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Sample records for acetamide

  1. 40 CFR 721.285 - Acetamide, N-[4-(pentyloxy)phenyl]-, acetamide, N-[2-nitro-4-(pentyloxy)phenyl]-, and acetamide...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., N- - (PMN P-92-31), acetamide, N- - (PMN P-92-32), and acetamide, N- - (PMN P-92-33) are subject to... specified in § 721.80(h). (ii) Release to water. Requirements as specified in § 721.90 (a)(4), (b)(4), and (c)(4) (where N = 90 ppb for PMNs P-92-31 and P-92-32, and N = 30 ppb for P-92-33). When...

  2. 40 CFR 721.285 - Acetamide, N-[4-(pentyloxy)phenyl]-, acetamide, N-[2-nitro-4-(pentyloxy)phenyl]-, and acetamide...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., N- - (PMN P-92-31), acetamide, N- - (PMN P-92-32), and acetamide, N- - (PMN P-92-33) are subject to... specified in § 721.80(h). (ii) Release to water. Requirements as specified in § 721.90 (a)(4), (b)(4), and (c)(4) (where N = 90 ppb for PMNs P-92-31 and P-92-32, and N = 30 ppb for P-92-33). When...

  3. Orientational Jumps in (Acetamide + Electrolyte) Deep Eutectics: Anion Dependence.

    PubMed

    Das, Suman; Biswas, Ranjit; Mukherjee, Biswaroop

    2015-08-27

    All-atom molecular dynamics simulations have been carried out to investigate orientation jumps of acetamide molecules in three different ionic deep eutectics made of acetamide (CH3CONH2) and lithium salts of bromide (Br(–)), nitrate (NO3(–)) and perchlorate (ClO4(–)) at approximately 80:20 mole ratio and 303 K. Orientational jumps have been dissected into acetamide–acetamide and acetamide–ion catagories. Simulated jump characteristics register a considerable dependence on the anion identity. For example, large angle jumps are relatively less frequent in the presence of NO3(–) than in the presence of the other two anions. Distribution of jump angles for rotation of acetamide molecules hydrogen bonded (H-bonded) to anions has been found to be bimodal in the presence of Br(–) and is qualitatively different from the other two cases. Estimated energy barrier for orientation jumps of these acetamide molecules (H-bonded to anions) differ by a factor of ∼2 between NO3(–) and ClO4(–), the barrier height for the latter being lower and ∼0.5kBT. Relative radial and angular displacements during jumps describe the sequence ClO(4)– > NO3(–) > Br(–) and follow a reverse viscosity trend. Jump barrier for acetamide–acetamide pairs reflects weak dependence on anion identity and remains closer to the magnitude (∼0.7kBT) found for orientation jumps in molten acetamide. Jump time distributions exhibit a power law dependence of the type, P(tjump) ∝ A(tjump/τ)(−β), with both β and τ showing substantial anion dependence. The latter suggests the presence of dynamic heterogeneity in these systems and supports earlier conclusions from time-resolved fluorescence measurements. PMID:26131593

  4. 40 CFR 721.285 - Acetamide, N-[4-(pentyloxy)phenyl]-, acetamide, N-[2-nitro-4-(pentyloxy)phenyl]-, and acetamide...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for... substances and significant new uses subject to reporting. (1) The chemical substances identified as acetamide... reporting under this section for the significant new uses described in paragraph (a)(2) of this section....

  5. 40 CFR 721.285 - Acetamide, N-[4-(pentyloxy)phenyl]-, acetamide, N-[2-nitro-4-(pentyloxy)phenyl]-, and acetamide...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for... substances and significant new uses subject to reporting. (1) The chemical substances identified as acetamide... reporting under this section for the significant new uses described in paragraph (a)(2) of this section....

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

    PubMed

    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

  7. Acetamides: chemotherapeutic agents for inflammation-associated cancers.

    PubMed

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

    2016-08-01

    Now clear evidences are available to support the hypothesis that inflammation accelerates the conditions including events and molecules that reach to various types of cancers. Inflammation is a normal response to infection containing the innate and adaptive immune systems. However, when allowed to continue, unresolved, perturbation of cellular microenvironment takes place; therefore, it leads to adaptations in genes that are linked to cancer. In addition, a lot of data are accessible confirming the concept that tumour microenvironment is orchestrated by various inflammatory cells and goes to neoplastic process and finally invasion, migration and metastasis. However, infiltrations of leucocytes lead to angiogenesis, propagation and invasion. An inflammatory microenvironment that perhaps fostering impact of angiogenesis include cytokines, chemokines, enzymes and growth factors that play key role for expansion and invasion of cancer cells. This insight highlights the pathogenesis of inflammation-associated cancers and also touches and fosters the role of acetamides for the treatment and chemoprevention of carcinomas that are allied with inflammation. PMID:26198312

  8. New structure-activity relationships of N-acetamide substituted pyrazolopyrimidines as pharmacological ligands of TSPO.

    PubMed

    Li, Jun; Schulte, Michael L; Nickels, Michael L; Manning, H Charles

    2016-08-01

    Translocator protein (TSPO) represents an attractive target for molecular imaging and therapy due to its prevalence and critical roles played in oncology and other pathologies. Based upon our previously optimized pyrazolopyrimidine scaffold, we elucidated new structure activity relationships related to N,N-disubstitutions of the terminal acetamide on pyrazolopyrimidines and further explored the impacts of these substituents on lipophilicity and plasma protein binding. Several novel chemical probes reported here exhibited significantly increased binding affinity, suitable lipophilicity and protein binding compared with contemporary TSPO ligands. We illustrate that N,N-acetamide disubstitution affords opportunities to introduce diverse chemical moieties distal to the central pyrazolopyrimidine core, without sacrificing TSPO affinity. We anticipate that further exploration of N-acetamide substitutions may yield additional TSPO ligands capable of furthering the field of precision medicine. PMID:27353534

  9. Synthesis and local anaesthetic activity of 2-substituted-N-(2-diethylaminoethyl)-acetamides.

    PubMed

    Jindal, Dharam Paul; Coumar, Mohane S; Singh, Babita; Ismail, Mohammed Muhiyiden Mohammed; Zambare, Girish Nilkanth; Bodhankar, Subhash Laxmanrao

    2003-01-01

    The synthesis of 2-substituted-N-(2-diethylaminoethyl)acetamide oxalates (6a, 6b) and the evaluation of their in vivo local anaesthetic activities are described. The compounds 6a and 6b were obtained starting from 4-acetamidophenol and 1-naphthol, respectively. The in vivo local anesthetic activity was evaluated by infiltration anaesthesia, sciatic nerve block and corneal anaesthesia models. N-(2-Diethylaminoethyl)-2-(naphthalen-1-yloxy)acetamide oxalate (6b) was found to have potency, onset and duration of action comparable to that of lidocaine (2) (lidocaine hydrochloride, CAS 6108-05-0). Procaine (1) (procaine hydrochloride, CAS 51-05-8) was also used for comparison. Dissociation constants (pKa) of compounds 5a and 5b (2-substituted-N-(2-diethylaminoethyl)acetamide) have been determined to be 8.9 and 8.6, respectively. PMID:12608012

  10. Slow-to-fast transition of hydrogen bond dynamics in acetamide hydration shell formation.

    PubMed

    D'Amico, Francesco; Rossi, Barbara; Camisasca, Gaia; Bencivenga, Filippo; Gessini, Alessandro; Principi, Emiliano; Cucini, Riccardo; Masciovecchio, Claudio

    2015-04-28

    The formation of a hydration shell in acetamide aqueous solution has been investigated by means of UV Raman spectroscopy. The experimental results reveal the existence of two distinct regimes of water dynamics. At high acetamide concentration water molecules show a structural and dynamical behavior consistent with the so-called iceberg model. Upon increasing the amount of water we observe the formation of a hydration shell marked by fastening of hydrogen-bond dynamics. Such a behavior may help to shed light on the scientific debate on how water rearranges around the hydrophobic portions of solute molecules (iceberg vs. non-iceberg models). PMID:25824617

  11. 40 CFR 721.225 - 2-Chloro-N-methyl-N-substituted acetamide (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 2-Chloro-N-methyl-N-substituted... Specific Chemical Substances § 721.225 2-Chloro-N-methyl-N-substituted acetamide (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance...

  12. 40 CFR 721.225 - 2-Chloro-N-methyl-N-substituted acetamide (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Chloro-N-methyl-N-substituted... Specific Chemical Substances § 721.225 2-Chloro-N-methyl-N-substituted acetamide (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance...

  13. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  14. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  15. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  16. 40 CFR 721.225 - 2-Chloro-N-methyl-N-substituted acetamide (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Chloro-N-methyl-N-substituted... Specific Chemical Substances § 721.225 2-Chloro-N-methyl-N-substituted acetamide (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance...

  17. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical...

  18. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical...

  19. Parametrisation of a force field of acetamide for simulations of the liquid phase

    NASA Astrophysics Data System (ADS)

    Aguilar-Pineda, Jorge A.; Arlette Méndez-Maldonado, G.; Núñez-Rojas, Edgar; Alejandre, José

    2015-09-01

    Molecular dynamics simulations are performed to develop new parameters for acetamide using a systematic procedure proposed by Salas et al., where the atomic charges were fitted to reproduce the experimental dielectric constant and the Lennard-Jones parameters to match the surface tension and density. The parameters for formamide recently calculated by Pérez et al. were used to obtain the new parameters of acetamide where atoms of the amine group and carbon kept the same intermolecular parameter values in both molecules. The parameters of the methyl group, taken as united atom, and the oxygen atom were fitted to reproduce the dielectric constant, surface tension and density at 358.15 K. The new set of parameters, based on the optimised potential for liquids simulations with all atoms, was able to predict results of the target properties as a function of temperature as a pure component and the dielectric constant and density of binary mixtures with water and formamide as a function of acetamide concentration at 298.15 K. The polymer chains formed by hydrogen bond interactions were analysed to understand the maximum of dielectric constant in acetamide-water mixtures.

  20. Crystal structures of two (±)-exo-N-isobornyl­acetamides

    PubMed Central

    Stepanovs, Dmitrijs; Posevins, Daniels; Turks, Maris

    2015-01-01

    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]. PMID:26594386

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

    NASA Astrophysics Data System (ADS)

    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.

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

    PubMed Central

    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

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

    PubMed

    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

  4. Design, synthesis and evaluation of benzofuran-acetamide scaffold as potential anticonvulsant agent.

    PubMed

    Shakya, Ashok K; Kamal, Mehnaz; Balaramnavar, Vishal M; Bardaweel, Sanna K; Naik, Rajashri R; Saxena, Anil K; Siddiqui, H H

    2016-09-01

    A series of N-(2-(benzoyl/4-chlorobenzoyl)-benzofuran- 3-yl)-2-(substituted)-acetamide derivatives (4a-l, 5a-l) was synthesized in good yield. All synthesized compounds were in agreement with elemental and spectral data. The anticonvulsant activity of all synthesized compounds was assessed against the maximal electroshock induced seizures (MES) model in mice. Neurotoxicity was evaluated using the rotarod method. The majority of compounds exhibited anticonvulsant activity at a dose of 30 mg kg-1 body mass during 0.5-4 h, indicating their ability to prevent seizure spread at low doses. Relative to phenytoin, [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(cyclohexyl( methyl) amino)-acetamide] (5i) and [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-methylpiperidin-1- yl)-acetamide] (5c) demonstrated comparable relative anticonvulsant potency of 0.74 and 0.72, respectively, whereas [(N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-(furan-2-carbonyl)-piperazin-1-yl)-acetamide] (5f) exhibited the lowest relative potency of 0.16. The ALD50 of tested compounds ranged from 1.604 to 1.675 mmol kg-1 body mass. The ED50 of synthesized compounds ranged from 0.055 to 0.259 mmol kg-1 (~23.4 to 127.6 mg kg-1) body mass. The pharmacophore mapping of the examined compounds on standard drugs (phenobarbital, phenytoin, ralitolin and carbamazepine) strongly suggests that these compounds may exert their anticonvulsant activity via the same established mechanism as that of known drugs. PMID:27383885

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

    PubMed Central

    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

  6. Acetamide herbicides and their degradation products in ground water and surface water of the United States, 1993-2003

    USGS Publications Warehouse

    Scribner, Elisabeth A.; Dietze, Julie E.; Thurman, Michael

    2004-01-01

    During 1993 through 2003, the U.S. Geological Survey conducted a number of studies to investigate and document the occurrence, fate, and transport of acetamide herbicides and their degradation products in ground and surface water. As part of these studies, approximately 5,100 water samples were collected and analyzed for the acetamide parent herbicides acetochlor, alachlor, dimethenamid, flufenacet, and metolachlor and their degradation products ethanesulfonic acid, oxanilic acid, and sulfinyl acetic acid. During this period, various analytical methods were developed to detect and measure concentrations of acetamide herbicides and their degradation products in ground water and surface water. Results showed that the degradation products of acetamide herbicides in ground water were detected more frequently and occurred at higher concentrations than their parent compounds. Further study showed that the acetamide herbicides and their degradation products were detected more frequently in surface water than in ground water. In general, the parent compounds were detected at similar or greater frequencies than the degradation products in surface water. The developed methods and data were valuable for acquiring information about the occurrence, fate, and transport of the herbicides and their degradation products and the importance of analyzing for both parent compounds and their degradate products in water-quality studies.

  7. Peptide bond formation through gas-phase reactions in the interstellar medium: formamide and acetamide as prototypes

    SciTech Connect

    Redondo, Pilar; Barrientos, Carmen; Largo, Antonio

    2014-09-20

    A theoretical study of the reactions of NH{sub 4}{sup +} with formaldehyde and CH{sub 5}{sup +} with formamide is carried out. The viability of these gas-phase ion-molecule reactions as possible sources of formamide and acetamide under the conditions of interstellar medium is evaluated. We report a theoretical estimation of the reaction enthalpies and an analysis of their potential energy surfaces. Formation of protonated formamide from the reaction between ammonium cation and formaldehyde is an exothermic process, but all the channels located on the potential energy surface leading to this product present net activation energies. For the reaction between methanium and formamide, different products are possible from a thermodynamic point of view. An analysis of its potential energy surface showed that formation of protonated acetamide and amino acetaldehyde takes place through barrier-free paths. Therefore, this reaction could be a feasible source of acetamide and amino acetaldehyde in space.

  8. Copper(I)-Catalyzed Asymmetric Dearomatization of Indole Acetamides with 3-Indolylphenyliodonium Salts.

    PubMed

    Liu, Chuan; Yi, Ji-Cheng; Liang, Xiao-Wei; Xu, Ren-Qi; Dai, Li-Xin; You, Shu-Li

    2016-07-25

    The rapid and direct asymmetric synthesis of 3-(3a-indolyl)hexahydropyrroloindoline motifs is an extremely important part of the total synthesis of several alkaloid structures. Herein, an intermolecular, asymmetric cascade dearomatization reaction of indole acetamides with 3-indolylphenyliodonium salts has been developed. This protocol provides a straightforward access to 3-(3a-indolyl)hexahydropyrroloindolines bearing an all-carbon quaternary stereocenter at the C3 position of the indoline ring with high enantioselectivities. The utility of the protocol has been demonstrated by the formal asymmetric synthesis of folicanthine. PMID:27171171

  9. Oxidation Reactivity Channels for 2-(Pyridin-2-yl)-N,N-diphenyl-acetamides

    SciTech Connect

    Pailloux, Sylvie; Binyamin, Iris; Kim, Sung-jun; Deck, Lorraine M.; Rapko, Brian M.; Hay, Benjamin; Duesler, Eileen N.; Paine, Robert T.

    2007-11-01

    Synthetic routes to 2-(pyridin-2-yl)-N,N-diphenylacetamide and 2-(6-methylpyridin-2-yl)-N,N-diphenyl-acetamide are described along with results from the chemical oxidation of these compounds with peracetic acid, m-chloroperbenzoic acid, and OXONE. In each case, oxidations generate four products in varying amounts depending on the oxidant and reaction conditions. Each product has been characterized by spectroscopic methods and the molecular structures of several of the new compounds have been confirmed by X-ray crystallography.

  10. Acetamide derivatives with antioxidant activity and potential anti-inflammatory activity.

    PubMed

    Autore, Giuseppina; Caruso, Anna; Marzocco, Stefania; Nicolaus, Barbara; Palladino, Chiara; Pinto, Aldo; Popolo, Ada; Sinicropi, Maria S; Tommonaro, Giuseppina; Saturnino, Carmela

    2010-03-01

    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. PMID:20336030

  11. Growth and characterization of new organic nonlinear optical crystal (R)-2-cyano-N-(1-phenylethyl) acetamide

    SciTech Connect

    Hemaraju, B. C.; Gnana Prakash, A. P.; Madhukar, B. S.; Bhadregowda, D. G.

    2014-04-24

    (R)-2-Cyano-N-(1-phenylethyl) acetamide (RCNPA) single crystals were grown by slow evaporation of the aqueous solution at room temperature (300K) using ethanol. The grown crystals were characterized by single crystal X-ray diffraction, powder X-ray diffraction, FTIR, UV-Vis-NIR transmittance, scanning electron microscopy (SEM) and powder second harmonic generation (SHG)

  12. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 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...

  13. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 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...

  14. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 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...

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

    NASA Astrophysics Data System (ADS)

    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

  16. 2-(Quinolin-4-yloxy)acetamides Are Active against Drug-Susceptible and Drug-Resistant Mycobacterium tuberculosis Strains.

    PubMed

    Pissinate, Kenia; Villela, Anne Drumond; Rodrigues-Junior, Valnês; Giacobbo, Bruno Couto; Grams, Estêvão Silveira; Abbadi, Bruno Lopes; Trindade, Rogério Valim; Roesler Nery, Laura; Bonan, Carla Denise; Back, Davi Fernando; Campos, Maria Martha; Basso, Luiz Augusto; Santos, Diógenes Santiago; Machado, Pablo

    2016-03-10

    2-(Quinolin-4-yloxy)acetamides have been described as potent in vitro inhibitors of Mycobacterium tuberculosis growth. Herein, additional chemical modifications of lead compounds were carried out, yielding highly potent antitubercular agents with minimum inhibitory concentration (MIC) values as low as 0.05 μM. Further, the synthesized compounds were active against drug-resistant strains and were devoid of apparent toxicity to Vero and HaCat cells (IC50s ≥ 20 μM). In addition, the 2-(quinolin-4-yloxy)acetamides showed intracellular activity against the bacilli in infected macrophages with action similar to rifampin, low risk of drug-drug interactions, and no sign of cardiac toxicity in zebrafish (Danio rerio) at 1 and 5 μM. Therefore, these data indicate that this class of compounds may furnish candidates for future development to, hopefully, provide drug alternatives for tuberculosis treatment. PMID:26985307

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

    USGS Publications Warehouse

    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.

  18. Transport Properties of LiTFSI-Acetamide Room Temperature Molten Salt Electrolytes Applied in an Li-Ion Battery

    NASA Astrophysics Data System (ADS)

    Yang, Chao-Chen; Hsu, Hsin-Yi; Hsu, Chen-Ruei

    2007-11-01

    In the present work some transport properties of the binary room temperature molten salt (RTMS) lithium bis(trifluoromethane sulfone)imide (LiTFSI)-acetamide [LiN(SO2CF3)2-CH3CONH2], applied in an Li-ion battery, have been investigated. The phase diagram was determined by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The result reveals that the binary RTMS has an eutectic point at 201 K and the 30 mol% LiTFSI composition. The electric conductivity was measured using a direct current computerized method. The result shows that the conductivities of the melts increase with increasing temperature and acetamide content. The densities of all melts decrease with increasing temperature and acetamide content. The equivalent conductivities were fitted by the Arrhenius equation, where the activation energies were 18.15, 18.52, 20.35, 25.08 kJ/mol for 10, 20, 30, 40 mol% LiTFSI, respectively. Besides the relationships between conductivity, density composition and temperature, of the ion interaction is discussed.

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

    PubMed

    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

  20. Dielectric Relaxations of (Acetamide + Electrolyte) Deep Eutectic Solvents in the Frequency Window, 0.2 ≤ ν/GHz ≤ 50: Anion and Cation Dependence.

    PubMed

    Mukherjee, Kallol; Das, Anuradha; Choudhury, Samiran; Barman, Anjan; Biswas, Ranjit

    2015-06-25

    Dielectric relaxation (DR) measurements in the frequency range 0.2 ≤ ν/GHz ≤ 50 have been carried out for neat molten acetamide and six different (acetamide + electrolyte) deep eutectic solvents (DESs) for investigating ion effects on DR dynamics in these ionic DESs. Electrolytes used are lithium salts of bromide (LiBr), nitrate (LiNO3), and perchlorate (LiClO4); sodium salts of perchlorate (NaClO4) and thiocyante (NaSCN); and potassium thiocyanate (KSCN). With these electrolytes acetamide forms DESs approximately at an 80:20 mol ratio. Simultaneous fits to the measured permittivity (ε′) and loss (ε″) spectra of these DESs at ∼293 K require a sum of four Debye (4-D) processes with relaxation times spread over picosecond to nanosecond regime. In contrast, DR spectra for neat molten acetamide (∼354 K) depict 2-D relaxation with time constants ∼50 ps and ∼5 ps. For both the neat and ionic systems, the undetected dispersion, ε∞ – n(D)2, remains to be ∼3–4. Upon comparison, measured DR dynamics reveal pronounced anion and cation effects. Estimated static dielectric constants (ε0) from fits for these DESs cover the range 12 < ε0 < 30 and are remarkably lower than that (ε0 ∼ 64) measured for molten acetamide at ∼354 K. Hydrodynamic effective rotation volumes (Veff) estimated from the slowest DR relaxation time constants vary with ion identity and are much smaller than the molecular volume of acetamide. This decrease of ε0 and Veff is attributed respectively to the pinning of acetamide molecules by ions and orientation jumps and undetected portion to the limited frequency coverage employed in these measurements PMID:26012789

  1. A HPLC method for the quantification of butyramide and acetamide at ppb levels in hydrogeothermal waters

    SciTech Connect

    Gracy Elias; Earl D. Mattson; Jessica E. Little

    2012-01-01

    A quantitative analytical method to determine butyramide and acetamide concentrations at the low ppb levels in geothermal waters has been developed. The analytes are concentrated in a preparation step by evaporation and analyzed using HPLC-UV. Chromatographic separation is achieved isocratically with a RP C-18 column using a 30 mM phosphate buffer solution with 5 mM heptane sulfonic acid and methanol (98:2 ratio) as the mobile phase. Absorbance is measured at 200 nm. The limit of detection (LOD) for BA and AA were 2.0 {mu}g L{sup -1} and 2.5 {mu}g L{sup -1}, respectively. The limit of quantification (LOQ) for BA and AA were 5.7 {mu}g L{sup -1} and 7.7 {mu}g L{sup -1}, respectively, at the detection wavelength of 200 nm. Attaining these levels of quantification better allows these amides to be used as thermally reactive tracers in low-temperature hydrogeothermal systems.

