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Sample records for acetamide

  1. Compound list: acetamide [Open TG-GATEs

    Full Text Available acetamide AAA 00169 ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Human/in_vitro/aceta...mide.Human.in_vitro.Liver.zip ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Rat/in_vivo/Liver/Repeat/acetamide.Rat.in_vivo.Liver.Repeat.zip ...

  2. N-(4-Chlorophenyl)-2-(hydroxyimino)acetamide

    Jie Sun; Zaisheng Cai

    2009-01-01

    The title compound, C8H7ClN2O2, is an intermediate in the synthesis of 5-chloroisatin, which can be further transformed to 5-chloro-2-indolinone via a Wolff–Kishne reduction. The C2N acetamide plane forms a dihedral angle of 6.3 (3)° with the benzene ring. An intramolecular C—H...O interaction results in the formation of a six-membered ring. In the crystal, intermolecular N—H...O, N—H...N and O—H...O hydrogen bonds link the ...

  3. Nanomorphology in thin films of acetamide end-functionalised quaterthiophene

    Zeilmann, Nina; Rösner, Benedikt; Späth, Andreas [Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) Department Chemie und Pharmazie, Physikalische Chemie 2 and ICMM, Egerlandstraße 3, 91058 Erlangen (Germany); Schmidt, Ute [WITec GmbH, Lise-Meitner-Straße 6, 89081 Ulm (Germany); Fink, Rainer H., E-mail: rainer.fink@fau.de [Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) Department Chemie und Pharmazie, Physikalische Chemie 2 and ICMM, Egerlandstraße 3, 91058 Erlangen (Germany)

    2015-05-29

    α,ω-Functionalised oligothiophenes are promising materials for organic field effect transistors due to their high degree of molecular ordering, crystallinity and π-π stacking. We employ several complementary microspectroscopic probes to investigate the formation of thermally evaporated films of 5,5‴-bis(N-acetamido-2-ethyl)-2,2′:5′,2″:5″,2‴quaterthiophene on inert substrates. These films were found to grow in a mixed fashion, featuring layer-by-layer domains with thicknesses of several monolayers and needle-shaped three-dimensional crystals. Detailed analysis of atomic force microscopy (AFM) and photoluminescence microscopy reveals the micro- and nanomorphology of the films. Linear dichroism in the near edge x-ray absorption fine structure and polarisation-dependent laser excitation corroborate the findings of AFM, i.e., upright standing molecules in the multilayer regime. The shape of the 3-dimensional crystallites and multilayer domains indicates strongly anisotropic growth favoured by the herringbone-arrangement of the thiophene moieties and additional stabilisation by hydrogen bonding of the acetamide end groups. - Highlights: • Growth study of end-functionalised quaterthiophene on inert substrates is presented. • Complementary nanoprobes were employed to investigate the growth behaviour. • The molecular orientation was revealed by the use of linearly polarised light.

  4. Nanomorphology in thin films of acetamide end-functionalised quaterthiophene

    α,ω-Functionalised oligothiophenes are promising materials for organic field effect transistors due to their high degree of molecular ordering, crystallinity and π-π stacking. We employ several complementary microspectroscopic probes to investigate the formation of thermally evaporated films of 5,5‴-bis(N-acetamido-2-ethyl)-2,2′:5′,2″:5″,2‴quaterthiophene on inert substrates. These films were found to grow in a mixed fashion, featuring layer-by-layer domains with thicknesses of several monolayers and needle-shaped three-dimensional crystals. Detailed analysis of atomic force microscopy (AFM) and photoluminescence microscopy reveals the micro- and nanomorphology of the films. Linear dichroism in the near edge x-ray absorption fine structure and polarisation-dependent laser excitation corroborate the findings of AFM, i.e., upright standing molecules in the multilayer regime. The shape of the 3-dimensional crystallites and multilayer domains indicates strongly anisotropic growth favoured by the herringbone-arrangement of the thiophene moieties and additional stabilisation by hydrogen bonding of the acetamide end groups. - Highlights: • Growth study of end-functionalised quaterthiophene on inert substrates is presented. • Complementary nanoprobes were employed to investigate the growth behaviour. • The molecular orientation was revealed by the use of linearly polarised light

  5. Leuckart Synthesis and Pharmacological Assessment of Novel Acetamide Derivatives.

    Rani, Priyanka; Pal, Dilipkumar; Hegde, Rahul Rama; Hashim, Syed Riaz

    2016-01-01

    A new concatenation of N-(1-(4-bromophenyl)ethyl)-2-phenoxyacetamide and N-(1-(4-methoxyphenyl) ethyl)-2-phenoxyacetamide derivatives having 2-phenoxy-N-(1-phenylethyl)acetamide nucleus as common in both the types was synthesized for the sake of achieve titled compounds as potential cytotoxic, anti-inflammatory, analgesic and antipyretic agents. All the novel derivatives have been synthesized through multi-step reaction sequence starting from Leuckart reaction. The structural assignments of the new compounds have been determined by virtue of their IR, 1H NMR, 13C NMR, elemental analysis and mass spectrum analysis. All the synthesized compounds were assessed for cytotoxicity and anti-inflammatory, analgesic and antipyretic effects. Among the series, compounds 3a, 3c, 3g and 3h possess cytotoxic, anti-inflammatory, analgesic and antipyretic activities comparable with standard drugs. The synthesized compounds were found to be active because of the presence of bromo, tert- butyl and nitro groups at position 4 of phenoxy nucleus. PMID:26555612

  6. Resonance Raman spectroscopy with chemical state selectivity on histidine and acetamide using synchrotron radiation

    We report on ultraviolet resonance Raman scattering experiments carried out on two model substances: histidine and acetamide using a UV synchrotron radiation source. In the case of aqueous histidine solution each protonated state of histidine tautomers was selectively excited by tuning the incident wavelength and the vibrational state of each protonated state was studied. We also demonstrated that the local pH condition of histidine can be identified directly from the spectra above pH 9. In the case of acetamide, the resonance Raman bands of acetamide with a stronger hydrogen bond at the NH2 site and weaker hydrogen bond at the C=O site were selectively observed. These findings will extend the selectivity and sensitivity of RR spectroscopy that is helpful to understanding protein functionality. (author)

  7. X-ray diffraction study of uranyl sulfate complexes with acetamide

    X-ray diffraction study of UO2SO4xLx2H2O (1), UO2SO4x2Lx2H2O (2) and UO2SO4x3LxH2O (3) (L-acetamide) complexes, which crystals were prepared by slow evaporation at room temperature uranyl sulfate and acetamide aqueous solutions with a definite molar ratio, is carried out. The lattice parameters for (1) are: a=17.520; b=6.917; c=8.759 A; β=104.40 deg sp.gr. s2/mC2 or Cm; for (2): a=7.248; b=9.451; c=10.623 A; α=109.15; β=107.79; γ=74.55 deg; sp.gr. P1-bar; for (3): a=8.494; b=10.170; c=10.606 A; α=118.81; β=102.92; γ=90.10 deg; sp.gr. P1-bar. Peculiarities of crystal-structure transformations in acetamide and carbamide uranyl sulfate complexes with change of UO2SO4:L ratio (L-acetamide or carbamide) are discussed

  8. Amino and Acetamide Functional Group Effects on the Ionization and Fragmentation of Sugar Chains in Positive-Ion Mass Spectrometry

    Yamagaki, Tohru; Sugahara, Kohtaro; Watanabe, Takehiro

    2014-01-01

    To elucidate the influence of amino (-NH2) and acetamide (-NHCOCH3, -NAc) groups in sugar chains on their ionization and fragmentation, cycloamyloses (cyclodextrins, CyDs) and lacto-oligosaccharide are analyzed by MALDI TOF/TOF and ESI Q-TOF mass spectrometry. CyD derivatives substituted by amino or acetamide groups are ideal analytes to extract the function group effects, which are amino-CyD with one hexosamine (HexNH2) and acetamide-CyD with one N-acetyl hexosamine (HexNAc). Interestingly, the relative ion intensities and isotope-like patterns in their product ion spectra depend on the functional groups and ion forms of sugar chains. Consequently, the results indicate that a proton (H+) localizes on the amino group of the amino sugar, and that the proton (H+) induces their fragmentation. Sodium cation (Na+) attachment is independent from amino group and exerts no influence on their fragmentation patterns in amino group except for mono- and disaccharide fragment ions because there is the possibility of the reducing end effect. In contrast, a sodium cation localizes much more frequently on the acetamide group in acetamide-CyDs because the chemical species with HexNAc are stable. Thus, their ions with HexNAc are abundant. These results are consistent with the fragmentation of lacto-neo- N-tetraose and maltotetraose, suggesting that a sodium cation generally localizes much more frequently on the acetamide group in sugar chains.

  9. Synthesis of N-acetamide C60 nitride and its performance of optical limiting

    2000-01-01

    N-acetamide C60 nitride (N-acetamide-1,2-dihydro-1,2-aza-fullerene[60]) has been synthesized by the reaction of C60 and azidoacetamide and initially characterized. Its mechanism was that the objective product is formed through intermediate triazoline. The computational study shows that N-nitride structure is thermodynamically more stable by using the semi-empirical AM1 SCF-MO method. The properties of optical limiting were tested by using double frequency Nd∶YAG pulse laser system and showed that the optical limiting mechanism is reverse saturation absorption. A wavelength of 532 nm, compared with optical limiting for ns pulse, this new material has good optical limiting character for ps pulse. At wavelength of 707 nm, the capacity of optical limiting of the derivative is prior to C60.

  10. Anticancer, anti-inflammatory, and analgesic activities of synthesized 2-(substituted phenoxy) acetamide derivatives.

    Rani, Priyanka; Pal, Dilipkumar; Hegde, Rahul Rama; Hashim, Syed Riaz

    2014-01-01

    The aphorism was to develop new chemical entities as potential anticancer, anti-inflammatory, and analgesic agents. The Leuckart synthetic pathway was utilized in development of novel series of 2-(substituted phenoxy)-N-(1-phenylethyl)acetamide derivatives. The compounds containing 1-phenylethylamine as basic moiety attached to substituted phenols were assessed for their anticancer activity against MCF-7 (breast cancer), SK-N-SH (neuroblastoma), anti-inflammatory activity, and analgesic activity. These investigations revealed that synthesized products 3a-j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity. Among all, compound 3c N-(1-(4-chlorophenyl)ethyl)-2-(4-nitrophenoxy)acetamide exhibited anticancer, anti-inflammatory, and analgesic activities. In conclusion, 3c may have potential to be developed into a therapeutic agent. PMID:25197642

  11. Acetylphosphonate as a Surrogate of Acetate or Acetamide in Organocatalyzed Enantioselective Aldol Reactions

    Guang, Jie; Guo, Qunsheng

    2012-01-01

    Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods. PMID:22650245

  12. Anticancer, Anti-Inflammatory, and Analgesic Activities of Synthesized 2-(Substituted phenoxy) Acetamide Derivatives

    Priyanka Rani; Dilipkumar Pal; Rahul Rama Hegde; Syed Riaz Hashim

    2014-01-01

    The aphorism was to develop new chemical entities as potential anticancer, anti-inflammatory, and analgesic agents. The Leuckart synthetic pathway was utilized in development of novel series of 2-(substituted phenoxy)-N-(1-phenylethyl)acetamide derivatives. The compounds containing 1-phenylethylamine as basic moiety attached to substituted phenols were assessed for their anticancer activity against MCF-7 (breast cancer), SK-N-SH (neuroblastoma), anti-inflammatory activity, and analgesic activ...

  13. Electrochemical study of nickel from urea-acetamide-LiBr low-temperature molten salt

    Highlights: • CV results show that the charge transfer process of Ni(II)/Ni in urea-acetamide-LiBr is irreversible. • The reduction process is a single step two-electron transfer process. • Chronoamperometry indicates that the reaction on tungsten electrode involves progressive nucleation. • EDS and XRD analyses confirm that the obtained deposits are pure nickel. -- Abstract: The electrochemical behavior of nickel was studied by cyclic voltammetry and chronoamperometry techniques at 353 K using a tungsten electrode in urea-acetamide-LiBr low-temperature molten salt. The cyclic voltammograms indicate that the reduction of Ni(II) to Ni proceeds via a single-step, two-electron transfer process. Chronoamperometric measurements show that the electrodeposition of nickel on the tungsten electrode involves three-dimensional (3D) progressive nucleation under diffusion-controlled growth at 353 K. Nickel coatings were prepared at different cathodic potentials (−0.70 to −0.85 V) and different temperatures (343–373 K) in urea-acetamide-LiBr molten salt. The deposits were characterized by scanning electron microscope (SEM), energy dispersive spectroscopy (EDS), and X-ray diffraction (XRD). The SEM images reveal that uniform, dense, and compact deposits were obtained at more positive cathodic potentials within the temperature range of 343–363 K. The EDS and XRD analyses confirm that the obtained deposits are pure nickel

  14. Acetamide Derivatives with Antioxidant Activity and Potential Anti-Inflammatory Activity

    Giuseppina Tommonaro

    2010-03-01

    Full Text Available This study reports the synthesis and antioxidant activity of some new acetamide derivatives. The compounds’ structures were elucidated by NMR analysis and their melting points were measured. The in vitro antioxidant activity of these compounds was tested by evaluating the amount of scavenged ABTS radical and estimating ROS and NO production in tBOH- or LPS-stimulated J774.A1 macrophages. All compounds were tested for their effect on cell viability by an MTT assay and by a Brine Shrimp Test.

  15. N-[4-(2-Propyn-1-yl­oxy)phen­yl]acetamide

    Yonas H. Belay; Kinfe, Henok H.; Muller, Alfred

    2012-01-01

    The title compound, C11H11NO2, was synthesized by chemoselective N-acetyl­ation of 4-amino­phenol followed by reaction with propargyl bromide in the presence of K2CO3. the acetamide and propyn-1-yloxy substituents form dihedral angles of 18.31 (6) and 7.01 (10)°, respectively, with the benzene ring. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into chains along [010]. C—H⋯O and C—H⋯π inter­actions also occur.

  16. SYNTHESIS OF BIOLOGICALLY ACTIVE 2-CHLORO-N-ALKYL/ARYL ACETAMIDE DERIVATIVES

    S.A.Katke; S.V.Amrutkar; R.J.Bhor; M.V.Khairnar

    2011-01-01

    Medicinal chemistry plays an important role in development of drug for cure; maintain and improved health of human being. It is also equally important to design chemical entities for prevent the growth of micro-organism, which come in contact with human being in day-to-day life. We have synthesized 2-chloro-N-alkyl/aryl Acetamide derivatives with an aim as new bioactive agent, which can be used as anti microbial agents such as herbicides, antifungal, disinfectant. The present study involves t...

  17. Electrochemical studies on La-Co alloy film in acetamide-urea-NaBr melt system

    GUO Cheng-yu; WANG Jian-chao; CHEN Bi-qing; WANG Jing-gui

    2005-01-01

    The kinetics of La-Co alloy film in acetamide-urea-NaBr molten salt electrolyte at 353 K was investigated. It is shown that the reduction of Co( Ⅱ ) to Co is irreversible reaction with the transfer coefficient of 0.28 and the diffusion coefficient of 7.46 × 10-5cm2/s. While La( Ⅲ ) cannot be reduced to La directly; but can be codeposited with cobalt. The content of La in the uncrystallized La-Co alloy film increases with increasing cathodic overpotential, molar ratio of La3+ to Co2+ and electrolysis time as well, and reaches the maximum of 66.32%.

  18. SYNTHESIS OF BIOLOGICALLY ACTIVE 2-CHLORO-N-ALKYL/ARYL ACETAMIDE DERIVATIVES

    S.A.Katke

    2011-07-01

    Full Text Available Medicinal chemistry plays an important role in development of drug for cure; maintain and improved health of human being. It is also equally important to design chemical entities for prevent the growth of micro-organism, which come in contact with human being in day-to-day life. We have synthesized 2-chloro-N-alkyl/aryl Acetamide derivatives with an aim as new bioactive agent, which can be used as anti microbial agents such as herbicides, antifungal, disinfectant. The present study involves the synthesis, purification and characterization of various N-substituted chloroacetamide derivatives. The chloroacetyl chloride treated with various aliphatic and aromatic amines at room temperature with stirring for few hours with monitoring reaction by thin layer chromatography gave 2-chloro-N-alkyl/aryl Acetamide as solid compounds. We checked the melting point of synthesized compounds with an open ended capillary tube method. The spectral techniques like Infra red and GC-MS have been used for characterization and establishment of structure of synthesized compounds. The antimicrobial screening of the synthesized chloroacetamides have shown excellent antibacterial and antifungalactivity.

  19. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false N- diallylamino-4- substituted phenyl] acetamide (generic name). 721.267 Section 721.267 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  20. Elucidation of Structural Elements for Selectivity across Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues

    Okunola-Bakara, Oluyomi; Cao, Jianjing; Kopajtic, Theresa;

    2014-01-01

    2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil, (±)-1) is a unique dopamine uptake inhibitor that binds the dopamine transporter (DAT) differently than cocaine and may have potential for the treatment of psychostimulant abuse. To further investigate structural requirements for this divergent...

  1. Colorimetric sensing of iodide based on triazole-acetamide functionalized gold nanoparticles

    We have modified gold nanoparticles (AuNPs) with triazole acetamide to obtain a material for the sensitive and selective colorimetric determination of iodide. The functionalized AuNPs were prepared by a reductive single chemical step using a Cu(I)-catalyzed click reaction. The presence of iodide ions induces the aggregation of these AuNPs and results in a color change from wine-red to purple. The iodide-induced aggregation can be detected visually with bare eyes, but also by photometry. The detection limit is as low as 15 nM. The method displays excellent selectivity for iodide over other anions due to the selective interaction with the amido groups of the triazole. The method was applied to the determination of iodide in spiked lake waters. (author)

  2. N-(4-Chloro­phen­yl)-2-(hydroxy­imino)acetamide

    Sun, Jie; Cai, Zaisheng

    2009-01-01

    The title compound, C8H7ClN2O2, is an inter­mediate in the synthesis of 5-chloro­isatin, which can be further transformed to 5-chloro-2-indolinone via a Wolff–Kishne reduction. The C2N acetamide plane forms a dihedral angle of 6.3 (3)° with the benzene ring. An intra­molecular C—H⋯O inter­action results in the formation of a six-membered ring. In the crystal, inter­molecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonds link the mol­ecules into multimers, forming sheets.

  3. The Microwave Spectrum of Monodeuterated Acetamide CH_2DC(=O)NH_2

    Konov, I. A.; Coudert, L. H.; Gutle, C.; Huet, T. R.; Margulès, L.; Motiyenko, R. A.; Møllendal, H.; Guillemin, J.-C.

    2014-06-01

    Acetamide is an oblate asymmetric top displaying almost free internal rotation of its methyl group. The microwave spectrum of the normal species (CH_3C(=O)NH_2) has already been studied and a value of only 25 wn was retrieved for the height of the potential barrier hindering the internal rotation. No spectroscopic results are available about the monodeutared species with a partially deuterated CH_2D methyl group which will be the subject of the present talk. The effects of deuteration on the hindering potential will be investigated first. They lead to qualitative changes of the hindering potential no longer resembling that of the normal species and displaying several inequivalent minima. A determination of the torsional potential will be attempted through an analysis of the microwave spectrum of the monodeuterated species in which torsion-rotation energies are calculated with the approach developed for monodeuterated methanol, accounting for the torsion-rotation Coriolis coupling and for the dependence of the inertia tensor on the torsional angle. A low temperature spectrum, recorded with the MB-FTMW spectrometer in Lille, has already been analyzed and 14 transitions could be assigned up to J=6. Room temperature spectra have also been recorded in the 7-91 and 150-165 GHz frequency ranges and more than 100 transitions have been assigned up to J=16 for the ground torsional state. In the paper, deuteration effects will be discussed and we hope to assign a sufficient number of microwave transitions in order to obtain the first quantitative information about the hindering potential of monodeuterated acetamide. Ilyushin, Alekseev, Dyubko, Kleiner, and Hougen, J. Molec. Spectrosc. 227 (2004) 115 Lauvergnat, Coudert, Klee, and Smirnov, J. Molec. Spectrosc. 256 (2009) 204 Margulès, Coudert, Møllendal, Guillemin, Huet and Janečková, J. Molec. Spectrosc. 254 (2009) 55 Coudert, Zemouli, Motiyenko, Margulès, and Klee, J. Chem. Phys. 140 (2014) 064307

  4. Changes in concentrations of triazine and acetamide herbicides by bank filtration, ozonation, and chlorination in a public water supply

    Verstraeten, Ingrid M.; Thurman, E.M.; Lindsey, M.E.; Lee, E.C.; Smith, R.D.

    2002-01-01

    The changes in triazine and acetamide concentrations in water during natural and artificial treatment by bank filtration, ozonation, filtration, and chlorination were measured at the well field and drinking water treatment plant of Lincoln, Nebraska, USA. The city's groundwater supply is affected by induced infiltration and transport of triazines and acetamide herbicides from the Platte River in late spring and early summer. The objective of the study was to evaluate the effect of infiltration and treatment on the presence of triazines and acetamides in drinking water. Samples of river water, well water, and public supply water at various stages of water treatment were collected from 1997-1999 during spring-runoff when the presence of herbicides in the Platte River is largest. In 1999, parent compounds were reduced by 76% of the concentration present in river water (33% by bank filtration, 41% by ozonation, and 1.5% by chlorination). Metabolites of herbicides for which analytical techniques existed were reduced by 21% (plus 26% by bank filtration, minus 23% by ozonation, and minus 24% by chlorination). However, increases in concentrations of specific metabolite compounds were identified after bank filtration and ozonation. After bank filtration, increases in cyanazine amide, cyanazine acid, and deethylcyanazine acid were identified. After ozonation, concentrations of deisopropylatrazine, deethylatrazine, didealkylatrazine, atrazine amide-I, hydroxydeethylatrazine, hydroxydeisopopylatrazine, deethylcyanazine acid, and deethylcyanazine increased. Concentrations of cyanazine acid and ethanesulfonic and oxanilic acids of acetamides decreased during ozonation. Our findings suggest that bank filtration and ozonation of water in part can shift the assessment of risk to human health associated with the consumption of the water from the parent compounds to their degradation products.

  5. Synthesis of N-(6-Arylbenzo[d]thiazole-2-acetamide Derivatives and Their Biological Activities: An Experimental and Computational Approach.

    Gull, Yasmeen; Rasool, Nasir; Noreen, Mnaza; Altaf, Ataf Ali; Musharraf, Syed Ghulam; Zubair, Muhammad; Nasim, Faiz-Ul-Hassan; Yaqoob, Asma; DeFeo, Vincenzo; Zia-Ul-Haq, Muhammad

    2016-01-01

    A new series of N-(6-arylbenzo[d]thiazol-2-yl)acetamides were synthesized by C-C coupling methodology in the presence of Pd(0) using various aryl boronic pinacol ester/acids. The newly synthesized compounds were evaluated for various biological activities like antioxidant, haemolytic, antibacterial and urease inhibition. In bioassays these compounds were found to have moderate to good activities. Among the tested biological activities screened these compounds displayed the most significant activity for urease inhibition. In urease inhibition, all compounds were found more active than the standard used. The compound N-(6-(p-tolyl)benzo[d]thiazol-2-yl)acetamide was found to be the most active. To understand this urease inhibition, molecular docking studies were performed. The in silico studies showed that these acetamide derivatives bind to the non-metallic active site of the urease enzyme. Structure-activity studies revealed that H-bonding of compounds with the enzyme is important for its inhibition. PMID:26927044

  6. Blending Behavior of Polysulfone, Polyvinyl Acetate and Amines in Dimethyl Acetamide Solvent

    Asim Mushtaq

    2014-02-01

    Full Text Available In this study, research will be carried out to classify the blending behavior of glassy and rubbery polymer in solvent with amines. Commercially preface of a polymer prepared from a new monomer is uncertain and enormously expensive. A strategy to introduce new products into the market without a large investment is to take dissimilar polymers, amines and blend them together to make a new product with unique properties. The blending of polyvinyl acetate, polysulfone and diethanol amine, methyl diethanol amine, mono ethanol amine are examined with dimethyl acetamide solvent, which gives the results of appearance, pH and viscosity values by using measuring device viscometer and general pH testing technique. Through getting these results, the intrinsic miscibility of the mixture was finally established which shows that the homogenous or heterogeneous blends are depending on the blend preparation method and percentage of polymers and amines. The achievement of this advance has been restricted, because the mechanical properties of the blend with amines are classically worse than a simple mixing law would predict.

  7. Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanylpyridin-2-yl]acetamide hemihydrate

    Mehmet Akkurt

    2015-03-01

    Full Text Available The title compound, C9H10N4OS·0.5H2O, crystallizes with two independent molecules (A and B in the asymmetric unit, together with a water molecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95 (16° in molecule A and by 1.77 (16° in molecule B. In the crystal, the A and B molecules are linked by two N—H...Ocarbonyl hydrogen bonds, forming a dimer. The dimers are linked via N—H...N hydrogen bonds, forming ribbons that are linked by N—H...Owater hydrogen bonds to form sheets parallel to (110. The sheets are linked by O—H...N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel π–π interactions [inter-centroid distance = 3.734 (2 Å, interplanar distance = 3.3505 (11 Å and slippage = 1.648 Å], forming a three-dimensional structure.

  8. VUV photoionization of acetamide studied by electron/ion coincidence spectroscopy in the 8–24 eV photon energy range

    Highlights: ► We study the VUV photoionization of acetamide in the 8–24 eV photon energy range. ► Electron/ion coincidence measurements are performed using synchrotron radiation. ► The adiabatic ionization energy of acetamide is determined by TPEPICO measurements. ► VUV induced fragmentation pathways of acetamide are assigned and discussed. - Abstract: A VUV photoionization study of acetamide was carried out over the 8–24 eV photon energy range using synchrotron radiation and photoelectron/photoion coincidence (PEPICO) spectroscopy. Threshold photoelectron photoion coincidence (TPEPICO) measurements were also made. Photoion yield curves and branching ratios were measured for the parent ion and six fragment ions. The adiabatic ionization energy of acetamide was determined as I.E. (12A′) = (9.71 ± 0.02) eV, in agreement with an earlier reported photoionization mass spectrometry (PIMS) value. The adiabatic energy of the first excited state of the ion, 12A″, was determined to be ≈10.1 eV. Assignments of the fragment ions and the pathways of their formation by dissociative photoionization were made. The neutral species lost in the principal dissociative photoionization processes are CH3, NH2, NH3, CO, HCCO and NH2CO. Heats of formation are derived for all ions detected and are compared with literature values. Some astrophysical implications of these results are discussed.

  9. Dielectric relaxation studies of N,N-dimethyl formamide and N,N-dimethyl acetamide on complexation with phenols

    Dielectric absorption studies of H-bonded complexes of N,N-dimethyl formamide and N,N-dimethyl acetamide with p-cresol, p-chlorophenol, 2,4-dichlorophenol and p-nitrophenol in benzene have been made at 308 K using 9.37 GHz dielectric relaxation set up. The validity of the single frequency equation of Higasi et al. for multiple relaxation time τ(1) is found to be function of the hydrogen bonding strength of the phenolic hydrogen, whereas the group rotation relaxation time τ(2) is a function of the steric interactions of the proton donor. The relaxation time is maximum at 50:50 mol% ratio

  10. Collective dynamic dipole moment and orientation fluctuations, cooperative hydrogen bond relaxations, and their connections to dielectric relaxation in ionic acetamide deep eutectics: Microscopic insight from simulations.

    Das, Suman; Biswas, Ranjit; Mukherjee, Biswaroop

    2016-08-28

    The paper reports a detailed simulation study on collective reorientational relaxation, cooperative hydrogen bond (H-bond) fluctuations, and their connections to dielectric relaxation (DR) in deep eutectic solvents made of acetamide and three uni-univalent electrolytes, lithium nitrate (LiNO3), lithium bromide (LiBr), and lithium perchlorate (LiClO4). Because cooperative H-bond fluctuations and ion migration complicate the straightforward interpretation of measured DR timescales in terms of molecular dipolar rotations for these conducting media which support extensive intra- and inter-species H-bonding, one needs to separate out the individual components from the overall relaxation for examining the microscopic origin of various timescales. The present study does so and finds that reorientation of ion-complexed acetamide molecules generates relaxation timescales that are in sub-nanosecond to nanosecond range. This explains in molecular terms the nanosecond timescales reported by recent giga-Hertz DR measurements. Interestingly, the simulated survival timescale for the acetamide-Li(+) complex has been found to be a few tens of nanosecond, suggesting such a cation-complexed species may be responsible for a similar timescale reported by mega-Hertz DR measurements of acetamide/potassium thiocyanate deep eutectics near room temperature. The issue of collective versus single particle relaxation is discussed, and jump waiting time distributions are determined. Dependence on anion-identity in each of the cases has been examined. In short, the present study demonstrates that assumption of nano-sized domain formation is not required for explaining the DR detected nanosecond and longer timescales in these media. PMID:27586932

  11. Fluorescence spectroscopic studies of (acetamide + sodium/potassium thiocyanates) molten mixtures: composition and temperature dependence.

    Guchhait, Biswajit; Gazi, Harun Al Rasid; Kashyap, Hemant K; Biswas, Ranjit

    2010-04-22

    Steady state and time-resolved fluorescence spectroscopic techniques have been used to explore the Stokes' shift dynamics and rotational relaxation of a dipolar solute probe in molten mixtures of acetamide (CH(3)CONH(2)) with sodium and potassium thiocyanates (Na /KSCN) at T approximately 318 K and several other higher temperatures. The dipolar solute probe employed for this study is coumarin 153 (C153). Six different fractions (f) of KSCN of the following ternary mixture composition, 0.75 CH(3)CONH(2) + 0.25[(1 - f)NaSCN + fKSCN], have been considered. The estimated experimental dynamic Stokes' shift for these systems ranges between 1800 and 2200 cm(-1) (+/-250 cm(-1)), which is similar to what has been observed with the same solute probe in several imidazolium cation based room temperature ionic liquids (RTIL) and in pure amide solvents. Interestingly, this range of estimated Stokes' shift, even though not corresponding to the megavalue of static dielectric constant reported in the literature for a binary mixture of molten CH(3)CONH(2) and NaSCN, exhibits a nonmonotonic KSCN concentration dependence. The magnitudes of the dynamic Stokes' shift detected in the present experiments are significantly less than the estimated ones, as nearly 40-60% of the total shift is missed due to the limited time resolution employed (full-width at half-maximum of the instrument response function approximately 70 ps). The solvation response function, constructed from the detected shifts in these systems, exhibits triexponential decay with the fastest time constant (tau(1)) in the 10-20 ps range, which might be much shorter if measured with a better time resolution. The second time constant (tau(2)) lies in the 70-100 ps range, and the third one (tau(3)) ranges between 300 and 800 ps. Both these time constants (tau(2) and tau(3)) show alkali metal ion concentration dependence and exhibit viscosity decoupling at higher viscosity in the NaSCN-enriched region. Time dependent rotational

  12. Synthesis, potential anticonvulsant and antidepressant effects of 2-(5-methyl-2,3-dioxoindolin-1-yl)acetamide derivatives.

