular salt, C19H34N+·C10H7O5S−, is a charge-control agent used for toners in electrophotography. There are two formula units in the asymmetric unit. Both anions form inversion dimers connected by pairs of O—H⋯O hydrogen bonds between the –OH group of one anion and a sulfonic O atom of the neighboring one. The two dimers A and B are characterized by a step between the least-squares planes of the naphthalene atoms of 0.85 and 2.30 Å. Further O—H⋯O bonds link the dimers into a two-dimensional network propagating in (110) such that dimer A is hydrogen-bonded to four B units and vice versa. One of the tert-butyl chains in one of the cations is disordered over two sets of sites in a 0.56:0.44 ratio. PMID:21581928

  8. Benzyl-tributyl-ammonium 4,6-dihydroxy-naphthalene-2-sulfonate.

    Science.gov (United States)

    Uta, Kazuya; Mizuguchi, Jin

    2009-01-17

    The title mol-ecular salt, C(19)H(34)N(+)·C(10)H(7)O(5)S(-), is a charge-control agent used for toners in electrophotography with a high melting point of 508 K. In the crystal structure, the anions form inversion dimers, linked by pairs of O-H⋯O hydrogen bonds. Further O-H⋯O links between dimers generate anionic sheets propagating in (010). One of the n-butyl chains of the cation is disordered over two sets of sites in a 0.53:0.47 ratio.

  9. Benzyl­tributyl­ammonium 7-hydroxy­naphthalene-1-sulfonate

    Science.gov (United States)

    Sato, Yohei; Uta, Kazuya; Mizuguchi, Jin

    2009-01-01

    The title compound, C19H34N+·C10H7O4S−, is a charge-control agent used for toners in electrophotography. The anions form one-dimensional chains by O—H⋯O hydrogen bonds in a zigzag fashion along the c axis between the OH group of one anion and the sulfonate O atom of a neighboring anion. One of the n-butyl chains of the cation is disordered over two sites in a 0.77:0.23 ratio. PMID:21581926

  10. Benzyl-tributyl-ammonium 6,7-dihydroxy-naphthalene-2-sulfonate.

    Science.gov (United States)

    Uta, Kazuya; Mizuguchi, Jin

    2009-01-17

    The title mol-ecular salt, C(19)H(34)N(+)·C(10)H(7)O(5)S(-), is a charge-control agent used for toners in electrophotography. There are two formula units in the asymmetric unit. Both anions form inversion dimers connected by pairs of O-H⋯O hydrogen bonds between the -OH group of one anion and a sulfonic O atom of the neighboring one. The two dimers A and B are characterized by a step between the least-squares planes of the naphthalene atoms of 0.85 and 2.30 Å. Further O-H⋯O bonds link the dimers into a two-dimensional network propagating in (110) such that dimer A is hydrogen-bonded to four B units and vice versa. One of the tert-butyl chains in one of the cations is disordered over two sets of sites in a 0.56:0.44 ratio.

  11. Bis(N-benzyl-N-methyldithiocarbamato-κ2S,S′(pyridine-κNcadmium(II

    Directory of Open Access Journals (Sweden)

    Muhammad Ali Ehsan

    2016-01-01

    Full Text Available The title compound, [Cd(C9H10NS22(C5H5N], features a five-coordinate CdII atom, being coordinated by two nearly symmetrically chelating dithiocarbamate ligands and a pyridine N atom. The resulting NS4 donor set defines a distorted coordination geometry tending toward square pyramidal. In the molecular packing, centrosymmetric ten-membered {...HCNCS}2 synthons arise as a result of methylene-C—H...S interactions. These are connected into layers parallel to (10-2 via weak methyl-C—H...π(phenyl interactions.

  12. (−-Benzyl 2,3-dideoxy-β-d-erythro-hex-2-enopyranoside

    Directory of Open Access Journals (Sweden)

    Mitsuru Shoji

    2013-12-01

    Full Text Available In the title compound, C13H16O4, the six-membered ring of the sugar moiety shows a half-chair conformation. In the crystal, molecules are connected via O—H...O hydrogen bonds, forming columns around twofold screw axes along the b-axis direction. There is a disorder of the benzyloxy group, which has two possible orientations with the phenyl group lying on a common plane [site-occupancy factors = 0.589 (9 and 0.411 (9].

  13. (E)-1-Benzyl-idene-2,2-diphenyl-hydrazine.

    Science.gov (United States)

    Mendoza, Angel; Meléndrez-Luevano, Ruth; Cabrera-Vivas, Blanca M; Lozano-Márquez, Claudia D; Carranza, Vladimir

    2012-02-01

    The asymmetric unit of the title compound, C(19)H(16)N(2), contains two independent mol-ecules, both of which show an E configuration with respect to the C=N bond. The dihedral angles between the phenyl rings bonded to the hydrazine group are 81.00 (10) and 88.34 (8)° in the two mol-ecules. Inter-molecular C-H⋯π inter-actions are observed in the crystal structure.

  14. Synthesis and antiproliferative activities of novel O-benzyl salicylamide derivatives

    Czech Academy of Sciences Publication Activity Database

    Dušek, J.; Imramovský, A.; Pauk, K.; Jorda, Radek; Řezníčková, Eva; Kryštof, Vladimír

    2017-01-01

    Roč. 14, č. 6 (2017), s. 662-671 ISSN 1570-1808 R&D Projects: GA ČR(CZ) GA15-15264S; GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : Amines * Antiproliferative activity * Cytotoxic activity * Pharmacological activity * Salicylamides Subject RIV: FR - Pharmacology ; Medidal Chemistry OBOR OECD: Organic chemistry Impact factor: 1.170, year: 2016

  15. Preparation and characterization of N-benzyl-N,O-succinyl chitosan ...

    African Journals Online (AJOL)

    IND) were entrapped in the hydrophobic inner cores by evaporation method. ... Results: The critical micelle concentration of BSCS micelles was 0.0385 mg/mL and cytotoxicity on Caco-2 cells depends on the polymer concentration (IC50 = 3.23 ...

  16. Synthesis of Benzyl Acetate Catalyzed by Lipase Immobilized in Nontoxic Chitosan-Polyphosphate Beads

    Directory of Open Access Journals (Sweden)

    Ana D. Q. Melo

    2017-12-01

    Full Text Available Enzymes serve as biocatalysts for innumerable important reactions, however, their application has limitations, which can in many cases be overcome by using appropriate immobilization strategies. Here, a new support for immobilizing enzymes is proposed. This hybrid organic-inorganic support is composed of chitosan—a natural, nontoxic, biodegradable, and edible biopolymer—and sodium polyphosphate as the inorganic component. Lipase B from Candida antarctica (CALB was immobilized on microspheres by encapsulation using these polymers. The characterization of the composites (by infrared spectroscopy, thermogravimetric analysis, and confocal Raman microscopy confirmed the hybrid nature of the support, whose external part consisted of polyphosphate and core was composed of chitosan. The immobilized enzyme had the following advantages: possibility of enzyme reuse, easy biocatalyst recovery, increased resistance to variations in temperature (activity declined from 60 °C and the enzyme was inactivated at 80 °C, and increased catalytic activity in the transesterification reactions. The encapsulated enzymes were utilized as biocatalysts for transesterification reactions to produce the compound responsible for the aroma of jasmine.

  17. Isolation and identification of 4-a-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation

    NARCIS (Netherlands)

    Graaf, de R.M.; Krosse, S.; Swolfs, A.E.M.; Brinke, te E.; Prill, N.; Leimu, R.; Galen, van P.M.; Wang, Y.; Aarts, M.G.M.; Dam, van N.M.

    2015-01-01

    Glucosinolates are secondary plant compounds typically found in members of the Brassicaceae and a few other plant families. Usually each plant species contains a specific subset of the ~130 different glucosinolates identified to date. However, intraspecific variation in glucosinolate profiles is

  18. Low pressure carbonylation of benzyl chloride = Die carbonylierung von benzylchlorid bei niedrigen drücken

    NARCIS (Netherlands)

    Luggenhorst, H.J.; Westerterp, K.R.

    1986-01-01

    For carbonylations, metal carbonyls, particularly cobalt and iron carbonyls, are often used as catalysts. These reactions take place under rather drastic reaction conditions, e.g. 200–300 °C and 60–100 MPa. In some patents it is stated that similar reactions using the same catalysts can also be

  19. Mild and selective vanadium-catalyzed oxidation of benzylic, allylic, and propargylic alcohols using air

    Science.gov (United States)

    Hanson, Susan Kloek; Silks, Louis A; Wu, Ruilian

    2013-08-27

    The invention concerns processes for oxidizing an alcohol to produce a carbonyl compound. The processes comprise contacting the alcohol with (i) a gaseous mixture comprising oxygen; and (ii) an amine compound in the presence of a catalyst, having the formula: ##STR00001## where each of R.sup.1-R.sup.12 are independently H, alkyl, aryl, CF.sub.3, halogen, OR.sup.13, SO.sub.3R.sup.14, C(O)R.sup.15, CONR.sup.16R.sup.17 or CO.sub.2R.sup.18; each of R.sup.13-R.sup.18 is independently alkyl or aryl; and Z is alkl or aryl.

  20. Radiation Stability of Benzyl Tributyl Ammonium Chloride Towards Technetium-99 Extraction

    Energy Technology Data Exchange (ETDEWEB)

    Jared Horkley; Audrey Roman; Keri Campbell; Ana Nunez; Amparo Espartero

    2013-02-01

    A closed nuclear fuel cycle combining new separation technologies along with generation III and generation IV reactors is a promising way to achieve a sustainable energy supply. But it is important to keep in mind that future recycling processes of used nuclear fuel (UNF) must minimize wastes, improve partitioning process, and integrate waste considerations into processes. New separation processes are being developed worldwide to complement the actual industrialized PUREX process which selectively separates U(VI) and Pu(IV) from the raffinate. As an example, low nitric acid concentration in the aqueous phase of a UREX based process will co-extract U(VI) and Tc(VII) by tri-n-butyl phosphate (TBP). Technetium (Tc-99) is recognized to be one of the most abundant, long-lived radiotoxic isotopes in UNF (half-life, t1/2 = 2.13 × 105 years), and as such, it is targeted in UNF separation strategies for isolation and encapsulation in solid waste forms for final disposal in a nuclear waste repository. Immobilization of Tc-99 by a durable solid waste form is a challenge, and its fate in new advanced technology processes is of importance. It is essential to be able to quantify and locate 1) its occurrence in any new developed flow sheets, 2) its chemical form in the individual phases of a process, 3) its potential quantitative transfer in any waste streams, and consequently, 4) its quantitative separation for either potential transmutation to Ru-100 or isolation and encapsulation in solid waste forms for ultimate disposal. Furthermore, as a result of an U(VI)-Tc(VII) co-extraction in a UREX-based process, Tc(VII) could be found in low level waste (LLW) streams. There is a need for the development of new extraction systems that would selectively extract Tc-99 from LLW streams and concentrate it for feed into high level waste (HLW) for either Tc-99 immobilization in metallic waste forms (Tc-Zr alloys), and/or borosilicate-based waste glass. Studies have been launched to investigate the suitability of new macrocompounds such as crown-ethers, aza-crown ethers, and resorcinarenes for the selective extraction of Tc-99 from nitric acid solutions. The selectivity of the ligand is important in evaluating potential separation processes and also the radiation stability of the molecule is essential for minimization of waste and radiolysis products. In this paper, we are reporting the extraction of TcO4- by benzyltributyl ammonium chloride (BTBA). Experimental efforts were focused on determining the best extraction conditions by varying the ligand’s matrix conditions and concentration, as well as varying the organic phase composition (i.e., diluent variation). Furthermore, the ligand has been investigated for radiation stability. The ?-irradiation was performed on the neat organic phases containing the ligand at different absorbed doses to a maximum of 200 kGy using external Co-60 source. Post-irradiation solvent extraction measurements will be discussed.

  1. 1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2 ,4 ...

    Indian Academy of Sciences (India)

    been described as 'the single most important method for the construction of heterocyclic five-membered rings in organic ... be a class of substrates having biological importance along with their synthetic utility.9 Besides, using chi- ..... Mohali for spectral analysis. References. 1. Lawyer R W 1963 Chem. Rev. 63 489. 2.

  2. N-Benzyl-9-isopropyl-9H-purin-6-amine.

    Science.gov (United States)

    Gergela, David; Rouchal, Michal; Bartoš, Peter; Vícha, Robert

    2013-06-01

    The asymmetric unit of the title compound, C15H17N5, consists of two mol-ecules in which the dihedral angles between the best planes of the purine ring system (r.m.s. deviations = 0.0060 and 0.0190 Å) and the benzene ring are 89.21 (3) and 82.14 (4)°. The mol-ecules within the asymmetric unit are linked into dimers by pairs of N-H⋯N hydrogen bonds. Weak C-H⋯π contacts and π-π inter-actions [centroid-centroid = 3.3071 (1) Å] further connect the mol-ecules into a three-dimensional network.

  3. N-Benzyl-9-isopropyl-9H-purin-6-amine

    Directory of Open Access Journals (Sweden)

    David Gergela

    2013-06-01

    Full Text Available The asymmetric unit of the title compound, C15H17N5, consists of two molecules in which the dihedral angles between the best planes of the purine ring system (r.m.s. deviations = 0.0060 and 0.0190 Å and the benzene ring are 89.21 (3 and 82.14 (4°. The molecules within the asymmetric unit are linked into dimers by pairs of N—H...N hydrogen bonds. Weak C—H...π contacts and π–π interactions [centroid–centroid = 3.3071 (1 Å] further connect the molecules into a three-dimensional network.

  4. Characterization and bioactivity of novel calcium antagonists - N-methoxy-benzyl haloperidol quaternary ammonium salt

    OpenAIRE

    Chen, Yi-Cun; Zhu, Wei; Zhong, Shu-Ping; Zheng, Fu-Chun; Gao, Fen-Fei; Zhang, Yan-Mei; Xu, Han; Zheng, Yan-Shan; Shi, Gang-Gang

    2015-01-01

    BACKGROUND AND PURPOSE Calcium antagonists play an important role in clinical practice. However, most of them have serious side effects. We have synthesized a series of novel calcium antagonists, quaternary ammonium salt derivatives of haloperidol with N-p-methoxybenzyl (X1), N-m-methoxybenzyl (X2) and N-o-methoxybenzyl (X3) groups. The objective of this study was to investigate the bioactivity of these novel calcium antagonists, especially the vasodilation activity and cardiac side-effects. ...

  5. Design, synthesis, and antifungal activities of novel triazole derivatives containing the benzyl group

    Directory of Open Access Journals (Sweden)

    Xu K

    2015-03-01

    Full Text Available Kehan Xu,1,* Lei Huang,1,* Zheng Xu,2 Yanwei Wang,1,3 Guojing Bai,1 Qiuye Wu,1 Xiaoyan Wang,1 Shichong Yu,1 Yuanying Jiang1 1School of Pharmacy, Second Military Medical University, Shanghai, 2Shanghai Changzheng Hospital, Second Military Medical University, Shanghai, 3Number 422 Hospital of PLA, Zhanjiang, People’s Republic of China *These authors contributed equally to this work Abstract: In previous studies undertaken by our group, a series of 1-(1H-1,2,4-triazole-1-yl-2-(2,4-difluorophenyl-3-substituted-2-propanols (1a–r, which were analogs of fluconazole, was designed and synthesized by click chemistry. In the study reported here, the in vitro antifungal activities of all the target compounds were evaluated against eight human pathogenic fungi. Compounds 1a, 1q, and 1r showed the more antifungal activity than the others. Keywords: triazole, synthesis, antifungal activity, CYP51

  6. 2,4,6-Trimethyl-3,5-bis[(phenylcarbonothioylsulfanylmethyl]benzyl benzenecarbodithioate

    Directory of Open Access Journals (Sweden)

    M. Kannan

    2010-06-01

    Full Text Available In the title compound C33H30S6, the three pendant methylene benzodithioate groups lie to one side of the central benzene ring in a cis-cis-cis `tripod' arrangement. The dihedral angles between the central benzene ring and the three pendant rings are 72.54 (4, 89.68 (4 and 86.74 (4°. In the crystal structure, one of the benzene rings is disordered over two orientations in a 0.559 (13:0.441 (13 ratio.

  7. Synthesis, structure, and sunlight photolysis of benzyl- and tert-butyl-substituted octamethyltitanocene dihydrosulfides

    Czech Academy of Sciences Publication Activity Database

    Horáček, Michal; Císařová, I.; Gyepes, R.; Kubišta, Jiří; Pinkas, Jiří; Lamač, Martin; Mach, Karel

    2014-01-01

    Roč. 755, APR 2014 (2014), s. 141-150 ISSN 0022-328X R&D Projects: GA ČR(CZ) GAP207/12/2368; GA ČR GP203/09/P276 Institutional support: RVO:61388955 Keywords : titanium * titanocene * hydrosulphide Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 2.173, year: 2014

  8. The FEMA GRAS assessment of benzyl derivatives used as flavor ingredients

    NARCIS (Netherlands)

    Adams, T.B.; Cohen, S.M.; Doull, J.; Feron, V.J.; Goodman, J.I.; Marnett, L.J.; Munro, I.C.; Portoghese, P.S.; Smith, R.L.; Waddell, W.J.; Wagner, B.M.

    2005-01-01

    This publication is the eighth in a series of safety evaluations performed by the Expert Panel of the Flavor and Extract Manufacturers Association (FEMA). In 1993, the panel initiated a comprehensive program to re-evaluate the safety of more than 1700 GRAS flavoring substances under conditions of

  9. The FEMA GRAS assessment of hydroxy- and alkoxy-substituted benzyl derivatives used as flavor ingredients

    NARCIS (Netherlands)

    Adams, T.B.; Cohen, S.M.; Doull, J.; Feron, V.J.; Goodman, J.I.; Marnett, L.J.; Munro, I.C.; Portoghese, P.S.; Smith, R.L.; Waddell, W.J.; Wagner, B.M.

    2005-01-01

    This publication is the ninth in a series of safety evaluations performed by the Expert Panel of the Flavor and Extract Manufacturers Association (FEMA). In 1993, the Panel initiated a comprehensive program to re-evaluate the safety of more than 1700 GRAS flavoring substances under conditions of

  10. 1-Benzyl-3-[3-(naphthalen-2-yloxypropyl]imidazolium hexafluorophosphate

    Directory of Open Access Journals (Sweden)

    Kun Huang

    2011-08-01

    Full Text Available In the title salt, C23H23N2O+·PF6−, the PF6− anion is highly disordered (occupancy ratios of 0.35:0.35:0.3, 0.7:0.15:0.15, 0.7:0.3 and 0.35:0.35:0.15:0.15 with the four F atoms in the equatorial plane rotating about the axial F—P—F bond. The mean plane of the imidazole ring makes dihedral angles of 82.44 (17 and 14.39 (16°, respectively, with the mean planes of the benzene ring and the naphthalene ring system. The crystal structure is stabilized by C—H...F hydrogen bonds. In addition, π–π [centroid–centroid distances = 3.7271 (19–3.8895 (17 Å] and C—H...π interactions are observed.

  11. 1-Benzyl-2-(1H-indol-3-yl-5-oxopyrrolidine-2-carbonitrile

    Directory of Open Access Journals (Sweden)

    Raymond Schinazi

    2008-02-01

    Full Text Available In the title compound, C20H17N3O, a potential anti-human immunodeficiency virus type 1 (HIV-1 non-nucleoside reverse-transcriptase inhibitor, the pyrrolidine ring has an envelope conformation. In the crystal structure, adjacent molecules are connected into infinite chains via an N—H...O hydrogen bond.