  2. FORMATION OF PEPTIDE BONDS IN SPACE: A COMPREHENSIVE STUDY OF FORMAMIDE AND ACETAMIDE IN Sgr B2(N)

    SciTech Connect

    Halfen, D. T.; Ziurys, L. M.; Ilyushin, V. E-mail: lziurys@as.arizona.edu

    2011-12-10

    Extensive observations of acetamide (CH{sub 3}CONH{sub 2}) and formamide (NH{sub 2}CHO) have been conducted toward Sgr B2(N) at 1, 2, and 3 mm using the Submillimeter Telescope (SMT) and the 12 m antenna of the Arizona Radio Observatory. Over the frequency range 65-280 GHz, 132 transitions of acetamide have been observed as individual, distinguishable features, although in some cases they are partially blended. The unblended transitions in acetamide indicate V{sub LSR} = 63.2 {+-} 2.8 km s{sup -1} and {Delta}V{sub 1/2} = 12.5 {+-} 2.9 km s{sup -1}, line parameters that are very similar to that of formamide (NH{sub 2}CHO) and other organic species in Sgr B2(N). For formamide, 79 individual transitions were identified over the same frequency region. Rotational diagram analyses indicate the presence of two components for both species in Sgr B2(N). For acetamide, the colder component (E{sub u} < 40 K) exhibits a rotational temperature of T{sub rot} = 17 {+-} 4 K and a column density of N{sub tot} = 5.2 {+-} 3.5 Multiplication-Sign 10{sup 13} cm{sup -2}; the higher energy component has T{sub rot} = 171 {+-} 4 K and N{sub tot} = 6.4 {+-} 4.7 Multiplication-Sign 10{sup 14} cm{sup -2}. In the case of formamide, T{sub rot} = 26 {+-} 4 K and N{sub tot} = 1.6 {+-} 0.7 Multiplication-Sign 10{sup 14} cm{sup -2} for the colder component with T{sub rot} = 134 {+-} 17 K and N{sub tot} = 4.0 {+-} 1.2 Multiplication-Sign 10{sup 14} cm{sup -2} for the warmer region. The fractional abundances of acetamide are f (H{sub 2}) = 1.7 Multiplication-Sign 10{sup -11} and 2.1 Multiplication-Sign 10{sup -10} for the cold and warm components, and in formamide, f (H{sub 2}) = 5.3 Multiplication-Sign 10{sup -11} and 1.3 Multiplication-Sign 10{sup -10}. The similarity between the abundances and distributions of CH{sub 3}CONH{sub 2} and NH{sub 2}CHO suggests a synthetic connection. The abundance of acetamide, moreover, is only a factor of three lower than that of formaldehyde, and very similar to

  3. The effect of deuterium substitution in the amino group on the internal-rotation barrier of acetamide

    NASA Astrophysics Data System (ADS)

    Hirota, Eizi; Kawashima, Yoshiyuki; Usami, Tsuyoshi; Seto, Koichi

    2010-03-01

    Peptide molecules XCO-NYY' are characterized by low potential barrier V3 to internal rotation of a methyl group substituted for X and/or Y. A most conspicuous example is acetamide, for which V3 was previously reported to be 25.043857(19) cm -1[8]. The present study intended to clarify why V3 is so low in acetamide, by examining the effect of the out-of-plane bending or inversion of the amino group on the molecular structure through deuterium substitution for amino hydrogens. The potential barrier V3 in acetamide was found to decrease by 2.630, 2.986, and 5.532 cm -1, when H's at cis, trans, and both positions in the amino group were replaced by deuterium atoms, respectively. The reduction was proportional to the effective mass of the out-of-plane bending mode of the amino group (hereafter referred to as the amino inversion), which was in turn ascribed to the change in electronic resonance character of the peptide linkage. The amino inversion is coupled with the CH 3 internal rotation, producing an interaction term proportional to τ sin 3 α, where τ and α denote the amino inversion and methyl internal rotation angles, respectively. This coupling term, when the inversion is treated by second-order perturbation, yields a V6 term in the internal-rotation potential function of the methyl group, in agreement with the finding of Ilyushin et al. [8], who derived an unusually large V6 term of -10.044874(73) cm -1. It is quite interesting that even a small perturbation such as deuterium substitution causes a substantial change in electronic structure of the peptide linkage.

  4. Monitoring 2-phenylethanamine and 2-(3-hydroxyphenyl)acetamide sulfate in doping controls.

    PubMed

    Sigmund, Gerd; Dib, Josef; Tretzel, Laura; Piper, Thomas; Bosse, Christina; Schänzer, Wilhelm; Thevis, Mario

    2015-01-01

    2-Phenylethanamine (phenethylamine, PEA) represents the core structure of numerous drugs with stimulant-like properties and is explicitly featured as so-called specified substance on the World Anti-Doping Agency (WADA) Prohibited List. Due to its natural occurrence in humans as well as its presence in dietary products, studies concerning the ability of test methods to differentiate between an illicit intake and the renal elimination of endogenously produced PEA were indicated. Following the addition of PEA to the Prohibited List in January 2015, retrospective evaluation of routine doping control data of 10 190 urine samples generated by combined gas chromatography-mass spectrometry and nitrogen phosphorus-specific detection (GC-MS/NPD) was performed. Signals for PEA at approximate concentrations > 500 ng/mL were observed in 31 cases (0.3%), which were subjected to a validated isotope-dilution liquid chromatography-tandem mass spectrometry (ID-LC-MS/MS) test method for accurate quantification of the target analyte. Further, using elimination study urine samples collected after a single oral administration of 250 mg of PEA hydrochloride to two healthy male volunteers, two tentatively identified metabolites of PEA were observed and evaluated concerning their utility as discriminative markers for PEA intake. The ID-LC-MS/MS approach was extended to allow for the simultaneous detection of PEA and 2-(3-hydroxyphenyl)acetamide sulfate (M1), and concentration ratios of M1 and PEA were calculated for elimination study urine samples and a total of 205 doping control urine samples that returned findings for PEA at estimated concentrations of 50-2500 ng/mL. Urine samples of the elimination study with PEA yielded concentration ratios of M1/PEA up to values of 9.4. Notably, the urinary concentration of PEA did increase with the intake of PEA only to a modest extent, suggesting a comprehensive metabolism of the orally administered substance. Conversely, doping control

  5. 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.

    PubMed

    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

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

    PubMed

    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

  7. Thermal phase diagram of acetamide-benzoic acid and benzoic acid-phthalimide binary systems for solar thermal applications

    NASA Astrophysics Data System (ADS)

    Kumar, Rohitash; Kumar, Ravindra; Dixit, Ambesh

    2016-05-01

    Thermal properties of Acetamide (AM) - Benzoic acid (BA) and Benzoic acid (BA) - Phthalimide (PM) binary eutectic systems are theoretically calculated using thermodynamic principles. We found that the binary systems of AM-BA at 67.6 : 32.4 molar ratio, BA-PM at 89.7 : 10.3 molar ratio form eutectic mixtures with melting temperatures ~ 54.5 °C and 114.3 °C respectively. Calculated latent heat of fusion for these eutectic mixtures are 191 kJ/kg and 146.5 kJ/kg respectively. These melting temperatures and heat of fusions of these eutectic mixtures make them suitable for thermal energy storage applications in solar water heating and solar cooking systems.

  8. Comparison of the crystal structure and molecular models of N,N-dissobutyl-2-(octylphenylphosphinyl)acetamide(CMPO).

    SciTech Connect

    Rogers, R. D.; Rollins, A. N.; Gatrone, R. C.; Horwitz, E. P.; Chemistry; Northern Illinois Univ.

    1995-01-01

    The crystal structure of N,N-diisobutyl-2-(octylphenylphosphinyl)acetamide, or CMPO was recently determined. The compound crystallizes in the space group P2{sub 1}/c with a=13.446(6),b=22.280(7),c=17.217(7) Angstroms, {beta}=92.07(4) degrees, and D{sub calc}=1.05 g/cm3 for Z=8 @20 C. Molecular mechanics, molecular dynamics, and MNDO calculations were also performed on CMPO utilizing the SYBYL suite of programs. The results from these calculations are compared to the crystal structure and to similar calculations performed on CMPO using ALCHEMY. In general, the results from the calculations agree fairly well with the parameters from the crystal structure.

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

    PubMed

    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

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

    PubMed

    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

  11. 2-Chloro-N-[4-chloro-2-(2-chloro­benzo­yl)phen­yl]acetamide

    PubMed Central

    Dutkiewicz, Grzegorz; Siddaraju, B. P.; Yathirajan, H. S.; Narayana, B.; Kubicki, Maciej

    2010-01-01

    In the title compound, C15H10Cl3NO2, an intra­molecular N—H⋯O hydrogen bond forms a six-membered ring and enforces an almost coplanar conformation for the acetamido group, the central benzene ring and the bridging carbonyl C—C(=O)—C group: the dihedral angles between the benzene ring and the acetamide and carbonyl C—C(=O)—C planes are 7.06 (11) and 7.17 (12)°, respectively. The dihedral angle between the two benzene rings is 67.43 (9)°. Because a strong hydrogen-bond donor is involved in the intra­molecular inter­action, the crystal packing is determined by weak C—H⋯O and C—H⋯Cl inter­actions. PMID:21579901

  12. 3,6-O-[N-(2-Aminoethyl)-acetamide-yl]-chitosan exerts antibacterial activity by a membrane damage mechanism.

    PubMed

    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

  13. Design, synthesis and in vitro evaluation studies of sulfonyl-amino-acetamides as small molecule BACE-1 inhibitors.

    PubMed

    Jain, Priti; Wadhwa, Pankaj K; Gunapati, Sinduri; Jadhav, Hemant R

    2016-06-01

    The identification of a series of sulfonyl-amino-acetamides as BACE-1 (β-secretase) inhibitors for the treatment of Alzheimer's disease is reported. The derivatives were designed based on the docking simulation study, synthesized and assessed for BACE-1 inhibition in vitro. The designed ligands revealed desired binding interactions with the catalytic aspartate dyad and occupance of S1 and S2' active site regions. These in silico results correlated well with in vitro activity. Out of 33 compounds synthesized, 12 compounds showed significant inhibition at 10μM concentration. The most active compound 2.17S had IC50 of 7.90μM against BACE-1, which was concomitant with results of in silico docking study. PMID:27102162

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

    PubMed

    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

  15. 2-Amino-N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]acetamide

    PubMed Central

    Fun, Hoong-Kun; Chantrapromma, Suchada; Dayananda, A. S.; Yathirajan, H. S.; Ramesha, A. R.

    2012-01-01

    In the title compound, C15H15ClN2O2S, the 2-amino­acetamide N—C(=O)—C—N unit is approximately planar, with an r.m.s. deviation of 0.020 (4) Å. The central thio­phene ring makes dihedral angles of 7.84 (11) and 88.11 (11)°, respectively, with the 2-amino­acetamide unit and the 2-chloro­phenyl ring. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by an N—H⋯O hydrogen bond and weak C—H⋯O inter­actions into a chain along the c axis. A C—H⋯π inter­action is also present. PMID:22347140

  16. Variable temperature 1H and 13C NMR study of restricted rotation in N,N-bis(2-hydroxyethyl)acetamide

    NASA Astrophysics Data System (ADS)

    Aitken, R. Alan; Smith, Melanja H.; Wilson, Heather S.

    2016-06-01

    N,N-bis(2-hydroxyethyl)acetamide shows restricted rotation about the amide bond in both 1H and 13C NMR spectra rendering the two hydroxyethyl groups non-equivalent. A variable temperature study in CD3SOCD3 allowed estimation of the free energy barrier to rotation as 75.6 ± 0.2 kJ mol-1. Previously published data in CDCl3 appears to be erroneous.

  17. 2-(2,4-Dioxy-1,2,3,4-Tetrahydropyrimidin-1-yl)-N-(4-Phenoxyphenyl)-Acetamides as a Novel Class of Cytomegalovirus Replication Inhibitors

    PubMed Central

    Babkov, D. A.; Paramonova, M. P.; Ozerov, A. A.; Khandazhinskaya, A. L.; Snoeck, R.; Andrei, G.; Novikov, M. S.

    2015-01-01

    A series of novel uracil derivatives, bearing N-(4-phenoxyphenyl)acetamide moiety at N3 of a pyrimidine ring, has been synthesized. Their antiviral activity has been evaluated. It has been found that the novel compounds possess high inhibitory activity against replication of human cytomegalovirus (AD-169 and Davis strains) in HEL cell cultures. In addition, some of the derivatives proved to be inhibitory against varicella zoster virus. PMID:26798502

  18. Synthesis of nitro(benzo)thiazole acetamides and in vitro antiprotozoal effect against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis.

    PubMed

    Navarrete-Vázquez, Gabriel; Chávez-Silva, Fabiola; Colín-Lozano, Blanca; Estrada-Soto, Samuel; Hidalgo-Figueroa, Sergio; Guerrero-Álvarez, Jorge; Méndez, Sara T; Reyes-Vivas, Horacio; Oria-Hernández, Jesús; Canul-Canché, Jaqueline; Ortiz-Andrade, Rolffy; Moo-Puc, Rosa

    2015-05-01

    We synthesized four 5-nitrothiazole (1-4) and four 6-nitrobenzothiazole acetamides (5-8) using an easy two step synthetic route. All compounds were tested in vitro against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis, showing excellent antiprotozoal effects. IC₅₀'s of the most potent compounds range from nanomolar to low micromolar order, being more active than their drugs of choice. Compound 1 (IC₅₀=122 nM), was 44-times more active than Metronidazole, and 10-fold more effective than Nitazoxanide against G. intestinalis and showed good trichomonicidal activity (IC₅₀=2.24 μM). This compound did not display in vitro cytotoxicity against VERO cells. The in vitro inhibitory effect of compounds 1-8 and Nitazoxanide against G. intestinalis fructose-1,6-biphosphate aldolase (GiFBPA) was evaluated as potential drug target, showing a clear inhibitory effect over the enzyme activity. Molecular docking of compounds 1, 4 and Nitazoxanide into the ligand binding pocket of GiFBPA, revealed contacts with the active site residues of the enzyme. Ligand efficiency metrics of 1 revealed optimal combinations of physicochemical and antiprotozoal properties, better than Nitazoxanide. PMID:25801157

  19. Anticonvulsant efficacy/safety properties of 2-amino-N-(1,2-diphenylethyl)acetamide hydrochloride.

    PubMed

    Palmer, G C; Stagnitto, M L; Garske, G E; Napier, J J; Harris, E W; Kaiser, F C; Griffith, R C; Woodhead, J H; White, H S; Wolf, H H

    1995-06-01

    2-Amino-N-(1,2-diphenylethyl)-acetamide-hydrochloride (FPL 13950) was profiled preclinically in rodents for efficacy against convulsions, as well as for acute safety/behavioral observations. FPL 13950 exhibited good oral efficacy and duration of action with respect to prevention of seizures elicited by maximal electroshock-shock in both rats and mice. Tolerance to protection against maximal electroshock and hexobarbital-induced sleep-time was not evident after subchronic drug administration. FPL 13950 also prevented convulsions/mortality in mice after i.v. dosing with N-methyl-D, L-aspartate, however, it was ineffective against other types of chemically induced convulsions, as well as bicorneal kindling. High oral doses produced neural impairment in both mice and rats and hyperactivity in rats. Sequential administration of yet higher doses elicited tonic/clonic convulsions culminating in death. During i.v. infusion of metrazol in mice, high i.p. doses of FPL 13950 shortened the latency to first twitch and clonus. No increase in the startle response or phencyclidine-like behavior was evident after oral dosing in rats. PMID:7791072

  20. Hydrothermal preparation and characterization of ultralong strontium-substituted hydroxyapatite whiskers using acetamide as homogeneous precipitation reagent.

    PubMed

    Xu, Jianqiang; Yang, Yaoqi; Wan, Rong; Shen, Yuhui; Zhang, Weibin

    2014-01-01

    The ultralong strontium- (Sr-) substituted hydroxyapatite (SrHAp) whiskers were successfully prepared using acetamide as homogeneous precipitation reagent. The effect of the Sr substitution amount on the lattice constants and proliferation of human osteoblast cells (MG-63) was further investigated. The results showed that the SrHAp whiskers with diameter of 0.2-12 μm and ultralong length up to 200 μm were obtained and the Sr substitution level could be facilely tailored by regulating the initial molar ratio of Sr/(Sr + Ca) in raw materials. The Sr(2+) replaced part of Ca(2+) and the lattice constants increased apparently with the increase of the Sr substitution amount. Compared with the pure HAp whiskers, the Sr substitution apparently stimulated the proliferation of MG-63 at certain extracted concentrations. Our study suggested that the obtained SrHAp whiskers might be used as bioactive and mechanical reinforcement materials for hard tissue regeneration applications. PMID:24592192

  1. Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides.

    PubMed

    Beyeh, N Kodiah; Ala-Korpi, Altti; Cetina, Mario; Valkonen, Arto; Rissanen, Kari

    2014-11-10

    N-alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures, whereas in the presence of small guests the self-included dimers spontaneously reorganize to 1:1 host-guest complexes. These host compounds show an interesting ability to bind a series of N-alkyl acetamide guests through intermolecular hydrogen bonds involving the carbonyl oxygen (C=O) atoms and the amide (NH) groups of the guests, the chloride anions (Cl(-)) and ammonium (NH2(+)) cations of the hosts, and also through CH⋅⋅⋅π interactions between the hosts and guests. The self-included and host-guest complexes were studied by single-crystal X-ray diffraction, NMR titration, and mass spectrometry. PMID:25257765

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

    PubMed Central

    2015-01-01

    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 binding mode, novel thio- and sulfinylacetamide and ethanamine analogues of (±)-1 were synthesized wherein (1) the diphenyl rings were substituted with methyl, trifluoromethyl, and halogen substituents and (2) substituents were added to the terminal amide/amine nitrogen. Halogen substitution of the diphenyl rings of (±)-1 gave several amide analogues with improved binding affinity for DAT and robust selectivity over the serotonin transporter (SERT), whereas affinity improved at SERT over DAT for the p-halo-substituted amine analogues. Molecular docking studies, using a subset of analogues with DAT and SERT homology models, and functional data obtained with DAT (A480T) and SERT (T497A) mutants defined a role for TM10 in the substrate/inhibitor S1 binding sites of DAT and SERT. PMID:24494745

  3. Natural bond orbital analysis, electronic structure and vibrational spectral analysis of N-(4-hydroxyl phenyl) acetamide: A density functional theory

    NASA Astrophysics Data System (ADS)

    Govindasamy, P.; Gunasekaran, S.; Ramkumaar, G. R.

    2014-09-01

    The Fourier transform infrared (FT-IR) and FT-Raman spectra of N-(4-hydroxy phenyl) acetamide (N4HPA) of painkiller agent were recorded in the region 4000-450 cm-1 and 4000-50 cm-1 respectively. Density functional theory (DFT) has been used to calculate the optimized geometrical parameter, atomic charges, and vibrational wavenumbers and intensity of the vibrational bands. The computed vibrational wave numbers were compared with the FT-IR and FT-Raman experimental data. The computational calculations at DFT/B3LYP level with 6-31G(d,p), 6-31++G(d,p), 6-311G(d,p) and 6-311++G(d,p) basis sets. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using Vibrational energy distribution analysis (VEDA 4) program. The oscillator’s strength calculated by TD-DFT and N4HPA is approach complement with the experimental findings. The NMR chemical shifts 13C and 1H were recorded and calculated using the gauge independent atomic orbital (GIAO) method. The molecular electrostatic potential (MESP) and electron density surfaces of the molecule were constructed. The Natural charges and intermolecular contacts have been interpreted using Natural Bond orbital (NBO) analysis the HOMO-LUMO energy gap has been calculated. The thermodynamic properties like entropy, heat capacity and zero vibrational energy have been calculated.

  4. Hydrothermal Preparation and Characterization of Ultralong Strontium-Substituted Hydroxyapatite Whiskers Using Acetamide as Homogeneous Precipitation Reagent

    PubMed Central

    Xu, Jianqiang; Yang, Yaoqi; Wan, Rong; Zhang, Weibin

    2014-01-01

    The ultralong strontium- (Sr-) substituted hydroxyapatite (SrHAp) whiskers were successfully prepared using acetamide as homogeneous precipitation reagent. The effect of the Sr substitution amount on the lattice constants and proliferation of human osteoblast cells (MG-63) was further investigated. The results showed that the SrHAp whiskers with diameter of 0.2–12 μm and ultralong length up to 200 μm were obtained and the Sr substitution level could be facilely tailored by regulating the initial molar ratio of Sr/(Sr + Ca) in raw materials. The Sr2+ replaced part of Ca2+ and the lattice constants increased apparently with the increase of the Sr substitution amount. Compared with the pure HAp whiskers, the Sr substitution apparently stimulated the proliferation of MG-63 at certain extracted concentrations. Our study suggested that the obtained SrHAp whiskers might be used as bioactive and mechanical reinforcement materials for hard tissue regeneration applications. PMID:24592192

  5. 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

    NASA Astrophysics Data System (ADS)

    Das, Anuradha; Das, Suman; Biswas, Ranjit

    2015-01-01

    Temperature dependent relaxation dynamics, particle motion characteristics, and heterogeneity aspects of deep eutectic solvents (DESs) made of acetamide (CH3CONH2) and urea (NH2CONH2) have been investigated by employing time-resolved fluorescence measurements and all-atom molecular dynamics simulations. Three different compositions (f) for the mixture [fCH3CONH2 + (1 - f)NH2CONH2] 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 (α2) 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.