    Zhen, Xinghua; Peng, Zhou; Zhao, Shuilian; Han, Yan; Jin, Qinghao; Guan, Liping

    2015-07-01

    A new series of 2-(5-methyl-2,3-dioxoindolin-1-yl)acetamide derivatives were synthesized and evaluated for their anticonvulsive activity in a pentylenetetrazole (PTZ)-evoked convulsion model and antidepressant activity in the forced swimming test (FST) model. Eleven synthesized compounds were found to be protective against PTZ-induced seizure and showed the anticonvulsant activity. In addition, four of the synthesized compounds (4l, 4m, 4p and 4q) showed potent antidepressant-like activity. Among these compounds, compound 4l was found to have the most potent antidepressant-like activity, and significantly reduced the duration of immobility time at 100 mg/kg dose level when compared to the vehicle control, which is similar to the reference drug fluoxetine. PMID:26579465

  13. Synthesis of N-(6-Arylbenzo[d]thiazole-2-acetamide Derivatives and Their Biological Activities: An Experimental and Computational Approach

    Yasmeen Gull

    2016-02-01

    Full Text Available A new series of N-(6-arylbenzo[d]thiazol-2-ylacetamides were synthesized by C-C coupling methodology in the presence of Pd(0 using various aryl boronic pinacol ester/acids. The newly synthesized compounds were evaluated for various biological activities like antioxidant, haemolytic, antibacterial and urease inhibition. In bioassays these compounds were found to have moderate to good activities. Among the tested biological activities screened these compounds displayed the most significant activity for urease inhibition. In urease inhibition, all compounds were found more active than the standard used. The compound N-(6-(p-tolylbenzo[d]thiazol-2-ylacetamide was found to be the most active. To understand this urease inhibition, molecular docking studies were performed. The in silico studies showed that these acetamide derivatives bind to the non-metallic active site of the urease enzyme. Structure-activity studies revealed that H-bonding of compounds with the enzyme is important for its inhibition.

  14. Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides.

    Surineni, Goverdhan; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas

    2016-08-01

    A series of novel dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides, designed by assembling antitubercular pharmacophoric fragments, dibenzofuran, 2-aminothiazole and substituted triazoles in one molecular architecture, were evaluated against Mycobacterium tuberculosis. The new analogues 6a-p accomplished in four step synthetic sequence utilizing click chemistry in the penultimate step, was fully characterized by their NMR and mass spectral data. Among the compounds 6a-p screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, three compounds 6j (MIC: 1.56μg/mL); 6a and 6p (MIC: 3.13μg/mL) was found to be most active and exhibited lower cytotoxicity. Among these three, 6j could be a candidate to consider as a drug like hit analogue for further development. PMID:27317646

  15. 3,6-O-[N-(2-Aminoethyl)-acetamide-yl]-chitosan exerts antibacterial activity by a membrane damage mechanism.

    Yan, Feilong; Dang, Qifeng; Liu, Chengsheng; Yan, Jingquan; Wang, Teng; Fan, Bing; Cha, Dongsu; Li, Xiaoli; Liang, Shengnan; Zhang, Zhenzhen

    2016-09-20

    A novel chitosan derivative, 3,6-O-[N-(2-aminoethyl)-acetamide-yl]-chitosan (AACS), was successfully prepared to improve water solubility and antibacterial activity of chitosan. AACS had good antibacterial activity, with minimum inhibitory concentrations of 0.25mg/mL, against Escherichia coli and Staphylococcus aureus. Cell membrane integrity, electric conductivity and NPN uptake tests showed that AACS caused quickly increasing the release of intracellular nucleic acids, the uptake of NPN, and the electric conductivity by damaging membrane integrity. On the other hand, hydrophobicity, cell viability and SDS-PAGE experiments indicated that AACS was able to reduce the surface hydrophobicity, the cell viability and the intracellular proteins through increasing membrane permeability. SEM observation further confirmed that AACS could kill bacteria via disrupting their membranes. All results above verified that AACS mainly exerted antibacterial activity by a membrane damage mechanism, and it was expected to be a new food preservative. PMID:27261735

  16. Synthesis, cytotoxic study and docking based multidrug resistance modulator potential analysis of 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamides.

    Kumar, Rajesh; Kaur, Maninder; Bahia, Malkeet Singh; Silakari, Om

    2014-06-10

    The present study describes the synthesis of fifteen 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamide derivatives (13a-o) through condensation of 2-chloro-N-phenyl acetamides (12a-o) with acridone molecule (10). All the synthesized compounds were screened for their anti-cancer activity against three diverse cell lines including breast (MCF-7), cervical (HeLa) and lung adenocarcinoma (A-549) employing standard MTT assay. Among synthesized molecules, 13k and 13l showed good cytotoxicity activity against considered three cancer cell lines. Additionally, in silico studies of multidrug resistance modulator (MDR) effects of these compounds was performed by docking simulation in the ATP binding site of P-gp. The results of docking simulation displayed important interactions of these molecules in the active site of this protein and predicted their MDR modulator behavior. PMID:24769346

  17. Dielectric relaxation of ethanol and -methyl acetamide polar mixture in C6H6 at 9.90 GHz

    S Sahoo; T R Middya; S K Sit

    2014-10-01

    Debye relaxation times $(_{jk})$ and dipole moments $(_{jk})$ of binary ($jk$) polar mixtures of ethanol (EtOH) and -methyl acetamide (NMA) dissolved in benzene(i) are studied by studying conductivity of solution at 9.90 GHz for different temperatures, different mole fractions ($x_j$) of ethanol and different weight fractions $(w_{jk})$ of the mixtures, respectively. The variation of $_{jk}−x_j$ from linear slope of imaginary ($''_{ijk}$) against real ($'_{ijk}$) part of total conductivity ($^{*}_{ijk}$) curve reveals solute–solute (dimer) or solute–solvent (monomer) molecular associations up to $x_j$ = 0.0−0.3 and thereafter, solute–solvent molecular associations. $_{jk}$s from the ratio of slopes of $''_{ijk}$−w_{jk}$ and $'_{ijk}$−w_{jk}$ curves exhibit solute–solvent molecular association for all $x_j$s which are consistent with the $_{jk}−x_j$ curves at all temperatures except at 35°C. This signifies the validity of both the proposed methods in estimating and . The molecular dynamics of the polar mixture are ascertained from Eyring rate theory. Theoretical dipole moments from bond angles and bond moments ($_{\\text{theo}}$) are also calculated to predict associational aspects.

  18. Density relaxation and particle motion characteristics in a non-ionic deep eutectic solvent (acetamide + urea): Time-resolved fluorescence measurements and all-atom molecular dynamics simulations

    Das, Anuradha; Das, Suman; Biswas, Ranjit, E-mail: ranjit@bose.res.in [Chemical, Biological and Macromolecular Sciences, S. N. Bose National Centre for Basic Sciences, Block-JD, Sector-III, Salt Lake, Kolkata, West Bengal 700098 (India)

    2015-01-21

    Temperature dependent relaxation dynamics, particle motion characteristics, and heterogeneity aspects of deep eutectic solvents (DESs) made of acetamide (CH{sub 3}CONH{sub 2}) and urea (NH{sub 2}CONH{sub 2}) have been investigated by employing time-resolved fluorescence measurements and all-atom molecular dynamics simulations. Three different compositions (f) for the mixture [fCH{sub 3}CONH{sub 2} + (1 − f)NH{sub 2}CONH{sub 2}] have been studied in a temperature range of 328-353 K which is ∼120-145 K above the measured glass transition temperatures (∼207 K) of these DESs but much lower than the individual melting temperature of either of the constituents. Steady state fluorescence emission measurements using probe solutes with sharply different lifetimes do not indicate any dependence on excitation wavelength in these metastable molten systems. Time-resolved fluorescence anisotropy measurements reveal near-hydrodynamic coupling between medium viscosity and rotation of a dissolved dipolar solute. Stokes shift dynamics have been found to be too fast to be detected by the time-resolution (∼70 ps) employed, suggesting extremely rapid medium polarization relaxation. All-atom simulations reveal Gaussian distribution for particle displacements and van Hove correlations, and significant overlap between non-Gaussian (α{sub 2}) and new non-Gaussian (γ) heterogeneity parameters. In addition, no stretched exponential relaxations have been detected in the simulated wavenumber dependent acetamide dynamic structure factors. All these results are in sharp contrast to earlier observations for ionic deep eutectics with acetamide [Guchhait et al., J. Chem. Phys. 140, 104514 (2014)] and suggest a fundamental difference in interaction and dynamics between ionic and non-ionic deep eutectic solvent systems.

  19. Synthesis and evaluation of 2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)-N-(3-(trifluoromethyl)phenyl)acetamides and N-(4-chloro-3-fluorophenyl)-2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)acetamides as antimicrobial agents

    Kalpesh Parikh; Deepkumar Joshi

    2014-05-01

    A series of 2-mercapto-5-phenyl-1,3,4-oxadiazole derivatives have been condensed with different phenyl acetamide derivatives possessing fluorine atom at meta position; resulting in the formation of 2-(5-aryl- 1,3,4-oxadiazol-2-ylthio)-N-(3-(trifluoromethyl)phenyl)acetamide (5a-j) and N-(4-chloro-3-fluorophenyl)-2-(5-aryl-1,3,4-oxadiazol-2-ylthio)acetamide (5k-t) derivatives. The antimicrobial properties of the synthesized entities (5a-t) measured as their MIC (Minimum Inhibitory Concentration) values were evaluated by using the broth dilution method against Gram-positive bacteria (S. aureus and E. faecalis), Gram-negative bacteria (E. coli and P. aeruginosa) and fungi (C. albicans and A. niger). The results of antimicrobial activities (in g/ml) revealed the fact that the compounds 5a and g bearing a maximum number of fluorine atoms showed the highest potency among the synthesized compounds against the broad panel of bacterial and fungal strains. The presence of fluorine atom at the meta position in the phenyl ring of final derivatives (5a-t) brought about an enhancement of their antimicrobial properties to a notable extent.

  20. Electrochemical preparation of few layer-graphene nanosheets via reduction of oriented exfoliated graphene oxide thin films in acetamide-urea-ammonium nitrate melt under ambient conditions

    Electrochemical reduction of exfoliated graphene oxide, prepared from pre-exfoliated graphite, in acetamide-urea-ammonium nitrate ternary eutectic melt results in few layer-graphene thin films. Negatively charged exfoliated graphene oxide is attached to positively charged cystamine monolyer self-assembled on a gold surface. Electrochemical reduction of the oriented graphene oxide film is carried out in a room temperature, ternary molten electrolyte. The reduced film is characterized by atomic force microscopy (AFM), conductive AFM, Fourier-transform infrared spectroscopy and Raman spectroscopy. Ternary eutectic melt is found to be a suitable medium for the regulated reduction of graphene oxide to reduced graphene oxide-based sheets on conducting surfaces.

  1. Crystal structure of N-[4-amino-5-cyano-6-(methyl­sulfan­yl)pyridin-2-yl]-2-chloro­acetamide

    Shaaban K. Mohamed; Knight, Kyle S.; Akkurt, Mehmet; Hussein, Bahgat R. M.; Mustafa R. Albayati

    2015-01-01

    In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83 (12)°. The O=C—C—Cl torsion angle is 46.4 (3)° and an intra­molecular C—H⋯O inter­action generates an S(6) ring. In the crystal, mol­ecules are linked by N—H⋯O, N—H⋯N and C—H⋯N hydrogen bonds, generating sheets lying parallel to (120).

  2. Molecular cloning and characterization of an amidase from Arabidopsis thaliana capable of converting indole-3-acetamide into the plant growth hormone, indole-3-acetic acid

    Pollmann, Stephan; Neu, Daniel; Weiler, Elmar W.

    2003-01-01

    Acylamidohydrolases from higher plants have not been characterized or cloned so far. AtAMI1 is the first member of this enzyme family from a higher plant and was identified in the genome of Arabidopsis thaliana based on sequence homology with the catalytic-domain sequence of bacterial acylamidohydrolases, particularly those that exhibit indole-3-acetamide amidohydrolase activity. AtAMI1 polypeptide and mRNA are present in leaf tissues, as shown by immunoblotting and RT-PCR, respectively. AtAM...

  3. Occurrence of isoxaflutole, acetamide, and triazine herbicides and their degradation products in 10 Iowa rivers draining to the Mississippi and Missouri Rivers, 2004

    Scribner, Elisabeth A.; Meyer, Michael T.; Kalkhoff, Stephen J.

    2006-01-01

    During 2004, a study to document the occurrence of herbicides and herbicide degradation products was conducted for 10 major Iowa rivers draining to the Missouri and Mississippi Rivers. Seventy-five water-quality samples were collected to measure isoxaflutole, acetamide, and triazine herbicides and their herbicide degradation products. An analytical method to measure isoxaflutole and its degradation products, diketonitrile and benzoic acid, was developed by the U.S. Geological Survey Organic Geochemistry Research Laboratory in Lawrence, Kansas, using vacuum manifold solid-phase extraction and liquid chromatography/mass spectrometry/mass spectrometry and is described in this report.

  4. Sorption-Desorption Behavior of Newly synthesized N-(1H-Benzimidazole -2 ylmethyl) Acetamide (ABNZ) on Selected Soils and its Antifungal activity

    A batch equilibrium method has been utilized to investigate the adsorption-desorption behavior of a versatile commercially available fungicide N-(1H-benzimidazole-2ylmethyl) acetamide (ABNZ) on four Pakistani soils geographically distant, from hilly to desert areas. Both qualitative and quantitative analysis has been done for sorption-desorption behavior of ABNZ. These analyses are done in the different concentration of fungicide (0-0.25, 0.25-0.5, 0.5-0.75). Based on statistical analysis ABNZ execute the Freundlich adsorption isotherm in all four tested soils having values of slope n<1 resembling the L-type curve. The distribution co-efficient K/sub d(ads)/ ranges from (2.66 to 12.42 ml/meu g/sup -1/) indicating low adsorption of ABNZ overall. Sorption increases with soil organic carbon content, exhibited greater degree of adsorption for hilly soil and least adsorption on sandy soil of Multan, Punjab. Desorption studies reveal that the adsorbed fungicide is firmly retained by soil particles and present a certain degree of irreversibility. The results indicate that the soil organic matters followed by clay content are the most important soil properties governing the fungicide sorption capacity. Compound N-(1H- benzimidazole -2-ylmethyl) acetamide (ABNZ) showed maximum antifungal activity compared to rest of the tested compound. This anti-fungal activity is substantial in comparison to other pesticides. It causes 40% inhibition of Microsporum canis and Fusarium solani. (author)

  5. VUV photoionization of acetamide studied by electron/ion coincidence spectroscopy in the 8-24 eV photon energy range

    Schwell, Martin

    2012-01-01

    A VUV photoionization study of acetamide was carried out over the 8-24 eV photon energy range using synchrotron radiation and photoelectron/photoion coincidence (PEPICO) spectroscopy. Threshold photoelectron photoion coincidence (TPEPICO) measurements were also made. Photoion yield curves and branching ratios were measured for the parent ion and six fragment ions. The adiabatic ionization energy of acetamide was determined as I.E. (1 2A′) = (9.71 ± 0.02) eV, in agreement with an earlier reported photoionization mass spectrometry (PIMS) value. The adiabatic energy of the first excited state of the ion, 1 2A″, was determined to be ≈10.1 eV. Assignments of the fragment ions and the pathways of their formation by dissociative photoionization were made. The neutral species lost in the principal dissociative photoionization processes are CH 3, NH 2, NH 3, CO, HCCO and NH 2CO. Heats of formation are derived for all ions detected and are compared with literature values. Some astrophysical implications of these results are discussed. © 2011 Elsevier B.V. All rights reserved.

  6. Spectroscopic and theoretical studies of some N , N -diethyl-2-[(4‧-substituted)phenylsulfonyl]acetamides

    Vinhato, Elisângela; Olivato, Paulo R.; Rodrigues, Alessandro; Zukerman-Schpector, Julio; Colle, Maurizio Dal

    2011-09-01

    The analysis of the IR carbonyl band of the N, N-diethyl-2-[(4'-substituted)phenylsulfonyl]acetamides Et 2NC(O)CH 2S(O) 2sbnd C 6H 4sbnd Y (Y = OMe 1, Me 2, H 3, Cl 4, Br 5, NO 26) supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three pairs ( anti and syn) of cis ( c) and gauche ( g1 and g2) conformers in the gas phase, being the gauche conformers significantly more stable than the cis ones. The anti geometry is more stable than the syn one, for each pair of cis and gauche conformers. The summing up of the orbital (NBO analysis) and electrostatic interactions justifies quite well the populations and the νCO frequencies of the anti and syn pairs of c, g1 and g2 conformers. The IR higher carbonyl frequency component whose population is ca. 10%, in CCl 4, may be ascribed to the least stable and most polar cis conformer pair (in the gas phase) and the lower frequency component whose population is ca. 90%, to the summing up of the populations of the two most stable and least polar gauche conformer pairs ( g1 and g2) (in the gas phase). The reversal of the cis( c)/ gauche ( g1 + g2) population ratio observed in chloroform ca. 60% ( cis)/40% ( gauche) and the occurrence of the most polar cis( c) conformer only, in acetonitrile, strongly suggests the coalescence of the two gauche components in a unique carbonyl band in solution. A further support to this rationalization is given by the single point PCM solvation model performed by HF/6-31G(d,p) method, which showed a progressive increase of the c/( g1 + g2) ratio going from gas to CCl 4, to CHCl 3 and to CH 3CN. X-ray single crystal analysis of 4 indicates that this compound assumes, in the solid state, the syn-clinal ( gauche) conformation with respect to the [O dbnd C sbnd CH 2sbnd S] moiety, and the most stable anti geometry relative to the [C(O)N(CH 2CH 3) 2] fragment. In order to obtain larger energy gain from the crystal packing the molecules of 4 are linked in centrosymmetric dimers

  7. Density functional studies of molecular structures of N-methyl formamide, N,N-dimethyl formamide, and N,N-dimethyl acetamide

    V Renugopalakrishnan; G Madrid; G Cuevas; A T Hagler

    2000-02-01

    Density functional theory was applied to the calculation of molecular structures of N-methyl formamide (NMF), N,N-dimethyl formamide (DMF), and N,Ndimethyl acetamide (DMA). DFT calculations on NMF, DMF, and DMA were performed using a combination of the local functional of Vosko, Wilk, and Nusair (VWN) with the nonlocal exchange functional of Becke and the nonlocal correlational functional of Lee, Yang, and Parr (BLYP). The adiabatic connection method (ACM) of Becke has also been used, for the first time, for the calculation of molecular structures of NMF, DMF, and DMA. The calculated molecular structures are in excellent agreement with the experimental geometries of NMF and DMA derived from gas-phase electron-diffraction studies. Sparse experimental data on the gas-phase geometry of DMF reported in the literature compares well with the DFT results on DMF. DFT emerges as a powerful method to calculate molecular structures.

  8. Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide

    ZHANG Qunfeng; L(U) Jinghui; MA Lei; LU Chunshan; LIU Wei; LI Xiaonian

    2013-01-01

    Deactivation of Pd/C catalyst often occurs in liquid hydrogenation using industrial materials.For instance,the Pd/C catalyst is deactivated severely in the hydrogenation of N-(3-nitro-4-methoxyphenyl) acetamide.In this study,the chemisorption of sulfur on the surface of deactivated Pd/C was detected by energy dispersive spectrometer and X-ray photoelectron spectroscopy.Sulfur compounds poison the Pd/C catalyst and increase the formation of azo deposit,reducing the activity of catalyst.We report a mild method to regenerate the Pd/C catalyst:wash the deposit by N,N-dimethylformamide and oxidize the chemisorbed sulfur by hot air.The regenerated Pd/C catalyst can be reused at least ten runs with stable activity.

  9. Facilitated transport of tetravalent plutonium from nitric acid medium using a novel extractant - bis-(2-Ethylhexyl) Carbamoyl Methoxy Phenoxy-Bis-(Ethylhexyl) Acetamide (Benzodioxodiamide, BenzoDODA)

    We have recently reported the synthesis and Pu extraction behavior of a novel extractant, Bis-(2-ethylhexyl) carbamoylmethoxyphenoxy-bis-(2-ethylhexyl) acetamide (BenzoDODA), the first Pu(IV) selective ligand. The extractant was found to have selective extraction of Pu(IV) from other actinides and fission products, fast kinetics of extraction, no third phase formation, easy stripping, good hydrodynamic parameters, etc. In recent years liquid membrane technology have gained considerable importance as an alternative to solvent extraction due to low ligand inventory, low volume of secondary waste generation, alleviation of the third phase problem, etc. Being an exotic reagent, ligand inventory of BenzoDODA have to be minimized specially for streams having low concentrations of Pu. With this aim, in the present communication we report the transport studies of Pu(IV) using BenzoDODA as carrier in SLM (Supported Liquid Membrane) mode

  10. SYNTHESIS OF N-(ALKYL OR ARYL-2-(1H-BENZOTRIAZOL-1-YL-ACETAMIDES AS SELECTIVE COX-2 INHIBITOR

    Amruta Patil* and Gita Chaurasia

    2013-11-01

    Full Text Available Microwave assisted organic synthesis (MAOS has emerged as frontier in pharmaceutical research for synthesis of newer drugs and implementing GREEN chemistry. Arylacetamides are pharmaceutically interesting as they show various biological activities such as analgesic, local anesthetic, antiarthritic, antiarrhythmic activities, etc. In arylacetamides the nature of aromatic ring and its substituent is primary determinant for its activity. To serve this purpose, we have decided to substitute arylacetamide with benzotriazole which may exploit the analgesic potential of newly synthesized derivatives i.e N-(Alkyl or Aryl-2-(1H-benzotriazol-1-yl-acetamides and thus it may be helpful in reducing the pain without having side effect of ulcerogenicity.

  11. Synthesis of 2-(3-methyl-2-oxoquinoxalin-1(2)-yl)acetamide-based azetidinone derivatives as potent antibacterial and antifungal agents

    Shiv Kumar; Nitin Kumar; Sushma Drabu; Md Akram Minhaj

    2013-01-01

    Twelve compounds belonging to series N-[3-chloro-2-oxo-4-(substituted)phenylazetidin-1-yl]-2-(3-methyl-2-oxoquinoxalin-1(2)-yl)acetamide (5a-l) were synthesized. These compounds were evaluated for their in vitro antibacterial against E. coli, S. aureus, K. pneumoniae, P. aeruginosa and antifungal activity against C. albicans, A. niger and A. flavus by cup-plate method. Structures of all the newly synthesized compounds were confirmed by their spectral data interpretation. Compound 5g having -dimethylaminophenyl group on 4-position of azetidinone ring attached to N-atom of acetamido group on 1-position of 3-methyl-1-quinoxaline-2-one, was found to be active against all the bacterial and fungal strains under investigation.

  12. 2-[3,5-Bis-(2-fluorobenzylidene-4-piperidon-1-yl]-N-(4-fluorobenzyl-acetamide and Its Evaluation as an Anticancer Agent

    Pallavi Lagisetty

    2013-01-01

    Full Text Available Synthesis of 2-[3,5-bis-(2-fluorobenzylidene-4-piperidon-1-yl]-N-(4-fluorobenzyl-acetamide, a derivative of 3,5-bis-(2-fluorobenzylidene-4-piperidone (EF24, as an antiproliferative and imageable compound is described. The radioactive derivative was synthesized in 40–45% radiochemical yield using N-[4-fluoro(18Fbenzyl]-2-bromoacetamide (NFLOBA as a radiolabeled synthon for coupling with EF24. Cell proliferation assays showed that 2-[3,5-bis-(2-fluorobenzylidene-4-piperidon-1-yl]-N-(4-fluorobenzyl-acetamide (NFLOBA-EF24 had antiproliferative efficacy similar to that of EF24 in lung adenocarcinoma H441 cells. 18F-NFLOBA-EF24 was investigated in normal rats for whole-body PET imaging and biodistribution. At necropsy after 1 h of injection, about 12% of injected compound was still circulating in blood; liver, kidney, and muscle were other tissues with moderate amounts of accumulation. In order to assess the tumor-suppressive activity, nonradioactive NFLOBA-EF24 was administered in nude rats carrying xenograft H441 tumor. After 15 days of treatment, the tumor size decreased by approximately 83% compared to the tumors in control rats. The tumor regression was also confirmed by molecular imaging of glucose metabolism with 18F- fluorodeoxyglucose. The results suggest that EF24 could be efficiently modified with 18F-labeled synthon NFLOBA for convenient PET imaging without altering the antitumor efficacy of the original compound. This study provides visual kinetics of synthetic curcuminoid EF24 by positron emission tomography for the first time.

  13. Kirkwood-Buff analysis of aqueous N-methylacetamide and acetamide solutions modeled by the CHARMM additive and Drude polarizable force fields.

    Lin, Bin; Lopes, Pedro E M; Roux, Benoît; MacKerell, Alexander D

    2013-08-28

    Kirkwood-Buff analysis was performed on aqueous solutions of N-methylacetamide and acetamide using the Chemistry at HARvard Molecular Mechanics additive and Drude polarizable all-atom force fields. Comparison of a range of properties with experimental results, including Kirkwood-Buff integrals, excess coordination numbers, solution densities, partial molar values, molar enthalpy of mixing, showed both models to be well behaved at higher solute concentrations with the Drude model showing systematic improvement at lower solution concentrations. However, both models showed difficulties reproducing experimental activity derivatives and the excess Gibbs energy, with the Drude model performing slightly better. At the molecular level, the improved agreement of the Drude model at low solute concentrations is due to increased structure in the solute-solute and solute-solvent interactions. The present results indicate that the explicit inclusion of electronic polarization leads to improved modeling of dilute solutions even when those properties are not included as target data during force field optimization. PMID:24007020

  14. Glass transition dynamics and conductivity scaling in ionic deep eutectic solvents: The case of (acetamide + lithium nitrate/sodium thiocyanate) melts

    Tripathy, Satya N., E-mail: satyanarayantripathy@gmail.com; Wojnarowska, Zaneta; Knapik, Justyna; Paluch, Marian [Institute of Physics, University of Silesia, Uniwersytecka 4, 40-007 Katowice (Poland); Silesian Center for Education and Interdisciplinary Research, 75 Pulku Piechoty 1A, 41-500 Chorzow (Poland); Shirota, Hideaki [Department of Nanomaterial Science and Department of Chemistry, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522 (Japan); Biswas, Ranjit [Department of Chemical, Biological and Macromolecular Sciences, S. N. Bose National Centre for Basic Sciences, JD Block, Sector III, Salt Lake, Kolkata 700098 (India)

    2015-05-14

    A detailed investigation on the molecular dynamics of ionic deep eutectic solvents (acetamide + lithium nitrate/sodium thiocyanate) is reported. The study was carried out employing dielectric relaxation spectroscopy covering seven decades in frequency (10{sup −1}-10{sup 6} Hz) and in a wide temperature range from 373 K down to 173 K, accessing the dynamic observables both in liquid and glassy state. The dielectric response of the ionic system has been presented in the dynamic window of modulus formalism to understand the conductivity relaxation and its possible connection to the origin of localized motion. Two secondary relaxation processes appear below glass transition temperature. Our findings provide suitable interpretation on the nature of secondary Johari-Goldstein process describing the ion translation and orientation of dipoles in a combined approach using Ngai’s coupling model. A nearly constant loss feature is witnessed at shorter times/lower temperatures. We also discuss the ac conductivity scaling behavior using Summerfield approach and random free energy barrier model which establish the time-temperature superposition principle. These experimental observations have fundamental importance on theoretical elucidation of the conductivity relaxation and glass transition phenomena in molten ionic conductors.

  15. Glass transition dynamics and conductivity scaling in ionic deep eutectic solvents: The case of (acetamide + lithium nitrate/sodium thiocyanate) melts

    A detailed investigation on the molecular dynamics of ionic deep eutectic solvents (acetamide + lithium nitrate/sodium thiocyanate) is reported. The study was carried out employing dielectric relaxation spectroscopy covering seven decades in frequency (10−1-106 Hz) and in a wide temperature range from 373 K down to 173 K, accessing the dynamic observables both in liquid and glassy state. The dielectric response of the ionic system has been presented in the dynamic window of modulus formalism to understand the conductivity relaxation and its possible connection to the origin of localized motion. Two secondary relaxation processes appear below glass transition temperature. Our findings provide suitable interpretation on the nature of secondary Johari-Goldstein process describing the ion translation and orientation of dipoles in a combined approach using Ngai’s coupling model. A nearly constant loss feature is witnessed at shorter times/lower temperatures. We also discuss the ac conductivity scaling behavior using Summerfield approach and random free energy barrier model which establish the time-temperature superposition principle. These experimental observations have fundamental importance on theoretical elucidation of the conductivity relaxation and glass transition phenomena in molten ionic conductors

  16. Identification of N-phenyl-2-(N-phenylphenylsulfonamido)acetamides as new RORγ inverse agonists: Virtual screening, structure-based optimization, and biological evaluation.

    Song, Yu; Xue, Xiaoqian; Wu, Xishan; Wang, Rui; Xing, Yanli; Yan, Weiqun; Zhou, Yulai; Qian, Chao-Nan; Zhang, Yan; Xu, Yong

    2016-06-30

    Retinoic acid receptor-related orphan receptors (RORs) are ligand-dependent transcriptional factors and members of the nuclear receptor superfamily. RORs regulate inflammation, metabolic disorders and circadian rhythm. RORγ is a promising therapeutic drug target for treating Th17-mediated autoimmune diseases. In our study, we performed structure-based virtual screening and ligand-based virtual screening targeting the RORγ ligand-binding domain and successfully identified N-phenyl-2-(N-phenylphenylsulfonamido) acetamides as a type of RORγ inverse agonist. Among the 28 purchased compounds, C11 was confirmed to be active with micromolar IC50 values in both an AlphaScreen assay (62.58 μM) and a cell-based reporter gene assay (4.54 μM). Structure-guided optimization of the compound C11 led to the identification of compound 39, which significantly enhanced RORγ inhibition with an IC50 value of 630 nM. The RORγ antagonism of 39 was 7-fold higher than that of hit compound C11. These results represent a promising starting point for developing potent small molecule RORγ inverse agonists for the treatment of autoimmune diseases, such as rheumatoid arthritis, psoriasis, and multiple sclerosis. PMID:27043267

  17. A acetamida de pirrolidona como medicação auxiliar no tratamento da paralisia cerebral Pyrrolidone acetamide as an auxiliary drug in the treatment of cerebral palsy

    Francisca Salete Pinheiro Chagas Ribeiro

    1976-06-01

    Full Text Available Vinte crianças, com diagnóstico de paralisia cerebral (PC e sob tratamento clássico, fisioterápico e pedagógico, receberam piracetam (acetamida de pirrolidona como medicação auxiliar. O objetivo foi melhorar os problemas de espasticidade, apredizagem, neurolabilidade, visando a um rendimento melhor do tratamento global da PC. O grupo medicado foi comparado com um grupo controle de 20 crianças que só eram objeto do tratamento habitual. A comparação mostrou resultados favoráveis no grupo medicado. A droga foi administrada na dose de 80 mg/kg/dia durante 10 semanas. Os critérios de avaliação dos resultados foram psicológicos, clínico, fisioterápico e pedagógico. A droga foi administrada em nova forma de apresentação: solução, para uso oral, a 6%.Twenty children, with the diagnosis of cerebral palsy (CP and under classical, physiotherapeutical and pedagogical, treatment, received piracetam (pyrrolidine acetamide as an auxiliary drug. The goal was to better spasticity, learning and nervous instability problems aiming at better results of over-all treatment of CP. The group that received the drug has been compared to a control group of 20 children treated by the customary treatment only. The comparison showed favourable results for the medicated group. The drug was administered in the dose of 80 mg/kg/day during 10 weeks. The criteria for evaluation have been psychological, clinical, physiotherapeutical and pedagogical. The drug has been given in a new form of presentation: 6% solution for oral use.