  12. Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring

    DEFF Research Database (Denmark)

    Tolborg, Jakob Fjord; Jensen, Knud Jørgen

    2000-01-01

    A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could...

  13. N-Benzyl-1,3-dideoxy-1,3-imino-l-xylitol

    Directory of Open Access Journals (Sweden)

    Sarah F. Jenkinson

    2011-09-01

    Full Text Available The structure determination confirms the stereochemistry of the title compound, C12H17NO3, which contains a four-membered azetidine ring system. The absolute configuration was determined by the use of d-glucose as the starting material. In the crystal, O—H...O and O—H...N hydrogen bonds link the molecules into layers in the ab plane.

  14. Benzyl alcohol–ammonia (1:1) cluster structure investigated by ...

    Indian Academy of Sciences (India)

    Unknown

    22. Although it is simply a ... chamber in a counter-propagating fashion and coaxially focused by lenses (f = 250 mm for IR and f = 500 for UV) .... In the present case the level of calculation is not high enough but the trend in relative stability of the ...

  15. Crystal structure of benzyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Suvratha Krishnamurthy

    2015-07-01

    Full Text Available The title compound, C13H13NO4 (also known as N-benzyloxycarbonyl-4-hydroxy-l-proline lactone, crystallizes with two molecules in the asymmetric unit. They have slightly different conformations: the fused ring systems almost overlap, but different C—O—C—C torsion angles for the central chains of −155.5 (2 and −178.6 (2° lead to different twists for the terminal benzene ring. In the crystal, the molecules are linked by C—H...O interactions, generating a three-dimensional network. The absolute structure was established based on an unchanging chiral centre in the synthesis.

  16. 1-[(1-Benzyl-1H-1,2,3-triazol-4-ylmethyl]indoline-2,3-dione

    Directory of Open Access Journals (Sweden)

    Fatima-Zahrae Qachchachi

    2014-05-01

    Full Text Available In the title compound, C18H14N4O2, the triazole ring makes dihedral angles of 77.32 (8 and 75.56 (9°, respectively, with the indoline residue and the terminal phenyl group. In the crystal, molecules are linked by C—H...N hydrogen bonds into tapes parallel to the b axis. The tapes are linked together by π–π interactions between triazole rings [inter-centroid distance = 3.4945 (9 Å].

  17. Pervaporation Membranes with Poly(γ-Benzyl-L-Glutamate) Selective Layers for Separation of Toluene - n-Heptane Mixtures

    Czech Academy of Sciences Publication Activity Database

    Kononova, S.V.; Kremnev, R.V.; Suvorova, E.I.; Baklagina, Y.G.; Volchek, B.Z.; Uchytil, Petr; Shabsels, B.M.; Romashkova, K.A.; Setničková, Kateřina; Řezníčková Čermáková, Jiřina

    2015-01-01

    Roč. 477, MAR 1 (2015), s. 14-24 ISSN 0376-7388 Institutional support: RVO:67985858 Keywords : composite membrane * structure * hydrocarbons pervaporation Subject RIV: CI - Industrial Chemistry, Chemical Engineering Impact factor: 5.557, year: 2015

  18. [Ru(TPP)CO]-catalysed intramolecular benzylic C-H bond amination, affording phenanthridine and dihydrophenanthridine derivatives.

    Science.gov (United States)

    Intrieri, Daniela; Mariani, Matteo; Caselli, Alessandro; Ragaini, Fabio; Gallo, Emma

    2012-08-20

    Shedding light on azides: [Ru(TPP)CO] (TPP=tetraphenyl porphyrin dianion), white light and O(2) were found to be a suitable catalyst combination to perform the annulation of several biaryl azides. The high chemoselectivity of the process allows the synthesis of phenanthridines and dihydrophenanthridines in good yield and purity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Rapid small intestinal permeability assay based on riboflavin and lactulose detected by bis-boronic acid appended benzyl viologens.

    Science.gov (United States)

    Resendez, Angel; Abdul Halim, Md; Landhage, Caroline M; Hellström, Per M; Singaram, Bakthan; Webb, Dominic-Luc

    2015-01-15

    Although organoboronic acids are efficient high-throughput sugar sensors, they have not been pursued for gut permeability studies. A modification of the lactulose/mannitol assay is described by which small intestinal permeability is assessed at the time of urine collection using a lactulose/riboflavin ratio. Volunteers ingested 50mg riboflavin and either 5 g mannitol or 10 g lactulose. Urine was collected for 6 hrs. Riboflavin was assayed by autofluorescence. Riboflavin was removed by C18 solid phase extraction. Lactulose and mannitol were then assayed using 1,1'-bis(2-boronobenzyl)-4,4'-bipyridinium (4,4'oBBV) coupled to the fluorophore HPTS. The temporal profile over 6 hrs for riboflavin paralleled mannitol. Riboflavin recovery in urine was 11.1 ± 1.9 % (mean ± SEM, n=7), similar to mannitol. There was selective binding of 4,4'oBBV to lactulose, likely involving cooperativity between the fructose and galactose moieties. Lower limits of detection and quantification were 90 and 364 μM. The lactulose assay was insensitive to other permeability probes (e.g., sucrose, sucralose) while tolerating glucose or lactose. This assay can be adapted to automated systems. Stability of 4,4'oBBV exceeds 4 years. Riboflavin measured by autofluorescence combined with lactulose measured with 4,4'oBBV represents a useful new chemistry for rapid measurement of intestinal permeability with excellent stability, cost and throughput benefits. Copyright © 2014. Published by Elsevier B.V.

  20. Experimental Determination and Modeling of the Phase Behavior for the Selective Oxidation of Benzyl Alcohol in Supercritical CO2

    DEFF Research Database (Denmark)

    Tsivintzelis, Ioannis; Beier, Matthias Josef; Grunwaldt, Jan-Dierk

    2011-01-01

    –benzaldehyde–water ternary mixtures were experimentally determined. The cubic plus association (CPA) equation of state was used to model the phase behavior of the experimentally investigated systems as well as the phase behavior of relevant mixtures that can exist inside the reactor during the reaction time...

  1. 4-Benzyl-6-bromo-2-(4-chlorophenyl-4H-imidazo[4,5-b]pyridine

    Directory of Open Access Journals (Sweden)

    Selma Bourichi

    2017-06-01

    Full Text Available In the title compound, C19H13BrClN3, the chlorophenyl ring occupies an equatorial position with respect to the mean plane of the imidazopyridine unit, while the other phenyl ring is twisted by 4.1 (2° with respect to the mean plane of the imidazopyridine unit. In the crystal, pairwise C—H...Br interactions link the molecules into dimers, forming an R22(16 ring motif. In addition, weak π–π stacking interactions stabilize the crystal packing.

  2. Crystal structure of 4-benzyl-2H-benzo[b][1,4]thiazin-3(4H-one

    Directory of Open Access Journals (Sweden)

    N. K. Sebbar

    2015-12-01

    Full Text Available In the title compound, C15H13NOS, the thiazine ring adopts a twisted boat conformation and the dihedral angle between the aromatic rings is 86.54 (4°. In the crystal, molecules are linked by weak C—H...O interactions, resulting in chains along [010].

  3. TUD-1-encapsulated HY zeolite: A new hierarchical microporous/mesoporous composite with extraordinary performance in benzylation reactions

    NARCIS (Netherlands)

    Saad, M.H.; Mul, Guido

    2013-01-01

    A new composite material consisting of amorphous TUD-1 encapsulating crystalline zeolite Y was synthesized. Samples with different HY zeolite loadings (10, 20, 40, and 60 wt %) were prepared, and the resulting solid products were characterized with elemental analysis, XRD, N2 physisorption, 27Al MAS

  4. Bis{N-benzyl-N-[2-(thiophen-2-ylethyl]dithiocarbamato-κ2S,S′}lead(II

    Directory of Open Access Journals (Sweden)

    S. Selvanayagam

    2013-08-01

    Full Text Available The molecule of the title compound, [Pb(C14H14NS32], is located on a twofold rotation axis. The dithiocarbamate anion S,S′-chelates to the PbII atom, which shows a Ψ-trigonal–bipyramidal coordination. The thiophene ring is disordered over two positions, the major component having 71.3 (7% occupancy. The molecular conformation is stabilized by intramolecular C—H...S interactions.

  5. Interaction of bentonite with dodecyl-benzyl-dimethylammonium bromide and N(1-(ethoxy carbonyl)penta-decyl)trimethylammonium bromide

    Czech Academy of Sciences Publication Activity Database

    Kalousová, J.; Votinský, J.; Beneš, Ludvík; Melánová, Klára; Zima, Vítězslav

    1998-01-01

    Roč. 4, - (1998), s. 65-73 ISSN 1211-5541 R&D Projects: GA ČR GA203/97/1010; GA AV ČR KSK2050602 Grant - others:Klíčový projekt AV ČR(CZ) No.12 Institutional research plan: CEZ:MSM 253100101; CEZ:AV0Z4050913 Subject RIV: CA - Inorganic Chemistry

  6. Convergent [18]F-labeling and evaluation of N-benzyl-phenethylamines as 5-HT2A receptor PET ligands

    DEFF Research Database (Denmark)

    Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant

    2016-01-01

    Positron emission tomography (PET) investigations of the 5-HT2A receptor (5-HT2AR) system can be used as a research tool in diseases such as depression, Alzheimer's disease and schizophrenia. We have previously developed a (11)C-labeled agonist PET ligand ([(11)C]Cimbi-36), and the aim...... the pig brain. However, since within-scan intervention with ketanserin, a known orthosteric 5-HT2A receptor antagonist, did not result in significant blocking, the radioligands seem unsuitable for neuroimaging of the 5-HT2AR in vivo....

  7. Metal chelates of azo-pyridazine dyes Chelating tendencies of benzoylacetone-monohydrazone-3-hydrazino-4-benzyl-6-phenylpyridazine (bahp).

    Science.gov (United States)

    Ramadan, A A; Seada, M H; Rizkalla, E N

    1983-04-01

    The synthesis, acid-base equilibria and metal-ion chelating tendencies of BAHP are reported. From potentiometric equilibrium measurements of hydrogen-ion concentration at 30 degrees and ionic strength 0.10M (KNO(3)), in 75% dioxan-water medium, the values of the stability constants of some BAHP complexes with transition, non-transition and lanthanide ions have been evaluated. Probable structures of the metal chelates are inferred from the electronic absorption spectra and infrared examination of the solid copper complex. The use of BAHP as an analytical reagent for the spectrophotometric determination of copper, nickel and cobalt ions is discussed.

  8. Synthesis and antiproteasomal activity of novel O-benzyl salicylamide-based inhibitors built from leucine and phenylalanine

    Czech Academy of Sciences Publication Activity Database

    Jorda, Radek; Dušek, J.; Řezníčková, Eva; Pauk, K.; Magar, P. P.; Imramovský, A.; Kryštof, Vladimír

    2017-01-01

    Roč. 135, JUL 28 (2017), s. 142-158 ISSN 0223-5234 R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : Apoptosis * Inhibitor * Proteasome * Salicylamide * Ubiquitin Subject RIV: EB - Genetics ; Molecular Biology OBOR OECD: Biochemical research methods Impact factor: 4.519, year: 2016

  9. (3R,4R,5R-5-(Acetamidomethyl-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide

    Directory of Open Access Journals (Sweden)

    Michela I. Simone

    2010-11-01

    Full Text Available X-ray crystallographic analysis with Cu Kα radiation established the relative configurations of the stereogenic centers in the title compound, C15H20N2O5, and clarified mechanistic ambiguities in the synthesis. The conformation of the five-membered ring approximates twisted, about a C—O bond. The absolute configuration of this carbon-branched dipeptide isostere was known based on the use of d-ribose as the starting material. Refinement of the Flack parameter gave an ambiguous result but the refined Hooft parameter is in agreement with the assumed (d-ribose absolute structure. The crystal structure consists of N—H...O and O—H...O hydrogen-bonded bi-layers, with the terminal methyl and phenyl groups forming a hydrophobic inter-layer interface. Some weak C—H...O interactions are also present.

  10. Access to the substituted benzyl-1,2,3-triazolyl hesperetin derivatives expressing antioxidant and anticancer effects

    Czech Academy of Sciences Publication Activity Database

    Mistry, B.; Patel, Rahul V.; Keum, Y.S.

    2017-01-01

    Roč. 10, č. 2 (2017), s. 157-166 ISSN 1878-5352 R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : free-radical method * oxidative stress * hesperidin * prevention * diseases * Hesperidin * Hesperetin * Cycloaddition * Click chemistry * Anticancer * Antioxidant Subject RIV: EB - Genetics ; Molecular Biology OBOR OECD: Oncology Impact factor: 4.553, year: 2016

  11. Benzyl N-((S-2-hydroxy-1-{N′-[(E-2-methoxybenzylidene]hydrazinecarbonyl}ethylcarbamate from synchrotron data

    Directory of Open Access Journals (Sweden)

    Alessandra C. Pinheiro

    2010-04-01

    Full Text Available A U-shaped conformation is found in the title compound, C19H21N3O5, with the benzene rings lying to the same side of the molecule; the dihedral angle between them is 10.83 (16°. The dihedral angle formed between the hydrazinecarbonyl and carbamate residues is 68.42 (13°. The carbonyl groups lie approximately at right angles to each other [O—C...C—O pseudo torsion angle of 107.7 (3°], and the conformation about the C12=N3 bond [1.279 (4 Å] is E. An intramolecular Ncb—H...Ohy (cb = carbmate and hy = hydroxy hydrogen bond occurs, generating an S(6 loop. In the crystal, intermolecular Oh—H...Oca (ca = carbonyl and Nhz—H...Oca (hz = hydrazine hydrogen bonds lead to the formation of a supramolecular chain, two molecules thick, which propagates along the a axis; these are connected by C—H...Oca contacts.

  12. THE SYNTHESIS OF SOME DERIVATIVES BASED ON THE 4-BENZYL-1H-PYRAZOLE-3,5-DIAMINE CORE

    Czech Academy of Sciences Publication Activity Database

    Jedinák, L.; Kryštof, Vladimír; Cankař, Petr

    2011-01-01

    Roč. 88, č. 2 (2011), s. 371-383 ISSN 0385-5414 R&D Projects: GA ČR GA301/08/1649 Institutional research plan: CEZ:AV0Z50380511 Keywords : Knoevenagel Condensation * Olefin Reduction * CDK * Hydrazine Cycloaddition * Pyrazole-3,5-diamine Subject RIV: CE - Biochemistry Impact factor: 0.999, year: 2011

  13. Synthesis, antitumor activity, and cytotoxicity of 4-substituted 1-benzyl-5-diphenylstibano-1H-1,2,3-triazoles.

    Science.gov (United States)

    Yamada, Mizuki; Takahashi, Tsutomu; Hasegawa, Mai; Matsumura, Mio; Ono, Kanna; Fujimoto, Ryota; Kitamura, Yuki; Murata, Yuki; Kakusawa, Naoki; Tanaka, Motohiro; Obata, Tohru; Fujiwara, Yasuyuki; Yasuike, Shuji

    2018-01-15

    Trisubstituted 5-organostibano-1H-1,2,3-triazoles (3a-f) were synthesized by the Cu-catalyzed azide-alkyne cycloaddition of various ethynylstibanes (1) with benzylazide (2) in the presence of CuBr (5 mol%) under aerobic conditions. The reaction of 5-stibanotriazoles with HCl afforded C5-unsubstituted 1,2,3-triazoles (4a-f). The antitumor activity of trisubstituted 5-organostibano-1H-1,2,3-triazoles (3a-f) and their 5-unsubstituted 1,2,3-triazoles (4a-f) were evaluated in several tumor cell lines. All 5-stibanotriazoles (3a-f) exerted an excellent antitumor activity. On the contrary, 5-unsubstituted 1,2,3-triazoles (4a-f) without a diphenylantimony group in the molecule exhibited very low antitumor activity compared with 5-stibanotriazoles (3a-f). In compounds of both the series, the substituted 4-butyl group appeared to decrease antitumor activity. However, results suggested that organometal (antimony) in the molecule was required for greater antitumor activity. In addition, all 5-stibanotriazoles (3a-f), but not all 5-unsubstituted 1,2,3-triazoles (4a-f), exhibited cytotoxicity in normal vascular endothelial cells derived from bovine aorta. Among the compounds (3b-e) that exhibited excellent antitumor activity, those with 4-methylphenyl (3b) and 1-cyclohexenyl (3e) showed relatively low cytotoxicity to vascular endothelial cells. Together, these results suggest that trisubstituted 5-organostibano-1H-1,2,3-triazoles, including compounds 3b and 3e, may serve as potential anticancer therapeutic drugs in the future. Copyright © 2017 Elsevier Ltd. All rights reserved.

  14. 5-[(1-Benzyl-1H-1,2,3-triazol-4-ylmethyl]-5H-dibenzo[b,f]azepine

    Directory of Open Access Journals (Sweden)

    N. K. Lokanath

    2013-12-01

    Full Text Available In the title compound, C24H20N4, the azepine ring adopts a boat conformation. The dihedral angle between the benzene rings fused to the azepine ring is 49.40 (9°. The triazole ring makes a dihedral angle of 77.88 (9° with the terminal phenyl ring. In the crystal, molecules are linked via C—H...π interactions and a parallel slipped π–π interaction [centroid–centroid distance = 3.7324 (9, normal distance = 3.4060 (6 and slippage = 1.526 Å], forming a three-dimensional network.

  15. Download this PDF file

    African Journals Online (AJOL)

    9). HO. ... Meldrum's acid (6. Decarboxylative esterification of this compound with benzyl alcohol gave benzyl acetoacetate in good yield. Selective reduction of benzyl .... The combined extract was dried and the solvent removed to give 4.22.

  16. A Sequential Preparation of Organic Compounds for Senior Chemistry Classes

    Science.gov (United States)

    Merrigan, Cecilia; Crotty, Patricia

    1971-01-01

    Describes procedures suitable for student preparation of benzaldehyde, benzoic acid, and ethyl benzoate sequentially from benzyl alcohol. Preparation for benzyl chloride also given. All reagents except benzyl alcohol are common inorganic chemicals. (AL)

  17. Overcoming super-knock down resistance (super-kdr) mediated resistance: multi-halogenated benzyl pyrethroids are more toxic to super-kdr than kdr house flies.

    Science.gov (United States)

    Sun, H; Tong, K P; Kasai, S; Scott, J G

    2016-04-01

    Target site insensitivity because of mutations in the voltage-sensitive sodium channel gene (Vssc) is a major mechanism of resistance to pyrethroid insecticides in the house fly, Musca domestica. There are three known Vssc alleles that confer resistance to pyrethroids in the house fly: knock down resistance (kdr; L1014F), super-kdr (M918T + L1014F) and kdr-his (L1014H), but there has been no side-by-side comparison of the resistance levels that they confer. We compared the levels of resistance conferred by the three Vssc alleles in congenic strains to 19 structurally diverse pyrethroids, and compared the full-length Vssc cDNA sequences from each strain. Generally, the levels of resistance conferred were kdr-his pyrethroids. We also examined the levels of resistance in heterozygotes. Resistance in each of the hybrids was generally inherited as an incompletely recessive trait, except for the kdr-his/kdr hybrids, which showed incompletely to completely dominant resistance (ie had resistance levels comparable to kdr homozygotes). The importance of these results to understanding the frequencies of these resistance alleles in natural populations, the evolution of insecticide resistance and resistance management strategies are discussed. © 2015 The Royal Entomological Society.