  6. 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.

    PubMed

    Das, Anuradha; Das, Suman; Biswas, Ranjit

    2015-01-21

    Temperature dependent relaxation dynamics, particle motion characteristics, and heterogeneity aspects of deep eutectic solvents (DESs) made of acetamide (CH3CONH2) and urea (NH2CONH2) have been investigated by employing time-resolved fluorescence measurements and all-atom molecular dynamics simulations. Three different compositions (f) for the mixture [fCH3CONH2 + (1 - f)NH2CONH2] 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 (α2) 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. PMID:25612718

  7. 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

    SciTech Connect

    Das, Anuradha; Das, Suman; Biswas, Ranjit

    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.

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

    NASA Astrophysics Data System (ADS)

    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

  9. Synthesis, crystal structure and DFT studies of N-(4-acetyl-5,5-dimethyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide

    SciTech Connect

    Gautam, P.; Gautam, D.; Chaudhary, R. P.

    2013-12-15

    The title compound N-(4-acetyl-5,5-dimethyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (III) was obtained from the reaction of 2-(propan-2-ylidene)hydrazinecarbothioamide (II) with acetic anhydride instead of formation of the desired thiosemcarbazide derivative of Meldrum acid. The structures of II and III were established by elemental analysis, IR, NMR, Mass and X-ray crystallographic studies. II crystallizes in triclinic system, sp. gr. P-bar1 Z = 2; III crystallizes in the monoclinic system, sp. gr. P2{sub 1}/c, Z = 8. Density functional theory (DFT) calculations have been carried out for III. {sup 1}H and {sup 13}C NMR of III has been calculated and correlated with experimental results.

  10. A novel 2-(2-Formyl-4-methyl-phenoxy)-N-phenyl-acetamide-based fluorescence turn-on chemosensor for selenium determination with high selectivity and sensitivity

    NASA Astrophysics Data System (ADS)

    Song, Cairui; Fei, Qiang; Shan, Hongyan; Feng, Guodong; Cui, Minghui; Liu, Yameng; Huan, Yanfu

    2013-12-01

    A novel turn-on fluorescent chemosensor, 2-(2-Formyl-4-methyl-phenoxy)-N-phenyl-acetamide (FMPPA) was designed and synthesized, and its photophysical properties were characterized. Upon coordination with Se (IV), the chemosensor showed incredible fluorescence enhancement (turn-on), other alkali, alkaline earth, transitional metal ions, and common anions including Li+, Na+, K+, Rb+, Cs+, Be2+, Mg2+, Ca2+, Sr2+, Ba2+, Ni2+, Cu2+, Cd2+, Zn2+, Mn2+, As3+, Pt4+, V5+, Fe3+, Mo6+, Al3+, CO32-, Cl-, SCN-, AC-, NO3-, F-, SO42- had no significant interference on Se (IV) determination. The chemosensor exhibits a dynamic response range for Se (IV) from 3.32 × 10-7 to 2.63 × 10-6 M, with a detection limit of 9.38 × 10-9 M (3σ).

  11. Bis{N-[bis­(pyrrolidin-1-yl)phosphor­yl]-2,2,2-trichloro­acetamide}di­nitrato­dioxidouranium(VI)

    PubMed Central

    Znovjyak, Kateryna O.; Ovchynnikov, Vladimir A.; Moroz, Olesia V.; Shishkina, Svitlana V.; Amirkhanov, Vladimir M.

    2010-01-01

    The crystal structure of the title compound, [U(NO3)2O2(C10H17Cl3N3O2P)2], is composed of centrosymmetric [UO2(L)2(NO3)2] mol­ecules {L is N-[bis­(pyrrolidin-1-yl)phosphor­yl]-2,2,2-trichloro­acetamide, C10H17Cl3N3O2P}. The UVI ion, located on an inversion center, is eight-coordinated with axial oxido ligands and six equatorial oxygen atoms of the phosphoryl and nitrate groups in a slightly distorted hexa­gonal-bipyramidal geometry. One of the pyrrolidine fragments in the ligand is disordered over two conformation (occupancy ratio 0.58:0.42). Intra­molecular N—H⋯O hydrogen bonds between the amine and nitrate groups are found. PMID:21580260

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

    PubMed

    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

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

    PubMed

    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. Synthesis of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}-N-substituted acetamides as potential antimicrobial and hemolytic agents.

    PubMed

    Rehman, Aziz-ur; Abbasi, Muhammad Athar; Siddiqui, Sabahat Zahra; Ahmad, Irshad; Shahid, Muhammad; Subhani, Zinayyera

    2016-05-01

    A new series of N-substituted derivatives of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}acetamides was synthesized. The synthesis was carried out by converting benzoic acid (1) into ethyl benzoate (2), benzohydrazide (3) and then 5-pheny-1,3,4-Oxadiazol-2-thiol (4) step by st0ep. The target compounds 6a-p were synthesized by reaction of compound 4 with equimolar ratios of different N-alkyl/aryl substituted 2-bromoacetamide (5a-p) in the presence of DMF and sodium hydride (NaH). The spectral (EI-MS, IR, (1)H-NMR) characterization of all the synthesized compounds reveal their successful synthesis. The compounds were also screened for antimicrobial & hemolytic activity and most of them were found to be active against the selected microbial species at variable extent relative to reference standards. But 6h was the most active against the selected panel of microbes. This series showed less toxicity and may be considered for further biological screening and application trial except 6m, possessing higher cytotoxicity. PMID:27166551

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

    NASA Astrophysics Data System (ADS)

    Tripathy, Satya N.; Wojnarowska, Zaneta; Knapik, Justyna; Shirota, Hideaki; Biswas, Ranjit; Paluch, Marian

    2015-05-01

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

    PubMed

    Tripathy, Satya N; Wojnarowska, Zaneta; Knapik, Justyna; Shirota, Hideaki; Biswas, Ranjit; Paluch, Marian

    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(-1)-10(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. PMID:25978897

  17. A novel compound 2-(4-{2-[(phenylthio)acetyl]carbonohydrazonoyl}phenoxy)acetamide downregulates TSLP through blocking of caspase-1/NF-κB pathways.

    PubMed

    Moon, Phil-Dong; Han, Na-Ra; Ryu, Ka-Jung; Kang, Sang-Woo; Go, Ji-Hyun; Jang, Jae-Bum; Choi, Youngjin; Kim, Hyung-Min; Jeong, Hyun-Ja

    2016-09-01

    Thymic stromal lymphopoietin (TSLP) is regarded as the main factor responsible for the pathogenesis of allergic disorders such as atopic dermatitis, chronic obstructive pulmonary diseases, and allergic rhinitis. As part of our continuing search for novel anti-inflammatory compounds, 2-(4-{2-[(phenylthio)acetyl]carbonohydrazonoyl}phenoxy)acetamide (PA) was analyzed. In the present study, we examined how PA regulates the mRNA expression and production of TSLP in the human mast cell line, HMC-1 cells. Computer-aided docking simulation, enzyme-linked immunosorbent assay, quantitative polymerase chain reaction, caspase-1 assay, and Western blotting were used to investigate the effects of PA. PA decreased the mRNA expression and production of TSLP in HMC-1 cells. PA (1μM) inhibited the TSLP production up to 87.710±5.201%. PA also improved the activation and phosphorylation of nuclear factor-κB as well as the degradation and phosphorylation of IκBα. Caspase-1 activation was up-regulated in activated HMC-1 cells, whereas caspase-1 activation was down-regulated by PA. Finally, PA inhibited ear swelling response induced by phorbol myristate acetate in mice. These results indicate that PA would be effective to treat inflammatory and atopic disorders through the down-regulations of TSLP. PMID:27376852

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

    SciTech Connect

    Tripathy, Satya N. Wojnarowska, Zaneta; Knapik, Justyna; Paluch, Marian; Shirota, Hideaki; Biswas, Ranjit

    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.

  19. Hit to lead optimization of a series of N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamides as monoacylglycerol lipase inhibitors with potential anticancer activity.

    PubMed

    Afzal, Obaid; Akhtar, Md Sayeed; Kumar, Suresh; Ali, Md Rahmat; Jaggi, Manu; Bawa, Sandhya

    2016-10-01

    A total of thirty five new N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamide derivatives were synthesized and structures of all the compounds were confirmed on the basis of elemental analysis and collective use of IR, (1)H NMR, (13)C NMR and mass spectral data. Compounds were tested for their ability to inhibit human monoacylglycerol lipase (hMAGL) enzyme. Eight compounds 4, 19-21, 24-26, and 34 reduced the hMAGL activity less than 50% at 100 nM concentrations. The halogen substituted aniline derivatives 20, 21 and 24-26 were found to be most active among all the synthesized compounds having IC50 value in the range of 6.5-9 nM. Twenty five compounds were selected by NCI, USA for one dose anticancer screening. Compound 21 (NSC: 780167) and 24 (NSC: 780168) fulfilled prearranged doorstep growth inhibition criteria and further selected for NCI full panel five dose assay at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM). Both the compounds 21 and 24 were found to be most active against MCF7 and MDA-MB-468 breast cancer cell lines. The GI50 value of 32.5 nM (MCF7) and 23.8 nM (MDA-MB-468) was observed for compound 21. Compound 24 showed GI50 values of 37.1 nM against MCF7 breast cancer cell line and 25.1 nM against MDA-MB-468 breast cancer cell line. PMID:27267002

  20. 2-[4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy]-N-(methylsulfonyl)acetamide (NS-304), an orally available and long-acting prostacyclin receptor agonist prodrug.

    PubMed

    Kuwano, Keiichi; Hashino, Asami; Asaki, Tetsuo; Hamamoto, Taisuke; Yamada, Tetsuhiro; Okubo, Kaori; Kuwabara, Kenji

    2007-09-01

    Prostacyclin (PGI(2)) and its analogs are useful for the treatment of various vascular disorders, but their half-lives are too short for widespread clinical application. To overcome this drawback, we have synthesized a novel diphenylpyrazine derivative, 2-[4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy]-N-(methylsulfonyl)acetamide (NS-304), a prodrug of the active form [4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy]acetic acid (MRE-269). NS-304 is an orally available and potent agonist for the PGI(2) receptor (IP receptor). The inhibition constant (K(i)) of MRE-269 for the human IP receptor was 20 nM; in contrast, the K(i) values for other prostanoid receptors were >2.6 microM. MRE-269 was therefore a highly selective agonist for the IP receptor. The plasma concentrations of MRE-269 remained near peak levels for more than 8 h after oral administration of NS-304 to rats and dogs, and NS-304 increased femoral skin blood flow in rats in a long-lasting manner without affecting the hemodynamics. These findings indicate that NS-304 acts as a long-acting IP receptor agonist in vivo. The continuous vasodilation evoked by NS-304 was not attenuated by repeated treatment, indicating that NS-304 is unlikely to cause severe desensitization of the IP receptor in rats. Moreover, a microdose pharmacokinetic study in which NS-304 was orally administered to healthy male volunteers showed conversion of NS-304 to MRE-269 and a long plasma elimination half-life for MRE-269 (7.9 h). In conclusion, NS-304 is an orally available and long-acting IP receptor agonist prodrug, and its active form, MRE-269, is highly selective for the IP receptor. Therefore, NS-304 is a promising drug candidate for various vascular diseases, especially pulmonary arterial hypertension and arteriosclerosis obliterans. PMID:17545310

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

    PubMed

    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

  2. In situ direct photoproduction of ketenes from substituted coumarins isolated in solid argon: The case of N-(2-oxo-2 H-chromen-3-yl)acetamide

    NASA Astrophysics Data System (ADS)

    Kuş, N.; Breda, S.; Fausto, R.

    2009-04-01

    In this study, the infrared spectrum of N-(2-oxo-2 H-chromen-3-yl)acetamide (3-acetamidocoumarin; 3AC) isolated in solid argon, at 10 K, was obtained and assigned. In consonance with the relative energies of the three conformers predicted theoretically, only the most stable form was observed experimentally. This conformer is stabilized by two intramolecular hydrogen bonds and is similar to the structural unit of 3AC found in crystalline phase. Upon in situ UV ( λ > 215 nm) irradiation of the matrix-isolated compound, the characteristic IR intense band due to the antisymmetric stretching vibration of the ketene ( sbnd C dbnd C dbnd O) group was observed, indicating occurrence of the ring-opening isomerization reaction to the open-ring ketene isomeric of 3AC. In consonance with the theoretical structural predictions for the most stable isomers of this photoproduct, the experimental data indicates that it is produced in the E arrangement of the (O dbnd )C sbnd C dbnd C sbnd C( dbnd C dbnd O) fragment. There were also experimental indications pointing to occurrence of a second photoreaction channel, corresponding to decarbonylation. On the other hand, contrarily to what is generally observed for α-pyrones derivatives, including unsubstituted coumarin, no photochemical production of Dewar isomer of 3AC was observed. This last result, follows the trend observed for 2-pyrone-3-carboxylate, and seems to be a quite general rule for matrix-isolated α-pyrones bearing relatively volumous substituents at the position 3, as a consequence of the unfavorable relaxation of the matrix around the guest molecule that would be required to accommodate the Dewar isomers of these compounds, whose structure deviates strongly from planarity, thus mismatching the primarily occupied matrix sites.

  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.

    PubMed

    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. 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

    PubMed Central

    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

  5. 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

    USGS Publications Warehouse

    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

  6. Discovery of 2-((3-cyanopyridin-2-yl)thio)acetamides as human lactate dehydrogenase A inhibitors to reduce the growth of MG-63 osteosarcoma cells: Virtual screening and biological validation.

    PubMed

    Cui, Wei; Lv, Wei; Qu, Ying; Ma, Rui; Wang, Yi-Wei; Xu, Yong-Jun; Wu, Di; Chen, Xuanhuang

    2016-08-15

    Lactate dehydrogenase A (LDHA) has emerged as an attractive target in the oncology field. In this paper, we present the identification of 2-((3-cyanopyridin-2-yl)thio)acetamide-containing compounds as LDHA inhibitors. The in vitro enzymatic assay suggested that inhibitor 9 had good inhibitory potency against LDHA with IC50 value as 1.24μM. Cytotoxicity assay showed that inhibitor 9 strongly inhibited the proliferation of cancer cell MG-63 (EC50=0.98μM). These findings indicated that inhibitor 9 could be employed as a lead for developing more potent LDHA inhibitor with anti-proliferative potency. PMID:27406795

  7. Regioselective Copper-Catalyzed Dicarbonylation of Imidazo[1,2-a]pyridines with N,N-Disubstituted Acetamide or Acetone: An Approach to 1,2-Diketones Using Molecular Oxygen.

    PubMed

    Wang, Changcheng; Lei, Sai; Cao, Hua; Qiu, Shuxian; Liu, Jingyun; Deng, Hao; Yan, Caijuan

    2015-12-18

    A novel copper-catalyzed regioselective double carbonylation of imidazo[1,2-a]pyridines with N,N-disubstituted acetamide or acetone using molecular oxygen has been described. It has provided a new approach to synthesize 1,2-carbonyl imidazo[1,2-a]pyridines, which are important substrates and intermediates in preparation of fine chemicals. The product shares a skeleton similar to that of Zolpidem, one of the most prescribed drugs in the world. (18)O-labeling experiments unambiguously established that the oxygen source of products originated from O2 rather than H2O. PMID:26595127

  8. Crystal structures of 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(3-nitro­phen­yl)acetamide monohydrate and N-(2-chloro­phen­yl)-2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]acetamide

    PubMed Central

    Subasri, S.; Timiri, Ajay Kumar; Barji, Nayan Sinha; Jayaprakash, Venkatesan; Vijayan, Viswanathan; Velmurugan, Devadasan

    2016-01-01

    The title compounds, C12H12N6O3S·H2O, (I), and C12H12ClN5OS, (II), are 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]acetamides. Compound (I) crystallized as a monohydrate. In both compounds, the mol­ecules have a folded conformation, with the pyrimidine ring being inclined to the benzene ring by 56.18 (6)° in (I) and by 67.84 (6)° in (II). In both mol­ecules, there is an intra­molecular N—H⋯N hydrogen bond stabilizing the folded conformation. In (I), there is also a C—H⋯O intra­molecular short contact, and in (II) an intra­molecular N—H⋯Cl hydrogen bond is present. In the crystal of (I), mol­ecules are linked by a series of N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming undulating sheets parallel to the (100). The sheets are linked via an N—H⋯Owater hydrogen bond, forming a three-dimensional network. In the crystal of (II), mol­ecules are linked by a series of N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds, forming slabs parallel to (001). PMID:27536406

  9. Crystal structures of 2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]-N-(3-nitro-phen-yl)acetamide monohydrate and N-(2-chloro-phen-yl)-2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]acetamide.

    PubMed

    Subasri, S; Timiri, Ajay Kumar; Barji, Nayan Sinha; Jayaprakash, Venkatesan; Vijayan, Viswanathan; Velmurugan, Devadasan

    2016-08-01

    The title compounds, C12H12N6O3S·H2O, (I), and C12H12ClN5OS, (II), are 2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]acetamides. Compound (I) crystallized as a monohydrate. In both compounds, the mol-ecules have a folded conformation, with the pyrimidine ring being inclined to the benzene ring by 56.18 (6)° in (I) and by 67.84 (6)° in (II). In both mol-ecules, there is an intra-molecular N-H⋯N hydrogen bond stabilizing the folded conformation. In (I), there is also a C-H⋯O intra-molecular short contact, and in (II) an intra-molecular N-H⋯Cl hydrogen bond is present. In the crystal of (I), mol-ecules are linked by a series of N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, forming undulating sheets parallel to the (100). The sheets are linked via an N-H⋯Owater hydrogen bond, forming a three-dimensional network. In the crystal of (II), mol-ecules are linked by a series of N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds, forming slabs parallel to (001). PMID:27536406

  10. Synthesis and in vitro reactivation study of isonicotinamide derivatives of 2-(hydroxyimino)-N-(pyridin-3-yl)acetamide as reactivators of Sarin and VX inhibited human acetylcholinesterase (hAChE).

    PubMed

    Karade, Hitendra N; Raviraju, G; Acharya, B N; Valiveti, Aditya Kapil; Bhalerao, Uma; Acharya, Jyotiranjan

    2016-09-15

    Previously (Karade et al., 2014), we have reported the synthesis and in vitro evaluation of bis-pyridinium derivatives of pyridine-3-yl-(2-hydroxyimino acetamide), as reactivators of sarin and VX inhibited hAChE. Few of the molecules showed superior in vivo protection efficacy (mice model) (Kumar et al., 2014; Swami et al., 2016) in comparison to 2-PAM against DFP and sarin poisoning. Encouraged by these results, herein we report the synthesis and in vitro evaluation of isonicotinamide derivatives of pyridine-3-yl-(2-hydroxyimino acetamide) (4a-4d) against sarin and VX inhibited erythrocyte ghost hAChE. Reactivation kinetics of these compounds was studied and the determined kinetic parameters were compared with that of commercial reactivators viz. 2-PAM and obidoxime. In comparison to 2-PAM and obidoxime, oxime 4a and 4b exhibited enhanced reactivation efficacy toward sarin inhibited hAChE while oxime 4c showed far greater reactivation efficacy toward VX inhibited hAChE. The acid dissociation constant and IC50 values of these oximes were determined and correlated with the observed reactivation potential. PMID:27450532

  11. Inclusion of 1-naphthylacetic acid and 2-(1-naphthyl)acetamide into three typical multiresidue methods for LC/MS/MS analysis of tomatoes and zucchini.

    PubMed

    Lozano, Ana; Pérez-Parada, Andrés; Heinzen, Horacio; Fernández-Alba, Amadeo R

    2012-01-01

    In spite of high plant growth regulator application rates, little has been reported in the literature on determination of their residues in fruits and vegetables. This would be useful in monitoring good manufacturing practices and overall safety through the enforcement of maximum residue levels (MRLs). The present work describes method validation for the determination of 1-naphthylacetic acid (NAA) and 2(1-naphthyl)acetamide (NAAm) in tomato and zucchini using the mini-Luke, ethyl acetate (EtOAc) and acetate-buffered quick, easy, cheap, effective, rugged, and safe (QuEChERS) methods. Samples were spiked at two different levels: 50 and 100 pg/kg for NAA and 20 and 100 pg/kg for NAAm. These compounds were analyzed within the same chromatographic run with LC coupled to triple quadrupole MS (LC/(QqQ)MS/MS) in positive and negative electrospray ionization [ESI(+) and ESI(-)] modes for NAAm and NAA, respectively. For analyte confirmation, LC/ESI(-)QTOF-MS was also investigated given that NAA has only one multiple reaction monitoring transition (185.1-*140.9 m/z). These three common methods were used to determine linearity, recoveries, precision (RSD), matrix effects, repeatability, and reproducibility (n = 5) for the selected matrixes. In terms of the Directorate-General for Health and Consumers (DG-SANCO) guidelines, only insignificant differences were found for the multiresidue methods tested, regardless of the commodity. Matrix-matched calibration was used, and LODs were below 10.1 pg/kg for NAA and 6.0 pg/kg for NAAm, which were lower than the MRLs established in current European Union legislation for these compounds. Obtained recoveries for NAA ranged from 87 to 107% with RSD values below 10% for mini-Luke, 83 to 107% with RSD <11% for EtOAc, and 76 to 85% with RSD <7% for QuEChERS. NAAm recoveries ranged from 74 to 102% with RSD 5 15% for mini-Luke, 76 to 97% with RSD <4% for EtOAc, and 76 to 93% with RSD < 5% for QuEChERS. The linearity of the response over two

  12. Low-frequency collective dynamics in deep eutectic solvents of acetamide and electrolytes: A femtosecond Raman-induced Kerr effect spectroscopic study

    NASA Astrophysics Data System (ADS)

    Biswas, Ranjit; Das, Anuradha; Shirota, Hideaki

    2014-10-01

    In this study, we have investigated the ion concentration dependent collective dynamics in two series of deep eutectic solvent (DES) systems by femtosecond Raman-induced Kerr effect spectroscopy, as well as some physical properties, e.g., shear viscosity (η), density (ρ), and surface tension (γ). The DES systems studied here are [0.75CH3CONH2 + 0.25{f KSCN + (1 - f )NaSCN}] and [0.78CH3CONH2 + 0.22{f LiBr + (1 - f )LiNO3}] with f = 0, 0.2, 0.4, 0.6, 0.8, and 1.0. γ of these DES systems shows near insensitivity to f, while ρ shows a moderate dependence on f. Interestingly, η exhibits a strong dependence on f. In the low-frequency Kerr spectra, obtained via the Fourier transform of the collected Kerr transients, a characteristic band at ˜70 cm-1 is clear in [0.78CH3CONH2 + 0.22{f LiBr + (1 - f )LiNO3}] DES especially at the larger f. The band is attributed to the intermolecular hydrogen bond of acetamide. Because of less depolarized Raman activities of intermolecular/interionic vibrational motions, which are mostly translational (collision-induced or interaction-induced) motions, of spherical ions, the intermolecular hydrogen-bonding band is clearly observed. In contrast, the intermolecular hydrogen-bonding band is buried in the other intermolecular/interionic vibrational motions, which includes translational and reorientational (librational) motions and their cross-terms, in [0.75CH3CONH2 + 0.25{f KSCN + (1 - f )NaSCN}] system. The first moment (M1) of the intermolecular/interionic vibrational band in these DES systems is much higher than that in typical neutral molecular liquids and shows a weak but contrasting dependence on the bulk parameter sqrt {γ /ρ }. The time constants for picosecond overdamped Kerr transients in both the DES systems, which are obtained on the basis of the analysis fitted by a triexponential function, are rather insensitive to f for both the DES systems, but all the three time constants (fast: ˜1-3 ps; intermediate: ˜7-20 ps; and

  13. Low-frequency collective dynamics in deep eutectic solvents of acetamide and electrolytes: a femtosecond Raman-induced Kerr effect spectroscopic study.