  18. Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells.

    Kulabaş, Necla; Tatar, Esra; Bingöl Özakpınar, Özlem; Özsavcı, Derya; Pannecouque, Christophe; De Clercq, Erik; Küçükgüzel, İlkay

    2016-10-01

    In this study, a series of thiosemicarbazide derivatives 12-14, 1,2,4-triazol-3-thione derivatives 15-17 and compounds bearing 2-(4H-1,2,4-triazole-3-ylthio)acetamide structure 18-32 have been synthesized starting from phenolic compounds such as 2-naphthol, paracetamol and thymol. Structures and purity of the target compounds were confirmed by the use of their chromatographic and spectral data besides microanalysis. All of the synthesized new compounds 12-32 were evaluated for their anti-HIV activity. Among these compounds, three representatives 18, 19 and 25 were selected and evaluated by the National Cancer Institute (NCI) against the full panel of 60 human cancer cell lines derived from nine different cancer types. Antiproliferative effects of the selected compounds were demonstrated in human tumor cell lines K-562, A549 and PC-3. These compounds inhibited cell growth assessed by MTT assay. Compound 18, 19 and 25 exhibited anti-cancer activity with IC50 values of 5.96 μM (PC-3 cells), 7.90 μM (A549/ATCC cells) and 7.71 μM (K-562 cells), respectively. After the cell viability assay, caspase activation and Bcl-2 activity of the selected compounds were measured and the loss of mitochondrial membrane potential (MMP) was detected. Compounds 18, 19 and 25 showed a significant increase in caspase-3 activity in a dose-dependent manner. This was not observed for caspase-8 activity with compound 18 and 25, while compound 19 was significantly elevated only at the dose of 50 μM. In addition, all three compounds significantly decreased the mitochondrial membrane potential and expression of Bcl-2. PMID:27214512

  19. Synthesis and anti-Parkinson′s screening of some novel 2-(naphthalen-1-yl-N-[2-substituted (4-oxothiazolidin-3-yl]acetamide derivatives

    S Gomathy

    2012-01-01

    Full Text Available Context: The objective of this study is to synthesize some novel 2-(naphthalen-1-yl-N-[2-substituted (4-oxothiazolidin-3-yl] acetamide derivatives and to study their anti-Parkinson′s activity. Materials and Methods: Ethyl (naphthalen-1-yl acetate (1 was prepared from naphthalene-1-yl acetic acid in ethanol. Condensation of ethyl (naphthalen-1-yl acetate (1 with an equimolar quantity of hydrazine hydrate in methanol afforded 2-(naphthalen-1-yl acetohydrazide (2. Compound 2 which on condensation with different aromatic aldehydes yielded respective Schiff bases (3a-e. The Schiff bases are then cyclised with mercaptoacetic acid in dioxane to yield the corresponding naphthalene bearing 4-thiazolidinone derivatives (4a-e. The structures of the synthesized compounds have been established based on their analytical and spectral data such as FT-IR, Mass and NMR spectroscopy. Results: The synthesized compounds were evaluated for their anti-Parkinson′s screening using in vitro free radical scavenging assay. Compounds 4c, 4d, and 4e showed potent free radical scavenging activity giving 82%, 74% and 76% respectively. Three compounds 4c, 4d and 4e were taken for in vivo anti-Parkinson′s screening by 6-Hydroxydopamine lesioned rat′s model (6-OHDA. Among these, one of the 4-thiazolidinone derivatives having a 3-nitro phenyl group at 2 nd position 4c exhibited maximum anti-Parkinson′s activity. Conclusion: Thiazolidinone derivatives showed significant anti-Parkinson′s activity in the 6-OHDA lesioned rat model. The estimated parameters were closely relevant to clinical parkinsonism, and the drug treatment protected the diseased brain of a rat. We appreciate further detailed studies with these drugs in anti-Parkinson′s pharmacology and toxicology.

  20. Production of Indole-3-Acetic Acid via the Indole-3-Acetamide Pathway in the Plant-Beneficial Bacterium Pseudomonas chlororaphis O6 Is Inhibited by ZnO Nanoparticles but Enhanced by CuO Nanoparticles

    Dimkpa, Christian O.; Zeng, Jia; McLean, Joan E; Britt, David W.; Zhan, Jixun; Anderson, Anne J.

    2012-01-01

    The beneficial bacterium Pseudomonas chlororaphis O6 produces indole-3-acetic acid (IAA), a plant growth regulator. However, the pathway involved in IAA production in this bacterium has not been reported. In this paper we describe the involvement of the indole-3-acetamide (IAM) pathway in IAA production in P. chlororaphis O6 and the effects of CuO and ZnO nanoparticles (NPs). Sublethal levels of CuO and ZnO NPs differentially affected the levels of IAA secreted in medium containing tryptophan...

  1. Methods of Analysis by the U.S. Geological Survey Organic Geochemistry Research Group?Determination of acetamide herbicides and their degradation products in water using online solid-phase extraction and liquid chromatography/mass spectrometry

    Lee, E.A.; Strahan, A.P.

    2003-01-01

    An analytical method for the determination of 6 acetamide herbicides (acetochlor, alachlor, dimethenamid, flufenacet, metolachlor, and propachlor) and 16 of their degradation products in natural water samples using solid-phase extraction and liquid chromatography/mass spectrometry is described in this report. Special consideration was given during the development of the method to prevent the formation of degradation products during the analysis. Filtered water samples were analyzed using octadecylsilane as the solid-phase extraction media on online automated equipment followed by liquid chromatography/mass spectrometry. The method uses only 10 milliliters of sample per injection. Three different water-sample matrices, a reagent-water, a ground-water, and a surface-water sample spiked at 0.10 and 1.0 microgram per liter, were analyzed to determine method performance. Method detection limits ranged from 0.004 to 0.051 microgram per liter for the parent acetamide herbicides and their degradation products. Mean recoveries for the acetamide compounds in the ground- and surface-water samples ranged from 62.3 to 117.4 percent. The secondary amide of acetochlor/metolachlor ethanesulfonic acid (ESA) was recovered at an average rate of 43.5 percent. The mean recoveries for propachlor and propachlor oxanilic acid (OXA) were next lowest, ranging from 62.3 to 95.5 percent. Mean recoveries from reagent-water samples ranged from 90.3 to 118.3 percent for all compounds. Overall the mean of the mean recoveries of all compounds in the three matrices spiked at 0.10 and 1.0 microgram per liter ranged from 89.9 to 100.7 percent, including the secondary amide of acetochlor/metolachlor ESA and the propachlor compounds. The acetamide herbicides and their degradation products are reported in concentrations ranging from 0.05 to 2.0 micrograms per liter. The upper concentration limit is 2.0 micrograms per liter for all compounds without dilution. With the exception of the secondary amide of

  2. Characterization of an Indole-3-Acetamide Hydrolase from Alcaligenes faecalis subsp. parafaecalis and Its Application in Efficient Preparation of Both Enantiomers of Chiral Building Block 2,3-Dihydro-1,4-Benzodioxin-2-Carboxylic Acid.

    Pradeep Mishra

    Full Text Available Both the enantiomers of 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid are valuable chiral synthons for enantiospecific synthesis of therapeutic agents such as (S-doxazosin mesylate, WB 4101, MKC 242, 2,3-dihydro-2-hydroxymethyl-1,4-benzodioxin, and N-[2,4-oxo-1,3-thiazolidin-3-yl]-2,3-dihydro-1,4-benzodioxin-2-carboxamide. Pharmaceutical applications require these enantiomers in optically pure form. However, currently available methods suffer from one drawback or other, such as low efficiency, uncommon and not so easily accessible chiral resolving agent and less than optimal enantiomeric purity. Our interest in finding a biocatalyst for efficient production of enantiomerically pure 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid lead us to discover an amidase activity from Alcaligenes faecalis subsp. parafaecalis, which was able to kinetically resolve 2,3-dihydro-1,4-benzodioxin-2-carboxyamide with E value of >200. Thus, at about 50% conversion, (R-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid was produced in >99% e.e. The remaining amide had (S-configuration and 99% e.e. The amide and acid were easily separated by aqueous (alkaline-organic two phase extraction method. The same amidase was able to catalyse, albeit at much lower rate the hydrolysis of (S-amide to (S-acid without loss of e.e. The amidase activity was identified as indole-3-acetamide hydrolase (IaaH. IaaH is known to catalyse conversion of indole-3-acetamide (IAM to indole-3-acetic acid (IAA, which is phytohormone of auxin class and is widespread among plants and bacteria that inhabit plant rhizosphere. IaaH exhibited high activity for 2,3-dihydro-1,4-benzodioxin-2-carboxamide, which was about 65% compared to its natural substrate, indole-3-acetamide. The natural substrate for IaaH indole-3-acetamide shared, at least in part a similar bicyclic structure with 2,3-dihydro-1,4-benzodioxin-2-carboxamide, which may account for high activity of enzyme towards this un-natural substrate. To

  3. Characterization of an Indole-3-Acetamide Hydrolase from Alcaligenes faecalis subsp. parafaecalis and Its Application in Efficient Preparation of Both Enantiomers of Chiral Building Block 2,3-Dihydro-1,4-Benzodioxin-2-Carboxylic Acid.

    Mishra, Pradeep; Kaur, Suneet; Sharma, Amar Nath; Jolly, Ravinder S

    2016-01-01

    Both the enantiomers of 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid are valuable chiral synthons for enantiospecific synthesis of therapeutic agents such as (S)-doxazosin mesylate, WB 4101, MKC 242, 2,3-dihydro-2-hydroxymethyl-1,4-benzodioxin, and N-[2,4-oxo-1,3-thiazolidin-3-yl]-2,3-dihydro-1,4-benzodioxin-2-carboxamide. Pharmaceutical applications require these enantiomers in optically pure form. However, currently available methods suffer from one drawback or other, such as low efficiency, uncommon and not so easily accessible chiral resolving agent and less than optimal enantiomeric purity. Our interest in finding a biocatalyst for efficient production of enantiomerically pure 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid lead us to discover an amidase activity from Alcaligenes faecalis subsp. parafaecalis, which was able to kinetically resolve 2,3-dihydro-1,4-benzodioxin-2-carboxyamide with E value of >200. Thus, at about 50% conversion, (R)-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid was produced in >99% e.e. The remaining amide had (S)-configuration and 99% e.e. The amide and acid were easily separated by aqueous (alkaline)-organic two phase extraction method. The same amidase was able to catalyse, albeit at much lower rate the hydrolysis of (S)-amide to (S)-acid without loss of e.e. The amidase activity was identified as indole-3-acetamide hydrolase (IaaH). IaaH is known to catalyse conversion of indole-3-acetamide (IAM) to indole-3-acetic acid (IAA), which is phytohormone of auxin class and is widespread among plants and bacteria that inhabit plant rhizosphere. IaaH exhibited high activity for 2,3-dihydro-1,4-benzodioxin-2-carboxamide, which was about 65% compared to its natural substrate, indole-3-acetamide. The natural substrate for IaaH indole-3-acetamide shared, at least in part a similar bicyclic structure with 2,3-dihydro-1,4-benzodioxin-2-carboxamide, which may account for high activity of enzyme towards this un-natural substrate. To the best of

  4. In Vivo Quantification of Cerebral Translocator Protein Binding in Humans Using 6-Chloro-2-(4′-123I-Iodophenyl)-3-(N,N-Diethyl)-Imidazo[1,2-a]Pyridine-3-Acetamide SPECT

    Feng, Ling; Svarer, Claus; Thomsen, Gerda;

    2014-01-01

    UNLABELLED: This study provides the first comprehensive quantification of translocator protein (TSPO) binding using SPECT and 6-chloro-2-(4'-(123)I-iodophenyl)-3-(N,N-diethyl)-imidazo[1,2-a]pyridine-3-acetamide ((123)I-CLINDE) in neurologic patients. (123)I-CLINDE is structurally related to well...... TSPO, reference tissue models should be used with caution. The 2-tissue-compartment kinetic analysis of a 90-min dynamic scan with arterial blood sampling is recommended for the quantification of (123)I-CLINDE binding with SPECT....

  5. Preparation, crystal structure and luminescent properties of the (6,3) type network supramolecular lanthanide picrate complexes with 2,2'-[(1,2-naphthalene)bis(oxy)]bis[N-(phenylmethyl)]acetamide

    Solid complexes of lanthanide picrates with a new podand-type ligand, 2,2'-[(1,2-naphthalene)bis(oxy)]bis[N-(phenylmethyl)]acetamide (L) have been prepared and characterized by elemental analysis, conductivity measurements, IR and electronic spectroscopies. The crystal and molecular structures of the coordination polymer {[Eu2L3(Pic)6].(CHCl3)3.(H2O)0.5}n have been determined by single-crystal X-ray diffraction, and the structure displays a two-dimensional honeycomb-like framework in the ab plane, which can be regarded as a (6,3) topological network with europium atoms acting as 'three-connected' centers. Furthermore, the coordination layers are linked by the intermolecular hydrogen bonds to form a three-dimensional (3-D) netlike supermolecule. Under excitation, Eu complex exhibited characteristic emissions. The lowest triplet state energy level of the ligand indicates that the triplet state energy level of the ligand matches better to the resonance level of Eu(III) than Tb(III) ion. - Graphical abstract: The (6,3) type network supramolecular luminescent lanthanide picrate complexes {Ln2L3(Pic)6}n (L=2,2'-[(1,2-naphthalene)bis(oxy)]bis[N-(phenylmethyl)]acetamide) displaying a two-dimensional honeycomb-like framework have been designed and prepared.

  6. Hydrothermal oxidation of an epoxy resin through the study of two model molecules: N-methyl-acetamide and N,N-di[1(phenoxy)2-hydroxy propyl-3] propyl-amine

    The study consists in choosing and developing a technology to realize damage experiments of an epoxy resin which is used as coating of embedded nuclear samples. Hydrothermal oxidation is the chosen method. We first identified the chemical composition of the epoxy resin. Then we studied hydrolysis and oxidation of a molecule which contains a function of the epoxy network: N-methyl-acetamide. The comparison between our results and those already existing allowed to validate this degradation method. In a second part, we studied a model molecule of the polymer network: N, N-di[1(phenoxy)2-hydroxy propyl-3] propyl-amine. The hydrolysis temperatures are relatively high: the compound is totally destroyed at 300 deg C. Its oxidation leads to the formation of acetic acid from 220 deg C. In the third study, we determined the best experimental conditions to destroy the epoxy resin. Experiments were performed at different temperatures between 200 deg C and 410 deg C. The degradation rates are classically defined by amounts of constituents in liquid and gaseous phases. (author)

  7. DFT and experimental (FT-IR and FT-Raman) investigation of vibrational spectroscopy and molecular docking studies of 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl) acetamide

    El-Azab, Adel S.; Sheena Mary, Y.; Yohannan Panicker, C.; Abdel-Aziz, Alaa A.-M.; El-Sherbeny, Magda A.; Van Alsenoy, C.

    2016-06-01

    A comprehensive structural and vibrational study of 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl) acetamide is reported. FT-IR and FT-Raman wavenumbers were compared with the theoretical values obtained from DFT calculations. Theoretical values agree well with the experimental values. Molecular electrostatic potential, frontier molecular orbital analysis and nonlinear optical properties were investigated using theoretical calculations. Natural bond orbital analysis shows that charge in electron density in σ* and π* antibonding orbitals and E(2) energies confirms the occurrence of intermolecular charge transfer within the molecule. Nonlinear optical property has also observed by predicting the first and second order hyperpolarizability parameters. As can be seen from the molecular electrostatic potential map of the title molecule, negative region is mainly localized over the carbonyl groups and the mono substituted phenyl ring and the maximum positive region is localized on the NH and hydrogen atoms. Molecular docking results show that the docked ligand title compound forms a stable complex with BRCA2 complex and gives a binding affinity value of -7.6 kcal/mol and results suggest that the compound might exhibit inhibitory activity against BRCA2 complex.

  8. Design, Synthesis, Characterization and Anticancer Prope rties of Novel 2-Chloro- N -(Aryl Substituted Acetamide Derivatives of 5-[2-(4- Methoxyphenyl Pyridin-3-yl]-1, 3, 4-Oxadiazole-2-Thiol

    Adimule Vinayak

    2014-12-01

    Full Text Available In this linear synthesis, novel different 2-chloro N-aryl substitutedacetamide derivatives of 5-[2-(4-methoxyphenyl pyridin-3-yl]-1, 3, 4-oxadiazole-2-thiol have been synthesized and screened for their cytotoxicity on PANC-1, HepG2and MCF7cell lines and obtained the IC50and CC50values.All the synthesized compounds were characterized by LCMS, IR, 1H and 13C (proton and Carbon 13 spectroscopies and elemental analysis. These compounds were evaluated for invitroanticancer activity on three different human leukemic cell lines, namely PANC-1,HepG2and MCF7.In total five compounds were synthesized and studied for their MTT assay. Among five synthesized novel compounds, the compound N-[5-(4-Methoxy-phenyl-pyridin-2-yl]-2-{5-[2-(4-methoxy-phenyl-pyridin-3-yl][1,3,4]oxadiazol-2 ylsulfanyl}-acetamide6eis highly cytotoxic on PANC-1and HepG2cell lines having IC50of 4.6μM and 2.2μM respectively whereas the compound 6cis moderately cytotoxic on MCF7having IC5015.5μM respectively. Rest all the compounds showed less cytotoxicity on all the three cell lines as compared with the standard 5-FU.

  9. Different molecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions.

    Narayana, Badiadka; Yathirajan, Hemmige S; Rathore, Ravindranath S; Glidewell, Christopher

    2016-09-01

    4-Antipyrine [4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and its derivatives exhibit a range of biological activities, including analgesic, antibacterial and anti-inflammatory, and new examples are always of potential interest and value. 2-(4-Chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, C19H18ClN3O2, (I), crystallizes with Z' = 2 in the space group P\\overline{1}, whereas its positional isomer 2-(2-chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, (II), crystallizes with Z' = 1 in the space group C2/c; the molecules of (II) are disordered over two sets of atomic sites having occupancies of 0.6020 (18) and 0.3980 (18). The two independent molecules of (I) adopt different molecular conformations, as do the two disorder components in (II), where the 2-chlorophenyl substituents adopt different orientations. The molecules of (I) are linked by a combination of N-H...O and C-H...O hydrogen bonds to form centrosymmetric four-molecule aggregates, while those of (II) are linked by the same types of hydrogen bonds forming sheets. The related compound N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(3-methoxyphenyl)acetamide, C20H21N3O3, (III), is isomorphous with (I) but not strictly isostructural; again the two independent molecules adopt different molecular conformations, and the molecules are linked by N-H...O and C-H...O hydrogen bonds to form ribbons. Comparisons are made with some related structures, indicating that a hydrogen-bonded R2(2)(10) ring is the common structural motif. PMID:27585929

  10. Infrared spectra, Raman laser, XRD, DSC/TGA and SEM investigations on the preparations of selenium metal, (Sb2O3, Ga2O3, SnO and HgO) oxides and lead carbonate with pure grade using acetamide precursors

    Moamen S Refat; Khaled M Elsabawy

    2011-07-01

    Ga2O3, Se metal, SnO, Sb2O3, HgO and PbCO3 are formed upon the reaction of acetamide aqueous solutions with Ga(NO3)3, SeO2, SnCl2, SbCl3, HgCl2 and Pb(NO3)2, respectively, at 90°C. Different amorphous or crystalline phases can be obtained depending upon the experimental conditions (molar ratios, metal salts and temperature). The chemical mechanisms for the formations of this metal, oxides or carbonate are discussed and the X-ray diffraction, scanning electron microscopy (SEM) and atomic force microscope (AFM) are described. The type of metal ions plays an important role in the decomposition of acetamide, leading to the formation of solid stable (metal, oxides or carbonate), soluble and gases species. These new precursors are more stable preventing the rapid precipitation of metal, oxides or carbonate. Furthermore, this route allows the formation of pure compounds in solutions.

  11. Hydrothermal oxidation of an epoxy resin through the study of two model molecules: N-methyl-acetamide and N,N-di[1(phenoxy)2-hydroxy propyl-3] propyl-amine; Oxydation hydrothermale d'une resine epoxyde au travers de l'etude de deux molecules modeles: le N-methylacetamide et la N,N-di[1-(phenoxy) 2-hydroxy propyl-3] propylamine

    Moutonnet-Fromonteil, C. [CEA/Cadarache, Dept. d' Etudes des Combustibles (DEC), 13 - Saint-Paul-lez-Durance (France)]|[Bordeaux-1 Univ., 33 (France)

    2000-07-01

    The study consists in choosing and developing a technology to realize damage experiments of an epoxy resin which is used as coating of embedded nuclear samples. Hydrothermal oxidation is the chosen method. We first identified the chemical composition of the epoxy resin. Then we studied hydrolysis and oxidation of a molecule which contains a function of the epoxy network: N-methyl-acetamide. The comparison between our results and those already existing allowed to validate this degradation method. In a second part, we studied a model molecule of the polymer network: N, N-di[1(phenoxy)2-hydroxy propyl-3] propyl-amine. The hydrolysis temperatures are relatively high: the compound is totally destroyed at 300 deg C. Its oxidation leads to the formation of acetic acid from 220 deg C. In the third study, we determined the best experimental conditions to destroy the epoxy resin. Experiments were performed at different temperatures between 200 deg C and 410 deg C. The degradation rates are classically defined by amounts of constituents in liquid and gaseous phases. (author)

  12. N-(Adamantan-1-yl)-2-chloro­acetamide

    Oluseye K. Onajole; Thavendran Govender; Hendrik G. Kruger; Maguire, Glenn E. M.

    2011-01-01

    In the title compound, C12H18ClNO, which was synthesized as part of a study into potential antituberculosis agents, the adamantine skeleton displays shorter than normal C—C bond lengths ranging between 1.5293 (18) and 1.5366 (15) Å. The structure also displays intermolecular N—H...O hydrogen bonding, which forms an infinite chain in the a-axis direction.

  13. Synthesis of 2- [ (4-Hydroxylcarbomylphenyl) -methylamino ] - N- ( 2- aminophenyl ) acetamide

    YUE Guo-Ren; DU Zhen-Ting; MA Jun-Ying; QUAN Wei-Guo; PAN Xin-Fu

    2003-01-01

    @@ Early studies revealed that the hybrid polar/apolar compound N, N′-hexamethylene bisacetaamide (HMBA) was a very effective inducer of differentiation in a transformed cell lines. [1] The use of this polar/apolar compound to induce murine erythroleukemia cells (MELC) to undergo erythoid differentiation with suppression of oncogenicity has proved a useful model to study inducer-mediated differentiation of transformed cell. [2] To search more effective inducers, we utilized the computer to design a new target compound. Herein, we reported the synthesis of title compound.

  14. An Improved Method of Synthesis for N-(3-acetyphenyl) Acetamide

    LI Yuanxun; TANG Xianzhong; HE Wei

    2003-01-01

    3-acetaminoacephenone is synthesized from acetophenone by nitrating, reducing and acetylating through an improved method. The designed route is reasonable and the new procedure is simple. The overall yield is 43.1%, which is about 15% higher than literature reported, and the structure of the product is identified by IR, 1HNMR, MS and elemental analysis.

  15. N-[3-(tert-Butyldimethylsiloxymethyl-5-nitrophenyl]acetamide

    David Barker

    2008-10-01

    Full Text Available The title compound, C15H24N2O4Si, was prepared by the reaction of (3-acetamido-5-nitrobenzylmethanol with tert-butyldimethylsilyl chloride and is a key intermediate in the synthesis of novel nonsymmetrical DNA minor groove-binding agents. There are two independent molecules in the structure, which differ primarily in the rotation about the C—O bond next to the Si atom. Two strong N—H...O hydrogen bonds align the molecules into a wide ribbon extending approximately parallel to the b axis.

  16. Crystallographic and computational studies on 4-phenyl-N-(beta-D-glucopyranosyl)-1H-1,2,3-triazole-1-acetamide, an inhibitor of glycogen phosphorylase: comparison with alpha-D-glucose, N-acetyl-beta-D-glucopyranosylamine and N-benzoyl-N'-beta-D-glucopyranosyl urea binding.

    Alexacou, Kyra-Melinda; Hayes, Joseph M; Tiraidis, Costas; Zographos, Spyros E; Leonidas, Demetres D; Chrysina, Evangelia D; Archontis, Georgios; Oikonomakos, Nikos G; Paul, Jashuva V; Varghese, Babu; Loganathan, Duraikkannu

    2008-05-15

    4-Phenyl-N-(beta-D-glucopyranosyl)-1H-1,2,3-triazole-1-acetamide (glucosyltriazolylacetamide) has been studied in kinetic and crystallographic experiments with glycogen phosphorylase b (GPb), in an effort to utilize its potential as a lead for the design of potent antihyperglycaemic agents. Docking and molecular dynamics (MD) calculations have been used to monitor more closely the binding modes in operation and compare the results with experiment. Kinetic experiments in the direction of glycogen synthesis showed that glucosyltriazolylacetamide is a better inhibitor (K(i) = 0.18 mM) than the parent compound alpha-D-glucose (K(i) = 1.7 mM) or beta-D-glucose (K(i) = 7.4 mM) but less potent inhibitor than the lead compound N-acetyl-beta-D-glucopyranosylamine (K(i) = 32 microM). To elucidate the molecular basis underlying the inhibition of the newly identified compound, we determined the structure of GPb in complex with glucosyltriazolylacetamide at 100 K to 1.88 A resolution, and the structure of the compound in the free form. Glucosyltriazolylacetamide is accommodated in the catalytic site of the enzyme and the glucopyranose interacts in a manner similar to that observed in the GPb-alpha-D-glucose complex, while the substituent group in the beta-position of the C1 atom makes additional hydrogen bonding and van der Waals interactions to the protein. A bifurcated donor type hydrogen bonding involving O3H, N3, and N4 is seen as an important structural motif strengthening the binding of glucosyltriazolylacetamide with GP which necessitated change in the torsion about C8-N2 bond by about 62 degrees going from its free to the complex form with GPb. On binding to GP, glucosyltriazolylacetamide induces significant conformational changes in the vicinity of this site. Specifically, the 280s loop (residues 282-288) shifts 0.7 to 3.1 A (CA atoms) to accommodate glucosyltriazolylacetamide. These conformational changes do not lead to increased contacts between the inhibitor and the

  17. N-(4-((E)-3-arylacryloyl)phenyl)acetamide derivatives and their antileishmanial activity

    The antileishmanial activity of a series of enonic derivatives (chalcones) synthesized via Claisen-Schmidt condensation reactions assisted by ultrasonic radiation was characterized by analyzing their cytotoxicity against Leishmania (Viannia) panamensis promastigotes, a species responsible for over 90% of Leishmania cases in Colombia. Two compounds were active against Leishmania with selectivity indexes of LC50 EC50-1 (lethal concentration 50 and effective concentration 50) higher than 27 and 3, respectively. These results suggest that a substitution on one of the two chalcone rings (aromatic ring A) with oxygen is convenient. Compound 3g should be further investigated for its antileishmanial activity, especially for being easy to obtain in high yields, making it possible to produce drugs for the treatment of cutaneous leishmaniasis. (author)

  18. N-(4-((E)-3-arylacryloyl)phenyl)acetamide derivatives and their antileishmanial activity

    Pacheco, Dency J.; Trilleras, Jorge; Prent, Luis; Coaves, Tobinson, E-mail: jorgetrilleras@mail.uniatlantico.edu.co [Universidad del Atlantico, Barranquilla-Atlantico (Colombia). Facultad de Ciencias Basicas. Grupo de Investigacion en Compuestos Heterociclicos; Quiroga, Jairo [Universidad del Valle, Cali (Colombia). Dept. de Quimica. Grupo de Investigacion de Compuestos Heterociclicos; Gutierrez, Jennifer; Delgado, Gabriela [Universidad Nacional de Colombia, Bogota, D.C. (Colombia). Facultad de Ciencias. Departamento de Farmacia. Grupo de Investigacion en Inmunotoxicologia; Marin, Juan C. [Universidad Nacional de Colombia, Bogota, D.C. (Colombia). Facultad de Ciencias. Departamento de Farmacia. Grupo de Investigacion Farmacognosia y Fitoquimica

    2013-10-15

    The antileishmanial activity of a series of enonic derivatives (chalcones) synthesized via Claisen-Schmidt condensation reactions assisted by ultrasonic radiation was characterized by analyzing their cytotoxicity against Leishmania (Viannia) panamensis promastigotes, a species responsible for over 90% of Leishmania cases in Colombia. Two compounds were active against Leishmania with selectivity indexes of LC{sub 50} EC{sub 50} {sup -1} (lethal concentration 50 and effective concentration 50) higher than 27 and 3, respectively. These results suggest that a substitution on one of the two chalcone rings (aromatic ring A) with oxygen is convenient. Compound 3g should be further investigated for its antileishmanial activity, especially for being easy to obtain in high yields, making it possible to produce drugs for the treatment of cutaneous leishmaniasis. (author)

  19. Separation of lanthanides (III) and actinides (III) by calixarenes containing acetamide-phosphine oxides functions

    The carbamoyl methyl phosphine oxide CMPO is the well known extractant of the TRUEX process for extraction of actinides from highly salted acidic wastes. In the framework of an European research contract coordinated by CEA/DDCC. V. Boehmer (Mainz, Germany) synthesized calix(4)arenes bearing CMPO moieties either on the wide rim, or on the narrow rim. Some of these calixarenes used at a concentration 10-3 M are more efficient than CMPO used at a two hundred fifty fold higher concentration. Moreover, calixarene skeleton leads to a strong selectivity among lanthanides, this selectivity is much less obvious for CMPO. Selectivity order is reversed according to whether CMPO unit is borne by the wide rim or the narrow rim. The most efficient calixarenes allow actinides to be separated from most of the lanthanides except the lightest ones. (authors)

  20. Crystal structure of N-[(2-hydroxynaphthalen-1-yl(4-methylphenylmethyl]acetamide

    Sharanbasappa Khanapure

    2015-04-01

    Full Text Available In the title molecule, C20H19NO2, the naphthalene ring system subtends a dihedral angle of 82.50 (7° with the benzene ring and an intramolecular N—H...O hydrogen bond closes an S(6 ring. In the crystal, molecules are linked by O—H...O hydrogen bonds, which generate C(8 chains propagating in the [010] direction. The crystal structure also features weak π–π interactions [centroid–centroid separation = 3.7246 (10 Å].

  1. Addition compounds between lanthanides and yttrium methane sulfonates and N,N-dimethyl acetamide (DMA)

    Adducts of composition Ln(CH3SO3)3·xDMA (x=2,Ln-Dy,Y;x=1,Ln=Ho-Lu) were prepared and characterized by elemental analysis, electrolytic conductance data in methanol, X-ray powder patterns, infrared spectra, electronic absorption spectra of the neodymium compound at room temperature and at 77 K and emission spectrum of the europium compound at 77 K. (author)

  2. Anticancer, Anti-Inflammatory, and Analgesic Activities of Synthesized 2-(Substituted phenoxy Acetamide Derivatives

    Priyanka Rani

    2014-01-01

    Full Text Available The aphorism was to develop new chemical entities as potential anticancer, anti-inflammatory, and analgesic agents. The Leuckart synthetic pathway was utilized in development of novel series of 2-(substituted phenoxy-N-(1-phenylethylacetamide derivatives. The compounds containing 1-phenylethylamine as basic moiety attached to substituted phenols were assessed for their anticancer activity against MCF-7 (breast cancer, SK-N-SH (neuroblastoma, anti-inflammatory activity, and analgesic activity. These investigations revealed that synthesized products 3a–j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity. Among all, compound 3c N-(1-(4-chlorophenylethyl-2-(4-nitrophenoxyacetamide exhibited anticancer, anti-inflammatory, and analgesic activities. In conclusion, 3c may have potential to be developed into a therapeutic agent.