  18. Interrelation between the Structural and Transport Properties of Pervaporation Membranes with Diffusion Layers Based on Poly-γ-Benzyl-L-Glutamate

    Czech Academy of Sciences Publication Activity Database

    Kononova, S.V.; Kremnev, R.V.; Baklagina, Yu.G.; Volchek, B.Z.; Vlasova, E.N.; Shabsels, B.M.; Romashkova, K.A.; Romanov, D.P.; Arkhipov, S.N.; Bogomazov, A.V.; Uchytil, Petr

    2011-01-01

    Roč. 56, č. 3 (2011), s. 502-507 ISSN 1063-7745 R&D Projects: GA ČR GA104/09/1165 Institutional research plan: CEZ:AV0Z40720504 Keywords : transport properties * membranes * mixture Subject RIV: CI - Industrial Chemistry, Chemical Engineering Impact factor: 0.469, year: 2011

  19. Metabolism of the fungicide Denmert (S-n-butyl S'-p-tert-butyl-benzyl N-3-pyridyldithiocarbonimidate, S-1358) and Denmert sulfoxides in liver enzyme systems

    International Nuclear Information System (INIS)

    Ohkawa, Hideo; Okihara, Yukiko; Miyamoto, Junshi

    1976-01-01

    On incubation with rat liver microsomes plus MADPH, Denmert (S-n-butyl S'-p-tert-butylbenzyl N-3-pyridyldithiocarbonimidate) underwent at least two different types of oxidation; hydroxylation and sulfoxidation. Hydroxylation of Denmert at the tert-butyl group was one of the major metabolic attacks in mammalian metabolism. Sulfoxidation of Denmert gave two isomers of Denmert sulfoxides which were intermediates in the metabolism and readily transformed into 2-(3'-pyridylimino)-4-carboxylthiazolidine (HM) in the presence of L-cysteine without enzymatic mediation. This type of conjugation with cysteine appears to be a new class of metabolic reactions in mammals. Denmert S-oxide showed increased fungicidal activity when assayed in liquid cultures, but not on plant leaves. (auth.)

  20. Enantioselective Decarboxylation of 2-Methyl-2-aminomalonate Catalyzed by (S)-2-Hydroxy-2'-(3-phenyluryl-benzyl)-1,1'-binaphthyl-3-carboxaldehyde

    International Nuclear Information System (INIS)

    Park, Hyun Jung; Nandhakumar, Raju; Lee, Sun Min; Ahn, Yoon Su; Kim, Kwan Mook

    2010-01-01

    We have demonstrated that the chiral aldehyde 1 catalyzes the stereoselective decarboxylation of [MAM-H] - . The stereoselectivity is maximum in monoanionic form of MAM. The D-form-favor in the decarboxylation may be explained by the removal of the protonated carboxylate group and protonation at the same site. Aminomalonic acid (AM-H 2 ) is a biological intermediate appearing in the conversion course of serine to glycine. Amino-malonic decarboxylases, enzymes that catalyze decarboxylation of aminomalonic acid, have been found in many living systems. Serine hydroxymethyltransferase stereospecifically decarboxylates 2-amino-2-methyl-malonic acid (MAM-H 2 ) to produce D-alanine. Although stereoselective decarboxylation is a century old theme, the interest on it is growing recently owing to the development of chiral technology. Chemical approaches using metal complexes and cinchonine derivatives have been developed for stereospecific decarboxylation of MAM

  1. DIASTEREOSELECTIVE INDIUM-PROMOTED ADDITION OF FUNCTIONALIZED ALLYL BROMIDES TO N-BENZYL-2,3-AZETIDINEDIONE UNDER AQUEOUS CONDITIONS. (R824725)

    Science.gov (United States)

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  2. CCDC 820903: Experimental Crystal Structure Determination : (eta^5^-pentamethylcyclopentadienyl)-(1-benzyl-3-[tri(propan-2-yl)-phosphanylidene]triaz-1-ene)-chloro-ruthenium

    KAUST Repository

    Lamberti, Marina

    2013-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  3. 75 FR 770 - Acrylic acid-benzyl methacrylate-1-propanesulfonic acid, 2-methyl-2-[(1-oxo-2-propenyl)amino...

    Science.gov (United States)

    2010-01-06

    ....960. Akzo Nobel Surface Chemistry LLC submitted a petition to EPA under the Federal Food, Drug, and Cosmetic Act (FFDCA), requesting an exemption from the requirement of a tolerance. This regulation... the receipt of a pesticide petition (PP 9E7599) filed by Akzo Nobel Surface Chemistry LLC. The...

  4. (E-1-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl-3-phenylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Alagusundaram Ponnuswamy

    2011-10-01

    Full Text Available The asymmetric unit of the title compound, C19H17N3O, contains two independent molecules. In one molecule, the essentially planar triazole ring [maximum deviation = 0.003 (2 Å] forms dihedral angles of 5.57 (12 and 87.51 (12° with the two phenyl rings, while in the other molecule [maximum deviation in triazole ring = 0.001 (2 Å] these angles are 1.55 (10 and 82.73 (11°. The dihedral angles between the two phenyl rings in the two molecules are 87.77 (13 and 81.22 (11°. In the crystal, the independent molecules are connected via a weak C—H...N hydrogen bond, forming dimers. Further stabilization is provided by weak C—H...π interactions.

  5. 4-Benzyl-2-(4-chlorobenzylidene-3,4-dihydro-2H-1,4-benzothiazin-3(4H-one

    Directory of Open Access Journals (Sweden)

    Mohamed Ellouz

    2016-05-01

    Full Text Available The title compound, C22H16ClNOS, has three aromatic systems, viz. (i a phenyl ring, (ii a chlorobenzene ring and (iii a 1,4-benzothiazine fused-ring system (r.m.s. deviation of the ten fitted atoms = 0.023 Å. The dihedral angle between planes (ii and (iii is 1.68 (8°, indicating a coplanar arrangement, and between plane (i and each of (ii and (iii is 85.61 (8 and 86.74 (8°, respectively, indicating the phenyl ring is approximately perpendicular to the remaining residue. In the crystal, pairwise methylene-C—H...O(carbonyl hydrogen bonds form dimers which stack along the b-axis direction.

  6. Formulation and characterization of biocompatible and stable I.V. itraconazole nanosuspensions stabilized by a new stabilizer polyethylene glycol-poly(β-Benzyl-l-aspartate) (PEG-PBLA).

    Science.gov (United States)

    Zong, Lanlan; Li, Xiaohua; Wang, Haiyan; Cao, Yanping; Yin, Li; Li, Mengmeng; Wei, Zhihao; Chen, Dongxiao; Pu, Xiaohui; Han, Jihong

    2017-10-05

    Amphiphilic block copolymers, PEG-PBLA with different molecular weights, were synthesized and used as new stabilizers for Itraconazole nannosuspensions (ITZ-PBLA-Nanos). ITZ-PBLA-Nanos were prepared by the microprecipitation-high pressure homogenization method, and the particle size and zeta potential were measured using a ZetaSizer Nano-ZS90. Morphology and crystallinity were studied using TEM, DSC and powder X-ray. The effect of the PEG-to-PBLA ratio, and the drug-to-stabilizer ratio were investigated to obtain the optimal formulation. It was found that the optimal length of hydrophobic block was 25 BLA-NCA molecules and the optimal ratio of drug/stabilizer was 1:1, where the resulted average particle size of ITZ-PBLA-Nanos was 262.1±7.13nm with a PDI value of 0.163±0.011. The images of TEM suggest that ITZ-PBLA-Nanos were rectangular in shape. ITZ existed as crystals in the nanoparticles as suggested by the DSC and XRD results. Compared with the crude drug suspensions, the dissolution rate of ITZ nanocrystals, was significantly increased and was similar to Sporanox ® injection. The ITZ-PBLA-Nanos also demonstrated better dilution stability and storage stability compared with ITZ-F68-Nanos. The particle size of ITZ-PBLA-Nanos did not change significantly after incubated in rat plasma for 24h which is a good attribute for I.V. administration. Acute toxicity tests showed that ITZ-PBLA-Nanos has the highest LD 50 compared with ITZ-F68-Nanos and Sporanox ® injection. ITZ-PBLA-Nanos also showed stronger inhibiting effect on the growth of Candida albicans compared with Sporanox ® injection. Therefore, PEG-PBLA has a promising potential as a biocompatible stabilizer for ITZ nanosuspensions and potentially for other nanosuspensions as well. Copyright © 2017. Published by Elsevier B.V.

  7. Preparation of 2-[α-(2-ethoxyphenoxy)benzyl]-[5-14C]morpholine methanesulfonate ([14C]reboxetine):a new antidepressant agent

    International Nuclear Information System (INIS)

    Angiuli, P.; Fontana, E.; Vicario, G.P.

    1991-01-01

    The labelling with radiocarbon of the new antidepressant agent Reboxetine is described. The preparation has been carried out in a two step procedure using 2-chloro-N-(3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl)propyl-[1- 14 C]acetamide as starting material. The expected compound was prepared by cyclization of the above halogenoacylamido alcohol to the corresponding morpholone ring followed by reduction to the final [5- 14 C]morpholine derivative 4, 98% radiochemically pure and with specific radioactivity of 988 MBq/mmol. An overall radiochemical yield of 57.5% was achieved. (author)

  8. Rapid acidolysis of benzyl group as a suitable approach for syntheses of peptides naturally produced by oxidative stress and containing 3-nitrotyrosine

    Czech Academy of Sciences Publication Activity Database

    Niederhafner, Petr; Šafařík, Martin; Brichtová, Eva; Šebestík, Jaroslav

    2016-01-01

    Roč. 48, č. 4 (2016), s. 1087-1098 ISSN 0939-4451 R&D Projects: GA ČR(CZ) GA14-00431S Institutional support: RVO:61388963 Keywords : nitrotyrosine * peptide synthesis * alpha-synuclein * reaction rate Subject RIV: CE - Biochemistry Impact factor: 3.173, year: 2016

  9. Synthesis and Crystal Structure of Benzyl [(1S-1-(5-amino-1,3,4-oxadiazol-2-yl-2-phenylethyl]carbamate

    Directory of Open Access Journals (Sweden)

    Reik Löser

    2012-08-01

    Full Text Available The conversion of Z-phenylalanine hydrazide with cyanogen bromide resulted in the formation of the corresponding 2-amino-1,3,4-oxadiazole by spontaneous cyclization of the intermediary cyanohydrazide. The molecular structure of the product was confirmed by single crystal X-ray diffraction. Crystals of the title compound where obtained from a saturated solution in a mixture of petroleum ether and ethyl acetate and belong to the monoclinic space group P21 with unit cell parameters a = 9.8152(2 Å, b = 9.6305(2 Å, c = 9.8465(2 Å, β = 116.785(1°. The asymmetric unit contains one molecule.

  10. A monoclinic modification of (4Z-1-benzyl-4-(2-oxopropylidene-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

    Directory of Open Access Journals (Sweden)

    Mohamed Samba

    2018-02-01

    Full Text Available In the title molecule, C19H18N2O2, the orientation of the oxopropylidene substituent is largely determined by an intramolecular N—H...O hydrogen bond. In the crystal, C—H...O hydrogen bonds form zigzag chains, which are elaborated into sheets lying parallel to (101 by complementary C—H...π interactions. Comparisons to the structure of the triclinic modification are made.

  11. Chloridobis[N'-(2-meth-oxy-benzyl-idene)-4-nitro-benzohydrazidato-κO,N'](4-methyl-pyridine-κN)cobalt(III).

    Science.gov (United States)

    Wu, Qiong-Jie; Chen, Xiao-Hua; Jiang, Jiang; Cai, Bi-Qiong; Xie, Yong-Ping

    2011-02-02

    In the title complex, [Co(C(15)H(12)N(3)O(4))(2)Cl(C(6)H(7)N)], the Co(III) ion is coordinated by two N atoms and two O atoms from two deprotonated Schiff base ligands, one N atom from a 4-methyl-pyridine ligand and one Cl atom, forming a distorted octa-hedral geometry. The Co(III) ion is displaced by 0.038 (2) Å from the equatorial plane towards the axial Cl atom.

  12. Design, synthesis, and biological evaluation of a series of resorcinol-based N-benzyl benzamide derivatives as potent Hsp90 inhibitors.

    Science.gov (United States)

    Park, Sun You; Oh, Yong Jin; Lho, Yunmee; Jeong, Ju Hui; Liu, Kwang-Hyeon; Song, Jaeyoung; Kim, Soong-Hyun; Ha, Eunyoung; Seo, Young Ho

    2018-01-01

    Heat shock protein 90 (Hsp90) is a ubiquitous molecular chaperone that is responsible for the stabilization and maturation of many oncogenic proteins. Therefore, Hsp90 has emerged as an attractive target in the field of cancer chemotherapy. In this study, we report the design, synthesis, and biological evaluation of a series of Hsp90 inhibitors. In particular, compound 30f shows a significant Hsp90α inhibitory activity with IC 50 value of 5.3 nM and an excellent growth inhibition with GI 50 value of 0.42 μM against non-small cell lung cancer cells, H1975. Compound 30f effectively reduces the expression levels of Hsp90 client proteins including Her2, EGFR, Met, Akt, and c-Raf. Consequently, compound 30f promotes substantial cleavages of PARP, Caspase 3, and Caspase 8, indicating that 30f induces cancer cell death via apoptotic pathway. Moreover, cytochrome P450 assay indicates that compound 30f has weak inhibitory effect on the activities of five major P450 isoforms (IC 50  > 5 μM for 1A2, 2C9, 2C19, 2D6, and 3A), suggesting that clinical interactions between 30f and the substrate drugs of the five major P450 isoforms are not expected. Compound 30f also inhibits the tumor growth in a mouse xenograft model bearing subcutaneous H1975 without noticeable abnormal behavior and body weight changes. The immunostaining and western immunoblot analysis of EGFR, Met, Akt in xenograft tissue sections of tumor further demonstrate a good agreement with the in vitro results. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  13. Callus induction of leaf explant Piper betle L. Var Nigra with combination of plant growth regulators indole-3-acetic acid (IAA), benzyl amino purin (BAP) and kinetin

    Science.gov (United States)

    Junairiah, Zuraidassanaaz, Nabilah Istighfari; Izdihar, Fairuz Nabil; Manuhara, Yosephine Sri Wulan

    2017-09-01

    The purpose of this research was to determine the combination of plant growth regulators IAA, BAP and kinetin towards callus induction and growth of leaf explants Piper betle L. VarNigra. Explants from leaf of Piper betle L. VarNigra was cultured on MS medium with 24 treatment combinations of plant growth regulators IAA and BAP and 24 treatment combinations of plant growth regulators IAA and kinetin with 0.0;0.5;1.0;1.5;2.0 mg/L concentration respectively, the observed variable were the length of time the formation of callus, callus morphology, fresh and dry weight of callus. The results of this research showed that the combination of growth regulators IAA with BAP and kinetin had effects on leaf growth of Piper betle L. VarNigra. During 8 weeks observation, it indicated that the combination of concentration IAA 0.5 mg/L and BAP 2.0 mg/L showed fastest callus formation at 8.5 days. Combination of concentration IAA 1.0 mg/L and BAP 1.5 mg/L showed the highest of fresh weight at 0.6596 grams, and the highest dry weight was obtained from the combination of concentration IAA 0.5 mg/L and BAP 0.5 mg/L at 0.0727 grams. Combination of concentration IAA 1.0 mg/L and kinetin 1.5 mg/L had the highest of fresh weight at 0.2972 grams and the highest dry weight at 0.1660 grams. Callus of Piper betle L. VarNigra had two textures, that were compact and friable, and also showed various kind of colors, like white, greenish white, yellowish white, tanned white, brown and black. Based on this research, that concentration IAA 1.0 mg/L and 1.5 mg/L kinetin was the best combination for induction of callus from leaf of Piper betle L. Var Nigra.

  14. Regioselective synthesis of 3-benzyl substituted pyrimidino chromen-2-ones and evaluation of anti-microbial and anti-biofilm activities.

    Science.gov (United States)

    Emmadi, Narender Reddy; Atmakur, Krishnaiah; Bingi, Chiranjeevi; Godumagadda, Narender Reddy; Chityal, Ganesh Kumar; Nanubolu, Jagadeesh Babu

    2014-01-15

    Regioselective synthesis of a number of highly functionalized 3-benzylpyrimidino chromen-2-ones (4) were accomplished in a one pot three component reaction in acetic acid and determined their anti-microbial and anti-biofilm activities. Compounds 4o and 4p showed an excellent anti-microbial activity against Micrococcus luteus MTCC 2470 at a par with standard control (Ciprofloxacin) and exhibited best activity against Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 121. Further, compounds 4h, 4i, 4m, 4n and 4q showed promising activity against Micrococcus luteus MTCC 2470, Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 121. Whereas, compounds 4m showed very promising biofilm inhibition activity against Staphylococcus aureus MLS 16 MTCC 2940 and 4o, 4p showed very potent activity against Staphylococcus aureus MTCC 96 at a par with Ciprofloxacin used as standard control. Copyright © 2013 Elsevier Ltd. All rights reserved.

  15. Benzyl alcohol induces a reversible fragmentation of the Golgi apparatus and inhibits membrane trafficking between endosomes and the trans-Golgi network

    DEFF Research Database (Denmark)

    Simm, Roger; Kvalvaag, Audun Sverre; van Deurs, Bo

    2017-01-01

    OH is a membrane fluidizing agent that can affect membrane protein activity and cellular processes such as ligand binding to cell surface receptors, endocytosis and degradation of lysosomal cargo. In this study, we examined the effects of BnOH on intracellular transport using Shiga toxin (Stx), diphtheria toxin...

  16. Synthesis and Structure-Conductivity Relationship of Polystyrene-block-Poly(vinyl benzyl trimethylammonium) for Alkaline Anion Exchange Membrane Fuel Cells

    Science.gov (United States)

    2012-01-01

    morphologies on the ionic conductivity, meas- ured by impedance spectroscopy, were also investigated. EXPERIMENTAL Materials Styrene (>99%; Aldrich) was passed...50 Integrated GPC system. Infrared spectroscopy was performed on a Perkin-Elmer 100 FTIR spectrometer with universal ATR sampling accessory. SAXS...conver- sion of the reaction by 1H NMR. Synthesis of Polystyrene (PS-Br) by ATRP The polymerization of styrene was performed as reported in the literature

  17. Synthesis of metabolites of the insecticide Deltamethrine: 3-phenoxy (carboxyl-14C) benzoic acids and 3-phenoxy (hydroxymethyl-14C) benzyl alcohols

    International Nuclear Information System (INIS)

    Do-Cao-Thang; Nguyen-Hoang-Nam; Hoellinger, H.; Pichat, L.; CEA Centre d'Etudes Nucleaires de Saclay, 91 - Gif-sur-Yvette

    1985-01-01

    Procedures are described for the synthesis of the following metabolites of Deltamethrin, the pyrethroid insecticide: 3-phenoxy (carboxyl- 14 C) benzoic acid, 3-(4'-hydroxyphenoxy) (carboxyl- 14 C) benzoic acid, 3-(2'-hydroxyphenoxy) (carboxyl- 14 C) benzoic acid and the corresponding 3-phenoxybenzyl alcohols, specific activity = 47-57 mCi/mmol. (author)

  18. Synthesis, structural, optical band gap and biological studies on iron (III), nickel (II), zinc (II) and mercury (II) complexes of benzyl α-monoxime pyridyl thiosemicarbazone

    Science.gov (United States)

    Bedier, R. A.; Yousef, T. A.; Abu El-Reash, G. M.; El-Gammal, O. A.