    PubMed

    Biswas, Ranjit; Das, Anuradha; Shirota, Hideaki

    2014-10-01

    In this study, we have investigated the ion concentration dependent collective dynamics in two series of deep eutectic solvent (DES) systems by femtosecond Raman-induced Kerr effect spectroscopy, as well as some physical properties, e.g., shear viscosity (η), density (ρ), and surface tension (γ). The DES systems studied here are [0.75CH3CONH2 + 0.25{f KSCN + (1 - f )NaSCN}] and [0.78CH3CONH2 + 0.22{f LiBr + (1 - f )LiNO3}] with f = 0, 0.2, 0.4, 0.6, 0.8, and 1.0. γ of these DES systems shows near insensitivity to f, while ρ shows a moderate dependence on f. Interestingly, η exhibits a strong dependence on f. In the low-frequency Kerr spectra, obtained via the Fourier transform of the collected Kerr transients, a characteristic band at ∼70 cm(-1) is clear in [0.78CH3CONH2 + 0.22{f LiBr + (1 - f )LiNO3}] DES especially at the larger f. The band is attributed to the intermolecular hydrogen bond of acetamide. Because of less depolarized Raman activities of intermolecular/interionic vibrational motions, which are mostly translational (collision-induced or interaction-induced) motions, of spherical ions, the intermolecular hydrogen-bonding band is clearly observed. In contrast, the intermolecular hydrogen-bonding band is buried in the other intermolecular/interionic vibrational motions, which includes translational and reorientational (librational) motions and their cross-terms, in [0.75CH3CONH2 + 0.25{f KSCN + (1 - f )NaSCN}] system. The first moment (M1) of the intermolecular/interionic vibrational band in these DES systems is much higher than that in typical neutral molecular liquids and shows a weak but contrasting dependence on the bulk parameter √γ/ρ. The time constants for picosecond overdamped Kerr transients in both the DES systems, which are obtained on the basis of the analysis fitted by a triexponential function, are rather insensitive to f for both the DES systems, but all the three time constants (fast: ∼1-3 ps; intermediate:

  14. SYNTHESIS AND BIOLOGICAL EVALUATION OF N-(SUBSTITUTED PHENYL)-2-(5H-[1,2,4]TRIAZINO[5,6-b]INDOL-3-YLSULFANYL)ACETAMIDES AS ANTIMICROBIAL, ANTIDEPRESSANT AND ANTICONVULSANT AGENTS.

    PubMed

    Shruthi, N; Poojary, Boja; Kumar, Vasantha; Prathibha, A; Hussain, Mumtaz Mohammed; Revanasiddappa, B C; Joshi, Himanshu

    2015-01-01

    A new series of N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides were synthesized by condensation of tricyclic compound 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione with chloro N-phenylacetamides. The tricyclic compound was obtained by condensation of Isatin with thiosemicarbazide. Chloro N-phenylacetamides were obtained from different substituted anilines. Their structures were characterized by IR, 1H NMR, LC-MS and elemental analyses. Newly synthesized compounds were screened for antimicrobial, antidepressant and anticonvulsant activities. Preliminary results indicated that most of the compounds showed lesser MIC value than the standard drug used when tested for antimicrobial activity. Some of the compounds were endowed with very good antidepressant and anticonvulsant activity. PMID:26165132

  15. 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

    NASA Astrophysics Data System (ADS)

    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.

  16. Discovery of 2-(6-(5-Chloro-2-methoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamide (PF-06282999): A Highly Selective Mechanism-Based Myeloperoxidase Inhibitor for the Treatment of Cardiovascular Diseases.

    PubMed

    Ruggeri, Roger B; Buckbinder, Leonard; Bagley, Scott W; Carpino, Philip A; Conn, Edward L; Dowling, Matthew S; Fernando, Dilinie P; Jiao, Wenhua; Kung, Daniel W; Orr, Suvi T M; Qi, Yingmei; Rocke, Benjamin N; Smith, Aaron; Warmus, Joseph S; Zhang, Yan; Bowles, Daniel; Widlicka, Daniel W; Eng, Heather; Ryder, Tim; Sharma, Raman; Wolford, Angela; Okerberg, Carlin; Walters, Karen; Maurer, Tristan S; Zhang, Yanwei; Bonin, Paul D; Spath, Samantha N; Xing, Gang; Hepworth, David; Ahn, Kay; Kalgutkar, Amit S

    2015-11-12

    Myeloperoxidase (MPO) is a heme peroxidase that catalyzes the production of hypochlorous acid. Clinical evidence suggests a causal role for MPO in various autoimmune and inflammatory disorders including vasculitis and cardiovascular and Parkinson's diseases, implying that MPO inhibitors may represent a therapeutic treatment option. Herein, we present the design, synthesis, and preclinical evaluation of N1-substituted-6-arylthiouracils as potent and selective inhibitors of MPO. Inhibition proceeded in a time-dependent manner by a covalent, irreversible mechanism, which was dependent upon MPO catalysis, consistent with mechanism-based inactivation. N1-Substituted-6-arylthiouracils exhibited low partition ratios and high selectivity for MPO over thyroid peroxidase and cytochrome P450 isoforms. N1-Substituted-6-arylthiouracils also demonstrated inhibition of MPO activity in lipopolysaccharide-stimulated human whole blood. Robust inhibition of plasma MPO activity was demonstrated with the lead compound 2-(6-(5-chloro-2-methoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamide (PF-06282999, 8) upon oral administration to lipopolysaccharide-treated cynomolgus monkeys. On the basis of its pharmacological and pharmacokinetic profile, PF-06282999 has been advanced to first-in-human pharmacokinetic and safety studies. PMID:26509551

  17. Bis(N-{bis­[meth­yl(phen­yl)amino]phos­phor­yl}-2,2,2-trichloro­acetamide)di­nitrato­dioxidouranium(VI)

    PubMed Central

    Znovjyak, Kateryna O.; Ovchynnikov, Vladimir A.; Sliva, Tetyana Yu.; Shishkina, Svitlana V.; Amirkhanov, Vladimir M.

    2010-01-01

    In the title compound, [UO2 L 2(NO3)2] {L = N-{bis­[meth­yl(phen­yl)amino]phosphor­yl}-2,2,2-trichloro­acetamide, C16H17Cl3N3O2P}, the UVI ions are eight-coordinated by axial oxido ligands and six equatorial O atoms from the phosphoryl and nitrate groups in a distorted hexa­gonal–bipyramidal geometry. There are disordered fragments in the two coordinating L ligands: the trichloro­methyl group is rotationally disordered between two orientations [occupancy ratio 0.567 (15):0.433 (15)] in one ligand, and a meth­yl(phen­yl)amine fragment is disordered over two conformations [occupancy ratio 0.60 (4):0.40 (4)] in the other ligand. In the crystal structure, intra­molecular N—H⋯O hydrogen bonds between the amine and nitrate groups are observed. PMID:21580248

  18. (Acetonitrile){2-[bis­(pyridin-2-ylmethyl-κ2 N)amino-κN]-N-(2,6-dimethyl­phen­yl)acetamide-κO}(perchlorato-κO)zinc (acetonitrile){2-[bis­(pyridin-2-ylmethyl-κ2 N)amino-κN]-N-(2,6-dimethyl­phen­yl)acetamide-κO}zinc tris­(perchlorate)

    PubMed Central

    Åstrand, Ove Alexander Høgmoen; Görbitz, Carl Henrik; Kristoffersen, Kenneth Aase; Rongved, Pål

    2013-01-01

    In the title salt, [Zn(C22H24N4O)(CH3CN)][Zn(ClO4)(C22H24N4O)(CH3CN)](ClO4)3, two differently coordinated zinc cations occur. In the first complex, the metal ion is coordinated by the N,N′,N′′,O-tetra­dentate acetamide ligand and an acetonitrile N atom, generating an approximate trigonal–bipyramidal coordination geometry, with the O atom in an equatorial site and the acetonitrile N atom in an axial site. In the second complex ion, a perchlorate ion is also bonded to the zinc ion, generating a distorted trans-ZnO2N4 octa­hedron. Of the uncoordinating perchlorate ions, one lies on a crystallographic twofold axis and one lies close to a twofold axis and has a site occupancy of 0.5. N—H⋯O and N—H⋯(O,O) hydrogen bonds are observed in the crystal. Disordered solvent mol­ecules occupy about 11% of the unit-cell volume; their contribution to the scattering was removed with the SQUEEZE routine of the PLATON program [Spek (2009 ▶). Acta Cryst. D65, 148–155.]. PMID:23424407

  19. A theoretical investigation into the cooperativity effect between the H∙∙∙O and H∙∙∙F⁻ interactions and electrostatic potential upon 1:2 (F⁻:N-(Hydroxymethyl)acetamide) ternary-system formation.

    PubMed

    Tian, Qing-Ping; Wang, Yan-Hong; Shi, Wen-Jing; Song, Shu-Qin; Tang, Hai-Fei

    2013-12-01

    The cooperativity effects between the O/N-H∙∙∙F(-) anionic hydrogen-bonding and O/N-H∙∙∙O hydrogen-bonding interactions and electrostatic potentials in the 1:2 (F(-):N-(Hydroxymethyl)acetamide (signed as "ha")) ternary systems are investigated at the B3LYP/6-311++G** and MP2/6-311++G** levels. A comparison of the cooperativity effect in the "F(-)∙∙∙ha∙∙∙ha" and "FH∙∙∙ha(-)∙∙∙ha" systems is also carried out. The result shows that the increase of the H∙∙∙O interaction energy in the O-H∙∙∙O-H, N-H∙∙∙O-H or N-H∙∙∙O = C link is more notable than that in the O-H∙∙∙O = C contact upon ternary-system formation. The cooperativity effect is found in the complex formed by the O/N-H∙∙∙F(-) and O/N-H∙∙∙O interactions, while the anti-cooperativity effect is present in the system with only the O/N-H∙∙∙F(-) H-bond or the "FH∙∙∙ha(-)∙∙∙ha" complex by the N(-)∙∙∙H-F contact. Atoms in molecules (AIM) analysis and shift of electron density confirm the existence of cooperativity. The most negative surface electrostatic potential (V(S,min)) correlates well with the interaction energy E' int.(ha∙∙∙F-) and synergetic energy E(syn.), respectively. The relationship between the change of V(S,min) (i.e., ΔV(S,min)) and E(syn.) is also found. PMID:24114326

  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

    PubMed Central

    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 as the precursor. After 15 h of growth, CuO NP-exposed cells had metabolized more tryptophan than the control and ZnO NP-challenged cells. The CuO NP-treated cells produced higher IAA levels than control cultures lacking NPs. In contrast, ZnO NPs inhibited IAA production. Mixing of CuO and ZnO NPs resulted in an intermediate level of IAA production relative to the levels in the separate CuO and ZnO NP treatments. The effect of CuO NPs on IAA levels could be duplicated by ions at the concentrations released from the NPs. However, ion release did not account for the inhibition caused by the ZnO NPs. The mechanism underlying changes in IAA levels cannot be accounted for by effects on transcript accumulation from genes encoding a tryptophan permease or the IAM hydrolase in 15-h cultures. These findings raise the issue of whether sublethal doses of NPs would modify the beneficial effects of association between plants and bacteria. PMID:22210218

  1. 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.

    PubMed

    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

  2. Crystal structure of N-(2-{[2,6-bis­(2,2,2-tri­fluoro­acetamido)­phen­yl]disulfan­yl}-3-(2,2,2-tri­fluoro­acetamido)­phen­yl)-2,2,2-tri­fluoro­acetamide

    PubMed Central

    Awasabisah, Dennis; Powell, Douglas R.; Richter-Addo, George B.

    2015-01-01

    The title compound, C20H10F12N4O4S2, is an organic diaryl di­sulfide compound with tri­fluoro­acetamide substituents at the ortho-positions of each benzene ring. There are two mol­ecules (labeled A and B) in the asymmetric unit. The F atoms of three of the –CF3 groups exhibit rotational disorder over two positions each. The S—S bond distances are 2.0914 (7) and 2.0827 (6) Å for mol­ecules A and B, respectively. The dihedral angle between the S—S—C and S—C—C planes is 103.05 (15)° for mol­ecule A and 104.09 (15)° for mol­ecule B. The three-dimensional supra­molecular architecture of the crystal is sustained by numerous N—H⋯O, N—H⋯S and C—H⋯O inter­actions. PMID:26396879

  3. New spectrofluorimetric methods for determination of melatonin in the presence of N-{2-[1-({3-[2-(acetylamino)ethyl]-5-methoxy-1H-indol-2-yl}methyl)-5-methoxy-1H-indol-3-yl]- ethyl}acetamide: a contaminant in commercial melatonin preparations

    PubMed Central

    2012-01-01

    Background Melatonin (MLT) has many health implications, therefore it is of valuable importance to develop specific analytical methods for determination of MLT in the presence of its main contaminant, N-{2-[1-({3-[2-(acetylamino)ethyl]-5-methoxy-1H-indol-2-yl}methyl)-5-methoxy-1H-indol-3-yl]ethyl}acetamide (10). For development of these analytical methods, compound 10 had to be prepared in an adequate amount. Results Compound 10 was synthesized in six steps starting from 5-methoxyindole-2-carboxylic acid (1). Analytical performance of the proposed spectrofluorimetric methods was statistically validated with respect to linearity, accuracy, precision and specificity. The proposed methods were successfully applied for the assay of MLT in laboratory prepared mixtures containing up to 60 % of compound 10 and in commercial MLT tablets with recoveries not less than 99.00 %. No interference was observed from common pharmaceutical additives and the results were favorably compared with those obtained by a reference method. Conclusions This work describes simple, sensitive, and reliable second derivative spectrofluorimetric method in addition to two multivariate calibration methods, principal component regression (PCR) and partial least square (PLS), for the determination of MLT in the presence of compound 10. PMID:22551394

  4. A long-acting and highly selective prostacyclin receptor agonist prodrug, 2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide (NS-304), ameliorates rat pulmonary hypertension with unique relaxant responses of its active form, {4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}acetic acid (MRE-269), on rat pulmonary artery.

    PubMed

    Kuwano, Keiichi; Hashino, Asami; Noda, Kumiko; Kosugi, Keiji; Kuwabara, Kenji

    2008-09-01

    2-{4-[(5,6-Diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide (NS-304) is an orally available, long-acting nonprostanoid prostacyclin receptor (IP receptor) agonist prodrug. In a rat model of pulmonary hypertension induced by monocrotaline (MCT), NS-304 ameliorated vascular endothelial dysfunction, pulmonary arterial wall hypertrophy, and right ventricular hypertrophy, and it elevated right ventricular systolic pressure and improved survival. {4-[(5,6-Diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}acetic acid (MRE-269), the active form of NS-304, is much more selective for the IP receptor than are the prostacyclin analogs beraprost and iloprost, which also have high affinity for the EP(3) receptor. To investigate the effect of receptor selectivity on vasodilation of the pulmonary artery, we assessed the relaxant response to these IP agonists in rats. MRE-269 induced vasodilation equally in large pulmonary arteries (LPA) and small pulmonary arteries (SPA), whereas beraprost and iloprost induced less vasodilation in SPA than in LPA. An EP(3) agonist, sulprostone, induced SPA and LPA vasoconstriction, and an EP(3) antagonist attenuated the vasoconstriction. Beraprost showed EP(3) agonism and induced LPA and SPA vasoconstriction, whereas the EP(3) antagonist inhibited this vasoconstriction and enhanced beraprost- and iloprost-induced SPA vasodilation. These findings suggest that the EP(3) agonism of beraprost and iloprost interfered with the SPA vasodilation resulting from their IP receptor agonism. Endothelium removal markedly attenuated the vasodilation induced by beraprost, but not that induced by MRE-269 or iloprost. Moreover, the vasodilation induced by beraprost and iloprost, but not that induced by MRE-269, was more strongly attenuated in LPA from MCT-treated rats than from normal rats. NS-304 is a promising alternative medication for pulmonary arterial hypertension with prospects for good patient compliance. PMID:18552131

  5. 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.

    PubMed

    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

  6. N-[4-(Ethyl­sulfamo­yl)phen­yl]acetamide

    PubMed Central

    Rehman, Jeveria; Ejaz; Khan, Islam Ullah; Harrison, William T. A.; Farid, Sidra

    2011-01-01

    The title compound, C10H14N2O3S, crystallized with two mol­ecules (A and B) in the asymmetric unit. The terminal methyl group of the ethyl­sulfonamide moiety in mol­ecule B is disordered over two sets of sites with an occupancy ratio of 0.61 (1):0.39 (1). Both mol­ecules have L-shaped conformations. In mol­ecule A, the dihedral angles between the benzene ring and its ethyl­sulfonamide and methyl­amide substituents are 83.5 (3) and 13.34 (18)°, respectively. Equivalent values for mol­ecule B are 87.9 (3) and 6.32 (16)°, respectively. The C—S—N—C torsion angles are 66.5 (3)° for A and −64.4 (3)° for B, indicating similar twists about the S—N bonds, but in opposite senses. In the crystal, the A mol­ecules are linked by pairs of Ns—H⋯O (s = sulfonamide) hydrogen bonds, generating inversion dimers containing R 2 2(8) rings, while the B mol­ecules are linked by Ns—H⋯O hydrogen bonds into C(10) [100] chains. Finally, Na—H⋯O (a = amide) hydrogen bonds link the A-mol­ecule dimers and B-mol­ecule chains into a three-dimensional network. PMID:22059023

  7. 40 CFR 721.225 - 2-Chloro-N-methyl-N-substituted acetamide (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...) Chemical substance and significant new uses subject to reporting. (1) The chemical substance 2-chloro-N... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for... significant new uses described in paragraph (a)(2) of this section. (2) The significant new uses are:...

  8. 40 CFR 721.225 - 2-Chloro-N-methyl-N-substituted acetamide (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...) Chemical substance and significant new uses subject to reporting. (1) The chemical substance 2-chloro-N... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for... significant new uses described in paragraph (a)(2) of this section. (2) The significant new uses are:...

  9. N-(4-Chloro­phen­yl)-2-(naphthalen-1-yl)acetamide

    PubMed Central

    Fun, Hoong-Kun; Quah, Ching Kheng; Nayak, Prakash S.; Narayana, B.; Sarojini, B. K.

    2012-01-01

    In the title compound, C18H14ClNO, the naphthalene ring system [maximum deviation = 0.014 (9) Å] forms a dihedral angle of 74.8 (2)° with the benzene ring. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds into chains propagating along [010]. PMID:22904906

  10. Low energy electron induced reactions in fluorinated acetamide - probing negative ions and neutral stable counterparts*

    NASA Astrophysics Data System (ADS)

    Kopyra, Janina; König-Lehmann, Constanze; Illenberger, Eugen; Warneke, Jonas; Swiderek, Petra

    2016-06-01

    Electron impact to trifluoroacetamide (CF3CONH2, TFAA) in the energy range 0-12 eV leads to a variety of negative fragment ions which are formed via dissociative electron attachment (DEA). The underlying reactions range from single bond cleavages to remarkably complex reactions that lead to loss of the neutral units HF, H2O and HNCO as deduced from their directly observed ionic counterparts (M - H2O)-, (M - HF)- and (M - HNCO)-. Also formed are the pseudo-halogen ions CN- and OCN-. All these reactions proceed dominantly via a resonance located near 1 eV, i.e., electrons at subexcitation energies trigger reactions involving multiple bond cleavages. The electron induced generation of the neutral molecules HF, H2O and HNCO in condensed TFAA films is probed by temperature controlled thermal desorption spectrometry (TDS) which can be viewed as a complementary techniques to gas-phase experiments in DEA to directly probe the neutral counterparts. Contribution to the Topical Issue "Advances in Positron and Electron Scattering", edited by Paulo Limao-Vieira, Gustavo Garcia, E. Krishnakumar, James Sullivan, Hajime Tanuma and Zoran Petrovic.

  11. N-[(4-Chloro­phen­yl)sulfon­yl]acetamide

    PubMed Central

    Fun, Hoong-Kun; Chia, Tze Shyang; Jyothi, K.; Hegde, Poornima; D’Souza, Pramila Rita

    2012-01-01

    The asymmetric unit of the title compound, C8H8ClNO3S, consists of two crystallographically independent mol­ecules (A and B). The dihedral angles between the benzene ring and amide C—C(=O)—NH– plane are 87.6 (3) (mol­ecule A) and 86.0 (3)° (mol­ecule B). In the crystal, the independent mol­ecules are alternately linked by N—H⋯O hydrogen bonds into an infinite chain along the b axis. Short inter­molecular Cl⋯Cl contacts [3.2882 (5) and 3.2812 (5) Å] are also observed. PMID:22969527

  12. N-[4-(4-Chloro­benzene­sulfonamido)­phenyl­sulfon­yl]acetamide

    PubMed Central

    Khan, Islam Ullah; Ejaz; Farid, Sidra; Harrison, William T. A.