  3. N-{2-[2-(2,6-Dichloro-3,5-dimethoxyphenylethenyl]phenyl}acetamide

    Seik Weng Ng

    2009-02-01

    Full Text Available The C=C double bond in the title substituted stilbene, C18H17Cl2NO3, has a trans arrangement of the aryl substituents. The aromatic ring of the 2-acetylaminophenyl substituent is twisted by 39.9 (3° with respect to the central C—C=C—C unit and that of the 2,6-dichloro-3,5-dimethoxyphenyl substitutent is twisted by 42.7 (3°.

  4. Complementary hydrogen bonding of a carboxylato-barbiturate with urea and acetamide: Experimental and theoretical approach

    Hasan, Md. A.; Seshaditya, A.; Záliš, Stanislav; Mishra, L.

    2011-01-01

    Roč. 83, č. 1 (2011), s. 532-539. ISSN 1386-1425 Institutional research plan: CEZ:AV0Z40400503 Keywords : barbiturate derivative * binding study * 1H-NMR titration Subject RIV: CG - Electrochemistry Impact factor: 2.098, year: 2011

  5. Para-ter-butyl of calix(4)arene with acetamide-ether as inorganic-organic receiver

    A new functionalized calix(4)arene was designed and constructed with predetrmined properties to form lanthanides complexes and to sensibilize its luminescent properties. This, in addition to sensibilize that photophysical property and once formed the complex resulted a good receiver of organic molecules as it is demonstrated the crystal structure of the lutetium complex. (Author)

  6. N-[2-(1,3-Benzodioxol-5-yl)eth­yl]-2-chloro­acetamide

    Dong, Hui-Chao

    2008-01-01

    The title compound, C11H12ClNO3, crystallizes with two independent mol­ecules in the asymmetric unit. Inter­molecular N—H⋯O hydrogen bonds link the mol­ecules related by translation along the b axis into two independent hydrogen-bonded chains. The crystal studied exhibited inversion twinning.

  7. Crystal structure of N,N′-(1,2-phenyl­ene)bis­(2-chloro­acetamide)

    Tariq, Javaria; Murtaza, Shahzad; Tahir, Muhammad Nawaz; Zaheer, Muhammad

    2015-01-01

    In the title compound, C10H10Cl2N2O2, the secondary amide groups are differently twisted relative to the benzene ring, with dihedral angles between the respective planes of 21.03 (2) and 81.22 (2)°. In the crystal, the mol­ecules are connected by N—H⋯O and C—H⋯O hydrogen bonds, forming a two-dimensional polymeric network parallel to (001). One of the amide carbonyl O atoms accepts two H atoms in N—H⋯O and C—H⋯O inter­actions, forming an R 2 2(6) ring motif.

  8. In situ Determination of Fluoride in Groundwater Using N-Octyl Acetamide with Iron(III)-Thiocyanate Complex

    Sahin, R.; Tapadia, K.; Sharma, A.

    2016-07-01

    This paper describes the nanodrop spectrophotometric determination of fluoride (F-) in a ground water sample using the organic reagent N-octylacetamide (N-OAA) with iron(III)-thiocyanate complex. The iron(III)-thiocyanate complex was extracted with a chloroform solution of amide (N-phenylacetamide, N-alkylacetamide, alkyl = butyl, phenyl, hexyl, and octyl group). This method is based upon the bleaching effect of fluoride on the red-colored extracted complex of iron(III)-thiocyanate-OAA in chloroform. The absorbance of the extract was measured pre and post F- addition at λmax = 470 nm against the reagent blank. The limit of detection and %RSD of F- was 38 μg/L and ±1.6%. The designed work followed Beer's law between 0.5 to 10 μg/mL with slope, intercept, and correlation coefficient values of -0.1101, 1.116, and -0.997, respectively. Furthermore, the applicability of the present investigation was extended for the determination of F- in a groundwater sample, and the results obtained were compared with those from another reported method.

  9. N-[3-(tert-Butyl­dimethyl­siloxymeth­yl)-5-nitro­phen­yl]acetamide

    David Barker; Clark, George R.; Gul S. Khan

    2008-01-01

    The title compound, C15H24N2O4Si, was prepared by the reaction of (3-acetamido-5-nitrobenzyl)methanol with tert-butyldimethylsilyl chloride and is a key intermediate in the synthesis of novel nonsymmetrical DNA minor groove-binding agents. There are two independent molecules in the structure, which differ primarily in the rotation about the C—O bond next to the Si atom. Two strong N—H...O hydrogen bonds align the molecules into a wide ribbon extending approximately parallel to the...

  10. 2-[(3R,6R)-6-Methyl-2,5-dioxomorpholin-3-yl]-N-(propan-2-yl)acetamide

    Peng-xue Duan; Li-qiang Yang; Juan Luo; De-dai Lu; Hu Zhang

    2012-01-01

    The molecular conformation of the title compound, C10H16N2O4, is determined by an intramolecular N—H...O hydrogen bond involving the morpholine NH group and the amide O atom. In the crystal, molecules are linked by N—H...O hydrogen bonds into chains along the a-axis direction.

  11. X-Ray diffraction and vibrational spectroscopic study of 2-chloro-N-{4-[3-(2,5-dimethylphenyl)-3-methylcyclobutyl] -thiazol-2-yl}-acetamide

    The title compound C18H21ClN2SO crystallizes with Z = 4 in space group P21/c. The structure of the title compound was characterized by 1H-NMR, 13C-NMR, IR and single crystal diffraction. There are an intermolecular N-H-O hydrogen bond and a C-H-π interactions in crystal packing. In addition to the molecular geometry and packing obtained from X-ray experiment, the molecular geometry and vibrational frequencies of the title compound in ground state have been calculated using density functional theory method DFT (B3LYP) with 6-31G (d, p) basis set. Calculated frequencies, bond lengths, angles and dihedral angles are in good agreement with the corresponding experimental data.

  12. N-(2-Chloro­phen­yl)-2-(4,6-dimethyl­pyrimidin-2-ylsulfan­yl)acetamide

    Li, Qiang; Wang, Wei; Wang, Hui; Gao, Yan; Qiu, Hong

    2009-01-01

    In the title compound, C14H14ClN3OS, the 4,6-dimethyl­pyrimidine ring and the chloro­benzene ring subtend a dihedral angle of 80.0 (2)°. The length of the Csp 2—S bond is significantly shorter than that of the Csp 3—S bond. The crystal structure is stabilized by inter­molecular N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonding, and C—H⋯π inter­actions.

  13. N-[(3-Ethyl­phen­yl)carbamo­thio­yl]-2,2-di­phenyl­acetamide

    Yusof, Mohd Sukeri Mohd; Razali, Nur Rafikah; Arshad, Suhana; Rahman, Azhar Abdul; Razak, Ibrahim Abdul

    2013-01-01

    In the title mol­ecule, C23H22N2OS, the di­phenyl­acetyl and ethyl­benzene groups adopt a trans–cis conformation, respectively, with respect to the S atom across the (S=)C—N bonds. This conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond and a weak C—H⋯S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N—H⋯O hydrogen bonds link mol­ecules into chains along [100]. A weak C—H⋯π inter­act...

  14. Prosthetic labelling of double-stranded small interfering RNA (s.i.RNA) using the bromo-acetamide [18F]fpybra reagent

    Introduction. - Small interfering RNAs (s.i.RNA) are double-stranded oligonucleotides able to induce a specific post-transcriptional inhibition of genes. S.i.RNA is one of the most powerful tools to achieve gene silencing in cells, but is limited in vivo because of the poor pharmacological properties of RNAs. In order to evaluate the in vivo pharmacokinetics of some selected s.i.RNA with Positron Emission Tomography (PET), the corresponding oligonucleotidic sequences have been modified in order to increase their resistance toward nucleases and then labelled with fluorine-18. Methods. - S.i.RNA (21 mer, non-modified or the corresponding 20-Fluoro- and 2-OMe-modified sequences) have been labelled with fluorine using the following two-step process: (A) prosthetic conjugation of one strand with [18F]F.Py.Br.A. [1] which was carried out in a mixture of methanol and phosphate buffer saline (pH 7.4) at 80 degrees C for 15 min. The corresponding [18F]conjugated oligonucleotide was then HPLC-purified, desalted, and its concentration measured at 260 nm. (B) The [18F]conjugated oligonucleotide was then hybridized with its complementary strand in stoichiometric condition (in 100 m M NaCl at 90 degrees C for 1 min and 25 degrees C for 10 min) to give the desired [18F]conjugated s.i.RNA. Quality controls of single- and double stranded [18F]conjugated oligonucleotides were performed by non-denaturing polyacrylamide gel electrophoresis (P.A.G.E.) with the corresponding [19F]conjugated oligonucleotides as references, enzymatically labelled with [32P]phosphate at their 5 end. Results. - Typically, up to 0.55 GBq of pure [18F]conjugated s.i.RNA can be produced in 160 min with a specific radioactivity up to 212 GBq/micro-mol at the end of synthesis, starting from 20.3 to 24.0 GBq of a [18F]F batch. They were found to be at least 95% radiochemically pure. Complete hybridization of the two strands was confirmed by non-denaturing P.A.G.E. analysis. All the [18F]conjugated s.i.RNA have shown the same interference efficiency in cells as the non-labelled oligonucleotides. Conclusion. - The labelling procedure described above allows for the first time the study of s.i.RNA biodistribution by PET and let to evaluate their potential of non-modified and sugar-modified s.i.RNA. (authors)

  15. Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide

    Sharma, R. [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics (India); Nayak, P. S.; Narayana, B. [Mangalore University, Mangalagangotri, Department of Studies in Chemistry (India); Kant, R., E-mail: rkvk.paper11@gmail.com [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics (India)

    2015-12-15

    The title compound, C{sub 13}H{sub 14}O{sub 2}N{sub 3}Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P2{sub 1}/c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) Å, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N–H···O and C–H···O interactions, the former interactions result in the formation of dimers corresponding to R{sub 2}{sup 2} (10) graphset motif and the dimers are further connected by C–H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λ{sub max} = 298 nm was determined by UV-Vis spectrophotometer.

  16. Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide

    The title compound, C13H14O2N3Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P21/c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) Å, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N–H···O and C–H···O interactions, the former interactions result in the formation of dimers corresponding to R22 (10) graphset motif and the dimers are further connected by C–H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λmax = 298 nm was determined by UV-Vis spectrophotometer

  17. Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro- N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H-pyrazol-4-yl)acetamide

    Sharma, R.; Nayak, P. S.; Narayana, B.; Kant, R.

    2015-12-01

    The title compound, C13H14O2N3Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P21/ c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) Å, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N-H···O and C-H···O interactions, the former interactions result in the formation of dimers corresponding to R 2 2 (10) graphset motif and the dimers are further connected by C-H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λmax = 298 nm was determined by UV-Vis spectrophotometer.

  18. A simplified synthesis of the hypoxia imaging agent 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-[18F]pentafluoropropyl)-acetamide ([18F]EF5)

    Introduction: [18F]EF5 is a validated marker for PET imaging of tumor hypoxia. It is prepared by reacting a trifluoroallyl precursor with carrier-added [18F]F2 gas in trifluoroacetic acid (TFA) solvent. We report here an improved radiosynthesis and purification of [18F]EF5 by utilizing an electroformed nickel (Ni) target for [18F]F2 production, and Oasis® HLB cartridges for on-line solid phase extraction of [18F]EF5 prior to HPLC purification. Methods: [18F]F2 was produced by deuteron bombardment of neon plus F2 in an Ni target, and bubbled through the radiolabelling precursor solution. Purification was achieved by extracting the contents of the crude reaction mixture onto Oasis HLB cartridges, and subsequently eluted onto a semi-preparative HPLC column for further separation. Purified [18F]EF5 was evaluated in small animal PET studies using HCT116 tumor xenografts in nude mice. Results: The electroformed Ni target enabled recovery of > 75% of the radioactivity from the cyclotron target, resulting in 16.2 ± 2.2 GBq (438 ± 58 mCi) of [18F]F2 available for the synthesis. Use of Oasis cartridges yielded a less complex mixture for purification. On average, 1140 ± 200 MBq (30.8 ± 5.4 mCi) of [18F]EF5 were collected at EOS. Small animal PET imaging studies showed specific retention of [18F]EF5 in tumors, with tumor-to-muscle ratios of 2.7 ± 0.3 at about160 min after injection. Conclusion: A simple procedure has been developed for the routine synthesis of [18F]EF5 in amounts and purity required for clinical studies. This new method avoids the need for TFA evaporation and also enables facile automation of the synthesis using commercially available radiosynthesis modules.

  19. Invariant Oxidation State of Copper but not of Ruthenium in Complexes with Noninnocent N-(2-Methyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide: A Combined Structural, Electrochemical and Spectroelectrochemical Investigation

    Paretzki, A.; Das, H. S.; Weisser, F.; Scherer, T.; Bubrin, D.; Fiedler, Jan; Nycz, J. E.; Sarkar, B.

    -, č. 15 (2011), s. 2413-2421. ISSN 1434-1948 R&D Projects: GA ČR GA203/09/0705; GA ČR GA203/08/1157 Institutional research plan: CEZ:AV0Z40400503 Keywords : copper * ruthenium * quinones Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 3.049, year: 2011

  20. Experimental Investigation on an Energy Efficient Solar Tunnel Dryer

    M. R. Seshan Ram

    2012-01-01

    The research determines the effectiveness of the solar tunnel dryer developed and the product dried in the device is superior in quality and also it is compatible with branded products available in the market. The study also determines Acetamide as Phase Key words: Solar Tunnel Dryer, Acetamide as Phase Change Materials, Conversion into Thermal Energy, Thermocouple, and Pyranometer

  1. Studies of linear correlation factor of dielectric polarization and excess dipolar free energies of amides in apolar solvents

    M Malathi; R Sabesan; S Krishnan

    2005-09-01

    The Kirkwood–Frohlich correlation factor (), Eyring's parameters and * and the dipolar excess free energies of dilute solutions of formamide, acetamide, -methyl acetamide, , -dimethyl formamide and , -dimethyl acetamide in 1,4-dioxan/benzene were obtained from a measurement of their static dielectric permittivities at 308 K. The fluid structure of these amides is discussed. Both in formamide and acetamide a dimeric linear chain with the individual dipoles more or less parallely oriented is preferred. In -methyl acetamide, the antiparallel orientation of dipoles at lower concentrations turns into a parallel orientation with increase of concentration. In tertiary amides, with increase of concentration, parallel orientation of dipoles with global value of tending to unity is observed. The dipolar excess free energy of mixing in a given solvent is of the order primary amide > secondary amide > tertiary amide.

  2. Discovery of a Series of 2-phenyl-N-(2-(pyrrolidin-1-yl)phenyl)acetamides as Novel Molecular Switches that Modulate Modes of Kv7.2 (KCNQ2) Channel Pharmacology: Identification of (S)-2-phenyl-N-(2-(pyrrolidin-1-yl)phenyl)butanamide (ML252) as a Potent, Brain Penetrant Kv7.2 Channel Inhibitor

    Cheung, Yiu-Yin; Yu, Haibo; Xu, Kaiping; Zou, Beiyan; Wu, Meng; McManus, Owen B.; Li, Min; Lindsley, Craig W.; Hopkins, Corey R.

    2012-01-01

    A potent and selective inhibitor of KCNQ2, (S)-5 (ML252, IC50 = 69 nM), was discovered after a high-throughput screen of the MLPCN library was performed. SAR studies revealed a small structural change (ethyl group to hydrogen) caused a functional shift from antagonist to agonist activity (37, EC50 = 170 nM), suggesting an interaction at a critical site for controlling gating of KCNQ2 channels. PMID:22793372

  3. Structures of the anticancer compounds N-(2-hydroxyethyl)-2-(3-nitro-1,2,4-triazol-1-yl)-acetamide (RB-6110) and 5-(1-aziridinyl)-3-nitro-1-(3-oxo-1-butyl)-1,2,4- triazole (RB-6162).

    McKenna, R; Jenkins, T C; Neidle, S

    1988-12-01

    RB-6110: C6H9N5O4, Mr = 215.17, monoclinic, C2/c, a = 20.595 (3), b = 4.713 (1), c = 19.914 (4) A, beta = 110.69 (1) degree, V = 1808.3 A3, Z = 8, Dx = 1.588 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 0.838 mm-1, F(000) = 675, T = 298 K, final R = 0.042 for 1219 observed reflections with I greater than or equal to 1.5 sigma (I). RB-6162: C8H11N5O3, Mr = 225.21, monoclinic, P2(1)/c, a = 7.515 (1), b = 14.758 (2), c = 9.813 (1) A, beta = 108.49 (1) degree, V = 1032.1 A3, Z = 4, Dx = 1.450 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 0.927 mm-1, F(000) = 472, T = 298 K, final R = 0.042 for 1113 observed reflections with I greater than or equal to 1.5 sigma (I). RB-6110 and RB-6162 are 3-nitro-1,2,4-triazoles with potential application as anticancer agents. The nitro groups are in the plane of the aromatic triazole ring with dihedral angles of 1.2 (4) and 4.6 (4) degrees, respectively. The arizidine substituent of RB-6162 is almost perpendicular [dihedral angle 80.1 (4) degrees] to the triazole plane. Molecular-orbital calculations on RB-6162 have confirmed that this geometry is energetically favoured. The energy barrier to rotation about the triazole-aziridine bond has been determined as 51.5 (5) kJ mol-1 by the dynamic NMR method. PMID:3271560

  4. Biotransformation of Indole to 3-Methylindole by Lysinibacillus xylanilyticus Strain MA

    Pankaj Kumar Arora

    2015-01-01

    Full Text Available An indole-biotransforming strain MA was identified as Lysinibacillus xylanilyticus on the basis of the 16S rRNA gene sequencing. It transforms indole completely from the broth culture in the presence of an additional carbon source (i.e., sodium succinate. Gas-chromatography-mass spectrometry identified indole-3-acetamide, indole-3-acetic acid, and 3-methylindole as transformation products. Tryptophan-2-monooxygenase activity was detected in the crude extracts of indole-induced cells of strain MA, which confirms the formation of indole-3-acetamide from tryptophan in the degradation pathway of indole. On the basis of identified metabolites and enzyme assay, we have proposed a new transformation pathway for indole degradation. Indole was first transformed to indole-3-acetamide via tryptophan. Indole-3-acetamide was then transformed to indole-3-acetic acid that was decarboxylated to 3-methylindole. This is the first report of a 3-methylindole synthesis via the degradation pathway of indole.

  5. Electrolytic Synthesis of Benzoic Anhydride from Benzoic Acid

    TAKAHASHI, Takeshige; KAMADA, Mitsushi; タカハシ, タケシゲ; カマダ, ミツシ; 高橋, 武重; 鎌田, 三司

    1982-01-01

    Electrolysis of benzoic acid was investigated by means of controlled current operation in acetonitrile with platinum disk electrodes. Benzoic anhydride was obtained from an anolyte at 20-30% of current efficiency as one electron reaction. At the same time, acetamide and hydrogen perchlorate were obtained from the anolyte, and triethylamine was obtained from the catholyte. The yield of acetamide was nearly equal to benzoic anhydride. On the other hand, the yield of triethylamine ap...

  6. 40 CFR 261.33 - Discarded commercial chemical products, off-specification species, container residues, and spill...

    2010-07-01

    ... 100-02-7 p-Nitrophenol U171 79-46-9 2-Nitropropane (I,T) U172 924-16-3 N-Nitrosodi-n-butylamine U173... described in § 261.2(a)(2)(i), when they are mixed with waste oil or used oil or other material and applied...-08-2 Acetamide, N-(aminothioxomethyl)- P057 640-19-7 Acetamide, 2-fluoro- P058 62-74-8 Acetic...

  7. UREA TRANSPORT DURING GAMETOGENESIS OF THE UNICELLULAR GREEN ALGA CHLAMYDOMONAS REINHARDTII

    Zalutskaya, Zhanneta; Lapina, Tatyana; Von, Wiren; Ermilova, Elena

    2009-01-01

    Direct urea transport mechanisms are present in Chlamydomonas reinhardtii. Urea uptake system(s) are repressed by ammonium and they can be induced by urea or acetamide in ammonium-starved vegetative cells. Urea transport ability of the alga is altered during gametogenesis. Unlike vegetative cells, mature gametes showed a low urea uptake. Incubation of gametes with urea or acetamide resulted in the increasing of urea uptake ability and the regaining of chemotactic activity. The data suggest a ...

  8. Indole-3-Acetic Acid Biosynthesis in Colletotrichum gloeosporioides f. sp. aeschynomene

    M Robinson; Riov, J.; Sharon, A.

    1998-01-01

    We characterized the biosynthesis of indole-3-acetic acid by the mycoherbicide Colletotrichum gloeosporioides f. sp. aeschynomene. Auxin production was tryptophan dependent. Compounds from the indole-3-acetamide and indole-3-pyruvic acid pathways were detected in culture filtrates. Feeding experiments and in vitro assay confirmed the presence of both pathways. Indole-3-acetamide was the major pathway utilized by the fungus to produce indole-3-acetic acid in culture.

  9. Synthesis of new hypoxia markers EF1 and [18F]-EF1

    We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its 18F analog, 2-(2-nitroimidazol-1[H]-yl)-N-(3-[18F]fluoropropyl)acetamide ([18F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [18F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added 18F in DMSO at 120 deg. C. Our results demonstrate the preparation of clinically relevant amounts of [18F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET)

  10. Enantiomeric 4-Acylamino-6-alkyloxy-2 Alkylthiopyrimidines As Potential A3 Adenosine Receptor Antagonists: HPLC Chiral Resolution and Absolute Configuration Assignment by a Full Set of Chiroptical Spectroscopy.

    Rossi, Daniela; Nasti, Rita; Marra, Annamaria; Meneghini, Silvia; Mazzeo, Giuseppe; Longhi, Giovanna; Memo, Maurizio; Cosimelli, Barbara; Greco, Giovanni; Novellino, Ettore; Da Settimo, Federico; Martini, Claudia; Taliani, Sabrina; Abbate, Sergio; Collina, Simona

    2016-05-01

    The chiral separation of enantiomeric couples of three potential A3 adenosine receptor antagonists: (R/S)-N-(6-(1-phenylethoxy)-2-(propylthio)pyrimidin-4-yl)acetamide (), (R/S)-N-(2-(1-phenylethylthio)-6-propoxypyrimidin-4-yl)acetamide (), and (R/S)-N-(2-(benzylthio)-6-sec-butoxypyrimidin-4-yl)acetamide () was achieved by high-performance liquid chromatography (HPLC). Three types of chiroptical spectroscopies, namely, optical rotatory dispersion (ORD), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD), were applied to enantiomeric compounds. Through comparison with Density Functional Theory (DFT) calculations, encompassing extensive conformational analysis, full assignment of the absolute configuration (AC) for the three sets of compounds was obtained. Chirality 28:434-440, 2016. © 2016 Wiley Periodicals, Inc. PMID:27095007

  11. Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives

    Gaballah, Samir T.; El-Nezhawy, Ahmed O. H.; Amer, Hassan; Ali, Mamdouh Moawad; Mahmoud, Abeer Essam El-Din; Hofinger-Horvath, Andreas

    2015-01-01

    The design, synthesis, and in vitro antiproliferative activity of a novel series of sulfide (4a–i) and sulfoxide (5a–h) derivatives of benzimidazole, in which different aromatic and heteroaromatic acetamides are linked to benzimidazole via sulfide (4a–i) and sulfoxide (5a–h) linker, are reported and the structure-activity relationship is discussed. The new derivatives were prepared by coupling 2-(mercaptomethyl)benzimidazole with 2-bromo-N-(substituted) acetamides in dry acetone in the presen...

  12. Synthesis of Meso- and Racemic 1, 3-Diamino-1, 3-diphenylpropanes

    Lee, G. S.; Kammermeier, T; Kaiser, A; Eibler, E.; Wiegrebe, Wolfgang

    1991-01-01

    The Pt-complexes 2a, b are synthesized according to Scheme 2 including oximation of and 1,4-addition of H2N-OH to the chalcone 3 and separation of the diastereomers either as bis-acetamides 5 or - less favourable - at the diamine stage 6. Die Pt-Komplexe 2a, b wurden nach Schema 2 hergestellt, u.a. durch Oximierung und 1,4-Addition von H2N-OH an das Chalcon 3 und Trennung der Diastereomere entweder als Bis-Acetamide 5 oder - schwieriger - als Diamine 6.

  13. Synthesis and Characterization of Two Cyanoxime Ligands, Their Precursors, and Light Insensitive Antimicrobial Silver(I) Cyanoximates.

    Riddles, Courtney N.; Whited, Mark; Lotlikar, Shalaka R.; Still, Korey; Patrauchan, Marianna; Silchenko, Svitlana; Gerasimchuk, Nikolay

    2014-01-01

    High-yield syntheses of N-piperidine-cyanacetamide (1), N-morpholyl-cyanacetamide (4) and their oxime derivatives N-piperidine-2-cyano-2-oximino-acetamide (HPiPCO, 2) and N-morpholyc-2-cyano-2-oximino-acetamide (HMCO, 5) were developed using two-step preparations. At first, the reactions of neat cyanoacetic acid esters and the respective cyclic secondary amines such as piperideine and morpholine afforded pure cyanacetamides, which were converted into cyanoximes at room temperature using the n...

  14. Reaction pathways and free energy profiles for spontaneous hydrolysis of urea and tetramethylurea: Unexpected substituent effects

    Yao, Min; Tu, Wenlong; Chen, Xi; Zhan, Chang-Guo

    2013-01-01

    It has been difficult to directly measure the spontaneous hydrolysis rate of urea and, thus, 1,1,3,3-tetramethylurea (Me4U) was used as a model to determine the “experimental” rate constant for urea hydrolysis. The use of Me4U was based on an assumption that the rate of urea hydrolysis should be 2.8 times that of Me4U hydrolysis because the rate of acetamide hydrolysis is 2.8 times that of N,N-dimethyl-acetamide hydrolysis. The present first-principles electronic-structure calculations on the...

  15. Synthesis and Biological Evaluation of Chalcone Derivatives Linked Triazoles

    Ashvin D. Panchal; Prashant D. Kunjadia; Patel, Pravinkumar M.

    2011-01-01

    In this work, an attempt was made to synthesize chalcone 3-(Substitutedphenyl)-N-(4H-1, 2, 4-triazol-4-yl)acrylamide by condensation of substitutedbenzaldehyde with N-(4H-1,2,4-triazol-4-yl)acetamide under basic conditions. A simple condensation reaction of substitutedbenzaldehyde and N-(4H-1, 2, 4-triazol-4-yl)acetamide using Sodium hydroxide as a base was carried out for the study. The synthesized chalcone derivative was characterized by FTIR, 1H-NMR & 13C-NMR and studied for their Antimicr...

  16. 40 CFR Appendix Vi to Part 265 - Compounds With Henry's Law Constant Less Than 0.1 Y/X

    2010-07-01

    ... 40 Protection of Environment 25 2010-07-01 2010-07-01 false Compounds With Henry's Law Constant... TREATMENT, STORAGE, AND DISPOSAL FACILITIES Pt. 265, App. VI Appendix VI to Part 265—Compounds With Henry's Law Constant Less Than 0.1 Y/X Compound name CAS No. Acetaldol 107-89-1 Acetamide 60-35-5...

  17. Metabolism of acetochlor herbicide in tolerant and sensitive plant species

    Metabolism of acetochlor (2-chloro-N-)2-ethyl-6-methyl-phenyl(-N-)ethoxymethyl(acetamide) herbicide was traced in tolerant corn (Zea mays L.) and sensitive wheat (Triticum aestivum L.). Both resistant and susceptible plant species were found to be able to metabolize acetochlor absorbed. However, a faster metabolism of the herbicide was observed in the tolerant plants. (author)

  18. Mesoporous titanosilicates by templated non-hydrolytic sol–gel reactions

    Škoda, D.; Stýskalík, A.; Moravec, Z.; Bezdička, Petr; Barnes, C.E.; Pinkas, J.

    2015-01-01

    Roč. 74, č. 3 (2015), s. 810-822. ISSN 0928-0707 Institutional support: RVO:61388980 Keywords : Acetamide elimination * Catalysis * Epoxidation * Mesoporous * Non-hydrolytic sol-gel * Templating Subject RIV: CA - Inorganic Chemistry Impact factor: 1.532, year: 2014

  19. Effect of meteorology and soil condition on metolachlor and atrazine volatilization over a 10 year period

    A 10-year study was conducted to focus on the impact of soil and climatic factors governing herbicide volatilization from an agricultural field. For the first 5 years, metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] and atrazine [6-chloro-N-ethyl-N’-(1-methyl...

  20. Deuteration of acetanilides

    Chin, S.K.; Collier, R.; Hutchinson, D.W. (Warwick Univ., Coventry (UK). Dept. of Chemistry and Molecular Sciences)

    1982-09-01

    The base-catalysed exchange of a proton of the methyl groups in acetanilides can be used to incorporate deuterium into these amides. 4'-Hydroxyl-2(/sup 2/H)acetanilide (acetaminophen, paracetamol) can be prepared by the demethylation with boron tribromide of 4'-methoxy-2(/sup 2/H) acetamide obtained by this base-catalysed exchange.

  1. Enzymatic synthesis of 5-3H-indole-3-acetic acid and 5-3H-indole-3-acetyl-myo-inositol from 5-3H-L-trytophan

    Labeled 1-tryptophan is converted to indole-3-acetamide and then to indole-3-acetic acid by enzymes from Pseudomonas savastanoi. Labeled indole-3-acetic acid can be converted to indole-3-acetyl-1-O-β-D-glucose and to indole-3-acetyl-myo-inositol by enzymes from kernels of Zea mays sweet corn. (author)

  2. Metabolism of acetochlor herbicide in tolerant and sensitive plant species

    Jablonkai, I.; Dutka, F.

    1985-05-16

    Metabolism of acetochlor (2-chloro-N-)2-ethyl-6-methyl-phenyl(-N-)ethoxymethyl(acetamide) herbicide was traced in tolerant corn (Zea mays L.) and sensitive wheat (Triticum aestivum L.). Both resistant and susceptible plant species were found to be able to metabolize acetochlor absorbed. However, a faster metabolism of the herbicide was observed in the tolerant plants. (author). 5 refs.

  3. Ambient temperature deposition of gallium nitride/gallium oxynitride from a deep eutectic electrolyte, under potential control.