    2017-07-01

    New ligand, (E)-2-((E)-2-(hydroxyimino)-1,2-diphenylethylidene)-N-(pyridin-2 yl) hydrazinecarbothioamide (H2DPPT) and its complexes [Fe(DPPT)Cl(H2O)], [Ni(H2DPPT)2Cl2], [Zn(HDPPT)(OAc)] and [Hg(HDPPT)Cl](H2O)4 were isolated and characterized by various of physico-chemical techniques. IR spectra show that H2DPPT coordinates to the metal ions as neutral NN bidentate, mononegative NNS tridentate and binegative NNSN tetradentate, respectively. From the modeling studies, the bond length, bond angle, HOMO, LUMO and dipole moment had been calculated to confirm the geometry of the ligands and their investigated complexes. The thermal studies showed the type of water molecules involved in metal complexes Furthermore, the kinetic and thermodynamic parameters for the different decomposition steps were calculated using the Coats-Redfern and Horowitz-Metzger methods. Also, the optical band gap (Eg) has been calculated to elucidate the conductivity of the isolated complexes. The optical transition energy (Eg) is direct and equals 3.34 and 3.44 ev for Ni and Fe complexes, respectively. The ligand and their metal complexes were screened for antibacterial activity against the following bacterial species, Bacillus thuringiensis, Staphylococcus aureus, Pseudomonas aeuroginosa and Escherichia coli. The results revealed that the metal complexes have more potent antibacterial compared with the ligand. Also, the degradation effect of the investigated compounds was tested showing that, Ni complex exhibited powerful and complete degradation effect on DNA.

  19. N′-(2-Hy­droxy­benzyl­idene)-2-(hy­droxy­imino)­propano­hydrazide

    Science.gov (United States)

    Plutenko, Maxym O.; Lampeka, Rostyslav D.; Moroz, Yurii S.; Haukka, Matti; Pavlova, Svetlana V.

    2011-01-01

    The mol­ecule of the title compound, C10H11N3O3, adopts an all-trans conformation and is approxomately planar, the largest deviation from the least-squares plane through all non-H atoms being 0.261 (1) Å. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, the mol­ecules are packed into layers lying parallel to the ab plane by π-stacking inter­actions between the benzene ring of one molecule and the C—N bond of the oxime group of another molecule; the shortest inter­molecular C⋯C separation within the layer is 3.412 (1) Å. The layers are connected by O—H⋯O and N—H⋯O hydrogen bonds. PMID:22199788

  20. A monoclinic polymorph of (1E,5E)-1,5-bis-(2-hy-droxy-benzyl-idene)thio-carbono-hydrazide.

    Science.gov (United States)

    Schmitt, Bonell; Gerber, Thomas; Hosten, Eric; Betz, Richard

    2011-08-01

    The title compound, C(15)H(14)N(4)O(2)S, is a derivative of thio-ureadihydrazide. In contrast to the previously reported polymorph (ortho-rhom-bic, space group Pbca, Z = 8), the current study revealed monoclinic symmetry (space group P2(1)/n, Z = 4). The mol-ecule shows non-crystallographic C(2) as well as approximate C(s) symmetry. Intra-molecular bifurcated O-H⋯(N,S) hydrogen bonds, are present. In the crystal, inter-molecular N-H⋯S hydrogen bonds and C-H⋯π contacts connect the mol-ecules into undulating chains along the b axis. The shortest centroid-centroid distance between two aromatic systems is 4.5285 (12) Å.

  1. A monoclinic polymorph of (1E,5E)-1,5-bis­(2-hy­droxy­benzyl­idene)thio­carbono­hydrazide

    Science.gov (United States)

    Schmitt, Bonell; Gerber, Thomas; Hosten, Eric; Betz, Richard

    2011-01-01

    The title compound, C15H14N4O2S, is a derivative of thio­ureadihydrazide. In contrast to the previously reported polymorph (ortho­rhom­bic, space group Pbca, Z = 8), the current study revealed monoclinic symmetry (space group P21/n, Z = 4). The mol­ecule shows non-crystallographic C 2 as well as approximate C s symmetry. Intra­molecular bifurcated O—H⋯(N,S) hydrogen bonds, are present. In the crystal, inter­molecular N—H⋯S hydrogen bonds and C—H⋯π contacts connect the mol­ecules into undulating chains along the b axis. The shortest centroid–centroid distance between two aromatic systems is 4.5285 (12) Å. PMID:22091213

  2. Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

    DEFF Research Database (Denmark)

    Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof

    2015-01-01

    and the 13C nuclear magnetic shieldings were predicted at the relativistic level of theory using the Zeroth Order Regular Approximation (ZORA). The changes in the benzene and pyrrole rings compared to the unsubstituted carbazole or the parent molecules were discussed in terms of aromaticity changes using...

  3. The adsorption of alkyl-dimethyl-benzyl-ammonium chloride onto cotton nonwoven hydroentangled substrates at the solid-liquid interface is minimized by additive chemistries

    Science.gov (United States)

    Quaternary ammonium compounds, commonly referred to as quats, are cationic surfactants widely used as the active biocide ingredient for disposable disinfecting wipes. The cationic nature of quats results in a strong ionic interaction and adsorption onto wipes materials that have an anionic surface ...

  4. Efficient Synthesis of 5-(Substituted)benzyl-2,4-Dihydro-3H-1,2,4-Triazol-3-Ones Using Microwave Irradiation

    International Nuclear Information System (INIS)

    Kahveci, B.; Mentese, E.; Ozil, M.

    2013-01-01

    A growing body of literature has shown the effectiveness of using microwave irradiation in chemical reactions. The aim of this study is to demonstrate a rapid and highly efficient synthesis of some new 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones from ethoxycarbonylhydrazones in the presence of ammonium acetate by using microwave heating for the first time. (author)

  5. Discovery of a para-Acetoxy-benzyl Ester Prodrug of a Hydroxamate-Based Glutamate Carboxypeptidase II Inhibitor as Oral Therapy for Neuropathic Pain

    Czech Academy of Sciences Publication Activity Database

    Rais, R.; Vávra, Jan; Tichý, Tomáš; Dash, R. P.; Gadiano, A. J.; Tenora, Lukáš; Monincová, Lenka; Bařinka, Cyril; Alt, J.; Zimmermann, S. C.; Slusher, C. E.; Wu, Y.; Wozniak, K.; Majer, Pavel; Tsukamoto, T.; Slusher, B. S.

    2017-01-01

    Roč. 60, č. 18 (2017), s. 7799-7809 ISSN 0022-2623 R&D Projects: GA MŠk(CZ) LM2015043; GA MŠk(CZ) ED1.1.00/02.0109 Institutional support: RVO:61388963 ; RVO:86652036 Keywords : linked acidic dipeptidase * peripheral mononeuropathy * biological activity Subject RIV: CC - Organic Chemistry; CC - Organic Chemistry (BTO-N) OBOR OECD: Organic chemistry; Organic chemistry (BTO-N) Impact factor: 6.259, year: 2016

  6. Isotypic crystal structures of 1-benzyl-4-(4-bromophenyl-2-imino-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carbonitrile and 1-benzyl-4-(4-fluorophenyl-2-imino-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carbonitrile

    Directory of Open Access Journals (Sweden)

    R. A. Nagalakshmi

    2014-11-01

    Full Text Available The molecules of the two isotypic title compounds, C25H24BrN3, (I, and C25H24FN3, (II, comprise a 2-iminopyridine ring fused with a cyclooctane ring. In (I, the cyclooctane ring adopts a twisted chair–chair conformation, while in (II, this ring adopts a twisted boat–chair conformation. The dihedral angles between the planes of the pyridine ring and the bromobenzene and phenyl rings are 80.14 (12 and 71.72 (13°, respectively, in (I. The equivalent angles in (II are 75.25 (8 and 68.34 (9°, respectively. In both crystals, inversion dimers linked by pairs of C—H...N interactions generate R22(14 loops, which are further connected by weak C—H...π interactions, generating (110 sheets.

  7. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    800°C) has been used for the benzylation of toluene and other aromatic compounds by benzyl chloride. Hydrotalcite before and after its calcination was characterized for surface area, crystalline phases and basicity. Both the hydrotalcite ...

  8. Friedel-Crafts Alkylation of o-xylene over V2O5/ZrO2 Catalysts

    CSIR Research Space (South Africa)

    Kesavan Pillai, Sreejarani

    2012-01-01

    Full Text Available and considerably more selective than the conventional homogeneous Lewis acid catalysts. The investigation of vanadia systems-catalyzed benzylation of o-xylene with benzyl chloride revealed that the catalytic activity and product selectivity are sensitive...

  9. Highly active and reusable catalyst from Fe-Mg-hydrotalcite anionic ...

    Indian Academy of Sciences (India)

    800°C) has been used for the benzylation of toluene and other aromatic compounds by benzyl chloride. Hydrotalcite before and after its calcination was characterized for surface area, crystalline phases and basicity. Both the hydrotalcite ...

  10. 4-[(1-Benzyl-1H-1,2,3-triazol-4-ylmethoxy]benzene-1,2-dicarbonitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations

    Directory of Open Access Journals (Sweden)

    Norzianah Shamsudin

    2016-04-01

    Full Text Available In the solid state, the title compound, C18H13N5O, adopts a conformation whereby the phenyl ring and methoxy–benzene-1,2-dicarbonitrile residue (r.m.s. deviation of the 12 non-H atoms = 0.041 Å lie to opposite sides of the central triazolyl ring, forming dihedral angles of 79.30 (13 and 64.59 (10°, respectively; the dihedral angle between the outer rings is 14.88 (9°. This conformation is nearly 7 kcal mol−1 higher in energy than the energy-minimized structure which has a syn disposition of the outer rings, enabling intramolecular π–π interactions. In the crystal, methylene-C—H...N(triazolyl and carbonitrile-N...π(benzene interactions lead to supramolecular chains along the a axis. Supramolecular layers in the ab plane arise as the chains are connected by benzene-C—H...N(carbonitrile interactions; layers stack with no directional interactions between them. The specified intermolecular contacts along with other, weaker contributions to the supramolecular stabilization are analysed in a Hirshfeld surface analysis.

  11. Synthesis and Characterization of Bis-benzyl and Bis-allyl Complexes of Titanium(III) and Vanadium(III); Catalytic Isomerization of Alkenes with CpV(η3-C3H5)2

    NARCIS (Netherlands)

    Nieman, J.; Pattiasina, J.W.; Teuben, J.H.

    1984-01-01

    Reactions of CpTiCl2 (Cp = η5-C5H5) with RMgX (X = Cl, Br) yield the complexes CpTiR2 (R = CH2Ph, η3-C3H5). The complex Cp*Ti(η3-C3H5)2 (Cp* = η5-C5Me5) was prepared analogously from Cp*TiCl2(THF). CpVCl2(PEt3)2 and Cp´VCl2(PEt3)2 (Cp´ = η5-C5H4Me) were used for the preparation of CpV(CH2Ph)2,

  12. 5-Substituted 3-isopropyl-7-[4-(2-pyridyl)benzyl]amino-1(2)H-pyrazolo[4,3-d]pyrimidines with anti-proliferative activity as potent and selective inhibitors of cyclin-dependent kinases

    Czech Academy of Sciences Publication Activity Database

    Vymětalová, Ladislava; Havlíček, Libor; Šturc, Antonín; Skrášková, Zuzana; Jorda, Radek; Pospíšil, Tomáš; Strnad, Miroslav; Kryštof, Vladimír

    2016-01-01

    Roč. 110, MAR 3 (2016), s. 291-301 ISSN 0223-5234 R&D Projects: GA MŠk(CZ) LO1204; GA ČR(CZ) GA15-15264S Institutional support: RVO:61389030 Keywords : Cyclin-dependent kinase * Inhibitor * Selectivity Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 4.519, year: 2016

  13. Radiosynthesis and biodistribution of a histamine H{sub 3} receptor antagonist 4-[3-(4-piperidin-1-yl-but-1-ynyl)-[{sup 11}C]benzyl]-morpholine: evaluation of a potential PET ligand

    Energy Technology Data Exchange (ETDEWEB)

    Airaksinen, Anu J. [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Jablonowski, Jill A. [Johnson and Johnson Pharmaceutical Research and Development LLC, San Diego, CA 92121 (United States); Mey, Margreet van der [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Barbier, Ann J. [Johnson and Johnson Pharmaceutical Research and Development LLC, San Diego, CA 92121 (United States); Klok, Rob P. [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Verbeek, Joost [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Schuit, Robert [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Herscheid, Jacobus D.M. [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Leysen, Josee E. [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Carruthers, Nicholas I. [Johnson and Johnson Pharmaceutical Research and Development LLC, San Diego, CA 92121 (United States); Lammertsma, Adriaan A. [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands); Windhorst, Albert D. [Department of Nuclear Medicine and PET Research, Location Radionuclide Center, VU University Medical Center, PO Box 7057, 1007 MB Amsterdam (Netherlands)]. E-mail: bwindhorst@rnc.vu.nl

    2006-08-15

    The potent histamine H{sub 3} receptor antagonist JNJ-10181457 () was successfully labeled with {sup 11}C in a novel one-pot reaction sequence, with high chemical yield (decay-corrected yield, 28{+-}8%) and high specific radioactivity (56{+-}26 GBq/{mu}mol). The binding of [{sup 11}C] to H{sub 3} receptors was studied in vitro in rat brain and in vivo in rats and mice. The in vitro binding of [{sup 11}C] in rat coronal brain slices showed high binding in the striatum, and this binding was blocked by histamine and by two known H{sub 3} antagonists, JNJ-5207852 () and unlabeled Compound (), in a concentration-dependent manner. The biodistribution of [{sup 11}C] in rats was measured at 5, 10, 30 and 60 min. The uptake of [{sup 11}C] in regions rich in H{sub 3} receptors was highest at 30 min, giving 0.98%, 1.41%, 1.28% and 1.72% dose/g for the olfactory bulb, hippocampus, striatum and cerebral cortex, respectively. However, the binding of [{sup 11}C] in the rat brain could not be blocked by pretreatment with either Compound () (30 min or 24 h pretreatment) or cold Compound () (30-min pretreatment). The biodistribution of [{sup 11}C] in a second species (Balb/c mice) showed a higher overall uptake of the radioligand with an average brain uptake of 8.9% dose/g. In C57BL/6-H{sub 3}(-/-) knockout mice, a higher brain uptake was also observed. Analyses of metabolites and plasma protein binding were also undertaken. It appeared that [{sup 11}C] could not specifically label H{sub 3} receptors in rodent brain in vivo. Possible causes are discussed.

  14. 2-[(1RS,3RS,3aRS,6aSR-5-Benzyl-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]acetamide

    Directory of Open Access Journals (Sweden)

    Konstantin V. Kudryavtsev

    2011-12-01

    Full Text Available In the title compound, C21H21N3O3, the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7°. In the crystal, ribbons spread along the a axis are formed by N—H...O hydrogen bonds. C—H...π interactions also occur.

  15. 2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl-octa-hydro-pyrrolo-[3,4-c]pyrrol-1-yl]acetamide.

    Science.gov (United States)

    Kudryavtsev, Konstantin V; Churakov, Andrei V; Dogan, Ozdemir

    2011-12-01

    In the title compound, C(21)H(21)N(3)O(3), the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7)°. In the crystal, ribbons spread along the a axis are formed by N-H⋯O hydrogen bonds. C-H⋯π inter-actions also occur.

  16. 2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl­octa­hydro­pyrrolo­[3,4-c]pyrrol-1-yl]acetamide

    Science.gov (United States)

    Kudryavtsev, Konstantin V.; Churakov, Andrei V.; Dogan, Ozdemir

    2011-01-01

    In the title compound, C21H21N3O3, the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7)°. In the crystal, ribbons spread along the a axis are formed by N—H⋯O hydrogen bonds. C—H⋯π inter­actions also occur. PMID:22199707

  17. [N-Benzyl-N-(2-phenylethyldithiocarbamato-κ2S,S′]triphenyltin(IV and [bis(2-methoxyethyldithiocarbamato-κ2S,S′]triphenyltin(IV: crystal structures and Hirshfeld surface analysis

    Directory of Open Access Journals (Sweden)

    Rapidah Mohamad

    2016-10-01

    Full Text Available The crystal and molecular structures of two triphenyltin dithiocarbamates, [Sn(C6H53(C16H16NS2], (I, and [Sn(C6H53(C7H14NO2S2], (II, are described. In (I, the dithiocarbamate ligand coordinates the SnIV atom in an asymmetric manner, leading to a highly distorted trigonal–bipyramidal coordination geometry defined by a C3S2 donor set with the weakly bound S atom approximately trans to one of the ipso-C atoms. A similar structure is found in (II, but the dithiocarbamate ligand coordinates in an even more asymmetric fashion. The packing in (I features supramolecular chains along the c axis sustained by C—H...π interactions; chains pack with no directional interactions between them. In (II, supramolecular layers are formed, similarly sustained by C—H...π interactions; these stack along the b axis. An analysis of the Hirshfeld surfaces for (I and (II confirms the presence of the C—H...π interactions but also reveals the overall dominance of H...H contacts in the respective crystals.

  18. (4R-4-Benzyl-3-{(4S-4-chloro-4-[(S-2,2-dimethyl-1,3-dioxolan-4-yl]butanoyl}-1,3-oxazolidin-2-one

    Directory of Open Access Journals (Sweden)

    Sandra Börding

    2012-01-01

    Full Text Available The title compound, C19H24ClNO5, was synthesized and subsequently employed in an Evans alkylation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (–-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an antiperiplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an antiperiplanar arrangement with a torsion angle of 173.64 (14°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.