    2012-01-01

    In the title compound, C14H13ClN2O5S2, the dihedral angles between the central benzene ring and the pendant chloro­benzene ring and the N-acetyl group are 82.35 (5) and 79.71 (6)°, respectively, and the overall conformation of the mol­ecule approximates to a U shape. Both the C—S—N—C conformations are gauche, but with opposite senses [torsion angles = −59.29 (15) and 63.68 (16)°]. An intra­molecular C—H⋯O inter­action generates an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(20) loops. A second N—H⋯O hydrogen bond links the dimers into (101) layers. PMID:22719667

  13. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for... this section for the significant new uses described in paragraph (a)(2) of this section. (2)...

  14. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for... this section for the significant new uses described in paragraph (a)(2) of this section. (2)...

  15. Comparison of the crystal structure and molecular models of N,N-diisobutyl-2-(octylphenylphosphinyl)acetamide (CMPO)

    SciTech Connect

    Rogers, R.D.; Rollins, A.N.; Gatrone, R.C.; Horwitz, E.P.

    1994-06-01

    The compound crystallizes in the space group P2{sub 1}/c with a=13. 446(6), b=22.280(7) {Angstrom}, b=92.07(4){degrees}, and D{sub calc}=1.05 g/cm{sup 3} for Z=8 (@20{degrees}C). Molecular mechanics, molecular dynamics, and MNDO calculations were also performed on CMPO utilizing the SYBYL{sup 2} suite of programs. Results from these calculations are compared to the crystal structure and to similar calculations performed on CMPO using ALCHEMY. The calculations agree fairly well with the crystal structure.

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

    NASA Astrophysics Data System (ADS)

    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.

  17. Medium decoupling of dynamics at temperatures ˜100 K above glass-transition temperature: A case study with (acetamide + lithium bromide/nitrate) melts

    NASA Astrophysics Data System (ADS)

    Guchhait, Biswajit; Daschakraborty, Snehasis; Biswas, Ranjit

    2012-05-01

    Time-resolved fluorescence Stokes shift and anisotropy measurements using a solvation probe in [0.78CH3CONH2 + 0.22{f LiBr + (1-f) LiNO3}] melts reveal a strong decoupling of medium dynamics from viscosity. Interestingly, this decoupling has been found to occur at temperatures ˜50-100 K above the glass transition temperatures of the above melt at various anion concentrations (fLiBr). The decoupling is reflected via the following fractional viscosity dependence (η) of the measured average solvation and rotation times (⟨τs⟩ and ⟨τr⟩, respectively): ⟨τx⟩ ∝ (η/T)p (x being solvation or rotation), with p covering the range, 0.20 < p < 0.70. Although this is very similar to what is known for deeply supercooled liquids, it is very surprising because of the temperature range at which the above decoupling occurs for these molten mixtures. The kinship to the supercooled liquids is further exhibited via p which is always larger for ⟨τr⟩ than for ⟨τs⟩, indicating a sort of translation-rotation decoupling. Multiple probes have been used in steady state fluorescence measurements to explore the extent of static heterogeneity. Estimated experimental dynamic Stokes shift for coumarin 153 in these mixtures lies in the range, 1000 < Δνt/cm-1 < 1700, and is in semi-quantitative agreement with predictions from our semi-molecular theory. The participation of the fluctuating density modes at various length-scales to the observed solvation times has also been investigated.

  18. N-[(2-Hydr­oxy-1-naphth­yl)(2-hydroxy­phen­yl)meth­yl]acetamide

    PubMed Central

    NizamMohideen, M.; Thenmozhi, S.; SubbiahPandi, A.; Selvam, N. Panneer; Perumal, P. T.

    2009-01-01

    In the asymmetric unit of the title compound, C19H17NO3, there are two crystallographically independent mol­ecules, which are connected to each other by O—H⋯O hydrogen bonds, forming mol­ecular chains as well as cyclic centrosymmetric R 2 2(16) dimers. PMID:21582473

  19. DEVELOPMENT OF METHOD 535 FOR THE DETERMINATION OF CHLOROACETANILIDE AND OTHER ACETAMIDE HERBICIDE DEGRADATES IN DRINKING WATER BY SOLID PHASE EXTRACTION AND LIQUID CHROMATOGRAPHY/TANDEM MASS SPECTROMETRY

    EPA Science Inventory

    EPA Method 535 has been developed in order to provide a method for the analysis of "Alachlor ESA and other acetanilide degradation products" which are listed on U.S. EPA's 1998 Drinking Water Contaminant Candidate List. Method 535 uses solid phase extraction with a nonporous gr...

  20. 2-Chloro-N-[2-(2-fluoro­benzo­yl)-4-nitro­phen­yl]-N-methyl­acetamide

    PubMed Central

    Siddaraju, B. P.; Jasinski, Jerry P.; Golen, James A.; Yathirajan, H. S.; Raju, C. R.

    2011-01-01

    The title compound, C16H12ClFN2O4, crystallizes with two mol­ecules in the asymmetric unit in which the dihedral angles between the mean planes of the two benzene rings are 65.1 (7) and 65.6 (6)°. In each mol­ecule, the nitro group displays rotational disorder over two orientations in a 0.503 (11):0.497 (11) ratio and the Cl atom is disordered in a 0.432 (5):0.568 (5) ratio. In one mol­ecule, the F atoms is statistically disordered over two positions. The crystal packing features weak inter­molecular C—H⋯O and C—H⋯Cl inter­actions, which form a layered network. PMID:22064922

  1. Crystal structure of N-[(2-hy­droxy­naphthalen-1-yl)(4-methyl­phen­yl)meth­yl]acetamide

    PubMed Central

    Khanapure, Sharanbasappa; Rashinkar, Gajanan; Chhowala, Tarulata; Anthal, Sumati; Kant, Rajni

    2015-01-01

    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]. PMID:26029431

  2. Synthesis, crystal, computational study and in vitro anti-tuberculosis activity of N-(furan-2-yl-methyl)- N-(phenyl(quinolin-3-yl)methyl) acetamide derivatives

    NASA Astrophysics Data System (ADS)

    Bai, Yuefei; Wang, Lijuan; Chen, Yu; Yuan, Lei; Xu, Wei; Sun, Tiemin

    2011-11-01

    A one-pot synthesis of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)- N-(furan-2-yl-methyl)-2-morpholinoacetamide ( 1) and N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)- N-(furan-2-yl-methyl)-2-adamantylacetamide ( 2) was achieved in good yield for the first time. Compounds 1 and 2·H 2O were characterized by single crystal X-ray diffraction in solid state. The structures of two new derivatives have been confirmed by typical spectroscopic techniques, namely IR, 1H and 13C NMR. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. The experimental molecular structures are well reproduced by the computation. The geometrical parameters of the title compounds are similar to those of some reported derivatives. In addition, in vitro anti-tuberculosis activities of derivatives 1 and 2 were also investigated.

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

    SciTech Connect

    Caliskan, Nezihe Guentepe, Feyizan; Yueksektepe, Cigdem; Cukurovali, Alaaddin; Bueyuekguengoer, Orhan

    2010-12-15

    The title compound C{sub 18}H{sub 21}ClN{sub 2}SO crystallizes with Z = 4 in space group P2{sub 1}/c. The structure of the title compound was characterized by {sup 1}H-NMR, {sup 13}C-NMR, IR and single crystal diffraction. There are an intermolecular N-H-O hydrogen bond and a C-H-{pi} 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.

  4. 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

    SciTech Connect

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

    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.

  5. 2-(3,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

    PubMed

    Mahan, Aneeka; Butcher, Ray J; Nayak, Prakash S; Narayana, B; Yathirajan, H S

    2013-03-01

    In the title compound, C19H17Cl2N3O2, there are three mol-ecules (A, B and C) in the asymmetric unit and each differs in the conformation adopted. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 44.5 (2) and 56.2 (2)°, respectively in A, 51.1 (2) and 54.1 (2)° in B, and 53.8 (2) and 54.6 (2)° in C. The dihedral angles between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings are 54.8 (2), 76.2 (2) and 77.5 (2)° in mol-ecules A, B and C, respectively, while the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings make dihedral angles of 45.3 (2), 51.2 (2) and 42.8 (2)°, respectively. In the crystal, two of the mol-ecules are linked through N-H⋯O hydrogen bonding to an adjoining mol-ecule, forming dimers of the R2(2)(10) type, while the third mol-ecule forms such dimers with itself. C-H⋯O inter-actions link the dimers. PMID:23476584

  6. 2-(2,6-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

    PubMed

    Butcher, Ray J; Mahan, Aneeka; Nayak, P S; Narayana, B; Yathirajan, H S

    2013-01-01

    In the title compound, C19H17Cl2N3O2, the amide group is planar and, through N-H⋯O hydrogen bonding to an adjoining mol-ecule, forms dimers of the R2(2)(10) type. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 71.63 (11) and 57.93 (10)°, respectively. The dihedral angle between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 76.60 (10)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 49.29 (7)°. The crystal structure also features weak C-H⋯O inter-actions. PMID:23476430

  7. 2-(2,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

    PubMed

    Butcher, Ray J; Mahan, Aneeka; Nayak, P S; Narayana, B; Yathirajan, H S

    2013-01-01

    In the crystal structure of the title compound, C19H17Cl2N3O2, the mol-ecules form dimers of the R2(2)(10) type through N-H⋯O hydrogen bonding. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 80.70 (13) and 64.82 (12)°, respectively. The dihedral angle between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 48.45 (5)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 56.33 (6)°. PMID:23476425

  8. Crystal structure of 2-[4(E)-2,6-bis­(4-chloro­phen­yl)-3-ethyl­piperidin-4-yl­idene]acetamide

    PubMed Central

    Priya, K.; Saravanan, K.; Selvanayagam, S.; Kabilan, S.

    2015-01-01

    In the title piperidine derivative, C21H22Cl2N2O, the piperidine ring adopts a chair conformation. The chloro­phenyl rings are oriented at an angle of 45.59 (14)° with respect to each other. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds, forming C(4) chains along [100]. The chains are linked by C—H⋯O hydrogen bonds, forming sheets parallel to the ab plane. Within the sheets, there are N—H⋯π inter­actions present. The crystal studied was refined as an inversion twin. PMID:26594551

  9. Crystal structure of (+)-N-[(1R,5S,6S,9S)-5-hydroxy-methyl-3,3,9-trimethyl-8-oxo-2,4,7-trioxabi-cyclo-[4.3.0]nonan-9-yl]acetamide.

    PubMed

    Oishi, Takeshi; Tsuzaki, Shun; Sugai, Tomoya; Sato, Takaaki; Chida, Noritaka

    2016-05-01

    In the title compound, C12H19NO6, the six-membered 1,3-dioxane ring adopts a chair-like conformation. The seat of this chair, containing two O atoms, is essentially planar, with a maximum deviation of 0.0021 (12) Å. The five-membered oxolane ring cis-fused to the 1,3-dioxane ring adopts an envelope form. The bridgehead C atom at the flap, which is bonded to the tetra-substituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539 (4) Å. In the crystal, classical O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a sheet structure enclosing an R 4 (4)(24) graph-set motif. Weak inter-molecular C-H⋯O inter-actions support the sheet formation. PMID:27308035

  10. 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

    NASA Astrophysics Data System (ADS)

    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.

  11. 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

    PubMed Central

    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

  12. Discovery, Synthesis, And Structure-Based Optimization of a Series of N-(tert-Butyl)-2-(N-arylamido)-2-(pyridin-3-yl) Acetamides (ML188) as Potent Noncovalent Small Molecule Inhibitors of the Severe Acute Respiratory Syndrome Coronavirus (SARS-CoV) 3CL Protease

    SciTech Connect

    Jacobs, Jon; Grum-Tokars, Valerie; Zhou, Ya; Turlington, Mark; Saldanha, S. Adrian; Chase, Peter; Eggler, Aimee; Dawson, Eric S.; Baez-Santos, Yahira M.; Tomar, Sakshi; Mielech, Anna M.; Baker, Susan C.; Lindsley, Craig W.; Hodder, Peter; Mesecar, Andrew; Stauffer, Shaun R.

    2012-12-11

    A high-throughput screen of the NIH molecular libraries sample collection and subsequent optimization of a lead dipeptide-like series of severe acute respiratory syndrome (SARS) main protease (3CLpro) inhibitors led to the identification of probe compound ML188 (16-(R), (R)-N-(4-(tert-butyl)phenyl)-N-(2-(tert-butylamino)-2-oxo-1-(pyridin-3-yl)ethyl)furan-2-carboxamide, Pubchem CID: 46897844). But, unlike the majority of reported coronavirus 3CLpro inhibitors that act via covalent modification of the enzyme, 16-(R) is a noncovalent SARS-CoV 3CLpro inhibitor with moderate MW and good enzyme and antiviral inhibitory activity. A multicomponent Ugi reaction was utilized to rapidly explore structure–activity relationships within S1', S1, and S2enzyme binding pockets. Moreover, the X-ray structure of SARS-CoV 3CLpro bound with 16-(R) was instrumental in guiding subsequent rounds of chemistry optimization. 16-(R) provides an excellent starting point for the further design and refinement of 3CLpro inhibitors that act by a noncovalent mechanism of action.

  13. Synthesis, SAR, and series evolution of novel oxadiazole-containing 5-lipoxygenase activating protein inhibitors: discovery of 2-[4-(3-{(r)-1-[4-(2-amino-pyrimidin-5-yl)-phenyl]-1-cyclopropyl-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-N,N-dimethyl-acetamide (BI 665915).

    PubMed

    Takahashi, Hidenori; Riether, Doris; Bartolozzi, Alessandra; Bosanac, Todd; Berger, Valentina; Binetti, Ralph; Broadwater, John; Chen, Zhidong; Crux, Rebecca; De Lombaert, Stéphane; Dave, Rajvee; Dines, Jonathon A; Fadra-Khan, Tazmeen; Flegg, Adam; Garrigou, Michael; Hao, Ming-Hong; Huber, John; Hutzler, J Matthew; Kerr, Steven; Kotey, Adrian; Liu, Weimin; Lo, Ho Yin; Loke, Pui Leng; Mahaney, Paige E; Morwick, Tina M; Napier, Spencer; Olague, Alan; Pack, Edward; Padyana, Anil K; Thomson, David S; Tye, Heather; Wu, Lifen; Zindell, Renee M; Abeywardane, Asitha; Simpson, Thomas

    2015-02-26

    The synthesis, structure-activity relationship (SAR), and evolution of a novel series of oxadiazole-containing 5-lipoxygenase-activating protein (FLAP) inhibitors are described. The use of structure-guided drug design techniques provided compounds that demonstrated excellent FLAP binding potency (IC50 < 10 nM) and potent inhibition of LTB4 synthesis in human whole blood (IC50 < 100 nM). Optimization of binding and functional potencies, as well as physicochemical properties resulted in the identification of compound 69 (BI 665915) that demonstrated an excellent cross-species drug metabolism and pharmacokinetics (DMPK) profile and was predicted to have low human clearance. In addition, 69 was predicted to have a low risk for potential drug-drug interactions due to its cytochrome P450 3A4 profile. In a murine ex vivo whole blood study, 69 demonstrated a linear dose-exposure relationship and a dose-dependent inhibition of LTB4 production. PMID:25671290

  14. Crystal structure of (+)-N-[(1R,5S,6S,9S)-5-hydroxy­methyl-3,3,9-trimethyl-8-oxo-2,4,7-trioxabi­cyclo­[4.3.0]nonan-9-yl]acetamide

    PubMed Central

    Oishi, Takeshi; Tsuzaki, Shun; Sugai, Tomoya; Sato, Takaaki; Chida, Noritaka

    2016-01-01

    In the title compound, C12H19NO6, the six-membered 1,3-dioxane ring adopts a chair-like conformation. The seat of this chair, containing two O atoms, is essentially planar, with a maximum deviation of 0.0021 (12) Å. The five-membered oxolane ring cis-fused to the 1,3-dioxane ring adopts an envelope form. The bridgehead C atom at the flap, which is bonded to the tetra­substituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539 (4) Å. In the crystal, classical O—H⋯O and N—H⋯O hydrogen bonds link the mol­ecules into a sheet structure enclosing an R 4 4(24) graph-set motif. Weak inter­molecular C—H⋯O inter­actions support the sheet formation. PMID:27308035

  15. Discovery of a Teraryl Oxazolidinone Compound (S)-N-((3-(3-Fluoro-4-(4-(pyridin-2-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide Phosphate as a Novel Antimicrobial Agent with Enhanced Safety Profile and Efficacies.

    PubMed

    Yang, Tao; Chen, Gong; Sang, Zitai; Liu, Yuanyuan; Yang, Xiaoyan; Chang, Ying; Long, Haiyue; Ang, Wei; Tang, Jianying; Wang, Zhenling; Li, Guobo; Yang, Shengyong; Zhang, Jingren; Wei, Yuquan; Luo, Youfu

    2015-08-27

    A series of novel teraryl oxazolidinone compounds was designed, synthesized, and evaluated for their antimicrobial activity and toxicities. The compounds with aromatic N-heterocyclic substituents at the 4-position of pyrazolyl ring showed better antibacterial activity against the tested bacteria than other compounds with different patterns of substitution. Among all potent compounds, 10f exhibited promising safety profile in MTT assays and in hERG K(+) channel inhibition test. Furthermore, its phosphate was found to be highly soluble in water (47.1 mg/mL), which is beneficial for the subsequent in vivo test. In MRSA systemic infection mice models, 10f phosphate exerted significantly improved survival protection compared with linezolid. The compound also demonstrated high oral bioavailability (F = 99.1%). Moreover, from the results of in vivo toxicology experiments, 10f phosphate would be predicted to have less bone marrow suppression. PMID:26212502

  16. Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors.

    PubMed

    Ayers, Benjamin J; Glawar, Andreas F G; Martínez, R Fernando; Ngo, Nigel; Liu, Zilei; Fleet, George W J; Butters, Terry D; Nash, Robert J; Yu, Chu-Yi; Wormald, Mark R; Nakagawa, Shinpei; Adachi, Isao; Kato, Atsushi; Jenkinson, Sarah F

    2014-04-18

    All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of β-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. β-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good α-N-acetylgalactosaminidase inhibitors. PMID:24641544

  17. New electrolyte may increase life of polarographic oxygen sensors

    NASA Technical Reports Server (NTRS)

    Albright, C. F.

    1967-01-01

    Electrolyte increases life on oxygen sensors in a polarograph used for measuring the partial pressure of oxygen in a gas mixture. It consists of a solution of lithium chloride, dimethyl acetamide and water.

  18. Feasibility study for a secondary Na/S battery

    NASA Technical Reports Server (NTRS)

    Abraham, K. M.; Schiff, R.; Brummer, S. B.

    1979-01-01

    The feasibility of a moderate temperature Na battery was studied. This battery is to operate at a temperature in the range of 100-150 C. Two kinds of cathode were investigated: (1) a soluble S cathode consisting of a solution of Na2Sn in an organic solvent and (2) an insoluble S cathode consisting of a transition metal dichalcogenide in contact with a Na(+)ion conducting electrolyte. Four amide solvents, dimethyl acetamide, diethyl acetamide, N-methyl acetamide and acetamide, were investigated as possible solvents for the soluble S cathode. Results of stability and electrochemical studies using these solvents are presented. The dialkyl substituted amides were found to be superior. Although the alcohol 1,3-cyclohexanediol was found to be stable in the presence of Na2Sn at 130 C, its Na2Sn solutions did not appear to have suitable electrochemical properties.

  19. 40 CFR Appendix Ix to Part 264 - Ground-Water Monitoring List

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... Acetamide, N-9H-fluoren-2-yl- Acrolein 107-02-8 2-Propenal Acrylonitrile 107-13-1 2-Propenenitrile Aldrin...) Lead Mercury (Total) Mercury Methacrylonitrile 126-98-7 2-Propenenitrile, 2-methyl- Methapyrilene...

  20. 40 CFR Appendix Ix to Part 264 - Ground-Water Monitoring List

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... Acetamide, N-9H-fluoren-2-yl- Acrolein 107-02-8 2-Propenal Acrylonitrile 107-13-1 2-Propenenitrile Aldrin...) Lead Mercury (Total) Mercury Methacrylonitrile 126-98-7 2-Propenenitrile, 2-methyl- Methapyrilene...

  1. 40 CFR Appendix Ix to Part 264 - Ground-Water Monitoring List

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... Acetamide, N-9H-fluoren-2-yl- Acrolein 107-02-8 2-Propenal Acrylonitrile 107-13-1 2-Propenenitrile Aldrin...) Lead Mercury (Total) Mercury Methacrylonitrile 126-98-7 2-Propenenitrile, 2-methyl- Methapyrilene...

  2. 40 CFR Appendix Ix to Part 264 - Ground-Water Monitoring List

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... Acetamide, N-9H-fluoren-2-yl- Acrolein 107-02-8 2-Propenal Acrylonitrile 107-13-1 2-Propenenitrile Aldrin...) Lead Mercury (Total) Mercury Methacrylonitrile 126-98-7 2-Propenenitrile, 2-methyl- Methapyrilene...

  3. 40 CFR Appendix Ix to Part 264 - Ground-Water Monitoring List

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... Acetamide, N-9H-fluoren-2-yl- Acrolein 107-02-8 2-Propenal Acrylonitrile 107-13-1 2-Propenenitrile Aldrin...) Lead Mercury (Total) Mercury Methacrylonitrile 126-98-7 2-Propenenitrile, 2-methyl- Methapyrilene...

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

    PubMed Central

    Robinson, M.; 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. PMID:9835603

  5. Synthesis and pharmacological evaluation of dual ligands for melatonin (MT1/MT2) and serotonin 5-HT2C receptor subtypes (II).