    Sarkar, Sujoy; Sampath, S

    2016-05-11

    A ternary, ionically conducting, deep eutectic solvent based on acetamide, urea and gallium nitrate is reported for the electrodeposition of gallium nitride/gallium indium nitride under ambient conditions; blue and white light emitting photoluminescent deposits are obtained under potential control. PMID:27074315

  4. The deuteration of acetanilides

    The base-catalysed exchange of a proton of the methyl groups in acetanilides can be used to incorporate deuterium into these amides. 4'-Hydroxyl-2[2H]acetanilide (acetaminophen, paracetamol) can be prepared by the demethylation with boron tribromide of 4'-methoxy-2[2H] acetamide obtained by this base-catalysed exchange. (author)

  5. Enhanced photocurrent generation in bacteriorhodopsin based bio-sensitized solar cells using gel electrolyte.

    Chellamuthu, Jeganathan; Nagaraj, Pavithra; Chidambaram, Sabari Girisun; Sambandam, Anandan; Muthupandian, Ashokkumar

    2016-09-01

    High purity light sensitive photoactive protein Bacteriorhodopsin (BR) was isolated successfully via a simple two phase extraction technique (ATPS) as an alternate method for the tedious sucrose gradient ultracentrifugation procedure (SGU). Bio sensitized solar cells (BSSCs) were fabricated by the integration of BR into TiO2 (photo anode) with acetamide based gel electrolytes and platinum (photo cathode) as a counter electrode. The structural and photoelectrical behaviours of BR and BSSCs were analyzed by Atomic Force Microscopy, Raman spectroscopy, photocurrent and photovoltage (IV) measurement and electrochemical impedance spectroscopy. The short circuit photocurrent (Jsc) and photoelectric conversion efficiency (η) of acetamide based gel electrolyte (AG) (1.08mAcm(-2), 0.49%) are twice higher than that of traditional triiodide based liquid electrolyte (LE) (0.62mAcm(-2), 0.19%). Also, quasi-Fermi level and lifetime of photogenerated electrons in acetamide based gel electrolyte is about four times higher than that observed in traditional triiodide redox electrolyte. A comparison of the observed results with similar BSSCs made of other natural photoactive protein systems shows that BR as sensitizer has better photovoltaic performance. The enhanced photocurrent generation of the BSSC constructed in our study could be due to the interaction of BR with acetamide based modified poly(ethylene)oxide (PEO) gel electrolyte. PMID:27380296

  6. Synthesis of Some New Thiazole Derivatives and Their Biological Activity Evaluation

    Leyla Yurttaş

    2015-01-01

    Full Text Available New 2-(4-arylpiperazine-1-yl-N-[4-(2-(4-substituted phenylthiazol-4-ylphenyl]acetamide derivatives were synthesized and evaluated for their antimicrobial and anticholinesterase activities. Acetylcholinesterase inhibitory activities of the compounds were found weak contrary to expectations. It is unlikely that antifungal activity of the compounds was found significant, especially against Candida parapsilosis.

  7. A New Alkaloid from Sinomenium acutum

    Wei Ming CHENG; Feng QIU; Li Jun WU; Xin Sheng YAO

    2005-01-01

    Sinomenium acutum is widely used in East and South Asia for the treatment of many diseases, especially rheumatoid arthritis (RA). The chemical research on Sinomenium acutum led to the isolation of a new alkaloid compound (1). On the basis of chemical evidences and spectral analysis, 1 was identified as N-(1, 7-dimethoxylphenanthren-2-yl)acetamide.

  8. ANTI INFLAMMATORY ACTIVITY OF SOME NEW THIO-ETHER DERIVATIVES OF QUINOXALINE

    Singh, Dharmchand Prasad

    2010-12-01

    Full Text Available A series of thioether derivatives of 2-Chloro-3-methylquinoxaline have been synthesized by reacting 3- methylquinoxalin-2-thiosodium with 2-chloro-N-(substituted aryl/alkyl-acetamides. The synthesis was initiated with the reaction of o-phenylenediamine (1 with ethyl pyruvate in n-butanol to yield 2-hydroxy-3-methyl quinoxaline (2, which on treatment with POCl3 ,yielded 2-chloro-3-methylquinoxaline(3.A mixture of the compound(3 and sodium sulphide in DMF was refluxed to yield 3-methylquinoxalin-2-thiosodium(4,which on treatment with different Nsubstituted chloroacetamides afforded the one pot synthesis of 2-(2-methylquinoxalin-3-ylthio-N-substitutedaryl/ alkyl-acetamides(5a-k. 2-chloro-N-substituted acetamides were prepared by treating substituted anilines in glacial acetic acid with chloroacetylchloride, warming on the water bath for half an hour and then precipitating, 2- chloro-N-substituted acetamides by addition of saturated aqueous solution of anhydrous sodium acetate. A compound 2-(benzylthio-3-methylquinoxaline 5l was also prepared. The newly synthesized compounds have been characterized by IR, and 1HNMR spectra, analysis. All compounds (5a-l were screened for their in vivo anti inflammatory activity by carrageenan induced rat paw edema method. Compounds 5a, 5b, 5d, 5e, 5g and 5k have been found to possess good anti inflammatory activity.

  9. Synthesis, characterization, fluorescence and DNA-binding studies of europium(Ⅲ) pirates complexes with amide-based 2,3-dihydroxynaphthalene derivatives

    LI Hanyu; YANG Tianlin; DING Ling; WANG Wenhua

    2012-01-01

    Two ligands 2,2'-[2,3-naphthylenebis(oxy)]-bis(N-benzyl(acetamide)(L1) and 22'-[23-naphthylenebis (oxy)]-bis(N,N-diphenyl (acetamide)(L2) and their europium(Ⅲ) picrate complexes were synthesized.The complexes were characterized by elemental analysis,infrared (IR),thermogravimetry and differential thermal analysis (TG-DTA) and molar conductivity.Fluorescent experiments showed that the resonance level of the Eu(Ⅲ) matched better to the triplet state energy level of the ligand L2 than that of the ligand L1 and the fluorescence intensifies of the complexes were reduced with the raising coordination ability of solvent.In addition,the interactions between the complexes and DNA were studied by means of spectrometry and cyclic voltammetry.The results suggested that the complexes could bind to DNA through intercalation and the complex 1 binded to DNA more strongly than the complex 2.

  10. Synthesis of some benzimidazole derivatives endowed with 1,2,3-triazole as potential inhibitors of hepatitis C virus.

    Youssif, Bahaa G M; Mohamed, Yaseen A M; Salim, Mohammed T A; Inagaki, Fuyuhiko; Mukai, Chisato; Abdu-Allah, Hajjaj H M

    2016-06-01

    New derivatives of 2-thiobenzimidazole incorporating triazole moiety were synthesized, characterized and tested in vitro for antiviral activity against hepatitis C virus (HCV) and hepatitis B virus (HBV). Their cytotoxicity was determined by the reduction in the number of viable cell. All of the synthesized compounds are inactive against HBV and some showed activity against HCV. In particular, two compounds showed significant activity, 2-{4-[(1-benzoylbenzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitro-phenyl)-acetamide (13) and 2-(4-{[1-(p-chlorobenzoyl)-benzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitrophenyl)-acetamide (17). The results give an insight into the importance of the substituent at position 2 of benzimidazole for the inhibition of HCV. PMID:27279065

  11. Synthetic approaches to multifunctional indenes

    López-Pérez, Sara; Dinarès, Immaculada

    2011-01-01

    Summary The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3-indenyl)acetamides as key intermediates. Although several multistep synthetic approaches can be applied to obtain these advanced intermediates, we describe herein their preparation by an aldol-type reaction between 5-nitroindan-1-ones and the lithium salt of N,N-disubstituted acetamides, followed immediately by dehydration with acid. This classical condensation process, which is neither simple nor trivial despite its apparent directness, permits an efficient entry to a variety of indene-based molecular modules, which could be adapted to a range of functionalized indanones. PMID:22238553

  12. Diphenamid metabolism in pepper and an ozone effect. II. Herbicide metabolite characterization

    Hodgson, R.H.; Hoffer, B.L.

    1977-07-01

    Metabolites of diphenamid (N,N-dimethyl-2,2-diphenyl-acetamide) were purified from extracts of pepper plants (Capsicum frutescens L. Early Calwonder) treated via nutrient solution with the herbicide or several of its analogs. The major metabolites were characterized. Diphenamid was metabolized partially via a previously unreported pathway to N,N-dimethyl-2-phenyl-2-((hydroxyphenyl)-..beta..-0-D-glucosyl) acetamide and its monomethyl analog, and to N-hydroxy-methyl glycosides previously reported in other species. Ozone fumigation stimulated the production of both types of glycoside-conjugates. Leaves of plants that had been treated with 30 ..mu..M diphenamid and fumigated with ozone for 146 to 149 h contained 304 and 560 nmoles per gram of fresh weight of the hydroxyphenyl and N-hydroxymethyl conjugates, respectively. 7 references, 1 figure, 3 tables.

  13. Radiolysis of paracetamol in dilute aqueous solution

    Szabó, László; Tóth, Tünde; Homlok, Renáta; Takács, Erzsébet; Wojnárovits, László

    2012-09-01

    Using radiolytic experiments hydroxyl radical (main reactant in advanced oxidation processes) was shown to effectively destroy paracetamol molecules. The basic reaction is attachment to the ring. The hydroxy-cyclohexadienyl radical produced in the further reactions may transform to hydroxylated paracetamol derivatives or to quinone type molecules and acetamide. The initial efficiency of aromatic ring destruction in the absence of dissolved O2 is c.a. 10%. The efficiency is 2-3 times higher in the presence of O2 due to its reaction with intermediate hydroxy-cyclohexadienyl radical and the subsequent ring destruction reactions through peroxi radical. Upon irradiation the toxicity of solutions at low doses increases with the dose and then at higher doses it decreases. This is due to formation of compounds with higher toxicity than paracetamol (e.g. acetamide, hidroquinone). These products, however, are highly sensitive to irradiation and degrade easily.

  14. N-(5-Benzylsulfanyl-1,3,4-thiadiazol-2-yl-2-(piperidin-1-ylacetamide

    D. S. Ismailova

    2014-03-01

    Full Text Available The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzylsulfanyl-5-chloroacetamido-1,3,4-thiadiazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thiadiazole units are twisted by 10.8 (4°. The thiadiazole S atom and the acetamide O atom are syn-oriented due to a hypervalent S...O interaction of 2.628 (4 Å. In the crystal, molecules form centrosymmetric dimers via N—H...N hydrogen bonds. These dimers are further connected by C—H...O interactions into (100 layers.

  15. Crystal structure of tetrakis(μ-N-phenylacetamidato-κ4N:O;κ4O:N-bis[(2-methylbenzonitrile-κNrhodium(II](Rh—Rh

    Cassandra T. Eagle

    2014-09-01

    Full Text Available The complex molecule of the title compound, [Rh2{N(C6H5COCH3}4(C8H7N2], exhibits inversion symmetry. The four acetamidate ligands bridging the dirhodium core are arranged in a 2,2-trans manner with two N atoms and two O atoms coordinating to each RhII atom trans to one another. The Neq—Rh—Rh—Oeq torsion angles on the acetamidate bridge vary between −4.07 (5 and −6.78 (7°. The axial nitrile ligands complete the distorted octahedral coordination sphere of each RhII atom and show a nonlinear coordination with Rh—N—C bond angles of 151.6 (3 and 152.5 (3°. The bond lengths of the two nitrile triple bonds are 1.133 (5 and 1.137 (5 Å.

  16. (3-Methylbenzonitrile-1κN-cis-tetrakis(μ-N-phenylacetamidato-1:2κ4N:O;1:2κ4O:N-dirhodium(II(Rh—Rh

    Cassandra T. Eagle

    2014-08-01

    Full Text Available The complex molecule of the title compound, [Rh2{N(C6H5COCH3}4(NCC7H7], has crystallographically-imposed mirror symmetry. The four acetamide ligands bridging the dirhodium core are arranged in a 2,2-cis manner with two N atoms and two O atoms coordinating to the unique RhII atom cis to one another. The Neq—Rh—Rh—Oeq torsion angles on the acetamide bridge are 0.75 (7 and 1.99 (9°. The axial nitrile ligand completes the distorted octahedral coordination sphere of one RhII atom and shows a nonlinear coordination, with an Rh—N—C bond angle of 162.8 (5°; the N—C bond length is 1.154 (7 Å.

  17. Piracetam and TRH analogues antagonise inhibition by barbiturates, diazepam, melatonin and galanin of human erythrocyte D-glucose transport

    Richard J Naftalin; Cunningham, Philip; Afzal-Ahmed, Iram

    2004-01-01

    Nootropic drugs increase glucose uptake into anaesthetised brain and into Alzheimer's diseased brain. Thyrotropin-releasing hormone, TRH, which has a chemical structure similar to nootropics increases cerebellar uptake of glucose in murine rolling ataxia. This paper shows that nootropic drugs like piracetam (2-oxo 1 pyrrolidine acetamide) and levetiracetam and neuropeptides like TRH antagonise the inhibition of glucose transport by barbiturates, diazepam, melatonin and endogenous neuropeptide...

  18. Transport methods for probing the barrier domain of lipid bilayer membranes.

    Xiang, T X; Chen, X.; Anderson, B. D.

    1992-01-01

    Two experimental techniques have been utilized to explore the barrier properties of lecithin/decane bilayer membranes with the aim of determining the contributions of various domains within the bilayer to the overall barrier. The thickness of lecithin/decane bilayers was systematically varied by modulating the chemical potential of decane in the annulus surrounding the bilayer using different mole fractions of squalene in decane. The dependence of permeability of a model permeant (acetamide) ...

  19. Disperse Dyes Based on Thiazole, Their Dyeing Application on Polyester Fiber and Their Antimicrobial Activity

    Zadafiya, S. K.; J. H. Tailor; Malik, G. M.

    2013-01-01

    Various diazotized aryl amines were coupled with N-(4-nitrophenyl)-2-[(4-phenyl-1,3-thiazol-2-yl)amino]acetamide to give the corresponding various azo disperse dyes (D1-D13). These dyes were applied to polyester fiber by HTHP method and their fastness properties were evaluated. Dyes were characterized by IR, elemental analysis, and NMR spectral studies. These dyes showed very good antibacterial and antifungal activities.

  20. One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br3 under solvent-free conditions

    Arash Ghorbani-Choghamarani; Shima Rashidimoghadam

    2014-01-01

    A facile and efficient method has been developed for the synthesis of 1-amidoalkyl-2-naphthols via the one-pot multi-component condensation of 2-naphthol with aromatic aldehydes and acetamide or thioacetamide in the presence of melamine-Br3 under solvent-free conditions. There are several advantages to this reaction, including high yields, short reaction time, and high catalytic efficiency.

  1. Methods for Cryopreservation of Guinea Fowl Sperm

    Váradi, Éva; Végi, Barbara; Liptói, Krisztina; Barna, Judit

    2013-01-01

    Conservation of indigenous poultry species is an important part of the new Hungarian agricultural strategy. Semen cryopreservation is the most practical method for the long term storage of poultry genetic material. The objective was to compare four protocols for cryopreservation of guinea fowl sperm (slow and fast programmable, freezing in nitrogen vapor, and pellet) and three cryoprotectants (10% ethylene glycol, 6% dimethyl-formamide and 6% dimethyl-acetamide). The efficiency of the methods...

  2. Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds.

    Vicario, Jose L; Rodriguez, Mónica; Badía, Dolores; Carrillo, Luisa; Reyes, Efraim

    2004-09-01

    [reaction: see text] The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aldehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones. PMID:15330615

  3. Synthesis and optical resolution of the neurotoxin 2-amino-3-([[sup 15]N]-methylamino)propanoic acid (BMAA)

    Yulin Hu; Ziffer, H. (National Inst. of Diabetes and Digestive and Kidney Diseases, Bethesda, MD (United States))

    1990-05-01

    The synthesis of 2-amino-3-([[sup 15]N]-methylamino)propanoic acid (synonyms, BMAA, [beta]-N-mehylamino-alanine) from [alpha]-acetamidoacrylic acid and [[sup 15]N]-methylamine is described. Enantioselective hydrolysis of the acetamide group, mediated by the enzyme Acylase 1 (EC 3.5.1.14), yielded (R)-BMAA and the (S)-[alpha]-acetamido derivative. Acid hydrolysis of the latter compound yielded (S)-BMAA. (author).

  4. Inducible nitric oxide synthase is involved in the modulation of depressive behaviors induced by unpredictable chronic mild stress

    Peng Yun-Li; Liu Yu-Ning; Liu Lei; Wang Xia; Jiang Chun-Lei; Wang Yun-Xia

    2012-01-01

    Abstract Background Experiences and inflammatory mediators are fundamental in the provocation of major depressive disorders (MDDs). We investigated the roles and mechanisms of inducible nitric oxide synthase (iNOS) in stress-induced depression. Methods We used a depressive-like state mouse model induced by unpredictable chronic mild stress (UCMS). Depressive-like behaviors were evaluated after 4 weeks of UCMS, in the presence and absence of the iNOS inhibitor N-(3-(aminomethyl)benzyl)acetamid...

  5. Synthesis and Antimicrobial Activity ofSome New Thioether Derivatives of Quinoxaline

    Singh, D. C. P.; S. R. Hashim; Singhal, R. G.

    2011-01-01

    2-Chloro-3-methylquinoxaline was selected as nucleus around which the molecular manipulations were carried out to get new compounds expected to possess better anti microbial activity. Various quinoxaline derivatives have been synthesized by replacing the chlorine at C-2 with a thioether linkage, which in turn attached to 2-(N-(substituted phenyl)acetamides. The synthesized compounds (5) were tested for their antimicrobial activity. Compounds 5b, 5c, 5d and 5i were found most active (comparabl...

  6. Effect of absorption and translocation on the acetochlor susceptibility of plants

    Absorption and translocation of acetochlor (2-chloro-N-)2-ethyl-6-methylphenyl(N-)ethoxymethyl(acetamide) herbicide were followed in experiments with tolerant corn (Zea mays L.) and sensitive wheat (Triticum aestivum L.) plants by using carbonyl-sup(14)C labelled compound. Tolerant plant species absorbed more radioactivity from the nutrient solution than susceptible plant species. However, the root-absorbed radioactivity was translocated to the shoot more readily in the sensitive plants. (author)

  7. Effect of absorption and translocation on the acetochlor susceptibility of plants

    Jablonkai, I.; Dutka, F. (Magyar Tudomanyos Akademia, Budapest. Koezponti Kemiai Kutato Intezete)

    1985-04-01

    Absorption and translocation of acetochlor (2-chloro-N-)2-ethyl-6-methylphenyl(N-)ethoxymethyl(acetamide) herbicide were followed in experiments with tolerant corn (Zea mays L.) and sensitive wheat (Triticum aestivum L.) plants by using carbonyl-sup(14)C labelled compound. Tolerant plant species absorbed more radioactivity from the nutrient solution than susceptible plant species. However, the root-absorbed radioactivity was translocated to the shoot more readily in the sensitive plants.

  8. Synthesis and optical resolution of the neurotoxin 2-amino-3-([15N]-methylamino)propanoic acid (BMAA)

    The synthesis of 2-amino-3-([15N]-methylamino)propanoic acid (synonyms, BMAA, β-N-mehylamino-alanine) from α-acetamidoacrylic acid and [15N]-methylamine is described. Enantioselective hydrolysis of the acetamide group, mediated by the enzyme Acylase 1 (EC 3.5.1.14), yielded (R)-BMAA and the (S)-α-acetamido derivative. Acid hydrolysis of the latter compound yielded (S)-BMAA. (author)

  9. Chemoselective hydrogenation of carbonyl compounds and acceptorless dehydrogenative coupling of alcohols.

    Spasyuk, Denis; Vicent, Cristian; Gusev, Dmitry G

    2015-03-25

    OsHCl(CO)[κ(3)-PyCH2NHC2H4NHPtBu2] is the first efficient catalyst for chemoselective reduction of challenging unsaturated esters to enols and for acceptorless coupling of amines with MeOH and EtOH affording formamides and acetamides. The NMR, ESI-MS, and DFT data indicate a mechanism proceeding in the metal coordination sphere and producing no free organic intermediates. PMID:25741992

  10. Disperse Dyes Based on Thiazole, Their Dyeing Application on Polyester Fiber and Their Antimicrobial Activity

    S. K. Zadafiya

    2013-01-01

    Full Text Available Various diazotized aryl amines were coupled with N-(4-nitrophenyl-2-[(4-phenyl-1,3-thiazol-2-ylamino]acetamide to give the corresponding various azo disperse dyes (D1-D13. These dyes were applied to polyester fiber by HTHP method and their fastness properties were evaluated. Dyes were characterized by IR, elemental analysis, and NMR spectral studies. These dyes showed very good antibacterial and antifungal activities.

  11. Spectroscopy of the amide-I modes of acetanilide

    Raman measurements were made on acetanilide (N-phenyl-acetamide). Data are presented of the integrated intensity of the 1650 cm-1 band as a function of temperature. The experimental procedures and data reduction were highly rigorous and are believed to be to most reliable data available. A concise theory of polaron states is presented and used to interpret the data. 22 refs., 4 figs., 1 tab

  12. In Planta Production of Indole-3-Acetic Acid by Colletotrichum gloeosporioides f. sp. aeschynomene

    Maor, Rudy; Haskin, Sefi; Levi-Kedmi, Hagit; Sharon, Amir

    2004-01-01

    The plant pathogenic fungus Colletotrichum gloeosporioides f. sp. aeschynomene utilizes external tryptophan to produce indole-3-acetic acid (IAA) through the intermediate indole-3-acetamide (IAM). We studied the effects of tryptophan, IAA, and IAM on IAA biosynthesis in fungal axenic cultures and on in planta IAA production by the fungus. IAA biosynthesis was strictly dependent on external tryptophan and was enhanced by tryptophan and IAM. The fungus produced IAM and IAA in planta during the ...

  13. CH Stretching Region: Computational Modeling of Vibrational Optical Activity

    Hudecová, Jana; Profant, V.; Novotná, P.; Baumruk, V.; Urbanová, M.; Bouř, Petr

    2013-01-01

    Roč. 9, č. 7 (2013), s. 3096-3108. ISSN 1549-9618 R&D Projects: GA ČR GAP208/11/0105; GA MŠk(CZ) LH11033 Grant ostatní: AV ČR(CZ) M200550902 Institutional support: RVO:61388963 Keywords : density-functional theory * circular-dichroism spectra * N-methyl acetamide * alpha-pinene * Raman Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 5.310, year: 2013

  14. Crystal structures of two (±-exo-N-isobornylacetamides

    Dmitrijs Stepanovs

    2015-10-01

    Full Text Available The title compounds consist of a bornane skeleton with attached acetamide, C12H21NO (±-(1 {systematic name: (±-N-[(1RS,2RS,4RS-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]acetamide}, and chloroacetamide, C12H20ClNO (±-(2 {systematic name: (±-2-chloro-N-[(1RS,2RS,4RS-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]acetamide}, functionalities to the 2-exo-position. The crystal structure of the first monoclinic polymorph of (±-(1 has been reported previously [Ung et al. (2014. Monatsh. Chem. 145, 983–992]. Compound (±-(1 crystallizes in the space group P21/n with two independent molecules in the asymmetric unit, in contrast to the above-mentioned polymorph which crystallized in the space group C2/c with one molecule in the asymmetric unit. In the title compounds, the bicyclic bornane moieties have normal geometries. In the crystals of both compounds, molecules are linked by N—H...O hydrogen bonds, reinforced by C—H...O contacts, forming trans-amide chains propagating along the a-axis direction. In the case of compound (±-(1, neighbouring chains are linked by further C—H...O contacts, forming double-chain ribbons along [100].

  15. Radiolysis of paracetamol in dilute aqueous solution

    Using radiolytic experiments hydroxyl radical (main reactant in advanced oxidation processes) was shown to effectively destroy paracetamol molecules. The basic reaction is attachment to the ring. The hydroxy-cyclohexadienyl radical produced in the further reactions may transform to hydroxylated paracetamol derivatives or to quinone type molecules and acetamide. The initial efficiency of aromatic ring destruction in the absence of dissolved O2 is c.a. 10%. The efficiency is 2–3 times higher in the presence of O2 due to its reaction with intermediate hydroxy-cyclohexadienyl radical and the subsequent ring destruction reactions through peroxi radical. Upon irradiation the toxicity of solutions at low doses increases with the dose and then at higher doses it decreases. This is due to formation of compounds with higher toxicity than paracetamol (e.g. acetamide, hidroquinone). These products, however, are highly sensitive to irradiation and degrade easily. - Highlights: ► Paracetamol is easily degraded in aqueous solution by low dose irradiation. ► Main degradation products are hydroxylated molecules, acetamide and hydroquinone. ► Toxicity of solutions goes through a maximum as a function of dose.

  16. Dielectric behaviour of some amides and formamides dissolved in nonpolar solvents under static electric field

    S Sahoo; S K Sit

    2011-08-01

    Structural and associational aspects of polar amides () like formamide, acetamide, Nmethyl acetamide (NMA), N,N-dimethyl formamide (DMF), N,N-dimethyl acetamide (DMA) and acetanilide dissolved in the nonpolar solvent () benzene or 1,4-dioxan have been estimated from the measured static relative permittivity 0 and high-frequency permittivity ∞ at different weight fractions s of polar solute at 35°C under static electric field using Debye model of polar liquid molecule. The static dipole moments s are compared with s reported from conductivity method and theoretical theos to get exact cal $\\cdot$ theos of the molecules are predicted from the available bond angles and bond moments where difference in electron affinity exists between two adjacent atoms of a polar group due to inductive, mesomeric and electromeric effects in them. Solute–solute molecular association for NMA in benzene and solute–solvent association for other amides are ascertained to arrive at their conformational structures.

  17. Synthesis of azepino[4,5-b]indol-4-ones via MCR/free radical cyclization and in vitro-in silico studies as 5-Ht6R ligands.

    Rentería-Gómez, Angel; Islas-Jácome, Alejandro; Díaz-Cervantes, Erik; Villaseñor-Granados, Tayde; Robles, Juvencio; Gámez-Montaño, Rocío

    2016-05-01

    A series of nine new 3-acetamide-azepino[4,5-b]indol-4-ones were synthesized in two steps: (i) multicomponent reaction (Ugi-4CR/SN2) and (ii) free radical-mediated cyclization. These compounds, along with their tetrazole-based analogs, were studied in vitro to assess their binding with the 5-hydroxytryptamine type 6 receptor (5-Ht6R). The 3-acetamide-azepino[4,5-b]indol-4-ones displayed moderate affinity, whereas the 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones affinity values are lower. However, one of the 3-acetamide-azepino[4,5-b]indol-4-ones exhibited a hit value of Ki (211.2nM) to the 5-Ht6R. Minimal-energy structures of one cis-amide and its tetrazole-based analog (calculated by means of the Density Functional Theory) were analyzed to assess some interesting bioisosterism aspects. Interactions and binding energies between all products and the 5-Ht6R were calculated through in silico molecular couplings. Finally, a QSAR model was proposed using the results of the in vitro assays. PMID:26996373

  18. Development of a Candida glabrata dominant nutritional transformation marker utilizing the Aspergillus nidulans acetamidase gene (amdS).

    Fu, Jianmin; Blaylock, Morganne; Wickes, Cameron F; Welte, William; Mehrtash, Adrian; Wiederhold, Nathan; Wickes, Brian L

    2016-05-01

    The gene encodingAspergillus nidulansacetamidase (amdS) was placed under control ofCandida albicans ACT1promoter and terminator sequences and then cloned into a plasmid containingC. glabrata ARS10,CEN8orARS10+CEN8sequences. All plasmids transformedC. glabratawild-type cells to acetamide+, with theARS-only containing plasmid transforming cells at the highest frequencies (>1.0 × 10(4)transformants μg(-1)). Plasmids were rapidly lost under non-selective conditions with the frequency dependent on chromosomal element, thus recycling the acetamide- phenotype. TheamdSplasmid was used to transform a set of clinical isolates resistant to a variety of antifungal drugs. All strains were successfully transformed to the acetamide+ phenotype at high frequency, confirming that this plasmid construct could be used as a simple dominant marker on virtually any strain. Gap repair experiments demonstrated that just as inSaccharomyces cerevisiae, gap repair functions efficiently inC. glabrata, suggesting thatC. glabratahas numerous similarities toS. cerevisiaewith regard to ease of molecular manipulation. TheamdSsystem is inexpensive and efficient, and combined with existingC. glabrataplasmid elements, confers a high transformation frequency forC. glabratawith a phenotype that can be easily recycled. PMID:26975388

  19. Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems

    Rafat Milad Mohareb

    2011-07-01

    Full Text Available A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated.

  20. Investigation of Uranyl Nitrate Ion Pairs Complexed with Amide Ligands using Electrospray Ionization Ion Trap Mass Spectrometry and Density Functional Theory

    Ion populations formed from electrospray of uranyl nitrate solutions containing different amides vary depending on ligand nucleophilicity and steric crowding at the metal center. The most abundant species were ion pair complexes having the general formula (UO2(NO3)(amide)n=2,3)+, and complexes containing the amide conjugate base, reduced uranyl UO2+, and a 2+ charge were also formed. The formamide experiment produced the greatest diversity of species that stems from weaker amide binding leading to dissociation and subsequent solvent coordination or metal reduction. Experiments using methyl formamide, dimethyl formamide, acetamide, and methyl acetamide produced ion pair and doubly charged complexes that were more abundant, and less abundant complexes containing solvent or reduced uranyl. This pattern is reversed in the dimethylacetamide experiment, which displayed reduced doubly charged complexes and augmented reduced uranyl complexes. DFT investigations of the tris-amide ion pair complexes showed that inter-ligand repulsion distorts the amide ligands out of the uranyl equatorial plane, and that complex stabilities do not increase with increasing amide nucleophilicity. Elimination of an amide ligand largely relieves the interligand repulsion, and the remaining amide ligands become closely aligned with the equatorial plane in the structures of the bis-amide ligands. The studies show that the phenomenological distribution of coordination complexes in a metal-ligand electrospray experiment is a function of both ligand nucleophilicity and interligand repulsion, and that the latter factor begins exerting influence even in the case of relatively small ligands like the substituted methyl-formamide and methyl-acetamide ligands.

  1. Investigation of Uranyl Nitrate Ion Pairs Complexed with Amide Ligands using Electrospray Ionization Ion Trap Mass Spectrometry and Density Functional Theory

    Gary S. Groenewold; Adriana Dinescu; Michael T. Benson; Garold L. Gresham; Michael J. van Stipdonk

    2011-04-01

    Ion populations formed from electrospray of uranyl nitrate solutions containing different amides vary depending on ligand nucleophilicity and steric crowding at the metal center. The most abundant species were ion pair complexes having the general formula [UO2(NO3)(amide)n=2,3]+, and complexes containing the amide conjugate base, reduced uranyl UO2+, and a 2+ charge were also formed. The formamide experiment produced the greatest diversity of species that stems from weaker amide binding leading to dissociation and subsequent solvent coordination or metal reduction. Experiments using methyl formamide, dimethyl formamide, acetamide, and methyl acetamide produced ion pair and doubly charged complexes that were more abundant, and less abundant complexes containing solvent or reduced uranyl. This pattern is reversed in the dimethylacetamide experiment, which displayed reduced doubly charged complexes and augmented reduced uranyl complexes. DFT investigations of the tris-amide ion pair complexes showed that inter-ligand repulsion distorts the amide ligands out of the uranyl equatorial plane, and that complex stabilities do not increase with increasing amide nucleophilicity. Elimination of an amide ligand largely relieves the interligand repulsion, and the remaining amide ligands become closely aligned with the equatorial plane in the structures of the bis-amide ligands. The studies show that the phenomenological distribution of coordination complexes in a metal-ligand electrospray experiment is a function of both ligand nucleophilicity and interligand repulsion, and that the latter factor begins exerting influence even in the case of relatively small ligands like the substituted methyl-formamide and –acetamide ligands.