  19. Discovery of an Oxybenzylglycine Based Peroxisome Proliferator Activated Receptor [alpha] Selective Agonist 2-((3-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methoxy)benzyl)(methoxycarbonyl)amino)acetic Acid (BMS-687453)

    Energy Technology Data Exchange (ETDEWEB)

    Li, Jun; Kennedy, Lawrence J.; Shi, Yan; Tao, Shiwei; Ye, Xiang-Yang; Chen, Stephanie Y.; Wang, Ying; Hernndez, Andrs S.; Wang, Wei; Devasthale, Pratik V.; Chen, Sean; Lai, Zhi; Zhang, Hao; Wu, Shung; Smirk, Rebecca A.; Bolton, Scott A.; Ryono, Denis E.; Zhang, Huiping; Lim, Ngiap-Kie; Chen, Bang-Chi; Locke, Kenneth T.; O’Malley, Kevin M.; Zhang, Litao; Srivastava, Rai Ajit; Miao, Bowman; Meyers, Daniel S.; Monshizadegan, Hossain; Search, Debra; Grimm, Denise; Zhang, Rongan; Harrity, Thomas; Kunselman, Lori K.; Cap, Michael; Kadiyala, Pathanjali; Hosagrahara, Vinayak; Zhang, Lisa; Xu, Carrie; Li, Yi-Xin; Muckelbauer, Jodi K.; Chang, Chiehying; An, Yongmi; Krystek, Stanley R.; Blanar, Michael A.; Zahler, Robert; Mukherjee, Ranjan; Cheng, Peter T.W.; Tino, Joseph A. (BMS)

    2010-04-12

    An 1,3-oxybenzylglycine based compound 2 (BMS-687453) was discovered to be a potent and selective peroxisome proliferator activated receptor (PPAR) {alpha} agonist, with an EC{sub 50} of 10 nM for human PPAR{alpha} and 410-fold selectivity vs human PPAR{gamma} in PPAR-GAL4 transactivation assays. Similar potencies and selectivity were also observed in the full length receptor co-transfection assays. Compound 2 has negligible cross-reactivity against a panel of human nuclear hormone receptors including PPAR{delta}. Compound 2 demonstrated an excellent pharmacological and safety profile in preclinical studies and thus was chosen as a development candidate for the treatment of atherosclerosis and dyslipidemia. The X-ray cocrystal structures of the early lead compound 12 and compound 2 in complex with PPAR{alpha} ligand binding domain (LBD) were determined. The role of the crystal structure of compound 12 with PPAR{alpha} in the development of the SAR that ultimately resulted in the discovery of compound 2 is discussed.

  20. 1-Benzyl-3′-[(1H-indol-3-ylcarbonyl]-1′-methyl-2-oxo-4′-(pyridin-3-ylspiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile

    Directory of Open Access Journals (Sweden)

    P. Seethalakshmi

    2016-11-01

    Full Text Available In the title compound, C34H27N5O2, the central pyrrolidine ring adopts an envelope conformation, with the N atom as the flap. The mean planes of the two indoline ring systems are inclined to the mean plane of the central pyrrolidine ring by 86.26 (9 and 69.30 (9°, respectively. The dihedral angle between the benzene and pyridine rings is 75.09 (11°. In the crystal, molecules are linked by N—H...N and C—H...N hydrogen bonds, forming sheets parallel to the ab plane.

  1. Crystal and mol-ecular structure of (2Z,5Z)-3-(2-meth-oxy-phen-yl)-2-[(2-meth-oxy-phen-yl)imino]-5-(4-nitro-benzyl-idene)thia-zolidin-4-one.

    Science.gov (United States)

    Djafri, Ahmed; Chouaih, Abdelkader; Daran, Jean-Claude; Djafri, Ayada; Hamzaoui, Fodil

    2017-04-01

    In the title compound, C 24 H 19 N 3 O 5 S, the thia-zole ring (r.m.s. deviation = 0.012 Å) displays a planar geometry and is surrounded by three fragments, two meth-oxy-phenyl and one nitro-phenyl. The thia-zole ring is almost in the same plane as the nitro-phenyl ring, making a dihedral angle of 20.92 (6)°. The two meth-oxy-phenyl groups are perpendicular to the thia-zole ring [dihedral angles of 79.29 (6) and 71.31 (7)° and make a dihedral angle of 68.59 (7)°. The mol-ecule exists in an Z , Z conformation with respect to the C=N imine bond. In the crystal, a series of C-H⋯N, C-H⋯O and C-H⋯S hydrogen bonds, augmented by several π-π(ring) inter-actions, produce a three-dimensional architecture of mol-ecules stacked along the b -axis direction. The experimentally derived structure is compered with that calculated theoretically using DFT(B3YLP) methods.

  2. Crystal structure of (4-methoxyphenyl[(4-methoxyphenylphosphonato]dioxidophosphate(1− 2-amino-6-benzyl-3-ethoxycarbonyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-6-ium

    Directory of Open Access Journals (Sweden)

    Joel T. Mague

    2015-12-01

    Full Text Available The asymmetric unit of the title molecular salt, C17H21N2O2S+·C14H15O7P2−, comprises two cations and two anions. Each cation features an intramolecular N—H...O hydrogen bond, which closes an S(6 ring; in each case the hydropyridine ring adopts a half-chair conformation. In the anions, the dihedral angles between the aromatic rings are 64.1 (2 and 54.9 (2°. In each case, the diphosphate groups are close to eclipsed [C—P...P—C pseudo-torsion angles = 11.6 (2 and −19.3 (2°]. One of the methoxy groups in each anion is disordered over two orientations in a 0.539 (18:0.461 (18 ratio in one anion and 0.82 (2:0.18 (2 in the other. In the crystal, O—H...O and N—H...O hydrogen bonds link the components into [100] chains. Numerous C—H...O interactions cross-link the chains into a three-dimensional network.

  3. Radiosynthesis and biodistribution of a histamine H3 receptor antagonist 4-[3-(4-piperidin-1-yl-but-1-ynyl)-[11C]benzyl]-morpholine: evaluation of a potential PET ligand

    International Nuclear Information System (INIS)

    Airaksinen, Anu J.; Jablonowski, Jill A.; Mey, Margreet van der; Barbier, Ann J.; Klok, Rob P.; Verbeek, Joost; Schuit, Robert; Herscheid, Jacobus D.M.; Leysen, Josee E.; Carruthers, Nicholas I.; Lammertsma, Adriaan A.; Windhorst, Albert D.

    2006-01-01

    The potent histamine H 3 receptor antagonist JNJ-10181457 () was successfully labeled with 11 C in a novel one-pot reaction sequence, with high chemical yield (decay-corrected yield, 28±8%) and high specific radioactivity (56±26 GBq/μmol). The binding of [ 11 C] to H 3 receptors was studied in vitro in rat brain and in vivo in rats and mice. The in vitro binding of [ 11 C] in rat coronal brain slices showed high binding in the striatum, and this binding was blocked by histamine and by two known H 3 antagonists, JNJ-5207852 () and unlabeled Compound (), in a concentration-dependent manner. The biodistribution of [ 11 C] in rats was measured at 5, 10, 30 and 60 min. The uptake of [ 11 C] in regions rich in H 3 receptors was highest at 30 min, giving 0.98%, 1.41%, 1.28% and 1.72% dose/g for the olfactory bulb, hippocampus, striatum and cerebral cortex, respectively. However, the binding of [ 11 C] in the rat brain could not be blocked by pretreatment with either Compound () (30 min or 24 h pretreatment) or cold Compound () (30-min pretreatment). The biodistribution of [ 11 C] in a second species (Balb/c mice) showed a higher overall uptake of the radioligand with an average brain uptake of 8.9% dose/g. In C57BL/6-H 3 (-/-) knockout mice, a higher brain uptake was also observed. Analyses of metabolites and plasma protein binding were also undertaken. It appeared that [ 11 C] could not specifically label H 3 receptors in rodent brain in vivo. Possible causes are discussed

  4. Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers

    OpenAIRE

    Kim, Moon Suk; Lee, Sang Bong

    2014-01-01

    In order to study the capability of pyrazinium salt derivatives to act as photo-initiators of epoxide monomers, benzyl pyrazinium hexafluoroantimonate (BPH), benzyl 3,5-dimethyl pyrazine hexafluoroantimonate (BDH) and benzyl quinoxalinium hexafluoroantimonate (BQH) were synthesized by the Menschutkin reaction of benzyl bromide with pyrazine, 2,6-dimethyl pyrazine, and quinoxaline, followed by exchanging with hexafluoroantimonate (SbF6). BPH, BDH, and BQH exhibited characteristic ultraviolet ...

  5. Performance Assessment of Hazardous Air Pollutant (HAP)Free Chemical Paint Strippers on Military Coatings for Validation to Federal Specification TT-R-2918A

    Science.gov (United States)

    2016-03-01

    hydrogen peroxide (᝿%), dioxolane (ក%), water (>20%) 5.5–6.0 D-Zolve 15–33 Solvent Kleene Benzyl alcohol Alkyl methyl ester, petroleum...naptha, benzyl alcohol, methyl phenyl ether 10.5 Socostrip A0103N Socomore Benzyl alcohol Benzyl alcohol, hydrogen peroxide solution, hydrocarbons...TECHNICAL (PDF) INFORMATION CTR DTIC OCA 2 DIRECTOR (PDF) US ARMY RESEARCH LAB RDRL CIO LL IMAL HRA MAIL & RECORDS MGMT 1 GOVT

  6. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Allyl and benzyl ethers of alcohols can be prepared conveniently and in high yield with allyl and benzyl bromide in the presence of solid potassium hydroxide without use of any solvent. Phenols can be converted to allyl ethers but are inert to benzylation under above conditions.

  7. Variation of kinetic energy release with temperature and electron energy for unimolecular ionic transitions

    International Nuclear Information System (INIS)

    Rabia, M.A.; Fahmy, M.A.

    1992-01-01

    The kinetic energy released during seven unimolecular ionic transitions, generated from benzyl alcohol and benzyl amine have been studied as a function of ion source temperature and ionizing electron energy. Only, the kinetic energy released during H CN elimination from fragment [C 7 H 8 N]+ ion of benzyl amine displays a temperature dependence. For only two transitions, generated from benzyl alcohol, the kinetic energy released show a significant ionizing electron energy dependence. These results may reveal the role of the internal energy of reacting ions in producing the kinetic energy released some transitions produced from benzyl alcohol

  8. Acylation of aromatic alcohols and phenols over InCl3 ...

    Indian Academy of Sciences (India)

    Unknown

    K-10) on the yield of benzyl benzoate in the benzoylation of benzyl alcohol (by benzoyl chlo- ride) at 50°C over the InCl3/Mont. K-10 catalyst. Table 1. Effect of InCl3 loading on the acidity (ammo- nia chemisorbed at 200°C) and yield in the benzoylation of benzyl alcohol (by benzoyl chloride) over InCl3/Mont. K-10 catalyst at ...

  9. Synthesis of a selectively protected trisaccharide building block of the capsular polysaccharide of Streptococcus pneumoniae types 6A and 6B

    NARCIS (Netherlands)

    Vliegenthart, J.F.G.; Slaghek, T.M.; Vliet, M.J. van; Maas, A.A.M.; Kamerling, J.P.

    1989-01-01

    4-Methoxybenzyl 2,4-di-O-benzyl-3-O-[2,4,6-tri-O-benzyl-3-O-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-α-D- glucopyranosyl]-α-L-rhamnopyranoside (22), a building block for the α-D-Galp-(1->3)-α-D-Glcp-(1->3)-α-L-Rhap fragment of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B

  10. A Química de Lauráceas Brasileiras. LXX. Estirilpironas de Aniba kappleri

    OpenAIRE

    Santos, Margarida M. dos; Mesquita, Antônio A. L.; Gottlieb, Otto R.

    1982-01-01

    Summary The trunk wood of Aniba kappleri Mez (family Lauraceae) contains besides sitosterol, octacosanoic acid and rhamnocitrin (7-O-methylkaempferol), three esters, namely benzyl benzoate, benzyl 2-hydroxybenzoate and benzyl 2,6-dihydroxybenzoate, and two α-pyrones, namely 4-methoxy-6- (E) -(3',4'-methy!enedioxystyryl)-2-pyrone and 4-methoxy-6-{E)-(3',4'-dimethoxystyryl]-2pyrone. A dimer of the latter compound, which was obtained additionally, is considered to be an artifact.

  11. Preparation of hyperbranched polymer via single electron transfer living radical polymerization

    International Nuclear Information System (INIS)

    Zhang, X; Chen, X H; Li, J; Cao, X X; Cheng, C J

    2015-01-01

    α-Trichloromethyl benzyl alcohol is converted to α-trichloromethyl benzyl methacrylate in 62% yield under esterification conditions. The ester proves to be a good inimer to prepare hyperbranched polymer by utilizing SET-LRP approach. The monomer conversion is about 72% at 60°C for 6 h. (paper)

  12. Preparation of hyperbranched polymer via single electron transfer living radical polymerization

    Science.gov (United States)

    Zhang, X.; Chen, X. H.; Li, J.; Cao, X. X.; Cheng, C. J.

    2015-07-01

    α-Trichloromethyl benzyl alcohol is converted to α-trichloromethyl benzyl methacrylate in 62% yield under esterification conditions. The ester proves to be a good inimer to prepare hyperbranched polymer by utilizing SET-LRP approach. The monomer conversion is about 72% at 60°C for 6 h.

  13. Selective discrimination of cyclodextrin diols using cyclic sulfates

    DEFF Research Database (Denmark)

    Petrillo, Marta; Marinescu, Lavinia; Rousseau, Cyril

    2009-01-01

    A method for selective monofunctionalition of readily available cyclodextrin diols (2(A-F),3(A-F),6(B,C,E,F)-hexadeca-O-benzyl-alpha-cyclodextrin and 2(A-G),3(A-G),6(B,C,E-G)-nonadeca-O-benzyl-beta-cyclodextrin) by regioselective nucleophilic opening of their cyclic sulfates is presented. Althoug...

  14. Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits

    Science.gov (United States)

    Bioassay-guided isolation and purification of the ethyl acetate extract of Moringa oleifera fruits yielded three new phenolic glycosides; 4-[(2'-O-acetyl-a-L-rhamnosyloxy) benzyl]isothiocyanate (1), 4-[(3'-O-acetyl-a-L-rhamnosyloxy)benzyl]isothiocyanate (2), and S-methyl-N-{4-[(a-L-rhamnosyloxy)benz...

  15. Three-dimensional imaging analysis of Yersinia ruckeri infected rainbow trout (Oncorhynchus mykiss) gills by optical projection tomography

    DEFF Research Database (Denmark)

    Otani, Maki; Raida, Martin Kristian

    incubated whole with rabbit anti-Y. ruckeri polyclonal antibody and Alexa Fluor®594 conjugated goat anti-rabbit IgG. After embedding in 1% low melting point agarose, specimens were dehydrated in 100% methanol and cleared in BABB (benzyl alcohol: benzyl benzoate) for OPT scanning. 3D imaging results showed...

  16. NITROAROMATICS ARE SUBSTRATES FOR THE TOL PLASMID UPPER-PATHWAY ENZYMES

    NARCIS (Netherlands)

    DELGADO, A; Wubbolts, Marcel; ABRIL, MA; RAMOS, JL

    Expression of the xylMA genes encoding for toluene monooxygenase from the lactose promoter in a broad-host-range plasmid allows the oxidation of toluene and m- and p-nitrotoluene to their corresponding benzyl alcohols and benzaldehydes in Pseudomonas putida and Escherichia coli. Benzyl alcohols

  17. Towards a fragment-based approach in gelator design: halogen effects leading to thixotropic, mouldable and self-healing systems in aryl-triazolyl amino acid-based gelators!

    Science.gov (United States)

    Srivastava, Bhartendu K; Manheri, Muraleedharan K

    2017-04-18

    A simple replacement of a H atom by Br transformed non-gelating aryl triazolyl amino acid benzyl ester into a versatile gelator, which formed shape-persistent, self-healing and mouldable gels. The 'bromo-aryl benzyl ester' fragment was then transplanted into another framework, which resulted in similar solvent preference and gelation efficiency.

  18. APPLICATION OF THE UNIFAC MODEL TO LIQUID-LIQUID EQUILIBRIA OF WATER-PROPIONIC ACID-SOLVENT TERNARIES*

    Directory of Open Access Journals (Sweden)

    Süheyla ÇEHRELİ

    2003-01-01

    Full Text Available The liquid-liquid equilibria of Water-Propionic Acid-Benzyl Alcohol, Water-Propionic Acid-Benzyl Acetate and Water-Propionic Acid-Dibenzyl Ether ternary systems were predicted by means of UNIFAC Model. For this purpose, multivariable Newton-Raphson convergence procedure was used. Experimental and model results were compared.

  19. Transition metal complexes supported on metal-organic frameworks for heterogeneous catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Farha, Omar K.; Hupp, Joseph T.; Delferro, Massimiliano; Klet, Rachel C.

    2017-02-07

    A robust mesoporous metal-organic framework comprising a hafnium-based metal-organic framework and a single-site zirconium-benzyl species is provided. The hafnium, zirconium-benzyl metal-organic framework is useful as a catalyst for the polymerization of an alkene.

  20. Synthesis, characterization and study of catalytic activity of Silver ...

    Indian Academy of Sciences (India)

    activity was tested using liquid-phase selective oxidation of benzylic alcohols to aldehydes. The influence of some parameters such as optimum weight of Ag, catalyst dosage, ... Ag/ZnO nanocomposite; selective oxidation; benzyl alcohol; heterogeneous catalysis. ..... Rodríguez-Reyes J C F, Friend C M and Madix R J 2012.

  1. Case Report: Infestation of Tunga penetrans in villages near Zomba ...

    African Journals Online (AJOL)

    Benzyl benzoate paint and liquid paraffin had been used in local Primary Healthcare settings previously and topical treatment with antiparasitic agents has been advocated in the literature, particularly for severe infestation. Benzyl benzoate and liquid paraffin were applied topically to four adults with numerous jigger flea ...

  2. Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability

    DEFF Research Database (Denmark)

    Leth-Petersen, Sebastian; Bundgaard, Christoffer; Hansen, Martin

    2014-01-01

    2,5-Dimethoxyphenethylamines and their N-benzylated derivatives are potent 5-HT2A agonists with psychedelic effects in humans. The N-benzylated derivatives are among the most selective 5-HT2A agonists currently available and their usage as biochemical and brain imaging tools is increasing, yet ve...

  3. Iodination of Alcohols over Keggin-type Heteropoly Compounds: A ...

    African Journals Online (AJOL)

    NICO

    way by replacing protons or by substituting framework transi- tion-metal atoms with different metals.25 Herein we describe a comprehensive study on the ..... the soft iodide ion on this cationic species, leads to the iodide product. 4. Conclusion. The conversion of benzyl alcohol into benzyl iodide has been investigated by a ...

  4. Multicomponent Synthesis of a N-Protected Alpha-Amino Ester: Ethyl 2-((4-Methoxyphenyl)Amino)-3-Phenylpropanoate

    Science.gov (United States)

    Le Gall, Erwan; Pignon, Antoine

    2012-01-01

    This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, "p"-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier…

  5. (E)-3-Hydr?oxy-13-methyl-16-[4-(methyl?sulfan?yl)benzyl?idene]-7,8,9,11,12,13,15,16-octa?hydro-6H-cyclo?penta?[a]phen?an????thren-17(14H)-one

    OpenAIRE

    Gunasekaran, B.; Murugan, R.; Narayanan, S. Sriman; Manivannan, V.

    2008-01-01

    In the title compound, C26H28O2S, the dihedral angles between the mean plane of the five membered ring and the 4-(methylsulfanyl)benzylidine ring in the two crystallographically independent molecules are 34.05 (10) and 40.53 (15)°. The packing is stabilized by intermolecular O—H...O and C—H...O interactions.

  6. EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF); Scientific Opinion on Flavouring Group Evaluation 20, Revision 3 (FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30

    DEFF Research Database (Denmark)

    Larsen, John Christian; Nørby, Karin Kristiane; Beltoft, Vibe Meister

    The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to consider in this revision 3 of Flavouring Group Evaluation 20, the SCF Opinion on benzoic acid. Furthermore information on stereoisomeric composition for two...... substances [FL-no: 06.104 and 09.570] and new information to support the re-allocation of the structural class for the candidate substance piperonyl alcohol [FL-no: 02.205] has been submitted. The 41 flavouring substances in Flavouring Group Evaluation 20 were evaluated using the Procedure in Commission...... Regulation (EC) No 1565/2000. None of the substances were considered to have genotoxic potential. The substances were evaluated through a stepwise approach (the Procedure) that integrates information on structure-activity relationships, intake from current uses, toxicological threshold of concern...