    PubMed

    Ettaoussi, Mohamed; Pérès, Basile; Errazani, Aïcha; Boutin, Jean A; Caignard, Daniel-Henri; Delagrange, Philippe; Melnyk, Patricia; Berthelot, Pascal; Yous, Saïd

    2015-01-27

    In this paper we report the investigation of C-3 and β-acetamide positions of agomelatine analogues. Concomitant insertion of a hydroxymethyl in the β-acetamide position and aliphatic groups in C-3 position produced a positive effect on both melatonin (MT1, MT2) and serotonin (5-HT2C) binding affinities. In particular, the allyl 6b and ethyl 15a represented the more interesting compounds of this series. Furthermore, the introduction of methyl cycloalkyl groups (compounds 11a, 12a) exhibited no change in both MT2 and 5-HT2C binding affinities while a decrease of MT1 binding affinity occurred leading to an MT2 selectivity. Finally, the acetamide modulation has led to methyl thiourea 11h, with a weak MT2 selectivity. PMID:25528336

  6. 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.

    PubMed

    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

  7. Synthesis and characterization of new metallophthalocyanines with four phenoxyacetamide units

    NASA Astrophysics Data System (ADS)

    Salih Ağırtaş, M.; Izgi, M. Sait

    2009-06-01

    N-(4-(3,4-dicyanophenoxy)phenyl)acetamide was obtained through the displacement reaction of 4-nitrophthalonitrile with 4-acetamidophenol. The zinc(II) Phthalocyanine (4) was prepared by the reaction of the N-(4-(3,4-dicyanophenoxy)phenyl)acetamide with ZnCl 2 in dimethyl formamide (DMF). Magnesium (II) and nickel (II) phthalocyanines ( 5,6) were prepared by the reaction of the N-(4-(3,4-dicyanophenoxy)phenyl)acetamide with MgCl 2, NiCl 2 salts without solvents at 300 °C. This newness on the periphery increased solubility compared to the unsubstituted phthalocyanines. These metallo-phthalocyanines are soluble in DMF, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), DMF/water (1/1). The structures of target compounds were confirmed by elemental analyses, IR, 1H NMR, UV-vis spectra.

  8. Benznidazole

    PubMed Central

    Soares-Sobrinho, José Lamartine; Cunha-Filho, Marcílio S. S.; Rolim Neto, Pedro José; Torres-Labandeira, Juan J.; Dacunha-Marinho, Bruno

    2008-01-01

    The conformation of the title compound [systematic name: N-benzyl-2-(2-nitro­imidazol-1-yl)acetamide], C12H12N4O3, can be described in terms of the relative orientation of three planar fragments, the imidazol group (A), benzyl group (B), and the acetamide fragment (C), with corresponding dihedral angles: A/C = 88.17 (4), B/C = 67.12 (5) and A/B = 21.11 (4)°. The crystal packing is enhanced by a network of strong inter­molecular N—H⋯O hydrogen bonds. PMID:21201965

  9. [A new indole derivative from endophyte Myrothecium roridum IFB-E091 in Artemisia annua].

    PubMed

    Shen, Li; Li, Ling-yu; Zhang, Xiao-jun; Li, Ming; Song, Yong-chun

    2015-10-01

    Three compounds were isolated from solid culture of endophyte Myrothecium roridum IFB-E091 in Artemisia annua. Their structures were determined as (S)-(-)-N-[2-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-ethyl]-acetamide (1), N-(4-hydroxyphenethyl)acetamide (2) and asperfumoid (3), in which compound 1 was a new indole derivative. In cytotoxicity assay, the compound 1 had no obvious inhibition activity in human hepatoma cell line SMMC-7721 and human cervical carcinoma cell line HeLa. PMID:26837178

  10. Conformational features of secondary N-cyclopropyl amides.

    PubMed

    González-de-Castro, Ángela; Broughton, Howard; Martínez-Pérez, José A; Espinosa, Juan F

    2015-04-17

    NMR studies in conjunction with ab initio calculations revealed unexpected conformational behavior of N-cyclopropylacetamide (1). This secondary amide displays 16-19% E-rotamer (cis) around the carbonyl-nitrogen bond in apolar solvents, in contrast to other aliphatic secondary acetamides in which significant E-rotamer populations are rare due to steric contacts between the substituents on the amide bond. In addition, 1 adopts an ortho conformation around the N-cPr bond instead of the anti conformation generally preferred by secondary acetamides. This distinct conformational behavior was also observed for other secondary N-cyclopropyl amides. PMID:25803271

  11. New methods for preparing n, n-dialkyltrifluoroacetamides

    NASA Technical Reports Server (NTRS)

    Hsu, L.

    1972-01-01

    The customary preparative methods for N,N-dialkyltrifluoroacetamides involve the acylation of an amine by trifluoroacetic acid or its derivatives. In this report the synthesis of N,N-dialkyltrifluoroacetamides by reacting trifluoroacetic anhydride or acid with disubstituted formamides and acetamides is discussed. These reactions are interpreted with the aid of gas chromatographic analysis. Different reaction mechanisms are proposed for the reactions of formamides and acetamides with trifluoroacetic anhydride or acid. The use of the proposed reaction mechanisms for the synthesis of other fluorinated compounds is discussed.

  12. New methods for preparing N,N-dialkyltrifluoroacetamides

    NASA Technical Reports Server (NTRS)

    Hsu, L.

    1972-01-01

    The customary preparative methods for N,N-dialkyltrifluoroacetamides involve the acylation of an amine by trifluoroacetic acid or its derivatives. The synthesis of N,N-dialkyltrifluoroacetamides by reacting trifluoroacetic anhydride or acid with disubstituted formamides and acetamides is discussed. These reactions were interpreted with the aid of gas chromatographic analysis. Different reaction mechanisms are proposed for the reactions of formamides and acetamides with trifluoroacetic anhydride or acid. The use of the proposed reaction mechanisms for the synthesis of other fluorinated compounds is discussed.

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  14. Disruption of Genes Involved in Butenolide and Culmorin Synthesis in Fusarium graminearum

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Butenolide (4-acetamide-4-hydroxy-2-butenoic acid '-lactone) and culmorin (a tricyclic sesquiterpene diol) are two less-studied mycotoxins produced by several Fusarium species, including Fusarium graminearum. A putative butenolide biosynthetic eight-gene cluster in F. graminearum includes fg08080 w...

  15. Synthesis and characterization of new thiazolidinones containing coumarin moieties and their antibacterial and antioxidant activities.

    PubMed

    Hamdi, Naceur; Al-Ayed, Abdullah Sulaiman; Ben Said, Ridha; Fabienne, Alary

    2012-01-01

    New coumarin derivatives, namely (2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-oxo-2-phenylthiazolidin-3-yl)acetamide, N-(2-(3-methoxyphenyl)-4-oxothiazolidin-3-yl)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetamide, 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-oxo-2-(2,3,4trimethoxyphenyl)thiazolidin-3-yl)acetamide and N-(2-(4-bromophenyl)-4-oxothiazolidin-3-yl)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetamide) were synthesized starting from 4-methyl-7-hydroxycoumarin. The structures of the obtained compounds were confirmed by analytical IR and NMR spectra to elucidate the different positions of protons and carbons and as well as theoretical studies (DFT/B3LYP). The new compounds were screened for antibacterial activity. Most of them are more active against E. coli S. aureus and B. subtilis than standard references. PMID:22864240

  16. 40 CFR 180.503 - Cymoxanil, tolerance for residues.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., subgroup 3-07B 1.1 Potato 0.05 Vegetable, cucurbit, group 9 0.05 Vegetable, fruiting, group 8 0.2 1There is... of the fungicide cymoxanil, 2-cyano -N- -2-(methoxyimino) acetamide) in or on the raw...

  17. 40 CFR 180.503 - Cymoxanil, tolerance for residues.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., subgroup 3-07B 1.1 Potato 0.05 Vegetable, cucurbit, group 9 0.05 Vegetable, fruiting, group 8 0.2 1There is... of the fungicide cymoxanil, 2-cyano -N- -2-(methoxyimino) acetamide) in or on the raw...

  18. 40 CFR Appendix Vi to Part 265 - Compounds With Henry's Law Constant Less Than 0.1 Y/X

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 26 2014-07-01 2014-07-01 false Compounds With Henry's Law Constant Less Than 0.1 Y/X VI Appendix VI to Part 265 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Law Constant Less Than 0.1 Y/X Compound name CAS No. Acetaldol 107-89-1 Acetamide 60-35-5...

  19. 40 CFR Appendix Vi to Part 265 - Compounds With Henry's Law Constant Less Than 0.1 Y/X

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 26 2011-07-01 2011-07-01 false Compounds With Henry's Law Constant Less Than 0.1 Y/X VI Appendix VI to Part 265 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Law Constant Less Than 0.1 Y/X Compound name CAS No. Acetaldol 107-89-1 Acetamide 60-35-5...

  20. Reduction and Acetylation of 2,4-Dinitrotoluene by a Pseudomonas aeruginosa Strain

    PubMed Central

    Noguera, D. R.; Freedman, D. L.

    1996-01-01

    Aerobic and anoxic biotransformation of 2,4-dinitrotoluene (DNT) was examined by using a Pseudomonas aeruginosa strain isolated from a plant treating propellant manufacturing wastewater. DNT biotransformation in the presence and absence of oxygen was mostly reductive and was representative of the type of cometabolic transformations that occur when a high concentration of an easily degradable carbon source is present. P. aeruginosa reduced both nitro groups on DNT, with the formation of mainly 4-amino-2-nitrotoluene and 2-amino-4-nitrotoluene and small quantities of 2,4-diaminotoluene. Acetylation of the arylamines was a significant reaction. 4-Acetamide-2-nitrotoluene and the novel compounds 2-acetamide-4-nitrotoluene, 4-acetamide-2-aminotoluene, and 2,4-diacetamidetoluene were identified as DNT metabolites. The biotransformation of 2,4-diaminotoluene to 4-acetamide-2-aminotoluene was 24 times faster than abiotic transformation. 2-Nitrotoluene and 4-nitrotoluene were also reduced to their corresponding toluidines and then acetylated. However, the yield of 4-acetamidetoluene was much higher than that of 2-acetamidetoluene, demonstrating that acetylation at the position para to the methyl group was favored. PMID:16535348

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

    PubMed

    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

  2. ACETANILIDE HERBICIDE DEGRADATION PRODUCTS BY LC/MS

    EPA Science Inventory

    Acetanilide herbicides are frequently applied in the U.S. on crops (corn, soybeans, popcorn, etc.) to control broadleaf and annual weeds. The acetanilide and acetamide herbicides currently registered for use in the U.S. are alachlor, acetochlor, metolachlor, propachlor, flufen...

  3. METHOD DEVELOPMENT FOR ALACHLOR ESA AND OTHER ACENTANILIDE HERBICIDE DEGRADATION PRODUCTS

    EPA Science Inventory

    Introduction: Acetanilide herbicides are frequently applied in the U.S. on crops (corn, soybeans, popcorn, etc.) to control broadleaf and annual weeds. The acetanilide and acetamide herbicides currently registered for use in the U.S. are alachlor, acetochlor, metolachlor, propa...

  4. Synthesis of carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives as new potential PET tracers for imaging of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1).

    PubMed

    Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang

    2016-03-01

    The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[(11)C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[(11)C]4a) and N-(4-[(11)C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[(11)C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[(11)C]methoxy-4-methoxyphenyl)acetamide (3-[(11)C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[(11)C]methoxy-3-methoxyphenyl)acetamide (4-[(11)C]8a), were prepared by O-[(11)C]methylation of their corresponding precursors with [(11)C]CH3OTf under basic condition (2N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [(11)C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555GBq/μmol. PMID:26856922

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

    PubMed

    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. METHOD 535: MEASUREMENT OF CHLOROACETANILIDE AND CHLOROACETAMIDE HERBICIDE DEGRADATES IN DRINKING WATER BY SOLID PHASE EXTRACTION AND LIQUID CHROMATOGRAPHY/TANDEM MASS SPECTROMETRY (LC/MS/MS)

    EPA Science Inventory

    Over the past several years, ethanesulfonic acid (ESA) and oxanilic acid (OA) degradation products of acetanilide/acetamide herbicides have been found in U.S. ground waters and surface waters. The substitution of the sulfonic acid or the carbonic acid for the chlorine atom great...

  7. Comparative metabolism of chloroacetamide herbicides and selected metabolites in human and rat liver microsomes.

    PubMed Central

    Coleman, S; Linderman, R; Hodgson, E; Rose, R L

    2000-01-01

    Acetochlor [2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide], alachlor [N-(methoxymethyl)-2-chloro-N-(2, 6-diethyl-phenyl)acetamide], butachlor [N-(butoxymethyl)-2-chloro-N-(2,6-diethyl-phenyl)acetamide], and metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] are pre-emergent herbicides used in the production of agricultural crops. These herbicides are carcinogenic in rats: acetochlor and alachlor cause tumors in the nasal turbinates, butachlor causes stomach tumors, and metolachlor causes liver tumors. It has been suggested that the carcinogenicity of these compounds involves a complex metabolic activation pathway leading to a DNA-reactive dialkylbenzoquinone imine. Important intermediates in this pathway are 2-chloro-N-(2,6-diethylphenyl)acetamide (CDEPA) produced from alachlor and butachlor and 2-chloro-N-(2-methyl-6-ethylphenyl)acetamide (CMEPA) produced from acetochlor and metolachlor. Subsequent metabolism of CDEPA and CMEPA produces 2,6-diethylaniline (DEA) and 2-methyl-6-ethylaniline (MEA), which are bioactivated through para-hydroxylation and subsequent oxidation to the proposed carcinogenic product dialkylbenzoquinone imine. The current study extends our earlier studies with alachlor and demonstrates that rat liver microsomes metabolize acetochlor and metolachlor to CMEPA (0.065 nmol/min/mg and 0.0133 nmol/min/mg, respectively), whereas human liver microsomes can metabolize only acetochlor to CMEPA (0.023 nmol/min/mg). Butachlor is metabolized to CDEPA to a much greater extent by rat liver microsomes (0.045 nmol/min/mg) than by human liver microsomes (< 0.001 nmol/min/mg). We have determined that both rat and human livers metabolize both CMEPA to MEA (0.308 nmol/min/mg and 0.541 nmol/min/mg, respectively) and CDEPA to DEA (0.350 nmol/min/mg and 0.841 nmol/min/mg, respectively). We have shown that both rat and human liver microsomes metabolize MEA (0.035 nmol/min/mg and 0.069 nmol/min/mg, respectively

  8. The biochemical pathway for the breakdown of methyl cyanide (acetonitrile) in bacteria.

    PubMed Central

    Firmin, J L; Gray, D O

    1976-01-01

    [2-14C]Methyl cyanide (acetonitrile) is metabolized to citrate, succinate, fumarate, malate, glutamate, pyrrolidonecarboxylic acid and aspartate. Non-radioactive acetamide and acetate compete with 14C from methyl cyanide, and [2-14C]acetate and [2-14C]methyl cyanide are metabolized at similar rates, giving identical products. This evidence, combined with the inhibitory effect of fluoroacetate and arsenite on methyl cyanide metabolism, indicates that the pathway is: methyl cyanide leads to acetamide leads to acetate leads to tricarboxylic acid-cycle intermediates. The pathway was investigated in a species of Pseudomonas (group III; N.C.I.B. 10477), but comparison of labelling patterns suggests that it also exists in several higher plants. PMID:985423

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

    PubMed

    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

  10. Crystal structure of 2-(4-acetyl­anilino)-2-oxoethyl 3-(4-hy­droxy­phen­yl)propionate

    PubMed Central

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

    2016-01-01

    In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms. The 4-hy­droxy­hydro­cinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12). The N—(C=O)—C plane of the acetamide group and the acetate O—(C=O)—C plane are almost co-planar; the acetamide plane makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the acetate planes of the major and minor occupancy components. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a supra­molecular sheet structure parallel to (102). PMID:27555934

  11. Aqua­[N-(1-naphth­yl)acetamido-κN]bis­[2-(2-pyrid­yl)phenyl-κ2 N,C 1]iridium(III) ethyl­ene glycol hemisolvate

    PubMed Central

    Fu, Hao; Ding, Yuqiang; Chen, Guoqing

    2008-01-01

    In the title compound, [Ir(C11H8N)2(C12H10NO)(H2O)]·0.5C2H6O2, the iridium center is coordinated by two N atoms and two C atoms from two 2-(2-pyrid­yl)phenyl (ppy) ligands, one N atom from the N-(1-naphth­yl)acetamide ligand and one water O atom, forming a distorted octa­hedral environment. Mol­ecules are linked by inter­molecular O—H⋯O hydrogen bonds formed by the coordinated water mol­ecule and the amide O atom of the N-(1-naphth­yl)acetamide ligands. PMID:21202254

  12. Radiolysis of paracetamol in dilute aqueous solution

    NASA Astrophysics Data System (ADS)

    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.

  13. Synthetic approaches to multifunctional indenes

    PubMed Central

    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

  14. Crystal structure of 2-(4-acetyl-anilino)-2-oxoethyl 3-(4-hy-droxy-phen-yl)propionate.

    PubMed

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

    2016-07-01

    In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms. The 4-hy-droxy-hydro-cinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12). The N-(C=O)-C plane of the acetamide group and the acetate O-(C=O)-C plane are almost co-planar; the acetamide plane makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the acetate planes of the major and minor occupancy components. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular sheet structure parallel to (102). PMID:27555934

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

    PubMed

    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

  16. Tough, Soluble, Aromatic, Thermoplastic Copolyimides

    NASA Technical Reports Server (NTRS)

    Bryant, Robert G. (Inventor)

    1998-01-01

    Tough, soluble, aromatic, thermoplastic copolyimides were prepared by reacting 4,4'-oxydiphthalic anhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydianiline. These copolyimides were found to be soluble in common amide solvents such as N,N'-dimethyl acetamide, N-methylpyrrolidinone, and dimethylformamide allowing them to be applied as the fully imidized copolymer and to be used to prepare a wide range of articles.

  17. Scaffold hopping: exploration of acetanilide-containing uracil analogues as potential NNRTIs.

    PubMed

    Babkov, Denis A; Valuev-Elliston, Vladimir T; Paramonova, Maria P; Ozerov, Alexander A; Ivanov, Alexander V; Chizhov, Alexander O; Khandazhinskaya, Anastasia L; Kochetkov, Sergey N; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe; Seley-Radtke, Katherine L; Novikov, Mikhail S

    2015-03-01

    In order to identify novel nonnucleoside inhibitors of HIV-1 reverse transcriptase two series of amide-containing uracil derivatives were designed as hybrids of two scaffolds of previously reported inhibitors. Subsequent biological evaluation confirmed acetamide uracil derivatives 15a-k as selective micromolar NNRTIs with a first generation-like resistance profile. Molecular modeling of the most active compounds 15c and 15i was employed to provide insight on their inhibitory properties and direct future design efforts. PMID:25638501

  18. Spectroscopy of the amide-I modes of acetanilide

    SciTech Connect

    Bigio, I.J.; Scott, A.C.; Johnston, C.T.

    1989-01-01

    Raman measurements were made on acetanilide (N-phenyl-acetamide). Data are presented of the integrated intensity of the 1650 cm/sup /minus/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.

  19. Synthesis of protein tyrosine phosphatase 1B inhibitors: model validation and docking studies.

    PubMed

    Saxena, Anil K; Pandey, Gyanendra; Gupta, Swati; Singh, Amar Bahadur; Srivastava, Arvind K

    2009-04-15

    The designed and synthesized 2-(4-methoxyphenyl) ethyl] acetamide derivatives (3a, 3b and 3c) were evaluated for their PTP1B inhibitory activity where they showed IC(50) values 69 microM, 87 microM and 71 microM, respectively. These results correlated well with the docking studies and in vivo screening of the compounds for their antidiabetic activity in SLM and STZ models. PMID:19282172

  20. Design and synthesis of a novel, orally active, brain penetrant, tri-substituted thiophene based JNK inhibitor

    SciTech Connect

    Bowers, Simeon; Truong, Anh P.; Neitz, R. Jeffrey; Neitzel, Martin; Probst, Gary D.; Hom, Roy K.; Peterson, Brian; Galemmo, Jr., Robert A.; Konradi, Andrei W.; Sham, Hing L.; Tóth, Gergley; Pan, Hu; Yao, Nanhua; Artis, Dean R.; Brigham, Elizabeth F.; Quinn, Kevin P.; Sauer, John-Michael; Powell, Kyle; Ruslim, Lany; Ren, Zhao; Bard, Frédérique; Yednock, Ted A.; Griswold-Prenner, Irene

    2012-02-28

    The SAR of a series of tri-substituted thiophene JNK3 inhibitors is described. By optimizing both the N-aryl acetamide region of the inhibitor and the 4-position of the thiophene we obtained single digit nanomolar compounds, such as 47, which demonstrated an in vivo effect on JNK activity when dosed orally in our kainic acid mouse model as measured by phospho-c-jun reduction.

  1. THE AMPHOTERIC PROPERTIES OF SOME AMINO-ACIDS AND PEPTIDES.

    PubMed

    Eckweiler, H; Noyes, H M; Falk, K G

    1921-01-20

    The titration curves of solutions of glycine, alanine, alpha-ammo-butyric acid, leucine, glycyl-glycine, alanyl-glycine, alanyl-alanine, acetone, acetamide, urea, acetic acid, and aceturic acid were determined and some of the relations as dependent upon the chemical structures discussed. The isoelectric points of some of the amphoteric electrolytes were found experimentally. The definition of isoelectric point, its theoretical significance, and method of calculation were considered in some detail. PMID:19871865

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

    PubMed

    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. Chemistry and toxicology of quinoxaline, organotin, organofluorine, and formamidine acaricides.

    PubMed Central

    Knowles, C O

    1976-01-01

    Quinoxaline, organotin, organofluorine, and formamidine compounds are among the newer pesticide chemicals used for acarine control. Included in these four classes are some of the most selective synthetic organic toxicants currently in the acaricide/insecticide arsenal. Oxythioquinox, Plictran (tricyclohexylhydroxytin), Nissol [2-fluoro-N-methyl-N-(1-naphthyl)acetamide], and chlordimeform are examples of quinoxaline, organotin, organofluorine, and formamidine acaricides, respectively. The chemistry and toxicology of these and related compounds are discussed. PMID:789072

  4. Graphite-supported perchloric acid (HClO4-C): an efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols.

    PubMed

    Lei, Zhen-Kai; Xiao, Li; Lu, Xiao-Quan; Huang, He; Liu, Chen-Jiang

    2013-01-01

    An efficient and direct protocol for the preparation of amidoalkylnaphthols employing a multi-component, one-pot condensation reaction of 2-naphthol, aromatic aldehydes and acetamide or benzamide in the presence of graphite supported perchloric acid under solvent-free conditions is described. The thermal solvent-free procedure offers advantages such as simple work-up, shorter reaction times and higher product yields, and the catalyst exhibited remarkable reactivity and can be recycled. PMID:23358323

  5. Extraction and spectrophotometric determination of molybdenum with thiocyanate and amides

    SciTech Connect

    Patel, K.S.; Khatri, H.; Mishra, K.