  2. Preparation and research of PAN/ZnO anti-static composite nano-fiber

    Hailing WEI; Wenyuan HE; Shen, Xiaohong; Feng, Xiaoyan

    2015-01-01

    In order to improve the anti-static performance of polyacrylonitrile(PAN) fiber, with PAN fiber as raw material, N, N-dimethyl acetamide (DMAC) as solvent, prepared PAN spinning solution.Then added different ratios of nano-ZnO, with good conductivity, to the PAN spinning solution by the method of ultrasound and mechanical stirring,prepared PAN/ZnO composite spinning solution. After that, PAN/ZnO nano-fibers with anti-static property were prepared by electrostatic spinning technique. The spin-...

  3. Highly Efficient N-Monomethylation of Primary Aryl Amines

    PENG, Yiyuan; LIU, Hanliang; TANG, Min; CAI, Lisheng; PIKE, Victor

    2009-01-01

    A highly efficient method for specific synthesis of N-monomethylarylamines is presented. Anilines were treated with acetic anhydride and triethylamine in dry CH2Cl2 to give the corresponding acetamides. The subsequent N-monomethylation of acetyl aryl amines with methyl iodide and Nail in THF introduced methyl group. Acid hy- drolysis of the N-methyl acetanilides in ethylene glycol generated the corresponding N-methyl-N-aryi amines in high yields. This method was also used to synthesize (E)-2-bromo-5-(4-methylaminostyryl)pyridine that may be useful as an amyloid imaging agent for Alzheimer's disease.

  4. 2-Heteroaryl Benzimidazole Derivatives as Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists

    Lim, Chae Jo; Kim, Jeong Young; Lee, Byung Ho; Oh, Kwangseok; Yi, Kyu Yang [Korea Research Institute of Chemical Technology, Daejeon (Korea, Republic of)

    2013-08-15

    A novel series of 2-heteroaryl substituted benzimidazole derivatives, containing the piperidinylphenyl acetamide group at the 1-position, were synthesized and evaluated as MCH-R1 antagonists. Extensive SAR investigation probing the effects of C-2 heteroaryl group led to the identification of 2-[2-(pyridin-3-yl)ethyl] analog 3o, which exhibits highly potent MCH-R1 binding activity with an IC{sub 50} value of 1 nM. This substance 3o also has low hERG binding activity, good metabolic stability, and favorable pharmacokinetic properties.

  5. Electrodeposition of luminescent composite metal coatings containing rare-earth phosphor particles

    Ganapathi, Murugan; Eliseeva, Svetlana V.; Brooks, Neil; Soccol, Dimitri; Fransaer, Jan; Binnemans, Koen

    2012-01-01

    Mixtures of acetamide and dimethylsulfone (DMSO2) with dissolved anhydrous transition metal chlorides are introduced as new non-aqueous electrolytes for the preparation of composite metal coatings with embedded hydrophilic particles via an electrolytic co-deposition process. Red-emitting (Eu2O3 and Y2O3:Eu3+), yellow-emitting (Y3Al5O12:Ce3+), green-emitting (Gd2O2S:Tb3+) and blue-emitting (BaMg2Al16O27:Eu2+) rare-earth phosphor particles and yttrium oxide particles have been embedded into thi...

  6. Role of pseudoephedrine as chiral auxiliary in the "acetate-type" aldol reaction with chiral aldehydes; asymmetric synthesis of highly functionalized chiral building blocks.

    Ocejo, Marta; Carrillo, Luisa; Vicario, Jose L; Badía, Dolores; Reyes, Efraim

    2011-01-21

    We have studied in depth the aldol reaction between acetamide enolates and chiral α-heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom-containing substituent of the chiral aldehyde is conveniently protected. Moreover, the obtained highly functionalized aldols have been employed as very useful starting materials for the stereocontrolled preparation of other interesting compounds and chiral building blocks such as pyrrolidines, indolizidines, and densely functionalized β-hydroxy and β-amino ketones using simple and high-yielding methodologies. PMID:21188970

  7. Catalytic behaviour in the ring-opening polymerisation of organoaluminiums supported by bulky heteroscorpionate ligands.

    Castro-Osma, Jose A; Alonso-Moreno, Carlos; Lara-Sánchez, Agustín; Otero, Antonio; Fernández-Baeza, Juan; Sánchez-Barba, Luis F; Rodríguez, Ana M

    2015-07-21

    A series of alkyl organoaluminium complexes based on bulky heteroscorpionate ligands were designed as catalysts for the ring-opening polymerisation of cyclic esters. Thus, the treatment of AlX3 (X = Me, Et) with bulky acetamide or thioacetamide heteroscorpionate ligands nbptamH (1) [nbptamH = N-naphthyl-2,2-bis(3,5-dimethylpyrazol-1-yl)thioacetamide], fbpamH (2) [fbpamH = N-fluorenyl-2,2-bis(3,5-dimethylpyrazol-1-yl)acetamide], ptbptamH (3) [ptbptamH = N-phenyl-2,2-bis(3,5-di-tert-butylpyrazol-1-yl)thioacetamide], ntbptamH (4) [ntbptamH = N-naphthyl-2,2-bis(3,5-di-tert-butylpyrazol-1-yl)thioacetamide], ptbpamH (5) [ptbpamH = N-phenyl-2,2-bis(3,5-di-tert-butylpyrazol-1-yl)acetamide] and (S)-mtbpamH (6) [(S)-mtbpamH = (S)-(−)-N-α-methylbenzyl-2,2-bis(3,5-di-tert-butylpyrazol-1-yl)acetamide] for 1 hour at 0 °C afforded the dialkyl aluminium complexes [AlX2{κ(2)-nbptam}] (X = Me 7, Et 8), [AlX2{κ(2)-fbpam}] (X = Me 9, Et 10), [AlX2{κ(2)-ptbptam}] (X = Me 11, Et 12), [AlX2{κ(2)-ntbptam}] (X = Me 13, Et 14), [AlX2{κ2(-)ptbpam}] (X = Me 15, Et 16) and [AlX2{κ(2)-(S)-mtbpam}] (X = Me 17, Et 18). The structures of the complexes were determined by spectroscopic methods and the X-ray crystal structure of 14 was also established. The alkyl-containing aluminium complexes 7–18 can act as efficient single-component initiators for the ring-opening polymerisation of ε-caprolactone and rac-lactide. The polymerisations are living, as evidenced by the narrow polydispersities of the isolated polymers and the linear nature of the number average molecular weight versus conversion plot. Finally, a comparative study of ring-opening polymerisation for new bulky heteroscorpionate aluminium initiators and the less congested aluminium analogues is reported. PMID:25534594

  8. Synthesis and in vitro Evaluation of New Benzothiazole Derivatives as Schistosomicidal Agents

    Mahran, Mona A; Samia William; Fatem Ramzy; Sembel, Amira M

    2007-01-01

    A series of benzothiazol-2-yl-dithiocarbamates 3a-d along with their copper complexes 4a-c were synthesized via the reaction of suitable alkyl, aralkyl or heteroaryl halides with the sodium salt of benzothiazol-2-yl-dithiocarbamic acid, followed by complexation with copper sulphate. N-(4-Acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl)-N-benzothiazol-2-yl-acetamides 7a-c were synthesized by cyclization of the appropriate thiosemicarbazones 6a-c in acetic anhydride. Selected compounds were scr...

  9. Preparation of 2-[α-(2-ethoxyphenoxy)benzyl]-[5-14C]morpholine methanesulfonate ([14C]reboxetine):a new antidepressant agent

    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-[1-14C]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 [5-14C]morpholine derivative 4, 98% radiochemically pure and with specific radioactivity of 988 MBq/mmol. An overall radiochemical yield of 57.5% was achieved. (author)

  10. N-(4-Sulfamoylphenylacetamide

    Abdullah M. Asiri

    2012-04-01

    Full Text Available In the title compound, C8H10N2O3S, the dihedral angle between the acetamide group and the benzene ring is 15.59 (12° and the amino group is close to being perpendicular to the benzene ring [N—S—Car—Car (ar = aromatic torsion angle = 109.4 (2°]. In the crystal, molecules are linked into supramolecular tubes parallel to [001] by amine–amide N—H...O interactions and these are connected into the three-dimensional architecture by amide–sulfonamide N—H...O hydrogen bonds. The crystal studied was a racemic twin.

  11. Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanylpyridin-2-yl]-2-chloroacetamide

    Shaaban K. Mohamed

    2015-03-01

    Full Text Available In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83 (12°. The O=C—C—Cl torsion angle is 46.4 (3° and an intramolecular C—H...O interaction generates an S(6 ring. In the crystal, molecules are linked by N—H...O, N—H...N and C—H...N hydrogen bonds, generating sheets lying parallel to (120.

  12. Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]-2-chloroacetamide

    Shaaban K. Mohamed; Knight, Kyle S.; Mehmet Akkurt; Hussein, Bahgat R. M.; Mustafa R. Albayati

    2015-01-01

    In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83 (12)°. The O=C—C—Cl torsion angle is 46.4 (3)° and an intramolecular C—H...O interaction generates an S(6) ring. In the crystal, molecules are linked by N—H...O, N—H...N and C—H...N hydrogen bonds, generating sheets lying parallel to (120).

  13. Synthesis of carbonyl-/sup 14/C labelled 'acetochlor'

    Jablonkai, I.; Marton, A.F.; Dutka, F. (Hungarian Academy of Sciences, Budapest. Central Research Inst. for Physics)

    1982-09-20

    Carbonyl-/sup 14/C labelled 'acetochlor' (2-chloro-N-ethoxymethyl-N-(2-ethyl-6-methylphenyl)acetamide) was prepared by chlorination of acetic-1-/sup 14/C acid obtained from barium radiocarbonate to monochloroacetic-1-/sup 14/C acid which was further chlorinated to monochloroacetyl-1-/sup 14/C chloride. The addition reaction of this latter with 2-ethyl-6-methylene aniline gave a chloromethyl derivative the ethanolysis of which resulted in 'acetochlor' labelled in its carbonyl carbon. The overall radiochemical yield is 51%.

  14. Synthesis of carbonyl-14C labelled 'acetochlor'

    Carbonyl-14C labelled 'acetochlor' (2-chloro-N-ethoxymethyl-N-(2-ethyl-6-methylphenyl)acetamide) was prepared by chlorination of acetic-1-14C acid obtained from barium radiocarbonate to monochloroacetic-1-14C acid which was further chlorinated to monochloroacetyl-1-14C chloride. The addition reaction of this latter with 2-ethyl-6-methylene aniline gave a chloromethyl derivative the ethanolysis of which resulted in 'acetochlor' labelled in its carbonyl carbon. The overall radiochemical yield is 51%. (author)

  15. 18F-EF5 PET Is Predictive of Response to Fractionated Radiotherapy in Preclinical Tumor Models

    Rehan Ali; Sandeep Apte; Marta Vilalta; Murugesan Subbarayan; Zheng Miao; Chin, Frederick T.; Graves, Edward E.

    2015-01-01

    We evaluated the relationship between pre-treatment positron emission tomography (PET) using the hypoxic tracer 18F-[2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3- pentafluoropropyl) acetamide] (18F-EF5) and the response of preclinical tumor models to a range of fractionated radiotherapies. Subcutaneous HT29, A549 and RKO tumors grown in nude mice were imaged using 18F-EF5 positron emission tomography (PET) in order to characterize the extent and heterogeneity of hypoxia in these systems. Based ...

  16. Concomitant Pseudopolymorphs of 10-Deacetyl Baccatin III

    Tatini, Lakshmi Kumar; Rao, N. Someswara; Khan, Muzaffar; Peraka, Krishna Sumanth; Reddy, K. V. S. R. Krishna

    2013-01-01

    Three new solvates [mono-dimethyl sulfoxide (mono-DMSO), mono-dimethyl acetamide (mono-DMA) and mono-dimethyl formamide (mono-DMF)] of 10-Deacetyl baccatin III, were generated by slow evaporation in DMSO, DMF, and DMSO/DMA (1:1) solvent systems respectively. Two concomitant forms mono-DMSO(a new form) and di-DMSO (a known form) were obtained in the DMSO solvent system. Yet two other concomitant forms mono-DMA (a new form) and di-DMSO (a known form) were obtained in DMSO/DMA (1:1) solvent syst...

  17. Two half-sandwiched ruthenium (II compounds containing 5-fluorouracil derivatives: synthesis and study of DNA intercalation.

    Zhao-Jun Li

    Full Text Available Two novel coordination compounds of half-sandwiched ruthenium(II containing 2-(5-fluorouracil-yl-N-(pyridyl-acetamide were synthesized, and their intercalation binding modes with calf thymus DNA were revealed by hyperchromism of ultraviolet-visible spectroscopy; the binding constants were determined according to a Langmuir adsorption equation that was deduced on the base of careful cyclic voltammetry measurements. The two compounds exhibited DNA intercalation binding activities with the binding constants of 1.13×106 M-1 and 5.35 ×105 M-1, respectively.

  18. Synthesis and Analgesic and Anti-Inflammatory Activity of New Pyridazinones

    DOĞRUER, Deniz S.; ŞAHİN, M. Fethi

    2003-01-01

    A new series of 2-(6-oxo-3,5-diphenyl-6H-pyridazin-1-yl)- acetamides and 3-[6-oxo-3,5-diphenyl-6H-pyridazin-1-yl)-propanamides were synthesized and evaluated in terms of their analgesic and anti-inflammatory activities. All compounds except for 7g were more potent than aspirin in a p-benzoquinone--induced writhing test at 100 mg/kg dose. Compounds 7b, 7c and 7e had the highest anti-inflammatory activity; compound 7e was the most potent in terms of analgesic and anti-inflammatory acti...

  19. Isolation and Characterisation of Degradation Impurities in the Cefazolin Sodium Drug Substance

    Sivakumar, Balasubramanian; Parthasarathy, Kannabiran; Murugan, Raman; Jeyasudha, Ramajeyabalan; Murugan, Saravanan; Saranghdar, Rajendira Janardhan

    2013-01-01

    Two unknown impurities were detected in the cefazolin sodium bulk drug substance using gradient reversed-phase high-performance liquid chromategraphy (HPLC). These impurities were isolated by preparative HPLC and characterized by using spectroscopic techniques like LC-MS, LC-MS/MS, 1D, 2D NMR, and FT-IR. Based on the spectral data, the impurities have been characterized as N-(2,2-dihydroxyethyl)-2-(1H-tetrazol-1-yl)acetamide (Impurity-I) and 2-{carboxy[(1H-tetrazol-1-ylacetyl)amino]methyl}-5-...

  20. N-(4-Chlorophenyl-2-(hydroxyiminoacetamide

    Jie Sun

    2009-09-01

    Full Text Available The title compound, C8H7ClN2O2, is an intermediate in the synthesis of 5-chloroisatin, which can be further transformed to 5-chloro-2-indolinone via a Wolff–Kishne reduction. The C2N acetamide plane forms a dihedral angle of 6.3 (3° with the benzene ring. An intramolecular C—H...O interaction results in the formation of a six-membered ring. In the crystal, intermolecular N—H...O, N—H...N and O—H...O hydrogen bonds link the molecules into multimers, forming sheets.

  1. Novel polymorphs of the anti-Trypanosoma cruzi drug benznidazole

    Honorato, Sara Braga; Mendonça, Jorge Souza; Boechat, Nubia; Oliveira, Alcemira Conceição; Mendes Filho, Josué; Ellena, Javier; Ayala, Alejandro Pedro

    2014-01-01

    Benznidazole (N-benzyl-2-(2-nitro-1H-imidazol-1-yl)acetamide), is a nitro-heterocyclic drug used in the treatment of Chagas disease. Despite the fact that this drug was released more than 30 years ago, little information about its solid state properties is available in the literature. In this study, it was verified that this drug exhibits three polymorphs, which were characterized in situ by X-ray powder diffraction, thermal analysis, hot stage microscopy and infrared spectroscopy. The thermodynamic relationships among these polymorphs were also discussed.

  2. Rhodium (II) carbene C-H insertion in water and catalyst reuse

    A five-session laboratory experiment is described for the synthesis of a beta-lactam via Rh(II) catalysed intramolecular C-H insertion of a alpha-diazo-alpha-ethoxycarbonyl acetamide. The metallo-carbene, responsible for the C-H bond activation, was generated from the diazo substrate and the catalyst Rh2(OAc)4. The high stability and solubility of the catalyst and the exclusive C-H insertion of the Rh-carbene allows the synthesis of this important heterocycle in water and the catalyst reutilization. (author)

  3. Antianxiety and antidepressant-like effects of AC-5216, a novel mitochondrial benzodiazepine receptor ligand

    Kita, Atsuko; Kohayakawa, Hitoshi; Kinoshita, Tomoko; Ochi, Yoshiaki; Nakamichi, Keiko; Kurumiya, Satoshi; Furukawa, Kiyoshi; Oka, Makoto

    2004-01-01

    We investigated the ability of N-benzyl-N-ethyl-2-(7,8-dihydro-7-methyl-8-oxo-2-phenyl-9H-purin-9-yl)acetamide (AC-5216), a novel mitochondrial benzodiazepine receptor (MBR) ligand, to produce anti-anxiety and antidepressant-like effects in various animal models.AC-5216 showed high affinity for MBRs prepared from rat whole brain (Ki 0.297 nM), rat glioma cells (IC50 3.04 nM) and human glioma cells (IC50 2.73 nM), but only negligible affinity for the other main receptors including central benz...

  4. Synthesis, Characterization, and BSA Binding Studies of Some New Benzamides Related to Schiff Base

    Prashanth, M. K.; Madaiah, M.; Revanasiddappa, H. D.; Amruthesh, K. N.

    2013-01-01

    Condensation of amine 1 with aldehyde 2 gives Schiff base, N-(4-((benzofuran-2-ylmethylene) amino)phenyl)acetamide 3. Schiff base on N-acylation with different substituted acid chlorides in the presence of triethylamine gives the corresponding benzamides, N-acetyl-N-(4-((benzofuran-2-ylmethylene)amino)phenyl)substitutedbenzamide (NABP) 5a–j. The structures of newly synthesized compounds were characterized by elemental analysis, 1H NMR, 13C NMR FT-IR, and mass spectral studies. Compounds 3 and...

  5. Prevention of myocardial enzyme release by ranolazine in a primate model of ischaemia with reperfusion.

    Allely, M. C.; Alps, B J

    1990-01-01

    In control anaesthetized baboons subjected to 30 min occlusion of the left anterior descending coronary artery, followed by 5.5 h reperfusion, total plasma levels for creatine kinase (CK) and lactate dehydrogenase (LDH) were markedly elevated in a time-related manner. In a second group of baboons pretreated 10 min prior to ischaemia with ranolazine [(+/-)-N-(2,6-dimethyl-phenyl)-4[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1 - piperazine acetamide dihydrochloride; RS-43285-193] at 500 micrograms k...

  6. Preferential binding of growth inhibitory prostaglandins by the target protein of a carcinogen.

    S H Khan; Sorof, S

    1990-01-01

    Liver fatty acid binding protein (L-FABP) is the principal target protein of the hepatic carcinogen N-(2-fluorenyl)acetamide (2-acetylaminofluorene) in rat liver. In addition, the cyclopentenone prostaglandins (PG), PGA, PGJ2, and delta 12-PGJ2, inhibit the growth of many cell types in vitro. This report describes the preferential binding of the growth inhibitory prostaglandins by L-FABP and the reversible inhibition of thymidine incorporation into DNA by PGA2 and delta 12-PGJ2 in primary cul...

  7. Cloning and analysis of the positively acting regulatory gene amdR from Aspergillus nidulans.

    Andrianopoulos, A; Hynes, M J

    1988-01-01

    The positively acting regulatory gene amdR of Aspergillus nidulans coordinately regulates the expression of four unlinked structural genes involved in acetamide (amdS), omega amino acid (gatA and gabA), and lactam (lamA) catabolism. By the use of DNA-mediated transformation of A. nidulans, the amdR regulatory gene was cloned from a genomic cosmid library. Southern blot analysis of DNA from various loss-of-function amdR mutants revealed the presence of four detectable DNA rearrangements, inclu...

  8. New thermally stable polyesters based on 2,5-pyridinedicarbonyl dichloride and aromatic diols: Synthesis and characterization

    Hossein Nasr Isfahani; Khalil Faghihi

    2009-01-01

    Six new thermally stable polyesters (4a-f) were synthesized through the solution polycondensation reaction of 2,5-pyridine dicarbonyldichloride (2) with six aromatic diols in N,N'-dimethyl acetamide (DMAc) solution and in the presence of pyridine as a base. The polycondensation reactions produce a series of new polyesters (4a-f) in high yields, and inherent viscosity between 0.30 and 0.55 dL/g. The resulting polyesters were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, Fourier transform infrared (FT-IR) spectroscopy and gel permeation chromatography (GPC).

  9. Synthesis and characterization of new polyesters based on 2,5-bis[(4-chloro carboxyanilino)carbonyl]pyridine and aromatic diols

    Khalil; Faghihi

    2010-01-01

    Six new polyesters 7a-f were synthesized through the solution polycondensation reaction of diacid chloride 5 with six aromatic diols 6a-f in N,N-dimethyl acetamide(DMAc) as solvent in the presence of pyridine as base.The polycondensation reaction produced a series of novel polyester containing pyridyl moiety in the main chain in high yields with inherent viscosities between 0.35 and 0.54 dL/g.The resulted polymers were fully characterized by means of FT-IR spectroscopy,elemental analyses,inherent viscosi...

  10. Influence of substituent on UV absorption and keto-enol tautomerism equilibrium of dibenzoylmethane derivatives

    Zawadiak, Jan; Mrzyczek, Marek

    2012-10-01

    UV absorption spectra of dibenzoylmethane and its 23 derivatives with acetamide, tert-butyl, chloride, fluoride, hydroxyl, methyl, methoxy and nitro substituents in aromatic rings were collected. General influence of substituent on absorption maxima and absorption intensity was defined. Hyperchromic effects were observed for diketones with electron-donating groups in para postion. The keto-enol tautomerism equilibrium constant of obtained compounds was investigated with 1H NMR spectroscopy. Significant changes of equilibrium were observed only for ortho substituted compounds. Results revealed dissimilarity of substituent effects on absorption and keto-enol tautomerism of aromatic β-diketones.

  11. ESI MS, spectroscopic and PM5 semiempirical studies of Colchicine complexes with lithium, sodium and potassium salts

    Kurek, Joanna; Boczoń, Władysław; Przybylski, Piotr; Brzezinski, Bogumił

    2007-11-01

    The colchicine complexes with Li +, Na + and K + cations have been synthesized and studied by ESI MS, 1H and 13C NMR, FT-IR and PM5 semiempirical methods. It has been shown that colchicine forms stable complexes of 1:1 stoichiometry with monovalent metal cations. For Li + cations also formation of the 2:1 stoichiometry complexes has been detected. The most stable structures of the complexes are those in which the acetamide groups are involved in the coordination process. The structures of the colchicine complexes with Li +, Na + and K + cations are visualized and discussed in details.

  12. The postprandial plasma rye fingerprint includes benzoxazinoid-derived phenylacetamide sulfates.

    Hanhineva, Kati; Keski-Rahkonen, Pekka; Lappi, Jenni; Katina, Kati; Pekkinen, Jenna; Savolainen, Otto; Timonen, Oskari; Paananen, Jussi; Mykkänen, Hannu; Poutanen, Kaisa

    2014-07-01

    The bioavailability of whole-grain rye-derived phytochemicals has not yet been comprehensively characterized, and different baking and manufacturing processes can modulate the phytochemical composition of breads and other rye products. The aim of our study was to find key differences in the phytochemical profile of plasma after the consumption of 3 breads containing rye bran when compared with a plain white wheat bread control. Plasma metabolite profiles of 12 healthy middle-aged men and women were analyzed using LC quadrupole time-of-flight mass spectrometry metabolomics analysis while fasting and at 60 min, 120 min, 240 min, and 24 h after consuming a meal that contained either 100% whole-grain sourdough rye bread or white wheat bread enriched with native unprocessed rye bran or bioprocessed rye bran. White wheat bread was used as the control. The meals were served in random order after a 12-h overnight fast, with at least 3 d between each occasion. Two sulfonated phenylacetamides, hydroxy-N-(2-hydroxyphenyl) acetamide and N-(2-hydroxyphenyl) acetamide, potentially derived from the benzoxazinoid metabolites, were among the most discriminant postprandial plasma biomarkers distinguishing intake of breads containing whole-meal rye or rye bran from the control white wheat bread. Furthermore, subsequent metabolite profiling analysis of the consumed breads indicated that different bioprocessing/baking techniques involving exposure to microbial metabolism (e.g., sourdough fermentation) have a central role in modulating the phytochemical content of the whole-grain and bran-rich breads. PMID:24812068

  13. Size effects on cation heats of formation. I. Methyl substitutions in nitrogenous compounds

    Graphical abstract: Heat of formation of cations as a function of ln(n) where n is the number of atoms in the ion: methyl substituted immonium cations. N = substitution at nitrogen sites, C = substitution at carbon sites. Highlights: ► Heats of formation of nitrogenous cations by graphical method relating to ion size. ► Methyl substitution in formamides, acetamides, immonium, amine, and imine cations. ► Methyl substitution in ammonium and amino cations. ► New studies ionization energies and heats of formation required in several cases. - Abstract: The heats of formation of molecular ions are often not known to better than 10 or 20 kJ/mol. The present study on nitrogenous compounds adopts the graphical approach of Holmes and Lossing which relates cation heats of formation to cation size. A study of methyl substitution in formamides and acetamides is followed by an examination of heat of formation data on carbon-site and nitrogen-site methyl substitution in immonium, amine, imine, ammonium and amino cations. The results provide tests of the validity of this graphical method and also suggest investigating or re-investigating the ionization energies and the heats of formation of several of the molecules studied.

  14. Isolation and characterization of an acrylamide-degrading Bacillus cereus.

    Shukor, M Y; Gusmanizar, N; Azmi, N A; Hamid, M; Ramli, J; Shamaan, N A; Syed, M A

    2009-01-01

    Several local acrylamide-degrading bacteria have been isolated. One of the isolate that exhibited the highest growth on acrylamide as a nitrogen source was then further characterized. The isolate was tentatively identified as Bacillus cereus strain DRY135 based on carbon utilization profiles using Biolog GP plates and partial 16S rDNA molecular phylogeny. The isolate grew optimally in between the temperatures of 25 and 30 degrees C and within the pH range of 6.8 to 7.0. Glucose, fructose, lactose, maltose, mannitol, citric acid and sucrose supported growth with glucose being the best carbon source. Different concentrations of acrylamide ranging from 100 to 4000 mg l(-1) incorporated into the growth media shows that the highest growth was obtained at acrylamide concentrations of between 500 to 1500 mg l(-1). At 1000 mg l(-1) of acrylamide, degradation was 90% completed after ten days of incubation with concomitant cell growth. The metabolite acrylic acid was detected in the media during degradation. Other amides such as methacrylamide, nicotinamide, acetamide, propionamide and urea supported growth with the highest growth supported by acetamide, propionamide and urea. Strain DRY135, however was not able to assimilate 2-chloroacetamide. The characteristics of this isolate suggest that it would be useful in the bioremediation of acrylamide. PMID:20112864

  15. ADSORPTION OF TANNIN FROM AQUEOUS SOLUTION ONTO MACROPOROUS CROSSLINKED POLY(N—VINYL—ACETAMIDE)VIA HYDROGEN BONDING

    XUMancai; XUMingcheng; 等

    2000-01-01

    A Strongly hydrophilic hydrogen-bonding adsorbent-macroporous crosslinked Poly(Nvinyl-acetamide),which contain both hydrogen bond acceptor and donator,was synthesized.Adsorption mechanism and dynamic adsorption of tannin from aqueous solution onto the adsorbent were investigated.Most of the differntial adsorption heats for various adsorption capacities calculated from the adsorption isotherms according to Clapeyron-Clausius equation lay in the range of hydrogen bond energy(8-50J/mol).Adsorption properties of the adsorbent were studied in detail.These results revealed a hydrogen bonding mechanism of the adsorption of tannin from aqueous solution onto the adsorbent.The result of the dynamic adsorption of tanning with the initial concentration under 600mg/L showed that the adsorption rate of tannin exceeded 90% when the flow rate was 3BV/h and the effluent volume reached 100BV.Therefore,the developed hydrogen-bonding adsorbent-macroporous crosslinked poly(N-vinyl-acetamide)-is an excellent adsorbent to remove tannin from extract of natural products,and has great value in application.

  16. A Green Ultrasound Synthesis, Characterization and Antibacterial Evaluation of 1,4-Disubstituted 1,2,3-Triazoles Tethering Bioactive Benzothiazole Nucleus.

    Rezki, Nadjet

    2016-01-01

    The synthesis of N-(benzo[d]thiazol-2-yl)-2-(4-substituted-1H-1,2,3-triazol-1-yl)acetamides 5a-r via the 1,3-dipolar cycloaddition reaction between 2-azido-N-(benzo[d]thiazol-2-yl)acetamide derivatives 3a-c and different alkynes were performed in the presence and absence of ultrasound irradiation. The synthesis was carried out using t-BuOH/H₂O (1:1, v/v) as reaction solvents and CuSO₄·5H₂O/sodium ascorbate as the catalyst. The copper catalyst was implemented to provide the regioselective 1,4-disubstituted 1,2,3-triazoles 5a-r. Significant reductions in reaction times with comparably higher yields were observed when the reactions were carried out under ultrasound irradiation. The structures of the newly synthesized 1,2,3-triazoles were elucidated by IR, NMR, MS, and elemental analyses. They were also screened for their antimicrobial activity against three gram-positive (Streptococcus pneumonia, Bacillus subtilis, and Staphylococcus aureus), three gram-negative (Pseudomonas aeuroginosa, Escherichia coli, and Klebsiella pneumonia), and two fungal strains (Aspergillus fumigates and Candida albicans). Most of the tested compounds displayed promising antimicrobial activities at a Minimum Inhibition Concentration (MIC) of 4-16 μg/mL. PMID:27096862

  17. Oxidation of amino groups by hydroxyl radicals in relation to the oxidation degree of the alpha-carbon.

    Leitner, N Karpel Vel; Berger, P; Legube, B

    2002-07-15

    Nitrogen organic compounds constitute a large class of aqueous pollutants. These compounds include not only azoic structures, nitrogen heterocycles, and nitrous groups but also amides and amines. This work consisted in studying the OH* induced oxidation of simple primary amines in dilute aqueous solution with special attention to mineralization of the nitrogen group as a function of the nature of the alpha-carbon. H2O2/UV and gamma-irradiation processes were used for the production of OH* radicals, and the molecules studied were one alpha-amino acid i.e., glycine (HOOCCH2NH2), and two primary amides i.e., acetamide (CH3CONH2) and oxamic acid (HOOCCONH2). It was shown that the oxidation of glycine leads to the formation of ammonia, whereas the acetamide molecule is first oxidized into oxamic acid ending in complete mineralization with production of nitrates. Reaction mechanisms are proposed which account for the observed inorganic nitrogen end product depending on the oxidation degree of the carbon atoms of the molecules. It follows that the present study will allow for prediction of the fate of nitrogen resulting from the oxidation of primary amino groups by OH* radicals. PMID:12141487

  18. Electrochemical stability of organic electrolytes in supercapacitors: Spectroscopy and gas analysis of decomposition products

    Kurzweil, P.; Chwistek, M. [University of Applied Sciences, Kaiser-Wilhelm-Ring 23, D-92224 Amberg (Germany)

    2008-02-01

    The fundamental aging mechanisms in double-layer capacitors based on alkylammonium electrolytes in acetonitrile were clarified for the first time. After abusive testing at cell voltages above 4 V, ultracapacitors cast out a crystalline mass of residual electrolyte, organic acids, acetamide, aromatics, and polymer compounds. The mixture could be reproduced by electrolysis. The decomposition products of active carbon electrodes and electrolyte solution after a heat treatment at 70 C were identified by infrared and ultraviolet spectroscopy, liquid and headspace GC-MS, thermogravimetric analysis, and X-ray diffraction. The alkylammonium cation is destroyed by the elimination of ethene. The fluoroborate anion works as source of fluoride and hydrogenfluoride, and boric acid derivates. Acetonitrile forms acetamide, acetic and fluoroacetic acid, and derivates thereof. Due to the catalytic activity of the electrode, heterocyclic compounds are generated in the liquid phase. The etched aluminium support under the active carbon layer is locally destroyed by fluorination. Exploring novel electrolytes, ionic liquids were characterized by impedance spectroscopy. (author)

  19. Electrochemical stability of organic electrolytes in supercapacitors: Spectroscopy and gas analysis of decomposition products

    Kurzweil, P.; Chwistek, M.