  7. Synthesis and enantiopreferential DNA-binding profile of late 3d transition metal R- and S-enantiomeric complexes derived from N,N-bis-(1-benzyl-2-ethoxyethane): Validation of R-enantiomer of copper(II) complex as a human topoisomerase II inhibitor.

    Science.gov (United States)

    Arjmand, Farukh; Sharma, Girish Chandra; Muddassir, Mohd; Tabassum, Sartaj

    2011-08-01

    To evaluate the biological preference of chiral drug candidates for molecular target DNA, new potential metal-based chemotherapeutic agents 1-3 (a and b) of late 3d transition metals Ni(II), Cu(II), and Zn(II), respectively, derived from (R)- and (S)-2-amino-2-phenylethanol with CH(2) CH(2)  linker were synthesized and thoroughly characterized. Interaction studies of 1-3 (a and b) with calf thymus DNA in Tris buffer were studied by electronic absorption titrations, luminescence titrations, cyclic voltammetry, and circular dichroism. The results reveal that the extent of DNA binding of R-enantiomer of copper 1a was highest in comparison to rest of the complexes via electrostatic interaction mode. The nuclease activity of 1(a and b) with supercoiled pBR322 DNA was further examined by gel electrophoresis, which reveals that complex 1a exhibits a remarkable DNA cleavage activity (concentration dependent) with pBR322DNA, and the cleavage activity of both enantiomers of complex 1 was significantly enhanced in the presence of activators. The activating efficiency follows the order Asc > H(2) O(2) > MPA for 1a, and reverse order was observed for 1b, because of the differences in enantioselectivity and conformation. Further, it was observed that cleavage reaction involves singlet oxygen species and superoxide radicals via oxidative cleavage mechanism. In addition, complex 1a exhibits significant inhibitory effects on the topoisomerase II (topo II) activity at a very low concentration ∼24 μM, which suggest that complex 1a is indeed catalytic inhibitor or (poison) of human topo II. Copyright © 2011 Wiley-Liss, Inc.

  8. Analysis of macamides in samples of Maca (Lepidium meyenii) by HPLC-UV-MS/MS.

    Science.gov (United States)

    McCollom, Megan M; Villinski, Jacquelyn R; McPhail, Kerry L; Craker, Lyle E; Gafner, Stefan

    2005-01-01

    The macamides are a distinct class of secondary metabolites that have so far been found only in Lepidium meyenii Walp. (Maca). Using HPLC-UV-MS/MS, the main macamides have been identified as n-benzylhexadecanamide, n-benzyl-(9Z)-octadecenamide, n-benzyl-(9Z, 12Z)-octadecadienamide, n-benzyl-(9Z, 12Z, 15Z)-octadecatrienamide and n-benzyloctadecanamide. The identities of n-benzyl-(9Z)-octadecenamide and n-benzyl-(9Z, 12Z)-octadecadienamide were confirmed by comparison of chromatographic and spectral properties with synthetic analogues. Total macamides have been quantified by HPLC-UV in plant material from different vendors using n-benzylhexadecanamide as an external standard. The amount of macamides in the dried plant material ranged from 0.0016 to 0.0123%.

  9. Chemical composition and acaricide activity of an essential oil from a rare chemotype of Cinnamomum verum Presl on Rhipicephalus microplus (Acari: Ixodidae).

    Science.gov (United States)

    Monteiro, Ildenice Nogueira; Monteiro, Odair Dos Santos; Costa-Junior, Lívio Martins; da Silva Lima, Aldilene; Andrade, Eloisa Helena de Aguiar; Maia, José Guilherme Soares; Mouchrek Filho, Victor Elias

    2017-04-30

    The Essential Oils (EOs) from the leaves of species Cinnamomum verum J. Presl are used in the pharmaceutical industry for their numerous biological activities. Currently, the main compound of C. verum EO is eugenol which has acaricidal activity; however, a rare chemotype with benzyl benzoate as the main component can be found. Benzyl benzoate is recognized as an acaricide; however, studies of the C. verum EOs benzyl benzoate chemotype on Rhipicephalus microplus were not reported. The aim of this study was to evaluate the acaricide activity of an EO from a rare chemotype of C. verum, as well as purified benzyl benzoate, against larvae and engorged females of R. microplus resistant to amidines and pyrethroids. The EO was extracted from C. verum leaves and the compounds present were identified using a gas phase chromatograph coupled to a mass spectrometer. Efficacy against R. microplus was assessed by the larval packet and the engorged female immersion tests. A rare chemotype of C. verum was found to produce EOs with benzyl benzoate (65.4%) as the main compound. The C. verum essential oil was 3.3 times more efficient on the R. microplus larvae than was benzyl benzoate. However, no differences were found on the R. microplus engorged females. This is the first report regarding the acaricidal activity of C. verum with chemotype benzyl benzoate, and this compound showed acaricidal activity on R. microplus larvae. Copyright © 2017 Elsevier B.V. All rights reserved.

  10. In vitro stability of EDTA and DTPA immunoconjugates of monoclonal antibody 2G3 labeled with indium-111

    Energy Technology Data Exchange (ETDEWEB)

    Reilly, R.; Lee, N.; Houle, S. (The Toronto Hospital (Canada)); Law, J.; Marks, A. (Toronto Univ., ON (Canada))

    1992-08-01

    Monoclonal antibody 2G3 directed against a high molecular weight glycoprotein on breast and ovarian cancer cells was conjugated with bicyclic DTPA (or EDTA) anhydride or benzyl isothiocyanate DTPA (benzyl DTPA) and labeled with {sup 111}In. DTPA anhydride was more reactive with the antibody than benzyl DTPA, and kinetics of labeling with {sup 111}In were more rapid for DTPA substituted 2G3 than for benzyl DTPA substituted 2G3. On the other hand, {sup 111}In-2G3 conjugates prepared using DTPA anhydride were subject to more extensive dimerization and higher losses in immunoreactivity than those prepared using benzyl DTPA. On the basis of measurement of transchelation to transferrin, the stability of {sup 111}In-2G3 prepared using DTPA anhydride or benzyl DTPA did not differ during incubation in human plasma for 6 days at 37{sup o}C. These results suggest that an important advantage of benzyl DTPA over DTPA anhydride for preparing {sup 111}In-labeled antibodies is the prevention of intermolecular (and intramolecular) crosslinking during conjugation which ultimately leads to alterations in conformation and losses in immunoreactivity of the radioimmunoconjugate. (author).

  11. Reactions of trapped electrons in methanol-isopropanol glasses irradiated at 77 K

    International Nuclear Information System (INIS)

    Kapoor, S.; Gopinathan, C.; Iyer, R.M.

    1989-01-01

    Trapped electron reactivity in methanol-isopropanol glasses irradiated at 77 K was studied as a function of trap-depth, the variation in the trap depth being achieved by variyng the methanol:isopropanol ratio. Benzyl chloride and carbon disulfide were used as scavengers. In the case of the glasses containing benzyl chloride, the observed yield of the benzyl radical correlated with the trapping efficiency of the matrix. The data are interpreted with the aim of assessing the relative importance of tunnelling in the scavenging of electrons in low temperature glassy matrices. (author) 20 refs.; 4 figs

  12. Catalytic properties of Thallium-containing mesoporous silicas

    Directory of Open Access Journals (Sweden)

    A. Baradji

    2017-02-01

    Full Text Available The benzylation of benzene by benzyl chloride over a series of Thallium-containing mesoporous silicas with different Tl contents has been investigated. These materials (Tl-HMS-n have been characterized by chemical analysis, N2 adsorption/desorption isotherm and X-ray diffraction (XRD. The mesoporous Thallium-containing materials showed both high activity and high selectivity for the benzylation of benzene. More interesting is the observation that these catalysts are always active and selective for large molecules like naphthenic compounds such as methoxynaphthalene.

  13. Mechanistic Investigation of Molybdate-Catalysed Transfer Hydrodeoxygenation

    DEFF Research Database (Denmark)

    Larsen, Daniel Bo; Petersen, Allan Robertson; Dethlefsen, Johannes Rytter

    2016-01-01

    The molybdate-catalysed transfer hydrodeoxygenation (HDO) of benzyl alcohol to toluene driven by oxidation of the solvent isopropyl alcohol to acetone has been investigated by using a combination of experimental and computational methods. A Hammett study that compared the relative rates...... for the transfer HDO of five para-substituted benzylic alcohols was carried out. Density-functional theory (DFT) calculations suggest a transition state with significant loss of aromaticity contributes to the lack of linearity observed in the Hammett study. The transfer HDO could also be carried out in neat PhCH2...... of benzyl alcohol, which is in line with the mechanism suggested by the DFT study....

  14. Jasminum flexile flower absolute from India--a detailed comparison with three other jasmine absolutes.

    Science.gov (United States)

    Braun, Norbert A; Kohlenberg, Birgit; Sim, Sherina; Meier, Manfred; Hammerschmidt, Franz-Josef

    2009-09-01

    Jasminum flexile flower absolute from the south of India and the corresponding vacuum headspace (VHS) sample of the absolute were analyzed using GC and GC-MS. Three other commercially available Indian jasmine absolutes from the species: J. sambac, J. officinale subsp. grandiflorum, and J. auriculatum and the respective VHS samples were used for comparison purposes. One hundred and twenty-one compounds were characterized in J. flexile flower absolute, with methyl linolate, benzyl salicylate, benzyl benzoate, (2E,6E)-farnesol, and benzyl acetate as the main constituents. A detailed olfactory evaluation was also performed.

  15. Thermal, dielectric and mechanical study of poly(vinyl chloride/olive pomace composites

    Directory of Open Access Journals (Sweden)

    2007-12-01

    Full Text Available Composites from PVC and chemically treated olive pomace have been prepared. The effect of the incorporation of virgin and benzylated olive pomace in the poly(vinyl chloride matrix on dielectric, mechanical and thermal stability properties, of /olive pomace composites was studied. The mechanical properties of the benzylated composites were improved. Furthermore, the thermal characterization of the different samples carried out by thermogravimetric analysis revealed an increase in the onset temperatures of decomposition for the treated composites. The dielectric investigation indicated that the samples containing olive pomace treated with the benzyl chloride can be used in electrical applications as insulators.

  16. [Preparation of leucine-methyl glutamate-glutamic acid copolymers].

    Science.gov (United States)

    Pan, S; Shi, F; Huang, L; Zhou, Q; Lin, Z; Yi, W

    1997-06-01

    The method for preparing leucine-methyl glutamate-glutamic acid copolymer was studied. In the first place benzyl glutamate and methyl glutamate were synthesized respectively. Then N-carboxy anhydrides (NCA) of leucine, benzyl glutamate or methyl glutamate were prepared in a closed container by phosgene-toluene solution method. After copolymerization the copolymers were debenzylated and demethylated by anhydrous hydrogen bromide. The free carboxyl group mole content in side chains of the copolymer was controlled by various standing periods following bubbling HBr. Analysis of infrared spectrogram and ultraviolet asorbance of copolymers indicated that this procedure resulted in the loss of almost all benzyl groups and some methyl groups.

  17. Proton transfer versus redox modulation in thiourea-phenanthrenequinone molecular and polymeric complexes.

    Science.gov (United States)

    Carroll, Joseph B; Gray, Mark; Cooke, Graeme; Rotello, Vincent M

    2004-02-21

    Phenanthrenequinone undergoes highly efficient proton transfer processes in the presence of a thiourea-functionalised polystyrene copolymer whereas interactions with a similar benzyl-thiourea monomer show strong redox modulation of the quinone without proton transfer.

  18. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Abstract. Alkyl/benzyl azides can be readily synthesized in excellent yields from their corresponding alcohols by stirring a solution of sodium azide in DMSO with a thoroughly ground equimolecular mixture of triphenylphosphine, iodine and imidazole.

  19. Preparation and characterization of aminobenzyl cellulose by two step synthesis from native cellulose

    Science.gov (United States)

    Synthesis and structural characterizations of nitro- and amino-benzyl cellulose were carried out. Cellulose derivatives were synthesized by etherification. Nitrobenzylation produced 80% yield by treating a mixture of microcrystalline cellulose, 4-dimethyl aminopyridine and 4-nitrobenzyl chloride at ...

  20. 40 CFR Table 8 to Subpart Ggg of... - Fraction Measured (Fm) for HAP Compounds in Wastewater Streams

    Science.gov (United States)

    2010-07-01

    ... POLLUTANTS FOR SOURCE CATEGORIES National Emission Standards for Pharmaceuticals Production Pt. 63, Subpt... Acrolein 107028 1.00 Acrylonitrile 107131 1.00 Allyl chloride 107051 1.00 Benzene 71432 1.00 Benzyl...

  1. Syntheses, Protonation Constants and Antimicrobial Activity of 2 ...

    African Journals Online (AJOL)

    carboxaldehyde and N-alkylimidazole-2-methanol derivatives [alkyl = benzyl, methyl, ethyl, propyl, butyl, heptyl, octyl and decyl] have been synthesized and the protonation constants determined. The antimicrobial properties of the compounds were tested ...

  2. Untitled

    Indian Academy of Sciences (India)

    1-Propyl alcohol. Iso-Propyl alcohol. Butyl alcohol. Amyl alcohol. Acetone. Acetic anlıy!ride . . Carbon disulphide. Chloroform. Chlorobyenzeme. Renzeme. Aniso. Carbo) tetrachloride. Acetophenone. Cyclohexane. (yellohexanone. Cyclohexanol. Paraldehyde. Formaldehyde (solution). Benzyl acetate. Amyl acetate. Water.

  3. New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

    Directory of Open Access Journals (Sweden)

    Daily Rodríguez-Padrón

    2017-09-01

    Full Text Available Polysaccharides from natural sources and iron precursors were applied to develop new bio-nanocomposites by mechanochemical milling processes. The proposed methodology was demonstrated to be advantageous in comparison with other protocols for the synthesis of iron oxide based nanostructures. Additionally, mechanochemistry has enormous potential from an environmental point-of-view since it is able to reduce solvent issues in chemical syntheses. The catalytic activity of the obtained nanocatalysts was investigated in both the oxidation of benzyl alcohol to benzaldehyde and in the alkylation of toluene with benzyl chloride. The microwave-assisted oxidation of benzyl alcohol reached 45% conversion after 10 min. The conversion of the alkylation of toluene in both microwave-assisted and conventional heating methods was higher than 99% after 3 min and 30 min, respectively. The transformation of benzyl alcohol and toluene into valuable product in both the oxidation and alkylation reaction reveals a potential method for the valorization of lignocellulosic biomass.

  4. Benzyllithiums bearing aldehyde carbonyl groups. A flash chemistry approach.

    Science.gov (United States)

    Nagaki, Aiichiro; Tsuchihashi, Yuta; Haraki, Suguru; Yoshida, Jun-ichi

    2015-07-14

    Reductive lithiation of benzyl halides bearing aldehyde carbonyl groups followed by reaction with subsequently added electrophiles was successfully accomplished without affecting the carbonyl groups by taking advantage of short residence times in flow microreactors.

  5. Highly active and reusable catalyst from Fe-Mg-hydrotalcite anionic ...

    Indian Academy of Sciences (India)

    Unknown

    hydrotalcite anionic clay for Friedel–Crafts type benzylation reactions. VASANT R CHOUDHARY*, RANI JHA and PANKAJ A CHOUDHARI. Chemical Engineering and Process Development Division, National Chemical Laboratory, Pune 411 008,. India.

  6. Recovery of uranium

    International Nuclear Information System (INIS)

    Clemens, D.H.; Walker, R.W.; Hurwitz, M.J.

    1974-01-01

    A process for recovering uranium from an uranium bearing liquid which comprises contacting the liquid with a crosslinkedvinyl benzyl chloride polymer, thereafter eluting from the resin the uranium in salt form

  7. 75 FR 17716 - Notice of Receipt of Requests to Voluntarily Cancel Certain Pesticide Registrations

    Science.gov (United States)

    2010-04-07

    ... Dichlorobenzen e 000748-00276 PPG Algae Calcium hypochlorite Destroyer 000769-00584 R & M Flea Tetramethrin &Tick...-20002 Nalco 92WT004 Sodium hypochlorite 001839-00109 20% Alkyl* dimethyl benzyl Veterinarian ammonium...

  8. Tsuji-Trost N-allylation with allylic acetates using cellulose-Pd catalyst

    Science.gov (United States)

    Allylic amines are synthesized using heterogeneous cellulose-Pd catalyst via N-allylation of amines; aliphatic and benzyl amines undergo facile reaction with substituted and unsubstituted allyl acetates in high yields.

  9. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    ethylpyridine -2-carboximidate ..... Synthesis and structures of two new Cu(I) frameworks bearing1,3-bis(4-pyridyl)propane and inorganic linkers ..... Effect of Isotacticity of Linear Poly(N-isopropylacrylamide) on its Gelation in Benzyl Alcohol.

  10. Development of Candidate Chemical Simulant List: The Evaluation of Candidate Chemical Simulants Which May Be Used in Chemically Hazardous Operations

    Science.gov (United States)

    1982-12-01

    exposure regimen was then changed to suspension of a sponge soaked with the dipentene inside the animal’s cage. The rabbits were treated in this manner for... almond oil. 0 Toxicity in Neonates "Although the above evidence suggests that benzyl alcohol can safely be used in adults, recent reports suggest that...average of 15 days, occurred in 18 trials involving 1-3 ml injections of 10% benzyl alcohol in sweet almond oil. In cases in which paralysis persisted

  11. Synthesis, Reactivity and Stability of Aryl Halide Protecting Groups towards Di-Substituted Pyridines

    Directory of Open Access Journals (Sweden)

    Ptoton Mnangat Brian

    2016-03-01

    Full Text Available This paper reports the synthesis and reactivity of different Benzyl derivative protecting groups. The synthesis and stability of Benzyl halides, 4-methoxybenzyl halides, 3,5-dimethoxybenzyl halides, 3,4-dimethoxybenzyl halides, 3,4,5-trimethoxybenzyl halide protecting groups and their reactivity towards nitrogen atom of a di-substituted pyridine ring in formation of pyridinium salts is also reported.