    1983-09-01

    The organic solution of commonly available amides (HAL), such as N-phenylacetamide, N-(methylphenyl) acetamide, N-(dimethylphenyl)acetamide, N-(diethylphenyl)acetamide, N-phenylpropionamide, N-phenylbutramide, and benzamide, is capable of extracting Mo(V) from SCN/sup -/ solutions. Mo(VI) was reduced to Mo(V) with mild reducing agents and allowed to react with SCN/sup -/ in strongly acidic media. The species formed was extracted with a benzene solution of amide dimers as a mixed-ligand complex. The special advantage of the method is that the HAL has good chemical stability with a very simple method of preparation. Moreover, it eliminates most of the drawbacks of established methods, such as interference from metal ions, variation of color intensity of the complex with respect to amounts of reagents, or prolonged extraction of the metal. The effect of various acids in the extraction of the metal was studied, as well as the effect of diverse ions in the determination of Mo. The ions and their tolerated amounts causing an error <2% are reported. The present method was accurately applied to ore, alloy steels, and synthetic matrices. 19 references, 3 figures, 2 tables.

  6. How does lithium oxalyldifluoroborate enable the compatibility of ionic liquids and carbon-based capacitors?

    NASA Astrophysics Data System (ADS)

    Chen, Renjie; Chen, Yan; Xu, Bin; Zhang, Rong; He, Zhouying; Wu, Feng; Li, Li

    2015-02-01

    Lithium oxalyldifluoroborate (LiODFB) has several unique characteristics, such as high ionic conductivity over a wide temperature range and the ability to form and stabilize solid electrolyte interface films on graphite surfaces. A series of binary, room-temperature, molten electrolytes composed of LiODFB and organic compounds with acylamino groups (acetamide, oxazolidinone or OZO) have been synthesized. Fourier-transform infrared (FT-IR) spectroscopy indicates that Cdbnd O and N-H functional groups undergo blue or red shifts upon addition of LiODFB. The electrolytes have excellent thermal stabilities and electrochemical characteristics that allow them to be promising electrolytes for electrochemical double layer capacitors (EDLCs). Here, we examine 1:5 molar ratio LiODFB and acetamide/OZO ionic liquid (IL) electrolytes in EDLCs. IL compatibility with two types of carbon-based electrodes is investigated theoretically and experimentally. We simulate possible structures and ion diameters for the ILs, which must be compatible with pore sizes of the carbon electrodes. Mesoporous activated carbon AC2, with a pore size similar to the ionic diameter of LiODFB-acetamide, has a specific capacitance of 154.2 Fg-1 at 20 m Ag-1. Additionally, typical capacitive and reversibility behaviors can be seen in the charge-discharge curves over 0-2 V. Finally, the EDLCs exhibit good charging/discharging performances.

  7. New analytical reagents for the determination of sulfur dioxide and carbon monoxide

    SciTech Connect

    Trump, E.L.

    1987-01-01

    Four solid reagent methods were developed for the determination of sulfur dioxide in air, and one method was developed to measure carbon monoxide. When applied to filter paper with acetamide as the humectant and 4-phenylcyclohexanone as a bisulfite absorbent, oxohydroxybis(8-hydroxyquinolinyl-) vanadium (V) changes from yellow to black in the presence of sulfur dioxide. The three other methods, also on a filter paper support, utilized the reduction of bromate to bromine which then changed 3-,3'-, 5-,5'-tetramethylbenzidine from yellow to blue, phenothiazine from white to green, and 4-dimethylamino-4'-,4/double prime/-dimethoxytriphenylmethanol from colorless to red-purple. Quantitative measurements were made by reflectance spectroscopy. The method for carbon monoxide involved the use of tetrakis (acetamide-) Pd(II) ditetrafluoroborate, sodium iodate, and leuco crystal violet all together on a filter paper support. Carbon monoxide reduced the Pd(II)-acetamide complex to metallic palladium. The metallic palladium then reduced iodate to hypoiodous acid, HOI, which, in turn, oxidized leuco crystal violet to crystal violet. The crystal violet color was then measured by reflectance.

  8. New analgesics synthetically derived from the paracetamol metabolite N-(4-hydroxyphenyl)-(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enamide.

    PubMed

    Sinning, Christian; Watzer, Bernhard; Coste, Ovidiu; Nüsing, Rolf M; Ott, Ingo; Ligresti, Alessia; Di Marzo, Vincenzo; Imming, Peter

    2008-12-25

    N-(4-hydroxyphenyl)-(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enamide (AM404) is a metabolite of the well-known analgesic paracetamol. AM404 inhibits endocannabinoid cellular uptake, binds weakly to CB1 and CB2 cannabinoid receptors, and is formed by fatty acid amide hydrolase (FAAH) in vivo. We prepared three derivatives of this new (endo)cannabinoid using bioisosteric replacement (1), homology (2), and derivatization (3) of the 4-aminophenol moiety in AM404 and tested them against CB1, CB2, and FAAH. We found affinities toward both cannabinoid receptors equal to or greater than that of AM404. Shortening the acyl chain from C20 to C2 led to three new paracetamol analogues: N-(1H-indazol-5-yl)acetamide (5), N-(4-hydroxybenzyl)acetamide (6), and N-(4-hydroxy-3-methoxyphenyl)acetamide (7). Again, 5, 6, and 7 were tested against CB1, CB2, and FAAH without significant activity. However, 5 and 7 behaved like inhibitors of cyclooxygenases in whole blood assays. Finally, 5 (50 mg/kg) and 6 (275 mg/kg) displayed analgesic activities comparable to paracetamol (200 mg/kg) in the mouse formalin test. PMID:19053765

  9. Induction of the acetamidase of Aspergillus nidulans by acetate metabolism.

    PubMed

    Hynes, M J

    1977-09-01

    Growth tests and enzyme determinations strongly suggest that the acetamidase of Aspergillus nidulans is induced by a product of acetate metabolism rather than the substrate, acetamide. The cis-dominant mutation, amdI9, which is closely linked to amdS, the structural gene for the acetamidase, results in greatly increased sensitivity to induction by acetate metabolism. Propionate, L-threonine, and ethanol also result in acetamidase induction. Mutations in the facA, facB, and facC genes, which lead to low levels of acetyl-coenzyme A synthase, are epistatic to the amdI9 mutation for strong growth on acetamide medium and abolish acetamide and propionamide induction of the acetamidase and isocitrate lyase enzymes. Acetate, L-threonine, and ethanol, however, can induce these enzymes in strains containing facA and facC lesions but not in strains containing a facB lesion. The evidence suggests that acetamidase and isocitrate lyase may be induced by a similar mechanism. PMID:19418

  10. Thiophene analogues of the carcinogens benzidine and 4-aminobiphenyl: evaluation in vitro.

    PubMed Central

    Ashby, J.; Styles, J. A.; Anderson, D.; Paton, D.

    1978-01-01

    A biologically active molecule with one or more aromatic rings often retains its activity when one of these rings is replaced by an isosteric and/or isoelectronic aromatic ring. Consideration has been given to whether this effect can be expected to apply to aromatic organic carcinogens. The literature relevant to this topic has been reviewed and the thiophene analogues of the carcinogens benzidine and 4-aminobiphenyl have been synthesized and evaluated for potential carcinogenicity. The compounds prepared were 5-p-acetamidophenyl-2-thiophenamine hydrochloride (XIII), 5-phenyl-2-thiophenamine hydrochloride (XIV), N-(5-p-acetamido-phenylthiophen-2-yl)acetamide (XV) and N-(5-phenylthiophen-2-yl)-acetamide (XVI) (see Chart for structures). Each compound was evaluated in the Salmonella reverse-mutation assay of Ames and the cell-transformation assay of Styles. The activity profiles observed for these compounds in vitro were consistent with their known chemistry, and indicate potential carcinogenicity. However, their overall chemical and biological behaviour casts doubt upon whether they would be capable of eliciting tumours in vivo. Because it is important to establish the degree of reliance which can be placed upon in vitro predictions of potential carcinogenicity generated for structurally new compounds, one of the thiophene derivatives, N-(5-phenylthiophen-2-yl)acetamide ((XVI), is currently being evaluated for carcinogenicity in mice. PMID:728339

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

    PubMed

    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

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

    PubMed

    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

  13. Bifurcate localization modes of excess electron in aqueous Ca(2+)amide solution revealed by ab initio molecular dynamics simulation: towards hydrated electron versus hydrated amide anion.

    PubMed

    Zhang, Ru; Bu, Yuxiang

    2016-07-28

    In this work, we conduct ab initio molecular dynamics simulations on the localization dynamics of an excess electron (EE) in acetamide/Ca(2+) aqueous solutions with three different interaction modes of Ca(2+) with acetamide: tight contact, solvent-shared state, and separated interaction. The simulated results reveal that an EE could exhibit two different localization behaviors in these acetamide/Ca(2+) aqueous solutions depending on different amideCa(2+) interactions featuring different contact distances. For the tight contact and solvent-shared state of amideCa(2+) solutions, vertically injected diffuse EEs follow different mechanisms with different dynamics, forming a cavity-shaped hydrated electron or a hydrated amide anion, respectively. Meanwhile, for the separated state, only one localization pattern of a vertically injected diffuse EE towards the formation of hydrated amide anion is observed. The hindrance of hydrated Ca(2+) and the attraction of the hydrated amide group originating from its polarity and low energy π* orbital are the main driving forces. Additionally, different EE localization modes have different effects on the interaction between the amide group and Ca(2+) in turn. This work provides an important basis for further understanding the mechanisms and dynamics of localizations/transfers of radiation-produced EEs and associated EE-induced lesions and damage to biological species in real biological environments or other aqueous solutions. PMID:27351489

  14. Interactions of amino acids, carboxylic acids, and mineral acids with different quinoline derivatives

    NASA Astrophysics Data System (ADS)

    Kalita, Dipjyoti; Deka, Himangshu; Samanta, Shyam Sundar; Guchait, Subrata; Baruah, Jubaraj B.

    2011-03-01

    A series of quinoline containing receptors having amide and ester bonds are synthesized and characterised. The relative binding abilities of these receptors with various amino acids, carboxylic acids and mineral acids are determined by monitoring the changes in fluorescence intensity. Among the receptors bis(2-(quinolin-8-yloxy)ethyl) isophthalate shows fluorescence enhancement on addition of amino acids whereas the other receptors shows fluorescence quenching on addition of amino acids. The receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy) propanamide has higher binding affinity for amino acids. However, the receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide having similar structure do not bind to amino acids. This is attributed to the concave structure of the former which is favoured due to the presence of methyl substituent. The receptor bis(2-(quinolin-8-yloxy)ethyl) isophthalate do not bind to hydroxy carboxylic acids, but is a good receptor for dicarboxylic acids. The crystal structure of bromide and perchlorate salts of receptor 2-bromo-N-(quinolin-8-yl)-propanamide are determined. In both the cases the amide groups are not in the plane of quinoline ring. The structure of N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide, N-(2-methoxyphenethyl)-2-(quinolin-8-yloxy)acetamide and their salts with maleic acid as well as fumaric acid are determined. It is observed that the solid state structures are governed by the double bond geometry of these two acid. Maleic acid forms salt in both the cases, whereas fumaric acid forms either salt or co-crystals.

  15. Enzymatic Characterization of a Prokaryotic Urea Carboxylase

    PubMed Central

    Kanamori, Takeshi; Kanou, Norihisa; Atomi, Haruyuki; Imanaka, Tadayuki

    2004-01-01

    We identified the first prokaryotic urea carboxylase (UCA) from a member of the alpha subclass of the class Proteobacteria, Oleomonas sagaranensis. This enzyme (O. sagaranensis Uca) was composed of 1,171 amino acids, and its N-terminal region resembled the biotin carboxylase domains of various biotin-dependent carboxylases. The C-terminal region of the enzyme harbored the Met-Lys-Met motif found in biotin carboxyl carrier proteins. The primary structure of the enzyme was 45% identical to that of the urea carboxylase domain of urea amidolyase from Saccharomyces cerevisiae. O. sagaranensis Uca did not harbor the allophanate hydrolase domain found in the yeast enzyme, but a separate gene with structural similarity was found to be adjacent to the uca gene. Purified recombinant O. sagaranensis Uca displayed ATP-dependent carboxylase activity towards urea (Vmax = 21.2 μmol mg−1 min−1) but not towards acetyl coenzyme A (acetyl-CoA) and propionyl-CoA, indicating that the gene encoded a bona fide UCA and not an acetyl-CoA or propionyl-CoA carboxylase. The enzyme also exhibited high levels of activity towards acetamide and formamide. Kinetic parameters of the enzyme reaction were determined with ATP, urea, acetamide, and formamide. O. sagaranensis could grow on urea, acetamide, and formamide as sole nitrogen sources; moreover, ATP-dependent urea-degrading activity was found in cells grown with urea but not in cells grown with ammonia. The results suggest that the UCA of this organism may be involved in the assimilation of these compounds as nitrogen sources. Furthermore, orthologues of the O. sagaranensis uca gene were found to be widely distributed among Bacteria. This implies that there are two systems of urea degradation in Bacteria, a pathway catalyzed by the previously described ureases and the UCA-allophanate hydrolase pathway identified in this study. PMID:15090492

  16. Synthesis and psychobiological evaluation of modafinil analogs in mice

    PubMed Central

    2013-01-01

    Background and the purpose of the study Modafinil, a novel wake-promoting agent with low potential for abuse and dependence, has a reliable structure to find some novel derivatives with better activity and lower potential for abuse and risk of dependency. This study was designed to evaluate psychobiological activity of some novel N-aryl modafinil derivatives. Methods Seven novel N-aryl modafinil derivatives were synthesized through three reactions: a) preparation of benzhydrylsulfanyl acetic acid through reaction of benzhydrol with thioglycolic acid, b) formation of desired amide by adding the substituted aniline to activated acid with EDC (1-ethyl-3-(3-dimethyl amino propyl) carbodiimide). This reaction was catalyzed by HOBt (N- hydroxylbenzotriazole), and c) oxidation of sulfur to sulfoxide group with H2O2. Then, their psychobiological effect on the performance of male albino mice were compared to that of modafinil as following: wakefulness by determining the effects of derivatives on phenobarbital-induced loss of the righting reflex (LOPR); exploratory activity by measuring activity in the open field test (OFT); depression by measuring immobility time (IT) during forced swimming test (FST) and the anxiogenic and anxiolytic like effects by using elevated plus-maze test (EPM). All tests were videotaped and analyzed for the frequency and duration of the behaviors during the procedures. Conclusions 2-(Benzhydrylsulfonyl)-N-(4-chlorophenyl)acetamide (4c) showed comparable result in LOPR test. However, all analogs were found to be stimulant except 2-(benzhydrylsulfinyl)-N-phenylacetamide (4a). Also 4c led the most exploratory activity in mice among derivatives. FST results showed that 4a had the longest IT while modafinil, 2-(benzhydrylsulfinyl)-N-(3-chlorophenyl) acetamide (4b) and 2-(benzhydrylsulfinyl)-N-(4-ethylphenyl) acetamide (4d) had the shortest IT. In EPM, all derivatives showed anxiogenic-like behavior since they decreased open arms time and open arms

  17. Elucidation of strain-specific interaction of a GII-4 norovirus with HBGA receptors by site-directed mutagenesis study

    SciTech Connect

    Tan Ming |; Xia Ming; Cao Sheng; Huang Pengwei; Farkas, Tibor |; Meller, Jarek |; Hegde, Rashmi S. |; Li Xuemei; Rao Zihe; Jiang Xi |

    2008-09-30

    Noroviruses interact with histo-blood group antigen (HBGA) receptors in a strain-specific manner probably detecting subtle structural differences in the carbohydrate receptors. The specific recognition of types A and B antigens by various norovirus strains is a typical example. The only difference between the types A and B antigens is the acetamide linked to the terminal galactose of the A but not to the B antigen. The crystal structure of the P dimer of a GII-4 norovirus (VA387) bound to types A and B trisaccharides has elucidated the A/B binding site on the capsid but did not explain the binding specificity of the two antigens. In this study, using site-directed mutagenesis, we have identified three residues on the VA387 capsid that are sterically close to the acetamide and are required for binding to A but not B antigens, indicating that the acetamide determines the binding specificity between the A and B antigens. Further mutational analysis showed that a nearby open cavity may also be involved in binding specificity to HBGAs. In addition, a systematic mutational analysis of residues in and around the binding interface has identified a group of amino acids that are required for binding but do not have direct contact with the carbohydrate antigens, implying that these residues may be involved in the structural integrity of the receptor binding interface. Taken together, our study provides new insights into the carbohydrate/capsid interactions which are a valuable complement to the atomic structures in understanding the virus/host interaction and in the future design of antiviral agents.

  18. Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations.

    PubMed

    An, Yuanyuan; Xia, Hongguang; Wu, Jie

    2016-08-16

    A base-controlled [3+3] cycloaddition reaction of isoquinoline N-oxides with azaoxyallyl cations is developed. 1,11b-dihydro-[1,2,4]oxadiazino[3,2-a]isoquinolin-2(3H)-ones are obtained when isoquinoline N-oxides are treated with α-halohydroxamates in the presence of sodium carbonate, while 2-(isoquinolin-1-yloxy)acetamides are unexpectedly produced when the base is changed to cesium carbonate. This transformation proceeds through an azaoxyallyl cation generated in situ from α-bromohydroxamate, and the [3+3] cycloaddition reaction is the key step for the final outcome. PMID:27484327

  19. Effect of combinations of additives on the performance of lithium ion batteries

    NASA Astrophysics Data System (ADS)

    Santee, Stuart; Xiao, Ang; Yang, Li; Gnanaraj, Joe; Lucht, Brett L.

    Commercial lithium-ion batteries have excellent performance at room temperature for a few years. However, the calendar life and thermal stability (>50 °C) need to be improved for many applications, including electric vehicles. We have conducted an investigation of the effect of thermal stabilizing additives, including dimethyl acetamide, vinylene carbonate, and lithium bis(oxalato) borate, on the performance of lithium ion batteries stored at 70 °C for one month. The reactions of the lithium hexafluorophosphate/carbonate electrolyte, with and without electrolyte additives, with the surface of the electrodes after initial formation cycling have been analyzed via a combination of IR-ATR and XPS.

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

    PubMed

    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

  1. Surface-water-quality assessment of the Yakima River basin, Washington; distribution of pesticides and other organic compounds in water, sediment, and aquatic biota, 1987-91; with a section on dissolved organic carbon in the Yakima River basin

    USGS Publications Warehouse

    Rinella, Joseph F.; McKenzie, Stuart W.; Crawford, J. Kent; Foreman, William T.; Fuhrer, Gregory J.; Morace, Jennifer L.; Aiken, George R.

    1999-01-01

    During 1987-91, chemical data were collected for pesticides and other organic compounds in surface water, streambed sediment, suspended sediment, agricultural soil, and aquatic biota to determine the occurrence, distribution, transport, and fate of organic compounds in the Yakima River basin in Washington. The report describes the chemical and physical properties of the compounds most frequently detected in the water column; organochlorine compounds including DDT, organophosphorus compounds, thiocarbamate and sulfite compounds, acetamide and triazine compounds, and chlorophenoxy-acetic acid and benzoic compounds. Concentrations are evaluated relative to chronic-toxicity water quality criteria and guidelines for the protection of human health and freshwater aquatic life.

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

    NASA Astrophysics Data System (ADS)

    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.

  3. Synthesis, characterization, theoretical prediction of activities and evaluation of biological activities of some sulfacetamide based hydroxytriazenes.

    PubMed

    Agarwal, Shilpa; Baroliya, Prabhat K; Bhargava, Amit; Tripathi, I P; Goswami, A K

    2016-06-15

    Six new N [(4-aminophenyl)sulfonyl]acetamide based hydroxytriazenes have been synthesized and characterized using elemental analysis, IR, 1H NMR, 13C NMR and MASS spectral analysis. Further, their theoretical predictions for probable activities have been taken using PASS (Prediction of Activity Spectra for Substance). Although a number of activities have been predicted but specifically anti-inflammatory, antiradical, anti-diabetic activities have been experimentally validated which proves that theoretical predictions agree with the experimental results. The object of the Letter is to establish Computer Aided Drug Design (CADD) using our compounds. PMID:27136718

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

    NASA Astrophysics Data System (ADS)

    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.

  5. Characterization and identification of gram-negative, nonfermentative bacteria.

    PubMed Central

    Oberhofer, T R; Rowen, J W; Cunningham, G F

    1977-01-01

    The morphological and physiological characteristics of 593 strains of nonfermentative, gram-negative bacteria are described. A battery of 46 tests was used to identify and differentiate strains representing 8 genera and 31 species of named and group-designated bacteria. Seven selected amides and organic salts were closely examined to determine their usefulness, individually or as a battery, in characterizing and identifying the organisms. Of these, allantoin and acetamide showed the most promise in differentiating the more commonly occurring organisms from biochemically similar species. Susceptiblilty patterns to 12 antimicrobics also proved useful in differentiation, especially among atypical strains. PMID:845246

  6. Total Synthesis of Brevisamide Using an Oxiranyl Anion Strategy.

    PubMed

    Sakai, Takeo; Fukuta, Ayumi; Nakamura, Kumiko; Nakano, Masato; Mori, Yuji

    2016-05-01

    A total synthesis of brevisamide, a marine monocyclic ether amide isolated from the dinoflagellate Karenia brevis, has been achieved in 18 steps starting from 4-(benzyloxy)butanol. The synthesis involves oxiranyl anion coupling between an epoxy sulfone and a triflate, intramolecular etherification of a hydroxy-bromoketone, diastereoselective introduction of the axial methyl group by hydroxyl-directed hydrogenation of an exocyclic olefin, and installation of an acetamide side chain by nucleophilic substitution of an N-acetyl carbamate. The dienal side chain is assembled using a Horner-Wadsworth-Emmons reaction to complete the synthesis. PMID:27057586

  7. Synthesis and characteristics of polyarylene ether sulfones

    NASA Technical Reports Server (NTRS)

    Viswanathan, R.; Johnson, B. C.; Ward, T. C.; Mcgrath, J. E.