    The fundamental aging mechanisms in double-layer capacitors based on alkylammonium electrolytes in acetonitrile were clarified for the first time. After abusive testing at cell voltages above 4 V, ultracapacitors cast out a crystalline mass of residual electrolyte, organic acids, acetamide, aromatics, and polymer compounds. The mixture could be reproduced by electrolysis. The decomposition products of active carbon electrodes and electrolyte solution after a heat treatment at 70 °C were identified by infrared and ultraviolet spectroscopy, liquid and headspace GC-MS, thermogravimetric analysis, and X-ray diffraction. The alkylammonium cation is destroyed by the elimination of ethene. The fluoroborate anion works as source of fluoride and hydrogenfluoride, and boric acid derivates. Acetonitrile forms acetamide, acetic and fluoroacetic acid, and derivates thereof. Due to the catalytic activity of the electrode, heterocyclic compounds are generated in the liquid phase. The etched aluminium support under the active carbon layer is locally destroyed by fluorination. Exploring novel electrolytes, ionic liquids were characterized by impedance spectroscopy.

  20. One-Step Preparation of N-Doped Nanowhisker TiO2 by Micro Arc Oxidation

    SU Yu-Cheng; ZHANG Gu-Ling; WANG Wen-Zhong; ZOU Bin; AO Le

    2011-01-01

    @@ Flowers, trees and coral like TiO2 Rlms are first produced by the micro-arc-oxidation method in electrolyte of phosphate.Nanowhiskers with high surface area grow at the tail ends of the coralloid film when the positive current density is set to be 17.14 A/dm2.With acetamide in electrolyte, N element is doped.The analysis results indicate that the ratio of anatase phase to rutile phases is about 2 : 1 in the micro-arc-oxidation produced N-TiO2 film.The optical absorption edge red shifts in the presence of N doping.%Flowers, trees and coral like TiO2 films are first produced by the micro-arc-oxidation method in electrolyte of phosphate. Nanowhiskers with high surface area grow at the tail ends of the coralloid film when the positive current density is set to be 17.14 A/dm2. With acetamide in electrolyte, N element is doped. The analysis results indicate that the ratio of anatase phase to rutile phases is about 2: 1 in the micro-arc-oxidation produced N-TiO2 film. The optical absorption edge red shifts in the presence of N doping.

  1. Urine metabolomics in rats after administration of ketamine

    Wen C

    2015-02-01

    Full Text Available Congcong Wen,1 Meiling Zhang,2 Jianshe Ma,2 Lufeng Hu,3 Xianqin Wang,2 Guanyang Lin31Laboratory Animal Centre, 2Analytical and Testing Center, 3First Affiliated Hospital of Wenzhou Medical University, Wenzhou, People’s Republic of ChinaAbstract: In this study, we developed a urine metabonomic method, based on gas chromatography–mass spectrometry (GC-MS, to evaluate the effect of ketamine on rats. Pattern recognition analysis, including both principal component analysis and partial least squares discriminate analysis revealed that ketamine (50 mg/kg induced metabolic perturbations. Compared with the control group, at day 7, the level of alanine, butanoic acid, glutamine, butanedioic, trimethylsiloxy, L-aspartic acid, D-glucose, cholesterol, acetamide, and oleic acid of the ketamine group was increased, while the level of 2,3,4-trihydroxybutyric acid, benzene­acetic acid, threitol, ribitol, xylitol, and glycine decreased. At day 14, the level of alanine, ethanedioic acid, L-proline, glycerol, tetradecanoic acid, l-serine, l-phenylalanine, L-aspartic acid, d-glucose, cholesterol, heptadecanoic acid, and acetamide in rat urine of the ketamine group was increased, while the 2,3,4-trihydroxybutyric acid, benzeneacetic acid, d-ribose, threitol, ribitol, glycine, pyrazine, and oleic acid levels decreased. Our results indicate that metabonomic methods based on GC-MS may be useful to elucidate ketamine abuse, through the exploration of biomarkers.Keywords: GC-MS, abuse, biomarker, metabolite

  2. Synthesis and crystal structures of the potential tyrosinase inhibitors N-(4-acetylphenyl)-2-chloroacetamide and 2-(4-acetylanilino)-2-oxoethyl cinnamate.

    Ashraf, Zaman; Kim, Daeyoung; Seo, Sung Yum; Kang, Sung Kwon

    2016-02-01

    Substituted benzoic acid and cinnamic acid esters are of interest as tyrosinase inhibitors and the development of such inhibitors may help in diminishing many dermatological disorders. The tyrosinase enzyme has also been linked to Parkinson's disease. In view of hydroxylated compounds having ester and amide functionalities to potentially inhibit tyrosinase, we herein report the synthesis and crystal structures of two amide-based derivatives, namely N-(4-acetylphenyl)-2-chloroacetamide, C10H10ClNO2, (I), and 2-(4-acetylanilino)-2-oxoethyl cinnamate, C19H17NO4, (II). In compound (I), the acetylphenyl ring and the N-(C=O)-C unit of the acetamide group are almost coplanar, with a dihedral angle of 7.39 (18)°. Instead of esterification, a cheaper and more efficient synthetic method has been developed for the preparation of compound (II). The molecular geometry of compound (II) is a V-shape. The acetamide and cinnamate groups are almost planar, with mean deviations of 0.088 and 0.046 Å, respectively; the dihedral angle between these groups is 77.39 (7)°. The carbonyl O atoms are positioned syn and anti to the amide carbonyl O atom. In the crystals of (I) and (II), N-H...O, C-H...O and C-H...π interactions link the molecules into a three-dimensional network. PMID:26846491

  3. Synthesis and Characterization of Two Cyanoxime Ligands, Their Precursors, and Light Insensitive Antimicrobial Silver(I) Cyanoximates.

    Riddles, Courtney N; Whited, Mark; Lotlikar, Shalaka R; Still, Korey; Patrauchan, Marianna; Silchenko, Svitlana; Gerasimchuk, Nikolay

    2014-03-01

    High-yield syntheses of N-piperidine-cyanacetamide (1), N-morpholyl-cyanacetamide (4) and their oxime derivatives N-piperidine-2-cyano-2-oximino-acetamide (HPiPCO, 2) and N-morpholyc-2-cyano-2-oximino-acetamide (HMCO, 5) were developed using two-step preparations. At first, the reactions of neat cyanoacetic acid esters and the respective cyclic secondary amines such as piperideine and morpholine afforded pure cyanacetamides, which were converted into cyanoximes at room temperature using the nitrosation reaction with gaseous CH3ONO. The synthesized compounds were investigated by means of IR, (1)H, (13)C and UV-visible spectroscopy. Crystal structures of two starting substituted cyan-acetamides and two target cyanoximes were determined. Silver(I) complexes of AgL composition (L = PipCO, 3; MCO, 6) were prepared in high yield. Both metal complexes are thermally stable above 100(o)C, and remarkably stable to high intensity visible light. The stability of dried AgL compounds towards short wavelength UV-radiation (a frequently used germicidal light) was examined using diffusion reflectance spectroscopy. Both complexes demonstrate slow photoreduction within ~3 hrs, observable as a gradual color change and darkening due to the formation of fine (nano-scale) particles of metallic silver. The complex Ag(MCO), 6, is about 2.6 times less stable towards UV-radiation than its more lypophyllic analog Ag(PipCO), 3. Antimicrobial and biofilm growth inhibition properties of the prepared solid acrylate-based polymeric composites containing embedded silver(I) cyanoximates were investigated using three human pathogens: P. aeruginosa PAO1 (wound isolate), S. aureus NRS70 (methicillin resistant respiratory isolate), and S. mutans UA159 (cariogenic dental isolate). Studies showed that both 3 and 6 compounds completely abolished the growth of PAO1 at 0.5 weight % concentration, and the growth of UA159 and NRS70 at 1% concentration. Moreover, data demonstrates that complexes 3 and 6 also

  4. Bidirectional water fluxes and specificity for small hydrophilic molecules in aquaporins 0-5

    Meinild, A K; Klærke, Dan Arne; Zeuthen, T

    1998-01-01

    for the osmotic water permeability (L p) were obtained in swelling as in shrinkage experiments demonstrating, for the first time, that aquaporins are bidirectional. The reflection coefficients (¿) of urea, glycerol, acetamide, and formamide at 23¿°C were: AQP0: 1, 1, 0.8, 0.6; AQP1: 1, 0.8, 1, 1; AQP2: 1, 0.8, 1......The dimensions of the aqueous pore in aquaporins (AQP) 0, 1, 2, 3, 4, and 5 expressed in Xenopus laevisoocytes were probed by comparing the ability of various solutes to generate osmotic flow. By improved techniques, volume flows were determined from initial rates of changes. Identical values...... and increased ¿glyc to 1 and ¿form to 0.6. We conclude that the pore of the various aquaporins are structurally different and that a simple steric model is insufficient to explain solute-pore interactions....

  5. Permeability of commercial solvents through living human skin

    Ursin, C; Hansen, C M; Van Dyk, J W;

    1995-01-01

    was characterized by calculation of the "percent error of the slope." The following permeability rates (g/m2h) of single solvents were measured: dimethyl sulfoxide (DMSO), 176; N-methyl-2-pyrrolidone, 171; dimethyl acetamide, 107; methyl ethyl ketone, 53; methylene chloride, 24; [3H]water, 14.......8; ethanol, 11.3; butyl acetate, 1.6; gamma-butyrolactone, 1.1; toluene, 0.8; propylene carbonate, 0.7; and sulfolane, 0.2. The effect of [3H]water saturation on the shape of the presteady state portion of the permeation curve was determined and found to be very dependent on the solvent. The permeability of...

  6. Thermal reactions of mesocarbon microbead (MCMB) particles in LiPF 6-based electrolyte

    Xiao, Ang; Li, Wentao; Lucht, Brett L.

    The thermal reaction of ternary electrolyte (1.0 M LiPF 6 in 1:1:1 ethylene carbonate/dimethyl carbonate/diethyl carbonate) with mesocarbon microbeads (MCMB) particles was investigated by the combined use of NMR, GC-MS, FTIR-ATR, TGA, XPS and SEM/EDS-element map. The thermal decomposition of ternary electrolyte is not inhibited by the presence of MCMB particles. The chemical composition and morphology of the surface of MCMB particles changes significantly upon storage in the presence of ternary electrolyte. Electrolyte decomposition products including oligocarbonates, oligoethylene oxides, polyethylene oxide (PEO), lithium fluorophosphates (Li xPO yF z), and lithium fluoride are deposited on the surface of MCMB particles. The concentration of decomposition products on the surface of MCMB increases with increased storage time and temperature. The addition of dimethyl acetamide (DMAc) impedes the thermal decomposition of the electrolyte and deposition of electrolyte decomposition products on the surface of MCMB.

  7. Synthesis and carbon-11-labeling of p-MeO-SSR180575, a novel indoleacetamide-based candidate for PET imaging of the peripheral benzodiazepine receptor (TSPO 18 kDa)

    Complete text of publication follows: Objectives: The 3-iso-quinolinecarboxamide [11C]PK11195, despite its low brain uptake and high level of nonspecific binding, is still the most widely used PET-radioligand for the in vivo imaging of the peripheral benzodiazepine receptor (PBR or TSPO 18 kDa). Several new PBR radioligands are currently developed to replace [11C]PK11195, e.g the pyrazolo[1, 5-a]pyrimidine-acetamides [11C]DPA-713 and [18F]DPA-714, the imidazo[1, 2-a]pyridine-acetamides [11C]CLINME and [18F]PBR111 and the N-benzyl-N-(2-phenoxy-aryl)- acetamides [11C]PBR28 and [18F]FEDAA1106. Another attractive newly identified chemical class of structures are the indole-acetamides and notably compounds derived from the lead compound SSR180575. Herein are reported the synthesis and the labelling with the positron-emitter carbon-11 (half-life: 20.38 min) of a novel derivative of SSR180575, bearing a para methoxy function on its phenyl ring. Methods: p-MeO-SSR180575 (1) was synthesized from commercially available 4-chloro-2-nitrotoluene in 10 steps. O-demethylation, performed with a boron tribromide solution in dichloromethane at low temperature, afforded the free phenol derivative 2. Carbon-11 labeling of p-MeO-SSR180575 (1) was performed using a TRACERLab FX-C Pro synthesizer (GEMS) and comprised (1) trapping of [11C]MeOTf at -10 C in acetone (0.3 mL) containing the nor-derivative 2 (O-demethylated, 0.6-0.9 mg) and aq. 3N NaOH (8 μL); (2) heating at 110 C for 2 min; (3) concentration to dryness and taking up the residue in 1.0 mL of the HPLC mobile phase; (4) purification using semi-preparative reversed-phase HPLC (Waters Symmetry C-18 - eluent: CH3CN / H2O / TFA: 50 / 50 / 0.1 (v:v:v) - flow rate: 5 mL/min - detection at 254 nm) and (5) SepPakR Plus C-18-based formulation for i.v. injection. Results: p-MeO-SSR180575 (1) was obtained in 10% overall yield. The tricky and low-yielding step in our approach was the pyridazine ring formation reaction that proceeded

  8. Cytotoxic diterpenoid pseudodimers from the Korean sponge Phorbas gukhulensis.

    Jeon, Ju-eun; Liao, Lijuan; Kim, Heegyu; Sim, Chung J; Oh, Dong-Chan; Oh, Ki-Bong; Shin, Jongheon

    2013-09-27

    Four new cytotoxic diterpenoid pseudodimers (2-5), along with a previously reported one, gukulenin A (1), were isolated from the marine sponge Phorbas gukhulensis collected off the coast of Gagu-do, Korea. These novel compounds, designated gukulenins C-F (2-5), were determined by extensive spectroscopic analyses to be pseudodimers of the gagunins, like gukulenin A. The termini of the tropolone-containing side chains in gukulenins C-E (2-4) were found to have diverse modifications involving acetamides or taurine, whereas gukulenin F (5) was formed from 1 by the ring-opening of a cyclic hemiketal. The relative and absolute configurations were assigned by Murata's and modified Snatzke's methods using a HETLOC experiment and a CD measurement of a dimolybdenum complex, respectively. All of these compounds exhibited significant cytotoxicity against the K562 and A549 cell lines. PMID:24025124

  9. Discovery of AZD8931, an Equipotent, Reversible Inhibitor of Signaling by EGFR, HER2, and HER3 Receptors.

    Barlaam, Bernard; Anderton, Judith; Ballard, Peter; Bradbury, Robert H; Hennequin, Laurent F A; Hickinson, D Mark; Kettle, Jason G; Kirk, George; Klinowska, Teresa; Lambert-van der Brempt, Christine; Trigwell, Cath; Vincent, John; Ogilvie, Donald

    2013-08-01

    Deregulation of HER family signaling promotes proliferation and tumor cell survival and has been described in many human cancers. Simultaneous, equipotent inhibition of EGFR-, HER2-, and HER3-mediated signaling may be of clinical utility in cancer settings where the selective EGFR or HER2 therapeutic agents are ineffective or only modestly active. We describe the discovery of AZD8931 (2), an equipotent, reversible inhibitor of EGFR-, HER2-, and HER3-mediated signaling and the structure-activity relationships within this series. Docking studies based on a model of the HER2 kinase domain helped rationalize the increased HER2 activity seen with the methyl acetamide side chain present in AZD8931. AZD8931 exhibited good pharmacokinetics in preclinical species and showed superior activity in the LoVo tumor growth efficacy model compared to close analogues. AZD8931 is currently being evaluated in human clinical trials for the treatment of cancer. PMID:24900741

  10. Design and synthesis of diamide-coupled benzophenones as potential anticancer agents.

    Zabiulla; Shamanth Neralagundi, H G; Bushra Begum, A; Prabhakar, B T; Khanum, Shaukath Ara

    2016-06-10

    A series of diamide-coupled benzophenone, 2-(4-benzoyl-phenoxy)-N-{2-[2-(4-benzoyl-phenoxy)-acetylamino]-phenyl}-acetamide analogues (9a-l) were synthesized by multistep reactions and all compounds were well characterized. Among the series (9a-l), compound 9k with three methyl groups at ortho position in rings A, B, and D and bromo group at the para position in ring E was selected as a lead compound by screening through multiple cancer cell types by in-vitro cytotoxic and antiproliferative assay systems. Also, the cytotoxic nature of the compound 9k resulted the regression of the tumor growth in-vivo, which could be due to decreased vascularisation in the peritoneum lining of the mice which regress the tumor growth. The results were reconfirmed in-vivo chorioallantoic membrane model which indicates a scope of developing 9k into potent anticancer drug in near future. PMID:27027818

  11. Cation Tuning toward the Inference of the Gelation Behavior of Supramolecular Gels

    Xue, Peng; Wu, Huiqiong; Wang, Xiaojuan; He, Ting; Shen, Rujuan; Yue, Fan; Wang, Jide; Zhang, Yi

    2016-01-01

    We serendipitously discovered that the tripeptide Asp–Phe–Phe trifluoroacetic acid salt (hereafter abbreviated as β-AspFF) formed a reversible thermotropic gel in chloroform solution (at temperatures higher than the boiling point of chloroform), and a stable gel in toluene solution (at equal to or lower than the room temperature). Experimental results indicate that doping metal ions into β-AspFF toluene gels can trigger morphological variations in the gel skeleton, thereby increasing gel volume and inducing the collapse of organogels. Investigation on the cation-tuned gelation behavior of β-AspFF can be used to elucidate heating-induced gel collapse (of normal gel) or reverse thermotropic gelation as well as select carbamide and acetamide as activators of β-AspFF gels in chloroform solution at room temperature. PMID:27138527

  12. Cation Tuning toward the Inference of the Gelation Behavior of Supramolecular Gels.

    Xue, Peng; Wu, Huiqiong; Wang, Xiaojuan; He, Ting; Shen, Rujuan; Yue, Fan; Wang, Jide; Zhang, Yi

    2016-01-01

    We serendipitously discovered that the tripeptide Asp-Phe-Phe trifluoroacetic acid salt (hereafter abbreviated as β-AspFF) formed a reversible thermotropic gel in chloroform solution (at temperatures higher than the boiling point of chloroform), and a stable gel in toluene solution (at equal to or lower than the room temperature). Experimental results indicate that doping metal ions into β-AspFF toluene gels can trigger morphological variations in the gel skeleton, thereby increasing gel volume and inducing the collapse of organogels. Investigation on the cation-tuned gelation behavior of β-AspFF can be used to elucidate heating-induced gel collapse (of normal gel) or reverse thermotropic gelation as well as select carbamide and acetamide as activators of β-AspFF gels in chloroform solution at room temperature. PMID:27138527

  13. Radiosynthesis of a chloroacetanilide herbicide ([phenyl-4-3 H] acetochlor) and a dichloroacetamide safener for herbicides [2,2-dimethyl-3 H]R-29148

    2-Chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl) acetamide (the chloroacetanilide herbicide acetochlor) and 3-(dichloroacetyl)-2,2,5-trimethyl-1, 3-oxazolidine (the dichloroacetamide safener R-29148) are required at high specific activity for studies on their metabolism and mode of action. [phenyl-4-3H]Acetochlor was obtained at 22 Ci/mmol in 71% yield by reductive dehalogenation of iodoacetochlor with tritium gas in ethanol in the presence of palladium on carbon and triethylamine. [2,2-dimethyl-3H]R-29148 was prepared at 15 Ci/mmol by treating acetone and 1-amino-2-propanol in pentane with two equivalents of NaOH in tritiated water (i.e. hydroxide ion-catalyzed enolization of acetone) followed by dichloroacetyl chloride. (Author)

  14. Cation Tuning toward the Inference of the Gelation Behavior of Supramolecular Gels

    Xue, Peng; Wu, Huiqiong; Wang, Xiaojuan; He, Ting; Shen, Rujuan; Yue, Fan; Wang, Jide; Zhang, Yi

    2016-05-01

    We serendipitously discovered that the tripeptide Asp–Phe–Phe trifluoroacetic acid salt (hereafter abbreviated as β-AspFF) formed a reversible thermotropic gel in chloroform solution (at temperatures higher than the boiling point of chloroform), and a stable gel in toluene solution (at equal to or lower than the room temperature). Experimental results indicate that doping metal ions into β-AspFF toluene gels can trigger morphological variations in the gel skeleton, thereby increasing gel volume and inducing the collapse of organogels. Investigation on the cation-tuned gelation behavior of β-AspFF can be used to elucidate heating-induced gel collapse (of normal gel) or reverse thermotropic gelation as well as select carbamide and acetamide as activators of β-AspFF gels in chloroform solution at room temperature.

  15. Synthetic approaches to multifunctional indenes

    Neus Mesquida

    2011-12-01

    Full Text Available The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethylinden-5-yl]amines, a reasonable pathway involves the (5-nitro-3-indenylacetamides as key intermediates. Although several multistep synthetic approaches can be applied to obtain these advanced intermediates, we describe herein their preparation by an aldol-type reaction between 5-nitroindan-1-ones and the lithium salt of N,N-disubstituted acetamides, followed immediately by dehydration with acid. This classical condensation process, which is neither simple nor trivial despite its apparent directness, permits an efficient entry to a variety of indene-based molecular modules, which could be adapted to a range of functionalized indanones.

  16. The Antitumor Components from Marine-derived Bacterium Streptoverticillium luteoverticillatum 11014 Ⅱ

    LI Dehai; ZHU Tianjiao; FANG Yuchun; LIU Hongbing; GU Qianqun; ZHU Weiming

    2007-01-01

    Eight known compounds were isolated from a marine-derived bacterium Streptoverticillium luteoverticillatum 11014 using bioassay-guided fractionations. Their structures were identified by spectral analysis as bis (4-hydroxybenzyl) ether (1), p-hydroxyphenylethyl alcohol (2), N-(4-hydroxyphenethyl) acetamide (3), indole-3 carboxylic acid methyl ester (4), dibenzo[b,e] [1,4]dioxine (5), thymine (6), cytosine deoxyribonucleoside (7) and 2, 3-butanediol (8). These compounds were evaluated for their cytotoxic activities against K562 cell line with the SRB method for the first time. Compounds 2 and 4 showed cytotoxcities with IC50 values of 101.1 and 165.3 μmolL-1, respectively. All compounds were isolated from S. luteoverticillatum 11014 for the first time.

  17. Synthesis and in vitro Evaluation of New Benzothiazole Derivatives as Schistosomicidal Agents

    Mona A Mahran

    2007-03-01

    Full Text Available A series of benzothiazol-2-yl-dithiocarbamates 3a-d along with their copper complexes 4a-c were synthesized via the reaction of suitable alkyl, aralkyl or heteroaryl halides with the sodium salt of benzothiazol-2-yl-dithiocarbamic acid, followed by complexation with copper sulphate. N-(4-Acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl-N-benzothiazol-2-yl-acetamides 7a-c were synthesized by cyclization of the appropriate thiosemicarbazones 6a-c in acetic anhydride. Selected compounds were screened for in vitro schistosomicidal activity against Schistosoma mansoni at three different dosage levels (10, 50 and 100 μg/ mL. Three of these products, 4a-c, showed schistosomicidal activity similar to praziquantel, with 100% worm mortality at 10 μg/mL. These compounds would constitute a new class of potent schistosomicidal agents.

  18. Urinary Metabolomic Approach Provides New Insights into Distinct Metabolic Profiles of Glutamine and N-Carbamylglutamate Supplementation in Rats.

    Liu, Guangmang; Cao, Wei; Fang, Tingting; Jia, Gang; Zhao, Hua; Chen, Xiaoling; Wu, Caimei; Wang, Jing

    2016-01-01

    Glutamine and N-carbamylglutamate can enhance growth performance and health in animals, but the underlying mechanisms are not yet elucidated. This study aimed to investigate the effect of glutamine and N-carbamylglutamate supplementation in rat metabolism. Thirty rats were fed a control, glutamine, or N-carbamylglutamate diet for four weeks. Urine samples were analyzed by nuclear magnetic resonance (NMR)-based metabolomics, specifically high-resolution ¹H NMR metabolic profiling combined with multivariate data analysis. Glutamine significantly increased the urine levels of acetamide, acetate, citrulline, creatinine, and methymalonate, and decreased the urine levels of ethanol and formate (p glutamine and N-carbamylglutamate could modify urinary metabolome related to nitrogen metabolism and gut microbiota metabolism. Moreover, N-carbamylglutamate could alter energy and lipid metabolism. These findings indicate that different arginine precursors may lead to differences in the biofluid profile in rats. PMID:27527211

  19. Investigating the structure-property relationship of aromatic-aliphatic polyamide/layered silicate hybrid films

    Zulfiqar, Sonia; Sarwar, Muhammad Ilyas

    2009-07-01

    Surface treated montmorillonite was used to prepare nanocomposites with aromatic-aliphatic polyamide by solution intercalation technique. The polyamide chains were produced through polycondensation of 4-aminophenyl sulfone with sebacoyl chloride in dimethyl acetamide. Compatibility between the polymer and organoclay was achieved through carbonyl chloride end-capped amide chains prepared by adding extra sebacoyl chloride near the end of polymerization reaction. The nanocomposites morphology and clay dispersion were investigated by X-ray diffraction (XRD) and transmission electron microscopy (TEM). Delaminated and intercalated morphologies were observed for different loading of organoclay. Tensile strength and modulus improved for nanocomposites with optimum organoclay content (10-wt.%). Thermal stability and glass transition temperature of nanocomposites increased relative to pristine polyamide with augmenting organoclay content. Water uptake of these materials decreased as compared to the neat polyamide indicating reduced permeability.

  20. PREPARATION OF POLYSULFONAMIDE/TiO2 NANOCOMPOSITES BY SOL-GEL

    WANG Xiaopeng; WANG Weitao; MA Ji; DENG Jie; LIU Li

    2006-01-01

    Polysulfonamide (PSA) was synthesized at room temperature, the polymerization based on terephthaloyl chloride and 3,3 '-diaminodiphenylsulfone in the common solvent N,N -Dimethyl-acetamide (DMAc). Polysulfonamide/titanium oxide nanocomposites were prepared by sol-gel method. Tetrabutyl titanate(TBT) was added into the polysulfonamide solution, at the same time ,some water was mixed to make the TBT hydrolyze. In the process, hydrochloric acid was used to catalyze the reaction. The polysulfonamide chemistry structure was characterized by FT-IR spectrum. Atomic force microscopy (AFM) was employed to observe the microstructure of the composite film. The thermal property was investigated by TGA.The results show that we have succeeded to synthesize the polysulfonamide, TiO2particles were well distributed in the composite film and average size was about 20 nm on average, the heat-resistance of nanocomposite was batter than the pure polysulfonamide.

  1. Effect of structure of N,N dialkyl amides on the extraction of U(VI) and Th(IV): a thermodynamic study

    The temperature effect on the extraction behaviour of U(VI) and Th(IV) from 3 M HNO3 employing 1 M solutions of N,N dialkyl amides with varying alkyl substituents on the Cα atom viz. di(2-ethylhexyl)acetamide (D2EHAA), di(2-ethylhexyl)propionamide (D2EHPRA), di(2-ethylhexyl)isobutyramide (D2EHIBA) and di(2-ethylhexyl)pivalamide (D2EHPVA) in n-dodecane has been investigated. These studies indicate that the extraction reactions of U(VI) and Th(IV) are enthalpy stabilised while the entropy factor counteracts the extraction. An attempt has been made to correlate the thermodynamic parameters with the structure of the extractant molecules. (orig.)

  2. amiA is a negative regulator of acetamidase expression in Mycobacterium smegmatis

    Turner Jane

    2001-08-01

    Full Text Available Abstract Background The acetamidase of Mycobacterium smegmatis is a highly inducible enzyme. Expression of this enzyme is increased 100-fold when the substrate acetamide is present. The acetamidase gene is found immediately downstream of three open reading frames. Two of these are proposed to be involved in regulation. Results We constructed a deletion mutant in one of the upstream ORFs (amiA. This mutant (Mad1 showed a constitutively high level of acetamidase expression. We identified four promoters in the upstream region using a β-galactosidase reporter gene. One of these (P2 was inducible in the wild-type, but was constitutively active in Mad1. Conclusions These results demonstrate that amiA encodes a negative regulatory protein which interacts with P2. Since amiA has homology to DNA-binding proteins, it is likely that it exerts the regulatory effect by binding to the promoter to prevent transcription.

  3. Structural Studies of N-(2,4,6-trisubstitutedphenyl)-Chloroacetamides, 2,4,6-X3C6 H2 -NHCO-CH3_y Cly, (X = CH3 or Cl and y = 1 -3)

    Gowda, B. Thimme; Svoboda, I.; Fuess, Hartmut

    2000-10-01

    The effect of side chain and ring substitutions on the crystal structures of N-(2,4,6-substitutedpheny)- chloroacetamides of the type, 2,4,6-X3C6H2-NHCO-CH3_yCly (X = CH3 or Cl and 1 ⩽ y ⩽ 3), has been studied by determining the crystal structures of N-(2,4,6-trimethylphenyl)- 2-chloroacetamide, 2,4,6-(CH3)3C6H2-NHCO-CH2Cl (TMPMCA); N-(2,4,6-trichlorophenyl)-2- chloroacetamide, 2,4,6-Cl3C6H2-NHCO-CH2Cl (TCPMCA); N-(2,4,6-trichlorophenyl)-2,2-dichloroacetamide, 2,4,6-Cl3C6H2-NHCO-CHCl2 (TCPDCA) and N-(2,4,6-trichlorophenyl)-2,2,2- trichloroacetamide, 2,4,6-Cl3C6H2-NHCO-CCl3 (TCPTCA). The crystal type, space group, formula units and lattice constants in A are: (TMiPMCA); monoclinic, P21,/n, Z = 8, a = 9.029(5), b = 15.688(2), c = 16.150(3), ß = 96.77(2)°; (TCPMCA): orthorhombic, Pna21, Z = 8, a = 30.708(4), b = 4.685(1), c = 14.506(2); (TCPDCA) orthorhombic, P212121 Z = 4, a = 16.459(3), b = 15.240(3), c = 4.640(1) and (TCPTCA): triclinic, P Ī , Z = 4, a = 9.828(2), b = 11.953(2), c = 12.278(2), a = 71,05( 1)°, ß = 75.26(2)°, g = 83.29( 1)°. The results have been analysed along with the structures of the ring unsubstituted N-phenylacetamide (PA), N-phenyl-2,2,2-trichloro-acetamide, side chain unsubstituted N-(2,4,6-trichlorophenyl)-acetamide, 2,4,6-Cl3C6H2-NHCO-CH3 (TCPA) and the corresponding di-substituted phenyl acetamides and chloroacetamides. The compounds TMPMCA, TCPMCA and TCPTCA have 2 molecules each in their asymmetric units. This is in agreement with the multiple lines observed in the 35CI NQR spectra of TCPTCA. Further, this compound shows disorder as indicated by the multiplicity of the C(side chain) - Cl bonds. The compound TCPMCA does not show 35C1 NQR spectra, while the compound TMPMCA shows a single frequency which fades out above 200 K, indicating that it may undergo a phase transition well below room temperature. Conversion of 2,4,6-trichloroaniline into 2,4,6-trichlorophenyl acetamide and gradual replacement of H-atoms in the side chain

  4. A carbon-13 NMR spin-lattice relaxation study of the molecular conformation of the nootropic drug 2-oxopyrrolidin-1-ylacetamide

    Baldo, M.; Grassi, A.; Guidoni, L.; Nicolini, M.; Pappalardo, G. C.; Viti, V.