  12. A thermodynamic study of ketoreductase-catalyzed reactions 5. Reduction of substituted ketones in n-hexane

    International Nuclear Information System (INIS)

    Tewari, Yadu B.; Vanderah, David J.; Schantz, Michele M.; Goldberg, Robert N.; Rozzell, J. David; Liebman, Joel F.; Hui, Raymond Wai-Man; Nissenbaum, Yitzy; Parniani, Ahmad Reza

    2008-01-01

    The equilibrium constants K for the ketoreductase-catalyzed reduction reactions of 1-benzyl-3-pyrrolidinone, ethyl 2-oxo-4-phenylbutyrate, ethyl 4-chloroacetoacetate, 1-benzyl-4-piperidone, and 1-benzyl-3-piperidone were measured in n-hexane at T = 298.15 K by using gas chromatography. The equilibrium constants for the reaction involving 1-benzyl-4-piperidone were also measured as a function of temperature (288.15 to 308.05) K. The calculated thermodynamic quantities for the reaction (1-benzyl-4-piperidone + 2-propanol = 1-benzyl-4-hydroxypiperidine + acetone) reaction carried out in n-hexane at T = 298.15 K are: K = (26.2 ± 1.7); Δ r G m 0 =-(8.10±0.16)kJ.mol -1 ; Δ r H m 0 =-(3.44±0.42)kJ.mol -1 ; and Δ r S m 0 =(15.6±1.4)J.K -1 .mol -1 . The chirality of the hydroxyl products of the reactions has also been investigated. The results showed that the stereoselectivity of the hydroxyl products formed can be controlled by the selection of the solvent and enzyme used in these reactions. The thermochemical results for these reactions are compared with the results for reactions that have analogous structural features as well as with the results of quantum chemical calculations

  13. Study of the effect of gamma radiation on the molecule of tetracycline concerning its behavior as complexing and extracting agent; Estudo do efeito da radiacao gama sobre a molecula de tetraciclina relativamente ao seu comportamento como agente complexante e extrator

    Energy Technology Data Exchange (ETDEWEB)

    Andrade e Silva, Leonardo Gondim de

    1982-07-01

    Both solvent extraction and spectrophotometric techniques were used to show the alterations that gamma radiation causes in the behavior of tetracycline molecule as far as its extracting and complexing power are concerned. The effect of gamma radiation on the solid tetracycline molecule, benzyl alcohol and on the solution of both was examined in solvent extraction systems whose aqueous phases were made up by {sup 152} Eu-{sup 154}Eu radioactive tracer solutions and whose organic phases were constituted by tetracycline-benzyl alcohol solutions. Experiments were performed in order to determine whether or not the water used for the pre-saturation of benzyl alcohol would influence the radiolysis of tetracycline. Solvent extraction and spectrophotometry were the techniques used to obtain the necessary data. Absorption spectra of irradiated tetracycline benzyl alcohol solutions submitted to several gamma radiation doses were examined and the alterations shown by these spectra were examined. The effect of gamma radiation on the tetracycline molecule was also studied when tetracycline-benzyl alcohol solutions were irradiated under several gaseous atmospheres, namely: O{sub 2}, N{sub 2}, SF{sub 6} and N{sub 2}O. The variation on the concentration of the tetracycline-benzyl alcohol solution caused by several doses of gamma radiation was determined by using the spectrophotometric technique. (author)

  14. Study of the effect of gamma radiation on the molecule of tetracycline concerning its behavior as complexing and extracting agent

    International Nuclear Information System (INIS)

    Andrade e Silva, Leonardo Gondim de

    1982-01-01

    Both solvent extraction and spectrophotometric techniques were used to show the alterations that gamma radiation causes in the behavior of tetracycline molecule as far as its extracting and complexing power are concerned. The effect of gamma radiation on the solid tetracycline molecule, benzyl alcohol and on the solution of both was examined in solvent extraction systems whose aqueous phases were made up by 152 Eu- 154 Eu radioactive tracer solutions and whose organic phases were constituted by tetracycline-benzyl alcohol solutions. Experiments were performed in order to determine whether or not the water used for the pre-saturation of benzyl alcohol would influence the radiolysis of tetracycline. Solvent extraction and spectrophotometry were the techniques used to obtain the necessary data. Absorption spectra of irradiated tetracycline benzyl alcohol solutions submitted to several gamma radiation doses were examined and the alterations shown by these spectra were examined. The effect of gamma radiation on the tetracycline molecule was also studied when tetracycline-benzyl alcohol solutions were irradiated under several gaseous atmospheres, namely: O 2 , N 2 , SF 6 and N 2 O. The variation on the concentration of the tetracycline-benzyl alcohol solution caused by several doses of gamma radiation was determined by using the spectrophotometric technique. (author)

  15. A thermodynamic study of ketoreductase-catalyzed reactions 5. Reduction of substituted ketones in n-hexane

    Energy Technology Data Exchange (ETDEWEB)

    Tewari, Yadu B. [Biochemical Science and Analytical Chemistry Division, National Institute of Standards and Technology, Gaithersburg, MD 20899 (United States)], E-mail: yadu.tewari@nist.gov; Vanderah, David J. [Biochemical Science and Analytical Chemistry Division, National Institute of Standards and Technology, Gaithersburg, MD 20899 (United States)], E-mail: david.vanderah@nist.gov; Schantz, Michele M. [Biochemical Science and Analytical Chemistry Division, National Institute of Standards and Technology, Gaithersburg, MD 20899 (United States)], E-mail: michele.schantz@nist.gov; Goldberg, Robert N. [Biochemical Science and Analytical Chemistry Division, National Institute of Standards and Technology, Gaithersburg, MD 20899 (United States)], E-mail: robert.goldberg@nist.gov; Rozzell, J. David [Codexis, Inc., 129 N. Hill Avenue, Pasadena, CA 91106 (United States)], E-mail: david.rozzell@codexis.com; Liebman, Joel F. [Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250 (United States)], E-mail: jliebman@umbc.edu; Hui, Raymond Wai-Man; Nissenbaum, Yitzy; Parniani, Ahmad Reza [Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250 (United States)

    2008-04-15

    The equilibrium constants K for the ketoreductase-catalyzed reduction reactions of 1-benzyl-3-pyrrolidinone, ethyl 2-oxo-4-phenylbutyrate, ethyl 4-chloroacetoacetate, 1-benzyl-4-piperidone, and 1-benzyl-3-piperidone were measured in n-hexane at T = 298.15 K by using gas chromatography. The equilibrium constants for the reaction involving 1-benzyl-4-piperidone were also measured as a function of temperature (288.15 to 308.05) K. The calculated thermodynamic quantities for the reaction (1-benzyl-4-piperidone + 2-propanol = 1-benzyl-4-hydroxypiperidine + acetone) reaction carried out in n-hexane at T = 298.15 K are: K = (26.2 {+-} 1.7); {delta}{sub r}G{sub m}{sup 0}=-(8.10{+-}0.16)kJ.mol{sup -1}; {delta}{sub r}H{sub m}{sup 0}=-(3.44{+-}0.42)kJ.mol{sup -1}; and {delta}{sub r}S{sub m}{sup 0}=(15.6{+-}1.4)J.K{sup -1}.mol{sup -1}. The chirality of the hydroxyl products of the reactions has also been investigated. The results showed that the stereoselectivity of the hydroxyl products formed can be controlled by the selection of the solvent and enzyme used in these reactions. The thermochemical results for these reactions are compared with the results for reactions that have analogous structural features as well as with the results of quantum chemical calculations.

  16. New imidazolidinic bioisosters: potential candidates for antischistosomal drugs

    Directory of Open Access Journals (Sweden)

    Maira GR Pitta

    2006-10-01

    Full Text Available The emergence of strains of Schistosoma resistant to praziquantel has drawn attention to the search for new schistosomacide drugs. Imidazolidinic derivatives have performed outstandingly against adult S. mansoni worms when evaluated in vitro. The molecular modification of imidazolidine by way of bioisosteric replacement gives rise to variations in its biological response. This study verifies the potential of substituent groups in the derivatives (Z3-benzyl-5-(2-fluoro-benzylidene-imidazolidine-2,4-dione NE4, 3-benzyl-5-(4-chloro-arylazo-4-thioxo-imidazolidin -2-ona PT5, 3-benzyl-5-(3-fluoro-benzylidene-1-methyl-2-thioxo-imidazolidin-4-one JT53; 3-benzyl-1-methyl-5-(4-methyl-benzylidene-2-thioxo-imidazolidin-4-one JT63; 3-benzyl-1-methyl-5-(4-methoxi-benzylidene-2-thioxo -imidazolidin-4-one JT68; 3-(4-chloro-benzyl-1-methyl-5-(4-methoxi-benzylidene-2-thioxo-imidazolidin-4-one JT69; 3-(4-phenyl-benzyl-1-methyl-5-(4-methoxi-benzylidene-2-thioxo-imidazolidin-4-one JT72 by determining the viability in vitro of adult S. mansoni worms in the presence of these derivatives. The susceptibility of the worms obtained from mice and kept in culture in the presence of different concentrations was determined by way of schistosomacide kinetic, observed every 24 h over a period of eight days. The results show that the worms were more sensitive to the PT5 derivative at a concentration of 58 µM which killed 100% of the worms after 24 h of contact, also giving rise to alterations in the tegument surface of the worms with the formation of bubbles and peeling. These observations suggest a strong electronic contribution of the arylazo grouping in the biological response.

  17. Larvicidal activity of ajowan ( Trachyspermum ammi ) and Peru balsam ( Myroxylon pereira ) oils and blends of their constituents against mosquito, Aedes aegypti , acute toxicity on water flea, Daphnia magna , and aqueous residue.

    Science.gov (United States)

    Seo, Seon-Mi; Park, Hye-Mi; Park, Il-Kwon

    2012-06-13

    This study evaluated the larvicidal activity of 20 plant essential oils and components from ajowan ( Trachyspermum ammi ) and Peru balsam ( Myroxylon pereira ) oils against the mosquito, Aedes aegypti . Of the 20 plant essential oils, ajowan and Peru balsam oils at 0.1 mg/mL exhibited 100 and 97.5% larval mortality, respectively. At this same concentration, the individual constituents, (+)-camphene, benzoic acid, thymol, carvacrol, benzyl benzonate, and benzyl trans-cinnamate, caused 100% mortality. The toxicity of blends of constituents identified in two active oils indicated that thymol and benzyl benzoate were major contributors to the larvicidal activity of the artificial blend. This study also tested the acute toxicity of these two active oils and their major constituents against the water flea, Daphnia magna . Peru balsam oil and benzyl trans-cinnamate were the most toxic to D. magna. Two days after the treatment, residues of ajowan and Peru balsalm oils in water were 36.2 and 85.1%, respectively. Less than 50% of benzyl trans-cinnamate and thymol were detected in the water at 2 days after treatment. The results show that the essential oils of ajowan and Peru balsam and some of their constituents have potential as botanical insecticides against Ae. aegypti mosquito larvae.

  18. Biodegradation of benzalkonium chlorides singly and in mixtures by a Pseudomonas sp. isolated from returned activated sludge

    Energy Technology Data Exchange (ETDEWEB)

    Khan, Adnan Hossain, E-mail: akhan462@uwo.ca [Department of Chemical and Biochemical Engineering, University of Western Ontario, London, ON N6A 5B9 (Canada); Topp, Edward, E-mail: Ed.Topp@AGR.GC.CA [Agriculture and Agri-Food Canada, London, ON N5V 4T3 (Canada); Department of Biology, University of Western Ontario, London, ON N6A 5B7 (Canada); Scott, Andrew, E-mail: Andrew.Scott@AGR.GC.CA [Agriculture and Agri-Food Canada, London, ON N5V 4T3 (Canada); Sumarah, Mark, E-mail: Mark.Sumarah@agr.gc.ca [Agriculture and Agri-Food Canada, London, ON N5V 4T3 (Canada); Macfie, Sheila M., E-mail: smacfie@uwo.ca [Department of Biology, University of Western Ontario, London, ON N6A 5B7 (Canada); Ray, Madhumita B., E-mail: mbhowmic@uwo.ca [Department of Chemical and Biochemical Engineering, University of Western Ontario, London, ON N6A 5B9 (Canada)

    2015-12-15

    Highlights: • Pseudomonas sp. degraded two benzalkonium chlorides: BDDA and BDTA. • Although BDTA biodegraded at low concentration, it inhibited the degradation of BDDA. • For BDDA, two transformation products indicate two sites of bacterial activity. • {sup 14}C-labelled BDDA was mineralized to {sup 14}CO{sub 2} within 300 h. - Abstract: Bactericidal cationic surfactants such as quaternary ammonium compounds (QACs) are widely detected in the environment, and found at mg kg{sup −1} concentrations in biosolids. Although individual QACs are amenable to biodegradation, it is possible that persistence is increased for mixtures of QACs with varying structure. The present study evaluated the biodegradation of benzyl dimethyl dodecyl ammonium chloride (BDDA) singly and in the presence of benzyl dimethyl tetradecyl ammonium chloride (BDTA) using Pseudomonas sp., isolated from returned activated sludge. Growth was evaluated, as was biodegradation using {sup 14}C and HPLC-MS methods. BDTA was more toxic to growth of Pseudomonas sp. compared to BDDA, and BDTA inhibited BDDA biodegradation. The benzyl ring of [U-{sup 14}C-benzyl] BDDA was readily and completely mineralized. The detection of the transformation products benzyl methyl amine and dodecyl dimethyl amine in spent culture liquid was consistent with literature. Overall, this study demonstrates the antagonistic effect of interactions on biodegradation of two widely used QACs suggesting further investigation on the degradation of mixture of QACs in wastewater effluents and biosolids.

  19. New alkamides from maca (Lepidium meyenii).

    Science.gov (United States)

    Zhao, Jianping; Muhammad, Ilias; Dunbar, D Chuck; Mustafa, Jamal; Khan, Ikhlas A

    2005-02-09

    Maca (Lepidium meyenii) has been used as a food in Peru for thousands of years. More recently a wide array of commercial maca products have gained popularity as dietary supplements, with claims of anabolic and aphrodisiac effects, although the biologically active principles are not fully known. In an earlier chemical investigation, two new alkamides and a novel fatty acid, as well as the N-hydroxypyridine derivative, macaridine, were isolated from L. meyenii. Further examination has led to the isolation of five additional new alkamides, namely, N-benzyl-9-oxo-12Z-octadecenamide (1), N-benzyl-9-oxo-12Z,15Z-octadecadienamide (2), N-benzyl-13-oxo-9E,11E-octadecadienamide (3), N-benzyl-15Z-tetracosenamide (4), and N-(m-methoxybenzyl)hexadecanamide (5). Their structures were established by spectrometric and spectroscopic methods including ESI-HRMS, EI-MS, (1)H, (13)C, and 2D NMR, as well as (1)H-(15)N 2D HMBC experiments. In addition, the identity of N-benzyl-15Z-tetracosenamide (4) was confirmed by synthesis. These compounds have been found from only L. meyenii and could be used as markers for authentication and standardization.

  20. Biodegradation of benzalkonium chlorides singly and in mixtures by a Pseudomonas sp. isolated from returned activated sludge

    International Nuclear Information System (INIS)

    Khan, Adnan Hossain; Topp, Edward; Scott, Andrew; Sumarah, Mark; Macfie, Sheila M.; Ray, Madhumita B.

    2015-01-01

    Highlights: • Pseudomonas sp. degraded two benzalkonium chlorides: BDDA and BDTA. • Although BDTA biodegraded at low concentration, it inhibited the degradation of BDDA. • For BDDA, two transformation products indicate two sites of bacterial activity. • 14 C-labelled BDDA was mineralized to 14 CO 2 within 300 h. - Abstract: Bactericidal cationic surfactants such as quaternary ammonium compounds (QACs) are widely detected in the environment, and found at mg kg −1 concentrations in biosolids. Although individual QACs are amenable to biodegradation, it is possible that persistence is increased for mixtures of QACs with varying structure. The present study evaluated the biodegradation of benzyl dimethyl dodecyl ammonium chloride (BDDA) singly and in the presence of benzyl dimethyl tetradecyl ammonium chloride (BDTA) using Pseudomonas sp., isolated from returned activated sludge. Growth was evaluated, as was biodegradation using 14 C and HPLC-MS methods. BDTA was more toxic to growth of Pseudomonas sp. compared to BDDA, and BDTA inhibited BDDA biodegradation. The benzyl ring of [U- 14 C-benzyl] BDDA was readily and completely mineralized. The detection of the transformation products benzyl methyl amine and dodecyl dimethyl amine in spent culture liquid was consistent with literature. Overall, this study demonstrates the antagonistic effect of interactions on biodegradation of two widely used QACs suggesting further investigation on the degradation of mixture of QACs in wastewater effluents and biosolids.

  1. Application of living radical polymerization to the synthesis of resist polymers for radiation lithography

    International Nuclear Information System (INIS)

    Shimizu, Takashi; Ichikawa, Tsuneki

    2005-01-01

    Poly(styrene) and poly(methyl acrylate) with benzyl ester of carboxylic acid at the center of the polymer skeletons were synthesized by living radical polymerization for developing a new type of radiation resist with high resistivity to plasma etching and high sensitivity and spatial resolution to ionizing radiations. The initiators were benzyl esters with two functional groups for living radical polymerization on the benzyl and the carboxylic sides. Introduction of benzyl ester to the polymer skeletons changed the polymers from cross-link type to scission type upon γ-irradiation. Irradiation of the polymers resulted in the binary change of the molecular weight, due to dissociative capture of secondary electrons by the benzyl ester, as M n R 1 COOCH(C 6 H 5 )R 2 M n +e - ->M n R 1 COO - + · CH(C 6 H 5 )R 2 M n . The generated polymer fragments were not decomposed by further irradiation, which suggests that the synthesized polymers have high resistivity to plasma etching

  2. Application of living radical polymerization to the synthesis of resist polymers for radiation lithography

    Energy Technology Data Exchange (ETDEWEB)

    Shimizu, Takashi [Nitto Denko Co. LTD., Shimohozumi 1-1-2, Ibaraki, Osaka 567-8680 (Japan); Ichikawa, Tsuneki [Division of Materials Chemistry, Graduate school of Engineering, Hokkaido University, Sapporo 060-8628 (Japan)]. E-mail: ichikawa@eng.hokudai.ac.jp

    2005-07-01

    Poly(styrene) and poly(methyl acrylate) with benzyl ester of carboxylic acid at the center of the polymer skeletons were synthesized by living radical polymerization for developing a new type of radiation resist with high resistivity to plasma etching and high sensitivity and spatial resolution to ionizing radiations. The initiators were benzyl esters with two functional groups for living radical polymerization on the benzyl and the carboxylic sides. Introduction of benzyl ester to the polymer skeletons changed the polymers from cross-link type to scission type upon {gamma}-irradiation. Irradiation of the polymers resulted in the binary change of the molecular weight, due to dissociative capture of secondary electrons by the benzyl ester, as M{sub n}R{sub 1}COOCH(C{sub 6}H{sub 5})R{sub 2}M{sub n}+e{sup -}->M{sub n}R{sub 1}COO{sup -}+{sup {center_dot}}CH(C{sub 6}H{sub 5})R{sub 2}M{sub n}. The generated polymer fragments were not decomposed by further irradiation, which suggests that the synthesized polymers have high resistivity to plasma etching.

  3. Raman spectroscopy, electronic microscopy and SPME-GC-MS to elucidate the mode of action of a new antimicrobial food packaging material.

    Science.gov (United States)

    Clemente, Isabel; Aznar, Margarita; Salafranca, Jesús; Nerín, Cristina

    2017-02-01

    One critical challenge when developing a new antimicrobial packaging material is to demonstrate the mode of action of the antimicrobials incorporated into the packaging. For this task, several analytical techniques as well as microbiology are required. In this work, the antimicrobial properties of benzyl isothiocyanate, allyl isothiocyanate and essential oils of cinnamon and oregano against several moulds and bacteria have been evaluated. Benzyl isothiocyanate showed the highest antimicrobial activity and it was selected for developing the new active packaging material. Scanning electron microscopy and Raman spectroscopy were successfully used to demonstrate the mode of action of benzyl isothiocyanate on Escherichia coli. Bacteria exhibited external modifications such as oval shape and the presence of septum surface, but they did not show any disruption or membrane damage. To provide data on the in vitro action of benzyl isothiocyanate and the presence of inhibition halos, the transfer mechanism to the cells was assessed using solid-phase microextraction-gas chromatography-mass spectrometry. Based on the transfer system, action mechanism and its stronger antimicrobial activity, benzyl isothiocyanate was incorporated to two kinds of antimicrobial labels. The labels were stable and active for 140 days against two mould producers of ochratoxin A; Penicillium verrucosum is more sensitive than Aspergillus ochraceus. Details about the analytical techniques and the results obtained are shown and discussed. Graphical Abstract Antimicrobial evaluation of pure compounds, incorporation in the packaging and study for mode of action on S. coli by Raman, SEM and SPME-GC-MS.