    The spin-lattice relaxation times ( T1) of carbon-13 resonances of the drug 2-oxopyrrolidin- 1-ylacetamide ( 2OPYAC) were determined in CDCl 3 + DMSO and H 2O solutions to investigate the internal conformational flexibility. The measured T1s for the hydrogen-bearing carbon atoms of the 2-pyrrolidone ring fragment were diagnostic of a rigid conformation with respect to the acetamide linked moiety. The model of anisotropic reorientation of a rigid body was used to analyse the measured relaxation data in terms of a single conformation. Owing to the small number of T1 data available the fitting procedure for each of the possible conformations failed. The structure corresponding to the rigid conformation was therefore considered to be the one that is strongly stabilized by internal hydrogen bonding as predicted on the basis of theoretical MO ab initio quantum chemical calculations.

  5. 4'-Acetamidochalcone Derivatives as Potential Antinociceptive Agents

    Valdir Cechinel-Filho

    2007-04-01

    Full Text Available Nine acetamidochalcones were synthesized and evaluated as antinociceptive agents using the mice writhing test. Given intraperitoneally all the compounds were more effective than the two reference analgesic drugs (acetylsalicylic acid and acetaminophen used for comparison. N-{4-[(2E-3-(4-nitrophenylprop-2-enoyl]phenyl}acetamide (6 was the most effective compound and was therefore selected for more detailed studies. It caused dose-related inhibition in the writhing test, being about 32 to 34-fold more potent than the standard drugs. It was also effective in the second phase of the formalin test and the capsaicin test. These acetamidochalcones, especially compound 6, might be further used as models to obtain new and more potent analgesic drugs.

  6. Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics

    Marco Marradi

    2012-06-01

    Full Text Available The preparation of low-generation dendrimers based on a simple calix[4]arene scaffold by insertion of the iminosugar-analogue C2-symmetric 3,4-dihydroxypyrrolidine is described. This methodology allows a rapid incorporation of a considerable number of iminosugar-like moieties in a reduced volume and in a well-defined geometry. The inclusion of alkali-metal ions (sodium and potassium in the polar cavity defined by the acetamide moieties at the lower rim of the calixarene was demonstrated, which allows also the rigidification of the dendrimer structure and the iminosugar presentation in the clusters. The combination of the supramolecular properties of calixarenes with the advantage of a dendrimeric presentation of repetitive units opens up the possibility of generating well-defined multivalent and multifaceted systems with more complex and/or biologically relevant iminosugars.

  7. Spectroscopic investigations of the chiral interactions of metolachlor and its (S)-isomer with lipase and phosphatase.

    Wen, Yue Z; Yuan, Yu L; Chen, Hui; Wang, He L; Liu, Hui J; Kang, Xiao D; Fu, Liu S

    2010-04-01

    Metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] is a chiral acetanilide herbicide. We investigated its enantioselective interactions, and that of its (S)-isomer, with Penicillium expansum alkaline lipase and phosphatase. UV differential spectroscopy and fluorescence spectrophotometry studies were conducted in phosphate buffered solution at pH 7. Chiral differences in the UV absorption and fluorescence spectra of lipase and phosphatase with metolachlor and its (S)-isomer were detected. The results showed that the interactions of metolachlor and its (S)-isomer with lipase and phosphatase occur statically through complex formation, and enantioselectivity was clearly observed. In addition, both UV absorption and fluorescence spectrophotometry showed that the (S)-isomer interacted more strongly with lipase and phosphatase than metolachlor. PMID:20390958

  8. Molar extinction coefficients of solutions of some organic compounds

    Singh, Kulwant; Sandhu, G. K.; Lark, B. S.

    2004-05-01

    Molar extinction coefficients of aqueous solutions of some organic compounds, viz. formamide (CH_{3}NO), N-methylformamide (C_{2}H_{5}NO), NN-dimethylformamide (C_{3}H_{7}NO), NN-dimethylacetamide (C_{4}H_{9}NO), 1,4-dioxane (C_{4}H_{8}O_{2}), succinimide (C_{4}H_{5}NO_{2}) and solutions of acetamide (C_{2}H_{5}NO) and benzoic acid (C_{7}H_{6}O_{2}) in 1,4-dioxane (C_{4}H_{8}O_{2}) have been determined by narrow beam gamma-ray transmission method at 81, 356, 511, 662, 1173 and 1332 keV. The experimental values of mass attenuation coefficients of these compounds have been used to calculate effective atomic numbers and electron densities. The additivity rule earlier used for aqueous solution has been extended to non-aqueous (1,4-dioxane) solutions.

  9. Analysis of Pyrolysates for Polysulphoneamide Fiber by Py-GC/MS

    QIAN He-sheng; LIN Dan-li

    2006-01-01

    Pyrolysis of polysulphoneamide fiber has been investigated using pyrolysis gas chromatography-mass spectroscopy at the different temperatures from 420℃ to 750℃. Its compositions of pyrolysates have been analyzed. At 420 ℃,pyrolysis of molecular chain could not completely take place, 12 compounds of pyrolysis have only been identified.When the temperature increases, the compositions of pyrolysate increase sharply. Several compounds, especially sulfur dioxide, benzene, aniline, benzoic acid, 1,4-benzene dicaronitrile, N-phenyl-acetamide, diphenylamine, benzo[g]isoquinoline, N-phenyl-benzamide, N-( 4-cyanophenyl )benzamide, could be formed. The degradation mechanisms which are determined by structure and amount of the thermal decomposition products are described. During pyrolysis, for polysulphoneamide, polymeric chain scissions take place as a successive removal of the monomer units from the polymeric chain. The chain scissions are followed by secondary reactions, which lead to a variety of compounds.Additional reactions can also take place during pyrolysis.

  10. Synthesis, characterization, and differentiation of high energy amine peroxides by MS and vibrational microscopy

    Peña-Quevedo, Alvaro J.; Mina-Calmide, Nairmen; Rodríguez, Nelmary; Nieves, Deborah; Cody, Robert B.; Hernández-Rivera, Samuel P.

    2006-05-01

    Synthesis and characterization of hexamethelene triperoxide diamine (HMTD), tetramethylene diperoxide dicarbamide (TMDD) and tetramethylene diperoxide acetamide (TMDA) using GC-MS, HPLC-MS, FT-IR and Raman Microscopy has been carried out. The study also centered in the synthesis and characterization of other cyclic amine peroxides, including and different forms of caged peroxides from other diaminoalkanes. Interest also was given to the secondary products of all syntheses and the effect of temperature in the composition mixtures of the preparations. Differentiation spectroscopy and spectrometry studies were also conducted. In these studies the differences in the ν(O-O), ν(N-C), ν(N-H), ν(C-O), δ(CH 3-C) and δ(C-O) bands for Raman and IR were established. For the GC/MS spectrometric studies retention times and fragmentation patterns for GC-MS and GC-FT-IR useful in amine peroxide differentiation were also established.

  11. Characterization of a tryptophan 2-monooxygenase gene from Puccinia graminis f. sp. tritici involved in auxin biosynthesis and rust pathogenicity.

    Yin, Chuntao; Park, Jeong-Jin; Gang, David R; Hulbert, Scot H

    2014-03-01

    The plant hormone indole-3-acetic acid (IAA) is best known as a regulator of plant growth and development but its production can also affect plant-microbe interactions. Microorganisms, including numerous plant-associated bacteria and several fungi, are also capable of producing IAA. The stem rust fungus Puccinia graminis f. sp. tritici induced wheat plants to accumulate auxin in infected leaf tissue. A gene (Pgt-IaaM) encoding a putative tryptophan 2-monooxygenase, which makes the auxin precursor indole-3-acetamide (IAM), was identified in the P. graminis f. sp. tritici genome and found to be expressed in haustoria cells in infected plant tissue. Transient silencing of the gene in infected wheat plants indicated that it was required for full pathogenicity. Expression of Pgt-IaaM in Arabidopsis caused a typical auxin expression phenotype and promoted susceptibility to the bacterial pathogen Pseudomonas syringae pv. tomato DC3000. PMID:24350783

  12. Automated synthesis of an 18F-labelled pyridine-based alkylating agent for high yield oligonucleotide conjugation

    Alkylating agents have been shown to be very promising for the radiolabelling of oligonucleotides with fluorine-18. In this report we describe the fully automated synthesis of 2-bromo-N-[3-(2-[18F]fluoropyridin-3-yloxy)propyl]acetamide ([18F]FPyBrA) utilizing a modular synthesis unit. Reaction conditions for the coupling of this pyridine-based alkylating agent at the 5' end of a fully phosphorothioated random 20-mer DNA sequence were optimized to achieve very high radiochemical yields (>90%) and a maximum specific activity of 5-6 GBq/μmoL. The potential for rapid purification by solid phase extraction without need of chromatographic isolation of the radiolabelled oligonucleotide presents an overall benefit for the application of oligonucleotides in preclinical studies and potential clinical applications.

  13. SYNTHESIS, COMPUTATIONAL STUDY AND PRELIMINARY PHARMACOLOGICAL EVALUATION OF 2-[4-(2-CHLOROBENZYL/BENZOYL SUBSTITUTED PIPERAZIN-1-YL]-N-PHENYLACETAMIDE: POTENTIAL ANTIPSYCHOTICS

    Tomar Amita

    2011-06-01

    Full Text Available Benzyl and benzoyl substituted acetamides have been synthesized and evaluated as potential antipsychotic agents. The target compounds (4a-b were prepared by reaction of substituted anilines with chloroacetylchloride which further treated with 2-chlorobenzyl or 2-chlorobenzoyl piperazine in presence of potassium carbonate and potassium iodide as catalyst in acetonitrile. The structures of the target compounds (4a-b were characterized on the basis of their M.P., TLC, IR and 1H-NMR data. Computational studies of target compounds (4a-b were carried out by using software programs. The target compounds showed good similarity with respect to standard drugs. The target compounds (4a-b showed inhibition of 5-HTP induced head twitches behavior and low induction of catalepsy in mice.

  14. Lethal or protective effects of prolonged treatment with hypoxic cell sensitizers

    AK-2123 [N-(2-methoxyethyl)-2-(3-nitro-1-triazolyl)acetamide] is a hypoxic cell radiosensitizer which is currently being tested in several oncology clinics and which has a lower toxicity than misonidazole (MISO) in vivo. The positive experiences reported recently certainly warrant further clinical evaluations. The experimental observations reported so far need further experimental studies to clarify the sensitization mechanism, especially as recent intratumoral strategies used in the clinical administration of the sensitizers can result in a large local concentration of the drug that may persist for a prolonged period of time between and after radiation exposures. Model experiments in vitro using V79 cells were performed with AK-2123 under these conditions. Misonidazole (MISO) and metronidazole (METRO), well known hypoxic cell radiosensitizers, were used for comparison of the effects. Clonogenic survival and induction and repair of DNA damage were used as end-points

  15. High brightness phosphorescent organic light emitting diodes on transparent and flexible cellulose films

    Organic light-emitting diodes (OLED) were fabricated on flexible and transparent reconstituted cellulose obtained from wood pulp. Cellulose is naturally available, abundant, and biodegradable and offers a unique substrate alternative for the fabrication of flexible OLEDs. Transparent cellulose material was formed by dissolution of cellulose in an organic solvent (dimethyl acetamide) at elevated temperature (165 °C) in the presence of a salt (LiCl). The optical transmission of 40-μm thick transparent cellulose sheet averaged 85% over the visible spectrum. High brightness and high efficiency thin film OLEDs were fabricated on transparent cellulose films using phosphorescent Ir(ppy)3 as the emitter material. The OLEDs achieved current and luminous emission efficiencies as high as 47 cd A−1 and 20 lm W−1, respectively, and a maximum brightness of 10 000 cd m−2. (paper)

  16. FTIR Study of Enhanced Polymeric Blend Membrane with Amines

    Asim Mushtaq

    2014-03-01

    Full Text Available In this study, research will be carried out to identify the functional group behavior of glassy and rubbery polymeric blend membrane with amines. Polymeric blend membranes with different blending ratios were prepared and the developed membranes were characterized by FTIR to see the effect of blend ratio on different functional groups. The developed membranes are flat dense sheet membrane of 20% wt/wt. The pure and blend membrane polysulfone, polyethersulfone, polyvinyl acetate with different composition, with 10% methyl diethanol amine, mono ethanol amine, diethanol amine are developed with dimethyl acetamide solvent. Fourier Transform Infrared (FTIR spectroscopy was utilized to study the interaction between two polymers and to analyze the type of bonding present. To observed frequencies were assigned to various mode of vibration in terms of fundamentals and combination. These spectral changes indicated the existence of molecular interaction among the enhanced polymeric blends; highlight the compatible nature among each other.

  17. Polyimidazoles via aromatic nucleophilic displacement

    Connell, John W. (Inventor); Hergenrother, Paul M. (Inventor)

    1992-01-01

    Polyimidazoles (PI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenyl) imidazole monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The reactions are carried out in polar aprotic solvents such as N,N-dimethyl acetamide, sulfolane, N-methylpyrrolidinone, dimethylsulfoxide, or diphenylsulfone using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl) imidazole monomers are prepared by reacting an aromatic aldehyde with a dimethoxybenzil or by reacting an aromatic dialdehyde with a methoxybenzil in the presence of ammonium acetate. The di(methoxyphenyl) imidazole is subsequently treated with aqueous hydrobromic acid to give the di(hydroxphenyl) imidazole monomer. This synthetic route has provided high molecular weight PI of new chemical structure, is economically and synthetically more favorable than other routes, and allows for facile chemical structure variation due to the availability of a large variety of activated aromatic dihalides and dinitro compounds.

  18. Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae

    Lourivaldo S. Santos

    2013-03-01

    Full Text Available Chemical investigation of Croton pullei (Euphorbiaceae collected in the Brazilian Amazon region was revisited. The chemical composition of the essential oils of leaves and stems was analyzed by GC/MS. It was found that both the oils comprise mainly terpenes, among which linalool was the major one (24.90 and 39.72%, respectively. Phytochemical investigation of the stem methanol extract led to the isolation of a new natural product from the glutarimide alkaloid group named N-[2,6-dioxo-1-(2-phenylethyl-3-piperidinyl]-acetamide, confirming that C. pullei is a rich source of this class of alkaloids. The hexane and methanol extracts of the stems of C. pullei showed moderate antibacterial and antifungal activity and the highest inhibition was observed when the methanol extract was tested against Staphylococcus aureus CCMB 262 and CCMB 263.

  19. Synthesis, characterization and biological evaluation of m-phenetidine derivatives

    The synthesis of compounds bearing sulfamoyl group and amide linkage is pharmacologically important due to their splendid biological activities. In the presented research work N-(3-ethoxyphenyl)-4-methylbenzenesulfonamide (3) was synthesized by the coupling of m-phenetidine (1) with 4-methylbenzenesulfonyl chloride (2) in basic aqueous media. Compound 3 on reaction with 2-bromo-N-aryl/aralkyl substituted acetamides, 5a-d, synthesized the products, 6a-d. The bromination of compound 3 yielded N-(2,4-dibromo-5-ethoxyphenyl)-4-methylbenzenesulfonamide (7) which on further treatment with different electrophiles, 8a-d yielded compound 9a-d. Enzyme inhibition activities of all the synthesized compounds were evaluated against acetylcholinesterase, butyrylcholinesterase, lipoxygenase, urease, chymotrypsin and tyrosinase enzymes; and found to be the most prominent inhibitor of tyrosinase enzyme. (author)

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

    Amini M.

    2008-03-01

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

  1. Synthesis and characterization of novel polyester containing Schiff-base unit

    Hossein Mighani

    2015-10-01

    Full Text Available Abstract A new Schiff base type of polyester containing 2,2-dimethyl-1,3-diaminopropane was prepared by solution polycondensation of 1,4-benzenedicarbonyl dichloride with Bis(4-hydroxybenzilaldehid-2,2-dimethyl-1,3-propildiimine (H2HB2P which is derived from a 2,2-dimethyl-1,3-diaminopropane Schiff base reacted with a 4-hydroxybenzaldehyde monomer. The monomer and the polyester were characterized by FTIR,1HNMR, and elemental analysis. The prepared polyester showed inherent viscosity of 0.29 dl/g in NMP at 25 °C, indicating their moderate molecular weight. The Polyester was completely soluble in aprotic polar solvents such asN -methylpyrolidone (NMP, dimethylformamide (DMF, Dimethyl Acetamid (DMAC, dimthylsulfoxide (DMSO. TGA determined the 10% weight loss temperature (T10 at 280 °C and residual weight at 600 °C ca. 41% under nitrogen atmosphere.

  2. [Cloning of new acylamidase gene from Rhodococcus erythropolis and its expression in Escherichia coli].

    2013-10-01

    The gene for new Rhodococcus erythropolis TA37 acylamidase, which possesses unique substrate specificity, has been cloned and expressed in E. coli. Substrates for this enzyme are not only simple amides, such as acetamide and propionamide, but also N-substituted amides, such as 4'-nitroacetanilide. The 1431-bp gene was expressed in E. coli BL21 (DE3) cells on pET16b plasmid under the control of a promoter of the φ 10 gene from the T7 phage. The molecular mass of recombinant acylamidase in E. coli was 55 kDa, which corresponded to that of native acylamidase from Rhodococcus erythropolis TA37. Recombinant acylamidase was able to hydrolize N-substituted amides. A search of a nucleotide database and multiple alignment revealed that acylamidase belonged to the Amidase protein family PF01425, but its nucleotide and amino acid sequences differed significantly from those of the described amidases. PMID:25508680

  3. Analysis of the Electronic Structure of Aqueous Urea and Its Derivatives: A Systematic Soft X-Ray-TD-DFT Approach.

    Tesch, Marc F; Golnak, Ronny; Ehrhard, Felix; Schön, Daniela; Xiao, Jie; Atak, Kaan; Bande, Annika; Aziz, Emad F

    2016-08-16

    Soft X-ray emission (XE), absorption (XA), and resonant inelastic scattering (RIXS) experiments have been conducted at the nitrogen K-edge of urea and its derivatives in aqueous solution and were compared with density functional theory and time-dependent density functional theory calculations. This comprehensive study provides detailed information on the occupied and unoccupied molecular orbitals of urea, thiourea, acetamide, dimethylurea, and biuret at valence levels. By identifying the electronic transitions that contribute to the experimental spectral features, the energy gap between the highest occupied and the lowest unoccupied molecular orbital of each molecule is determined. Moreover, a theoretical approach is introduced to simulate resonant inelastic X-ray scattering spectra by adding an extra electron to the lowest unoccupied molecular orbital, thereby mimicking the real initial state of the core-electron absorption before the subsequent relaxation process. PMID:27416871

  4. Water-soluble polymers as auxiliary contrivance for enhanced petroleum recovery

    Klein, J.

    1984-01-01

    In oil extraction, polymers are used above all as viscosity enhancers, fluid-loss additives, protective colloids, acid thickeners, flow accelerators and complex formers. The paper concentrates its discussion on the application of viscosity enhancers added to the flooding water in enhanced oil recovery. Vinyl polymers like acrylamide/Na-acrylate copolymers, and terpolymers from acrylamide, vinyl acetamide and vinyl sulphonic acid are used which bring about an increase of median viscosity but are resistent to microbial degradation. In addition, biopolysaccharides like xanthane or compounds from the scleroglucane group are applied which increase viscosity very much but are biodegradable. As a compromise between both types mentioned, vinyl polymers are being tested whose side chains consist of saccharides.

  5. Detection and Quantification of Nitrogen Compounds in the First Drilled Martian Solid Samples by the Sample Analysis at Mars (SAM) Instrument Suite on the Mars Science Laboratory (MSL)

    Stern, J. C.; Navarro-Gonzales, R.; Freissinet, C.; McKay, C. P.; Archer, P. D., Jr.; Buch, A.; Brunner, A. E.; Coll, P.; Eigenbrode, J. L.; Franz, H. B.; Glavin, D. P.; McAdam, A. C.; Ming, D.; Steele, A.; Sutter, B.; Szopa, C.; Wray, J. J.; Conrad, P.; Mahaffy, P. R.

    2014-01-01

    The Sample Analysis at Mars (SAM) instrument suite on the Mars Science Laboratory (MSL) Curiosity Rover detected both reduced and oxidized nitrogen-bearing compounds during the pyrolysis of surface materials at Yellowknife Bay in Gale Crater. Preliminary detections of nitrogen species include NO, HCN, ClCN, CH3CN, and TFMA (trifluoro-N-methyl-acetamide). Confirmation of indigenous Martian N-bearing compounds requires quantifying N contribution from the terrestrial derivatization reagents (e.g. N-methyl-N-tertbutyldimethylsilyltrifluoroacetamide, MTBSTFA and dimethylformamide, DMF) carried for SAM's wet chemistry experiment that contribute to the SAM background. Nitrogen species detected in the SAM solid sample analyses can also be produced during laboratory pyrolysis experiments where these reagents are heated in the presence of perchlorate, a compound that has also been identified by SAM in Mars solid samples.

  6. Antinociceptive properties of selective MT(2) melatonin receptor partial agonists.

    López-Canul, Martha; Comai, Stefano; Domínguez-López, Sergio; Granados-Soto, Vinicio; Gobbi, Gabriella

    2015-10-01

    Melatonin is a neurohormone involved in the regulation of both acute and chronic pain whose mechanism is still not completely understood. We have recently demonstrated that selective MT2 melatonin receptor partial agonists have antiallodynic properties in animal models of chronic neuropathic pain by modulating ON/OFF cells of the descending antinociceptive system. Here, we examined the antinociceptive properties of the selective MT2 melatonin receptor partial agonists N-{2-[(3-methoxyphenyl)phenylamino]ethyl}acetamide (UCM765) and N-{2-[(3-bromophenyl)-(4-fluorophenyl)amino]ethyl}acetamide (UCM924) in two animal models of acute and inflammatory pain: the hot-plate and formalin tests. UCM765 and UCM924 (5-40 mg/kg, s.c.) dose-dependently increased the temperature of the first hind paw lick in the hot-plate test, and decreased the total time spent licking the injected hind paw in the formalin test. Antinociceptive effects of UCM765 and UCM924 were maximal at the dose of 20mg/kg. At this dose, the effects of UCM765 and UCM924 were similar to those produced by 200 mg/kg acetaminophen in the hot-plate test, and by 3 mg/kg ketorolac or 150 mg/kg MLT in the formalin test. Notably, antinociceptive effects of the two MT2 partial agonists were blocked by the pre-treatment with the MT2 antagonist 4-phenyl-2-propionamidotetralin (4P-PDOT, 10 mg/kg) in both paradigms. These results demonstrate the antinociceptive properties of UCM765 and UCM924 in acute and inflammatory pain models and corroborate the concept that MT2 melatonin receptor may be a novel target for analgesic drug development. PMID:26162699

  7. Applicability of a carbamate insecticide multiresidue method for determining additional types of pesticides in fruits and vegetables.

    Krause, R T; August, E M

    1983-03-01

    Several fruits and vegetables were fortified at a low (0.02-0.5 ppm) and at a high (0.1-5 ppm) level with pesticides and with a synergist, and recoveries were determined. Analyses were performed by using 3 steps of a multiresidue method for determining N-methylcarbamates in crops: methanol extraction followed by removal of plant co-extractives by solvent partitioning and chromatography with a charcoal-silanized Celite column. Eleven compounds were determined by using a high performance liquid chromatograph equipped with a reverse phase column and a fluorescence detector. Twelve additional compounds were determined by using a gas-liquid chromatograph equipped with a nonpolar packed column and an electron capture or flame photometric detector. Recoveries of 10 pesticides (azinphos ethyl, azinphos methyl, azinphos methyl oxygen analog, carbaryl, carbofuran, naphthalene acetamide, naphthalene acetic acid methyl ester, napropamide, phosalone, and phosalone oxygen analog) and the synergist piperonyl butoxide, which were determined by high performance liquid chromatography, averaged 100% (range 86-117) at the low fortification level and 102% (range 93-115) at the high fortification level. Quantitative recovery of naphthalene acetamide through the method required that an additional portion of eluting solution be passed through the charcoal column. Recoveries of 7 additional pesticides (dimethoate, malathion, methyl parathion, mevinphos, parathion, phorate oxygen analog, and pronamide), which were determined by gas-liquid chromatography (GLC), averaged 108% (range 100-120) at the low fortification level and 107% (range 99-122) at the high fortification level. DDT, diazinon, dieldrin, phorate, and pirimiphos ethyl, which were determined by GLC, were not quantitatively recovered. PMID:6853408

  8. 35Cl NQR and Structural Studies of Chloroacetanilides C6H3Cl2NHCOCH3-xClx, 1 ≤ x ≤ 3

    Groke, Dirk; Dou, Shi-Qi; Weiss, Alarich

    1992-02-01

    The temperature dependence of 35Cl NQR frequencies and the phase transition behaviour of chloroacetanilides (N-[2,6-dichlorophenyl]-2-chloroacetamide, -2,2-dichloroacetamide, -2,2,2-trichloroacetamide) were investigated. The crystal structure determination of N-[2,6-dichlorophenyl]- 2-chloroacetamide leads to the following: a = 1893.8 pm, b = 1110.7 pm, c = 472.1 pm, space group P212121 = D24 with Z = 4 molecules per unit cell. The arrangement of the molecules and their geometry is comparable to the high temperature phase of the acetyl compound N-[2,6-dichlorophenyl]- acetamide. For N-[2,6-diclorophenyl]-2,2,2-trichloroacetamide it was found: a = 1016.6 pm, b = 1194.3 pm, c = 1006.7 pm, ß= 101.79°, space group P21/c = C52h, Z = 4. The structure is similar to the low temperature phase of N-[2,6-dichlorophenyl]-acetamide. Parallelism between the temperature dependence of the 35C1 NQR lines of the CCl3 group and the X-ray diffraction results concerning the different behaviour of the chlorine atoms was observed. The structures of the compounds show intermolecular hydrogen bonding of the N - H • • • O - C type. The phenyl group and the HNCO function are nearly planar. A bleaching out of several 35Cl NQR lines at a temperature far below the melting point of the substances was observed. The different types of chlorine atoms (aromatic, chloromethyl) can be distinguished by their temperature coefficients of the 35Cl NQR frequencies. All the resonances found show normal "Bayer" temperature behaviour. N-[2,6-dichlorophenyl]-2,2-diehloroacetamide shows several solid phases. One stable low temperature phase and an instable high temperature phase (at room temperature) were observed. The different phases were detected by means of 35Cl NQR spectroscopy and thermal analysis

  9. Synthesis, antifungal activity, and QSAR studies of 1,6-dihydropyrimidine derivatives

    Chirag Rami

    2013-01-01

    Full Text Available Introduction: A practical synthesis of pyrimidinone would be very helpful for chemists because pyrimidinone is found in many bioactive natural products and exhibits a wide range of biological properties. The biological significance of pyrimidine derivatives has led us to the synthesis of substituted pyrimidine. Materials and Methods: With the aim of developing potential antimicrobials, new series of 5-cyano-6-oxo-1,6-dihydro-pyrimidine derivatives namely 2-(5-cyano-6-oxo-4-substituted (aryl-1,6-dihydropyrimidin-2-ylthio-N-substituted (phenyl acetamide (C1-C41 were synthesized and characterized by Fourier transform infrared spectroscopy (FTIR, mass analysis, and proton nuclear magnetic resonance ( 1 H NMR. All the compounds were screened for their antifungal activity against Candida albicans (MTCC, 227. Results and Discussion: Quantitative structure activity relationship (QSAR studies of a series of 1,6-dihydro-pyrimidine were carried out to study various structural requirements for fungal inhibition. Various lipophilic, electronic, geometric, and spatial descriptors were correlated with antifungal activity using genetic function approximation. Developed models were found predictive as indicated by their square of predictive regression values (r 2pred and their internal and external cross-validation. Study reveals that CHI_3_C, Molecular_SurfaceArea, and Jurs_DPSA_1 contributed significantly to the activity along with some electronic, geometric, and quantum mechanical descriptors. Conclusion: A careful analysis of the antifungal activity data of synthesized compounds revealed that electron withdrawing substitution on N-phenyl acetamide ring of 1,6-dihydropyrimidine moiety possess good activity.

  10. A comparison of chemical shift sensitivity of trifluoromethyl tags: optimizing resolution in {sup 19}F NMR studies of proteins

    Ye, Libin; Larda, Sacha Thierry; Frank Li, Yi Feng [University of Toronto, UTM, Department of Chemistry (Canada); Manglik, Aashish [Stanford University School of Medicine, Department of Molecular and Cellular Physiology (United States); Prosser, R. Scott, E-mail: scott.prosser@utoronto.ca [University of Toronto, UTM, Department of Chemistry (Canada)

    2015-05-15

    The elucidation of distinct protein conformers or states by fluorine ({sup 19}F) NMR requires fluorinated moieties whose chemical shifts are most sensitive to subtle changes in the local dielectric and magnetic shielding environment. In this study we evaluate the effective chemical shift dispersion of a number of thiol-reactive trifluoromethyl probes [i.e. 2-bromo-N-(4-(trifluoromethyl)phenyl)acetamide (BTFMA), N-(4-bromo-3-(trifluoromethyl)phenyl)acetamide (3-BTFMA), 3-bromo-1,1,1-trifluoropropan-2-ol (BTFP), 1-bromo-3,3,4,4,4-pentafluorobutan-2-one (BPFB), 3-bromo-1,1,1-trifluoropropan-2-one (BTFA), and 2,2,2-trifluoroethyl-1-thiol (TFET)] under conditions of varying polarity. In considering the sensitivity of the {sup 19}F NMR chemical shift to the local environment, a series of methanol/water mixtures were prepared, ranging from relatively non-polar (MeOH:H{sub 2}O = 4) to polar (MeOH:H{sub 2}O = 0.25). {sup 19}F NMR spectra of the tripeptide, glutathione ((2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl] -2-sulfanylethyl]carbamoyl}butanoic acid), conjugated to each of the above trifluoromethyl probes, revealed that the BTFMA tag exhibited a significantly greater range of chemical shift as a function of solvent polarity than did either BTFA or TFET. DFT calculations using the B3LYP hybrid functional and the 6-31G(d,p) basis set, confirmed the observed trend in chemical shift dispersion with solvent polarity.