  4. Degradation of the fungicide denmert (S-n-butyl S'-p-tert-butylbenzyl N-3-pyridyldithiocarbonimidate, S-1358) by plants, soils and light

    International Nuclear Information System (INIS)

    Ohkawa, Hideo; Shibaike, Reiko; Okihara, Yukiko; Morikawa, Michihide; Miyamoto, Junshi

    1976-01-01

    14 C-Denmert(S-n-butyl S'-p-tert-butylbenzyl N-3-pyridyldithiocarbonimidate, S-1358) labeled at the methylene of the benzyl group was gradually decomposed to yield a number of products, when exposed to sunlight on thin-layer plates or in water solution, applied to plant foliage or nutrient solution, and added to soils under upland conditions. The identified products were almost common to plants, soils and light. The primary reactions occurred: (1), oxidation of the sulfur atoms; (2), cleavage of the dithiocarbonimidate linkage, and (3), oxidation of the methylene of the benzyl group. Also, hydroxylation at the tert-butyl group attached to the benzyl moiety slightly took place in soils. Although radioactivity was absorbed by the plant through leaves or roots, translocation into other parts of the plant occurred to a very small extent. Denmert and its degradation products were hardly leached through the acidic soils tested. (auth.)

  5. SYNTHESIS AND PHYSICAL-CHEMICAL PROPERTIES OF WATER-SOLUBLE 3-BENZYLXANTHINE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    K. V. Аleksandrova

    2015-04-01

    Full Text Available Introduction Nowadays, research of novel biological active compounds with low toxicity, are carried out among different classes of organic compounds of natural and synthetic genesis. One of the main ways of these studies is search of water-soluble compounds – convenient objects for pharmacological researches. In recent years researchers paid attention to xanthine derivatives, because of their high variativity of possible chemical modification and ability to form different salts with wide spectrum of biological action. Thus, among water-soluble xanthine derivatives were found compounds with pronounced antioxidant, diuretic and analeptic properties. Primary methods of obtaining water-soluble xanthine derivatives are direct interaction of bases with xanthine molecule or insertion basic or acidic residues in positions 7 or 8 of xanthine bicycle. According from the above, search of biologically active compounds among water-soluble substituted xanthines is prospective and actual. The aim of the study was development of synthetic ways of obtaining novel water-soluble derivatives of 3-benzyl-8-methylxanthine and studying their physical and chemical properties. Material and methods Melting points of obtained compounds were determined by capillary method on PTP (M device. ІR-spectra of synthesized compounds were recorded on the Bruker Alpha device (company «Bruker» – Germany on 4000-400 sm-1 with using console ATR (direct insertion of compound. 1Н NMR-spectra were recorded on the Varian Mercury VX-200 device (company «Varian» – USA solvent – (DMSO-d6, internal standart – ТМС. Elemental analysis was made on Elementar Vario L cube device. Chromatoraphic studies were made on the plates Sorbfil-AFV-UV (company «Sobrpolimer» –Russia. Systhems for chromatography: «acetone-propanol-2» in ratio 2:3, «propanol-2-benzene» in ratio 10:1 and exersized in UV-light in wave 200-300 nm. Results and discussion We developed methodic of synthesis

  6. Molecular interaction of a potent nonpeptide agonist with the chemokine receptor CCR8

    DEFF Research Database (Denmark)

    Jensen, Pia C; Nygaard, Rie; Thiele, Stefanie

    2007-01-01

    Most nonpeptide antagonists for CC-chemokine receptors share a common pharmacophore with a centrally located, positively charged amine that interacts with the highly conserved glutamic acid (Glu) located in position 6 of transmembrane helix VII (VII:06). We present a novel CCR8 nonpeptide agonist......, 8-[3-(2-methoxyphenoxy)benzyl]-1-phenethyl-1,3,8-triaza-spiro[4.5]decan-4-one (LMD-009), that also contains a centrally located, positively charged amine. LMD-009 selectively stimulated CCR8 among the 20 identified human chemokine receptors. It mediated chemotaxis, inositol phosphate accumulation......-binding pockets of CCR8 uncovered that the binding of LMD-009 and of four analogs [2-(1-(3-(2-methoxyphenoxy)benzyl)-4-hydroxypiperidin-4-yl)benzoic acid (LMD-584), N-ethyl-2-4-methoxybenzenesulfonamide (LMD-902), N-(1-(3-(2-methoxyphenoxy)benzyl)piperidin-4-yl)-2-phenyl-4-(pyrrolidin-1yl)butanamide (LMD-268...

  7. [Quality control of Maca (Lepidium meyenii)].

    Science.gov (United States)

    Shu, Ji-cheng; Cui, Hang-qing; Huang, Ying-zheng; Huang, Xiao-ying; Yang, Ming

    2015-12-01

    To control the quality of Maca, the quality standard was established in this study. According to the methods recorded in the Appendix of Chinese Pharmacopoeia (2010 Edition), the water, extract, total ash, acid insoluble substance, and heavy metals inspections in Lepidium meyenii were carried out. N-benzyl-9Z, 12Z-octadecadienamide in L. meyenii was identified by TLC, and it was determined by HPLC. The results showed that the N-benzyl-9Z, 12Z-octadecadienamide identification of TLC was a strong mark and specificity. In content determination experiment, the linearity of N-benzyl-9Z, 12Z-octadecadienamide was in the range of 0.01-2 microg (r = 0.9998), and the average recovery (n=9) was 99.27% (RSD 2.0%). The methods were simple, accurate, with good reproducibility. It is suitable for quality control L. meyenii.

  8. Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids

    Directory of Open Access Journals (Sweden)

    Rustum S. Boyce

    2004-05-01

    Full Text Available The synthesis of (2S-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl- propionic acid, (2S-2-benzyloxymethyl-3-(2-fluoro-4-methylphenylpropionic acid and (2S-2-benzyl-oxymethyl-3-(2,4-dimethylphenylpropionic acid has been achieved by TiCl4 mediated alkylation of the corresponding (4R-4-benzyl-3-[3-(2-fluoro-4-methoxyphenyl-, 2-fluoro-4-methylphenyl-, 2,4- dimethylphenyl-propionyl]-2-oxazolidinones, followed by hydrolysis of the chiral auxiliary. The stereochemistry of the alkylation reaction was confirmed by an X-ray crystal structure of (4R-4-benzyl-3-[(2S-2-benzyloxymethyl-3-(2- fluoro-4-methylphenylpropionyl]-2-oxazolidinone.

  9. Synthesis of tritium labeled MK-886, a leukotriene biosynthesis inhibitor; employment of epibromohydrin as a masked electrophilic acetone synthon

    International Nuclear Information System (INIS)

    Schmidt, S.J.; Garnes, K.T.; Heys, J.R.; Landvatter, S.W.; Adams, J.L.

    1991-01-01

    1-(4-Chloro-[3- 3 H]benzyl)-3-(t-butylthio)-α,α-dimethyl-5 -(i-propyl)-indole-2-propanoic acid (MK-886) was prepared by catalytic tritium/halogen exchange on 1-(4-chloro-3-iodobenzyl)-3-(t-butylthio)-α,α-dimethyl-5-(i-p propyl)-indole-2-propanoic acid(9). Compound 9 was prepared by a synthesis converging at the indole benzylation step. The required indole was prepared by means of a Fischer indole synthesis employing the highly functionalized unsymmetrical ketone 3. Ketone 3 was efficiently made in three steps using epibromohydrin as a masked electrophilic acetone synthon. The halogenated benzyl bromide moiety was prepared in three steps from 1-chloro-2-iodo-4-(trifluoromethyl)-benzene. (author)

  10. Nitroaromatics are substrates for the TOL plasmid upper-pathway enzymes

    Energy Technology Data Exchange (ETDEWEB)

    Delgado, A.; Abril, M.A.; Ramos, J.L. (Consejo Superior de Investigaciones Cientificas, Granada (Spain)); Wubbolts, M.G. (Univ. of Groningen (Netherlands))

    1992-01-01

    Expression of the xylMA genes encoding for toluene monoxygenase from the lactose promoter in a broad-host-range plasmid allows the oxidation of toluene and m- and p-nitrotoluene to their corresponding benzyl alcohols and benzaldehydes in Pseudomonas putida and Escherichia coli. Benzyl alcohols accumulate until reaching a concentration of about 80 {mu}M, while benzaldehydes accumulate steadily with time for at least 24 h. TOL-encoded benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase recognize m- and p-nitro-substituted compounds as substrates. In contrast, the XylR protein, which regulates the TOL plasmid-encoded upper-pathway operon, does not recognize nitro-substituted toluenes as effectors.

  11. Preparation of Color Filter Photo Resists for Generating Color Pixels in Liquid Crystal Displays by Synthesis and Applications of Polymeric Binders

    Energy Technology Data Exchange (ETDEWEB)

    Yoon, Chun [Sejong University, Seoul (Korea, Republic of); Choi, Jae Hong [Kyungpook National University, Daegu (Korea, Republic of)

    2010-09-15

    This study was carried out based on several purposes. First, introductions of new binders have been requested due to the recent trend of red pigments; that is, a dieketo-pyrrolo-pyrrole with a smaller particle size and less polarity for a high contrast ratio is desired. The pigments for a high contrast ratio usually have a particle size in the range of 40 - 60 nm, while conventional pigments of anthraquinone have a particle size of approximately 90 nm. For this reason, less polar styrene was introduced to increase affinity by replacing or reducing benzyl methacrylate. Traditionally, a binder prepared from benzyl methacrylate and methacrylic acid has been widely used. Second, introductions of less expensive materials, such as styrene and methyl methacrylate, have been requested to contribute to the extreme competitiveness of the LCD industry. For this study, styrene, methacrylic acid, methyl methacrylate and benzyl methacylate were employed to synthesize the random copolymer into polymeric binders.

  12. Enzyme-controlled nitrogen-atom transfer enables regiodivergent C-H amination.

    Science.gov (United States)

    Hyster, Todd K; Farwell, Christopher C; Buller, Andrew R; McIntosh, John A; Arnold, Frances H

    2014-11-05

    We recently demonstrated that variants of cytochrome P450BM3 (CYP102A1) catalyze the insertion of nitrogen species into benzylic C-H bonds to form new C-N bonds. An outstanding challenge in the field of C-H amination is catalyst-controlled regioselectivity. Here, we report two engineered variants of P450BM3 that provide divergent regioselectivity for C-H amination-one favoring amination of benzylic C-H bonds and the other favoring homo-benzylic C-H bonds. The two variants provide nearly identical kinetic isotope effect values (2.8-3.0), suggesting that C-H abstraction is rate-limiting. The 2.66-Å crystal structure of the most active enzyme suggests that the engineered active site can preorganize the substrate for reactivity. We hypothesize that the enzyme controls regioselectivity through localization of a single C-H bond close to the iron nitrenoid.

  13. On the specificity of sialidase. Synthesis and properties of N5-acetyl-beta-D-neuraminoylpeptides - AcNeu-Gly-OH, AcNeu-Glu-OH, AcNeu-Phe-OH - and the corresponding alpha-ketosides.

    Science.gov (United States)

    Eschenfelder, V; Brossmer, R; Wachter, M

    1983-10-01

    By means of the mixed anhydride procedure the benzyl alpha-ketoside of N5-acetyl-D-neuraminic acid was linked to L-glycine, L-glutamic acid and L-phenylalanine. Hydrogenolytic cleavage of the benzyl group resulted in the corresponding free N5-acetyl-beta-D-neuraminoylpeptides. This new class of compounds is no substrate for Vibrio cholerae sialidase. The enzyme does not split the benzyl alpha-ketosides of N5-acetyl-D-neuraminoylpeptides nor is its activity inhibited by these compounds. The results strongly support the assumption that in sialidase substrates the carboxy group must be located close to the ketosidic oxygen. N-(N5-acetyl-beta-D-neuraminoyl)-L-phenylalanine was readily hydrolysed by carboxypeptidase A from bovine pancreas.

  14. S-Substituted cysteine derivatives and thiosulfinate formation in Petiveria alliacea-part II.

    Science.gov (United States)

    Kubec, Roman; Kim, Seokwon; Musah, Rabi A

    2002-11-01

    Three cysteine derivatives, (R)-S-(2-hydroxyethyl)cysteine, together with (R(S)R(C))- and (S(S)R(C))-S-(2-hydroxyethyl)cysteine sulfoxides, have been isolated from the roots of Petiveria alliacea. Furthermore, three additional amino acids, S-methyl-, S-ethyl-, and S-propylcysteine derivatives, were detected. They were present only in trace amounts (<3 microg g(-1) fr. wt), precluding determination of their absolute configurations and oxidation states. In addition, four thiosulfinates, S-(2-hydroxyethyl) (2-hydroxyethane)-, S-(2-hydroxyethyl) phenylmethane-, S-benzyl (2-hydroxyethane)- and S-benzyl phenylmethanethiosulfinates, have been found in a homogenate of the roots. The formation pathways of various benzyl/phenyl-containing compounds previously found in the plant were also discussed.

  15. Initiation of MMA polymerization by iniferters based on dithiocarbamates

    Directory of Open Access Journals (Sweden)

    Jovanović Slobodan M.

    2005-01-01

    Full Text Available Twelve modified dithiocarbamates and a thiuramdisulfide used for the initiation of methyl methacrylate (MMA polymerization were synthesized in this study. The polymerization of MMA was followed by determine the yield and molar mass of the obtained PMMA as a function of polymerization time. Four of the synthesized dithiocarbamates S-benzyl-N,N-dibenzyldithiocarbamate, S-allyl-N,N-dibenzyldithiocarbamate S-benzyl-N,N-diisobutyldithiocarbamate and S-benzoyl-N,N-diisobutyldithiocarbamate, as well as N,N,N',N'-tetrabenzylthiuramdisulfide acted as iniferters. They were active as the initiators of the photo and/or thermally initiated radical polymerization of MMA in bulk and inert solvents (benzene and toluene. S Benzyl - N,N - dibenzyldithiocarbamate can be successfully used for the initiation of MMA polymerization in a polar solvent such as dimethylacetamide.

  16. Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities

    Directory of Open Access Journals (Sweden)

    NALILU SUCHETHA KUMARI

    2011-02-01

    Full Text Available Several 5-thio-substituted tetrazole derivatives were efficiently synthesized by a three-step process. The substituted tetrazol-5-thiol, namely, 1-benzyl-1H-tetrazole-5-thiol (2 was prepared by refluxing commercially available benzyl isothiocyanate (1 with sodium azide in water. The second step was the synthesis of 1-benzyl-5-[(3-bromopropylthio]-1H-tetrazole (3 by thioalkylation of tetrazole-5-thiol 2 with 1,3-dibromopropane in tetrahydrofuran. Finally, the 5-thio-substituted tetrazole derivatives 4a–i were prepared by condensation of 3 with the corresponding amine or thiol. The structures of the newly synthesized compounds were characterized by NMR, LC/MS/MS, IR spectral data and elemental analysis. All the synthesized compounds were screened for their antibacterial and antifungal activities.

  17. New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase.

    Science.gov (United States)

    Kun, Sándor; Bokor, Éva; Varga, Gergely; Szőcs, Béla; Páhi, András; Czifrák, Katalin; Tóth, Marietta; Juhász, László; Docsa, Tibor; Gergely, Pál; Somsák, László

    2014-04-09

    O-Perbenzoylated 5-(β-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (Ki 0.67 μM) and the 5-(2-naphthyl)-substituted (Ki 0.41 μM) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  18. Exploring the aglycone subsite of a GH11 xylanase for the synthesis of xylosides by transglycosylation reactions.

    Science.gov (United States)

    Brusa, C; Belloy, N; Gérard, D; Muzard, M; Dauchez, M; Plantier-Royon, R; Rémond, C

    2018-03-01

    Xylanases Tx-xyn10 and Tx-xyn11 were compared for their transxylosylation abilities in the presence of various acceptors. Tx-xyn10 exhibited a broad specificity for various acceptors, whereas xylanase Tx-xyn11 catalysed transxylosylation reactions only in presence of polyphenolic acceptors. A modelling approach was developed to study the molecular bottlenecks into the active site of the enzyme that could be responsible for this restricted specificity. The glycosyl-enzyme intermediate of Tx-xyn11 was modelled, and a rotamer of the Y78 residue was integrated. In silico mutations of some residues from the (+1) and (+2) subsites were tested for the deglycosylation step in the presence of non-polyphenolic acceptors. The results indicated that the mutant W126A was able to use aliphatic alcohols and benzyl alcohol as acceptors for transxylosylation. Experimental validation was tested by mutating the xylanase Tx-xyn11 at position W126 into alanine. The specific activity and catalytic efficiency of the W126A mutant during the hydrolysis of xylans decreased by 2-fold and 4-fold, respectively, compared to wild-type xylanase. Among tested acceptors, transxylosylation catalysed by mutant W126A was improved with benzyl alcohol leading to a 2-fold higher concentration of benzyl xylobioside, as predicted by in silico mutation. This improved transxylosylation in the presence of benzyl alcohol leading to higher synthesis of benzyl xylobioside could likely be explained by lowest steric hindrance in the aglycone subsite of the mutated xylanase. No secondary hydrolysis of benzyl xylobioside occurred for both wild-type and mutant xylanases. Finally, our results demonstrated that the modelling approach was limited and that accounting for protein dynamics can lead to improved models. Copyright © 2018. Published by Elsevier B.V.

  19. Use of mixed Li/K metal TMP amide (LiNK chemistry for the synthesis of [2.2]metacyclophanes

    Directory of Open Access Journals (Sweden)

    Marco Blangetti

    2011-09-01

    Full Text Available A new two-step general approach to [2.2]metacyclophane synthesis from substituted m-xylenes is described. The strategy employs a selective benzylic metalation and oxidative C–C bond formation for both synthetic operations. Regioselective benzylic metalation is achieved using the BuLi, KOt-Bu, TMP(H (2,2,6,6-tetramethylpiperidine combination (LiNK metalation conditions and oxidative coupling with 1,2-dibromoethane. The synthetic ease of this approach compares favourably with previously reported methods and allows for ready access to potentially useful planar chiral derivatives.

  20. Influence of substituents of nickel(II) complexes of Schiff bases of substituted (S)-2-N-(benzylpropyl)aminobenzophenones and amino-acids on their asymmetric induction

    International Nuclear Information System (INIS)

    Nadvornik, M.; Lycka, A.; Gee, A.; Popkov, A.

    1999-01-01

    The aim of this work was to study of influence of substituents on benzophenone substituent on thermodynamic controlled induction of complexes as well as influence of substituents on benzyl group and on benzophenone on kinetically controlled asymmetric induction of complexes. [ 13 C]methyl iodide was used in the synthesis. Replace of benzyl group by 2,4,6-trimethylbenzyl group increase kinetically controlled asymmetric induction of synthesis of (S)-α-[ 13 C]methylalanine from 43% d.e. to 66% d.e