    1981-01-01

    A method utilizing potassium carbonate/dimethyl acetamide, as base and solvent respectively, was used for the synthesis of several homopolymers and copolymers derived from various bisphenols. It is demonstrated that this method deviates from simple second order kinetics; this deviation being due to the heterogeneous nature of the reaction. Also, it is shown that a liquid induced crystallization process can improve the solvent resistance of these polymers. Finally, a Monte Carlo simulation of the triad distribution of monomers in nonequilibrium copolycondensation is discussed.

  8. Synthesis of Propionamide Pyridine and Pyridine N-oxide Ligands

    SciTech Connect

    Binyamin, Iris; Pailloux, Sylvie; Hay, Benjamin P; Rapko, Brian M; Duesler, Eileen N; Paine, Robert T

    2007-02-01

    A new set of pyridine and pyridine N-oxides functionalized with N,N-dimethylpropionamide pendant groups in the 2- and 2,6-positions have been prepared from the combination of 2-chloromethylpyridine and 2,6-bis(chloromethyl) pyridine with -lithio N,N-dimethyl acetamide. The coordination interaction between 2-(N,N-dimethylpropionamide) pyridine N-oxide (10) and Tb(NO3)3 has been unambiguously defined via single crystal X-ray diffraction analysis of Tb(10)(NO3)3(H2O). Battelle operates PNNL for the USDOE

  9. Alkyl Chlorides as Hydrogen Bond Acceptors

    SciTech Connect

    Nadas, Janos I; Vukovic, Sinisa; Hay, Benjamin

    2012-01-01

    To gain an understanding of the role of an alkyl chloride as a hydrogen bond acceptor, geometries and interaction energies were calculated at the MP2/aug-cc-pVDZ level of theory for complexes between ethyl chloride and representative hydrogen donor groups. The results establish that these donors, which include hydrogen cyanide, methanol, nitrobenzene, pyrrole, acetamide, and N-methylurea, form X-H {hor_ellipsis} Cl hydrogen bonds (X = C, N, O) of weak to moderate strength, with {Delta}E values ranging from -2.8 to -5.3 kcal/mol.

  10. Two-dimensional stimulated resonance Raman spectroscopy of molecules with broadband x-ray pulses

    PubMed Central

    Biggs, Jason D.; Zhang, Yu; Healion, Daniel; Mukamel, Shaul

    2012-01-01

    Expressions for the two-dimensional stimulated x-ray Raman spectroscopy (2D-SXRS) signal obtained using attosecond x-ray pulses are derived. The 1D- and 2D-SXRS signals are calculated for trans-N-methyl acetamide (NMA) with broad bandwidth (181 as, 14.2 eV FWHM) pulses tuned to the oxygen and nitrogen K-edges. Crosspeaks in 2D signals reveal electronic Franck-Condon overlaps between valence orbitals and relaxed orbitals in the presence of the core-hole. PMID:22583220

  11. The two conformers of acetanilide unraveled using LA-MB-FTMW spectroscopy

    NASA Astrophysics Data System (ADS)

    Cabezas, C.; Varela, M.; Caminati, W.; Mata, S.; López, J. C.; Alonso, J. L.

    2011-07-01

    Acetanilide has been investigated by laser ablation molecular beam Fourier transform microwave LA-MB-FTMW spectroscopy. The rotational spectrum of both trans and cis conformers have been analyzed to determine the rotational and 14N quadrupole coupling the constants. The spectrum of the less abundant cis conformer has been assigned for the first time. The doublets observed for this conformer have been interpreted in terms of the tunneling motion between two equivalent non-planar conformations through a small barrier in which the acetamide group and phenyl ring plane are perpendicular. The results are compared with those of the related formanilide.

  12. Lipopolythioureas: a new non-cationic system for gene transfer.

    PubMed

    Leblond, Jeanne; Mignet, Nathalie; Largeau, Céline; Spanedda, Maria-Vittoria; Seguin, Johanne; Scherman, Daniel; Herscovici, Jean

    2007-01-01

    A DNA-transfection protocol has been developed that makes use of thiourea non-cationic synthetic lipid, N-[1,3-bis(carbamothioylamino)propan-2-yl]-2-(dialkycarbamoylmethoxy)acetamide. It was found that these new compounds could be formulated without helper lipid and that the N-decanoyl and N-lauryl derivatives transfected B16 cells in the presence of serum with an efficiency at the same level as cationic lipids, under identical conditions. In vivo transfection using intratumoral injection was also investigated. It was found that compounds 18c and 19 showed an efficiency of the same magnitude as naked DNA and cationic lipid. PMID:17373770

  13. Two Half-Sandwiched Ruthenium (II) Compounds Containing 5-Fluorouracil Derivatives: Synthesis and Study of DNA Intercalation

    PubMed Central

    Li, Zhao-Jun; Hou, Yong; Qin, Da-An; Jin, Zhi-Min; Hu, Mao-Lin

    2015-01-01

    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. PMID:25789618

  14. Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine Sponge Aplysinella strongylata.

    PubMed

    Mándi, Attila; Mudianta, I Wayan; Kurtán, Tibor; Garson, Mary J

    2015-08-28

    The absolute configuration of psammaplysin A (1) has been assigned as (6R,7R) using experimental and calculated electronic circular dichroism (ECD) data and NMR analysis of MPA esters prepared from the acetamide derivative of 1. Detailed conformational analyses of a truncated model compound of 1 with an in vacuo method and with the PCM solvent model for MeOH have identified the major conformers and factors governing the ECD spectrum of 1. The correlation of the ECD data with the stereochemistry of 1 allows configurational assignment of related psammaplysin analogues on the basis of their ECD spectra. PMID:26237370

  15. Oxygen transfer from an intramolecularly coordinated diaryltellurium oxide to acetonitrile. Formation and combined AIM and ELI-D analysis of a novel diaryltellurium acetimidate.

    PubMed

    Mallow, Ole; Bolsinger, Jens; Finke, Pamela; Hesse, Malte; Chen, Yu-Sheng; Duthie, Andrew; Grabowsky, Simon; Luger, Peter; Mebs, Stefan; Beckmann, Jens

    2014-08-01

    The reaction of the intramolecularly coordinated diaryltellurium(IV) oxide (8-Me2NC10H6)2TeO with acetonitrile proceeds with oxygen transfer and gives rise to the formation of the novel zwitterionic diaryltelluronium(IV) acetimidate (8-Me2NC10H6)2TeNC(O)CH3 (1) in 57% yield. Hydrolysis of 1 with hydrochloric acid affords acetamide and the previously known diarylhydroxytelluronium(IV) chloride [(8-Me2NC10H6)2Te(OH)]Cl. PMID:25026100

  16. GABAA receptor pharmacology of fluorinated derivatives of the novel sedative-hypnotic pyrazolopyrimidine indiplon.

    PubMed

    Wegner, Florian; Deuther-Conrad, Winnie; Scheunemann, Matthias; Brust, Peter; Fischer, Steffen; Hiller, Achim; Diekers, Michael; Strecker, Karl; Wohlfarth, Kai; Allgaier, Clemens; Steinbach, Jörg; Hoepping, Alexander

    2008-02-01

    The function of gamma-aminobutyric acid type A receptors (GABA(A) receptors) is enhanced by various clinically important drugs including benzodiazepines that act on an allosteric site formed at the interface between the alpha and gamma subunits. In contrast to classical benzodiazepines, the novel pyrazolopyrimidine indiplon (N-methyl-N-{3-[7-(thiophene-2-carbonyl)-1,5,9-triazabicyclo[4.3.0]nona-2,4,6,8-tetraen-2-yl]phenyl}acetamide; N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidine-7-yl]phenyl}-acetamide) demonstrates relative binding selectivity for the alpha1 subunit containing receptor subtypes, which are the most frequently expressed in the mammalian central nervous system. To investigate the pharmacological properties at GABA(A) receptors and to promote the development of alpha1 subunit selective radiotracers for positron emission tomography imaging, we have started with the evaluation of various fluorinated indiplon derivatives. Binding affinities were determined in homogenates from newborn and adult rats suggesting an alpha1 preference of the reference compounds indiplon, zaleplon as well as for all newly synthesized indiplon derivatives. In homogenated cerebellar tissue obtained from adult rat brain, known to primarily express alpha1 containing GABA(A) receptors, the high affinity of the basic indiplon structure was only slightly affected by an elongation of the alkyl substituent of the amide N from methyl (indiplon; K(i) 3.1 nM) via ethyl (2a, N-(2-fluoro-ethyl)-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidine-7-yl]phenyl}-acetamide; K(i) 5.4 nM) to propyl (2b, N-(3-fluoro-propyl)-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidine-7-yl]phenyl}-acetamide; K(i) 2.4 nM). Whole cell patch-clamp recordings at neuronal and recombinant GABA(A) receptors indicated that the fluorinated derivatives 2a and 2b have a high potency at alpha1beta3gamma2L isoforms comparable to indiplon (EC(50): 105, 158, and 81 nM, respectively), with 2b

  17. Genotoxicity studies with the unstable Zeste-White (UZ) system of Drosophila melanogaster: Results with ten carcinogenic compounds

    SciTech Connect

    Batiste-Alentorn, M.; Xamena, N.; Creus, A.; Marcos, R. )

    1991-01-01

    To increase the number of chemicals tested using the Zeste-White (UZ) somatic mutation assay, ten selected carcinogens (acetamide, acrylamide, benzo({alpha})pyrene, cyclophosphamide, diethylstilbestrol, 4-nitroquinoline N-oxide, propyleneimine, safrole, thiourea, and o-toluidine) have been evaluated in this assay. The results show that all the compounds tested produce significant increases in the eye spot frequency at, at least, one of the concentrations assayed, indicating that the Zeste-White assay appears to be highly sensitive to these carcinogenic compounds. That is in agreement with data previously reported by other authors.

  18. Space thermal control development

    NASA Technical Reports Server (NTRS)

    Hoover, M. J.; Grodzka, P. G.; Oneill, M. J.

    1971-01-01

    The results of experimental investigations on a number of various phase change materials (PCMs) and PCMs in combination with metals and other materials are reported. The evaluations include the following PCM system performance characteristics: PCM and PCM/filler thermal diffusivities, the effects of long-term thermal cycling, PCM-container compatibility, and catalyst effectiveness and stability. Three PCMs demonstrated performance acceptable enough to be considered for use in prototype aluminum thermal control devices. These three PCMs are lithium nitrate trihydrate with zinc hydroxy nitrate catalyst, acetamide, and myristic acid. Of the fillers tested, aluminum honeycomb filler was found to offer the most increase in system thermal diffusivity.

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

    PubMed

    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

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

    NASA Astrophysics Data System (ADS)

    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.

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

    PubMed

    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 (1)H 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. PMID:22925908

  2. Electrochemical reduction of nitrate in the presence of an amide

    DOEpatents

    Dziewinski, Jacek J.; Marczak, Stanislaw

    2002-01-01

    The electrochemical reduction of nitrates in aqueous solutions thereof in the presence of amides to gaseous nitrogen (N.sub.2) is described. Generally, electrochemical reduction of NO.sub.3 proceeds stepwise, from NO.sub.3 to N.sub.2, and subsequently in several consecutive steps to ammonia (NH.sub.3) as a final product. Addition of at least one amide to the solution being electrolyzed suppresses ammonia generation, since suitable amides react with NO.sub.2 to generate N.sub.2. This permits nitrate reduction to gaseous nitrogen to proceed by electrolysis. Suitable amides include urea, sulfamic acid, formamide, and acetamide.

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

    PubMed

    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

  4. Benzimidazole-2-one: A Novel Anchoring Principle For Antagonizing p53-Mdm2

    PubMed Central

    Wang, Wei; Cao, Haiping; Wolf, Siglinde; Camacho-Horvitz, Miguel S.; Holak, Tad A.; Dömling, Alexander

    2013-01-01

    Herein we propose the benzimidazole-2-one substructure as a suitable tryptophan mimic and thus a reasonable starting point for the design of p53 Mdm2 antagonists. We devise a short multicomponent reaction route to hitherto unknown 2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)acetamides by reacting mono N-carbamate protected phenylenediamine in a Ugi-3CR followed by base induced cyclisation. Our preliminary synthesis and screening results are presented here. The finding of the benzimidazolone moiety as a tryptophan replacement in mdm2 is significant as it offers access to novel scaffolds with potentially higher selectivity and potency and improved biological activities. Observing low μM affinities to mdm2 by NMR and fluorescence polarization we conclude that the 2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)acetamide scaffold might be a good starting point to further optimize the affinities to Mdm2. PMID:22789708

  5. The Fps1p aquaglyceroporin facilitates the use of small aliphatic amides as a nitrogen source by amidase-expressing yeasts.

    PubMed

    Shepherd, Andrew; Piper, Peter W

    2010-08-01

    Saccharomyces cerevisiae acquires a resistance to high, toxic levels of acetic acid by destabilizing Fps1p, the plasma membrane aquaglyceroporin through which this acid - in its undissociated state - enters the cell. In this study, Fps1p loss was shown to confer resistances to acetic acid, acrolein and allyl alcohol, not just in S. cerevisiae but also in the osmotolerant spoilage yeast Zygosaccharomyces rouxii. However, in Z. rouxii, the loss of Fps1p severely compromised the use of acetamide and several other small amides as sources of nitrogen, an indication that these amides enter the cells of this yeast by passive diffusion through the Fps1p pore. Saccharomyces cerevisiae cannot grow on acetamide, but was conferred with an ability to use this and other small amides as nitrogen sources by heterologous expression of a Z. rouxii ORF (ZrAMD1) with protein sequence identity to the amdS-encoded amidase of Aspergillus nidulans. This capacity of ZrAMD1-expressing S. cerevisiae to assimilate amide nitrogen was severely compromised by the loss of Fps1p. ZrAMD1 appears to encode the major amidase of Z. rouxii as a Zramd1Delta deletant mutant had, like the Zrfps1Delta deletant, lost the ability to assimilate small amides as sources of nitrogen. PMID:20491941

  6. Amide coordination effects in organolithiums

    SciTech Connect

    Bachrach, S.M.; Ritchie, J.P. )

    1989-04-26

    Organolithiums containing the amide group are examined by ab initio molecular orbital calculations with the 3-21G basis set. Amide coordination with the metal cation results in a large thermodynamic stabilization of the ion pair. Basis set superposition errors at 3-21G are estimated to favor the complex by 10-15 kcal mol{sup {minus}1}; nevertheless, qualitative trends at this level are believed to be reliable. The calculations stabilization energy due to the amide drops off depending upon whether lithiation occurs {alpha}, {beta}, or {gamma} to the amide - provided the cation is accessible to the amide oxygen. Without correction for basis set superposition error, stabilization energies at 3-21G (in kcal mol{sup {minus}1}) are 45 in acetamide, 40 in benzamide, and 38 in syn-bicyclo(1.1.1)-pentane-2-carboxamide. Amide coordination effects in lithiocubanes are also estimated and found to be large. Thus, thermodynamics plays an important role in amide-assisted metalations. In addition, formation of an acetamide-methyllithium complex is found to be 37.5 kcal mol{sup {minus}1} exothermic relative to separated molecules, suggesting that formation of this complex lies along the metalation reaction pathways. This complexation facilitates the reaction kinetically. Analysis of electron density distributions and electrostatic potentials shows that the carbanion-lithium and the amide-lithium interactions are primarily closed-shell ones, being essentially ionic bonds.

  7. A perfusion study of the handling of urea and urea analogues by the gills of the dogfish shark (Squalus acanthias).

    PubMed

    Wood, Chris M; Liew, Hon Jung; De Boeck, Gudrun; Walsh, Patrick J

    2013-01-01

    The branchial mechanism of urea retention in elasmobranchs was investigated using an in vitro isolated-perfused head preparation, as well as in vivo samples, in the spiny dogfish shark. Both in vivo and in control saline perfusions containing 350 mmol L(-1) urea, calculated intracellular urea concentrations in gill epithelial cells were close to extracellular concentrations. Urea efflux to the external water fell only non-significantly, and calculated gill intracellular urea concentration did not change when perfusate urea concentration was reduced from 350 to 175 mmol L(-1) with osmotic compensation by 175 mmol L(-1) mannitol. However, when the urea analogues thiourea or acetamide were present in the perfusate at concentrations equimolar (175 mmol L(-1)) to those of urea (175 mmol L(-1)), urea efflux rates were increased 4-fold and 6.5-fold respectively, and calculated gill intracellular urea concentrations were depressed by about 55%. Analogue efflux rates were similar to urea efflux rates. Previous studies have argued that either the basolateral or apical membranes provided the limiting permeability barrier, and/or that a back-transporter on the basolateral membranes of gill cells is responsible for urea retention. The present results provide new evidence that the apical membrane is the limiting factor in maintaining gill urea impermeability, and raise the prospect that a urea back-transporter, which can be competitively inhibited by thiourea and acetamide, operates at the apical membrane. PMID:23638369

  8. Characterization of Four Bifunctional Plant IAM/PAM-Amidohydrolases Capable of Contributing to Auxin Biosynthesis

    PubMed Central

    Sánchez-Parra, Beatriz; Frerigmann, Henning; Pérez Alonso, Marta-Marina; Carrasco Loba, Víctor; Jost, Ricarda; Hentrich, Mathias; Pollmann, Stephan

    2014-01-01

    Amidases [EC 3.5.1.4] capable of converting indole-3-acetamide (IAM) into the major plant growth hormone indole-3-acetic acid (IAA) are assumed to be involved in auxin de novo biosynthesis. With the emerging amount of genomics data, it was possible to identify over forty proteins with substantial homology to the already characterized amidases from Arabidopsis and tobacco. The observed high conservation of amidase-like proteins throughout the plant kingdom may suggest an important role of theses enzymes in plant development. Here, we report cloning and functional analysis of four, thus far, uncharacterized plant amidases from Oryza sativa, Sorghum bicolor, Medicago truncatula, and Populus trichocarpa. Intriguingly, we were able to demonstrate that the examined amidases are also capable of converting phenyl-2-acetamide (PAM) into phenyl-2-acetic acid (PAA), an auxin endogenous to several plant species including Arabidopsis. Furthermore, we compared the subcellular localization of the enzymes to that of Arabidopsis AMI1, providing further evidence for similar enzymatic functions. Our results point to the presence of a presumably conserved pathway of auxin biosynthesis via IAM, as amidases, both of monocot, and dicot origins, were analyzed. PMID:27135507

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

    PubMed

    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

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

    PubMed

    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

  11. Animal Toxicity of Hairpin Pyrrole-Imidazole Polyamides Varies with the Turn Unit

    PubMed Central

    2013-01-01

    A hairpin pyrrole-imidazole polyamide (1) targeted to the androgen receptor consensus half-site was found to exert antitumor effects against prostate cancer xenografts. A previous animal study showed that 1, which has a chiral amine at the α-position of the γ-aminobutyric acid turn (γ-turn), did not exhibit toxicity at doses less than 10 mg/kg. In the same study, a polyamide with an acetamide at the β-position of the γ-turn resulted in animal morbidity at 2.3 mg/kg. To identify structural motifs that cause animal toxicity, we synthesized polyamides 1–4 with variations at the α- and β-positions in the γ-turn. Weight loss, histopathology, and serum chemistry were analyzed in mice post-treatment. While serum concentration was similar for all four polyamides after injection, dose-limiting liver toxicity was only observed for three polyamides. Polyamide 3, with an α-acetamide, caused no significant evidence of rodent toxicity and retains activity against LNCaP xenografts. PMID:24015881

  12. Bilirubin oxidation products (BOXes): synthesis, stability and chemical characteristics

    PubMed Central

    Wurster, W. L.; Pyne-Geithman, G. J.; Peat, I. R.; Clark, J. F.

    2009-01-01

    Summary Bilirubin oxidation products (BOXes) have been a subject of interest in neurosurgery because they are purported to be involved in subarachnoid hemorrhage induced cerebral vasospasm. There is a growing body of information concerning their putative role in vasospasm; however, there is a dearth of information concerning the chemical and biochemical characteristics of BOXes. A clearer understanding of the synthesis, stability and characteristics of BOXes will be important for a better understanding of the role of BOXes post subarachnoid hemorrhage. We used hydrogen peroxide to oxidize bilirubin and produce BOXes. BOXes were extracted and analyzed using conventional methods such as HPLC and mass spectrometry. Characterization of the stability BOXes demonstrates that light can photodegrade BOXes with a t1/2 of up to 10 h depending upon conditions. Mixed isomers of BOXes have an apparent extinction coefficient of ε = 6985, and a λmax of 310 nm. BOXes are produced by the oxidation of bilirubin, yielding a mixture of isomers: 4-methyl-5-oxo-3-vinyl-(1,5-dihydropyrrol-2-ylidene)acetamide (BOX A) and 3-methyl-5-oxo-4-vinyl-(1,5-dihydropyrrol-2-ylidene)acetamide (BOX B). The BOXes are photodegraded by ambient light and can be analyzed spectrophotometrically with their extinction coefficient as well as with HPLC or mass spectrometry. Their small molecular weight and photodegradation may have made them difficult to characterize in previous studies. PMID:18456996

  13. Defining the Structural Parameters that Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2- Amino-3-methylbutanamide

    PubMed Central

    King, Amber; De Ryck, Marc; Kaminski, Rafal; Valade, Anne; Stables, James P.; Kohn, Harold

    2011-01-01

    Primary Amino Acid Derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to Functionalized Amino Acids (FAAs) (N′-benzyl 2- substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogs of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s). PMID:21861466

  14. Key role of intramolecular metal chelation and hydrogen bonding in the cobalt-mediated radical polymerization of N-vinyl amides.

    PubMed

    Debuigne, Antoine; Morin, Aurélie N; Kermagoret, Anthony; Piette, Yasmine; Detrembleur, Christophe; Jérôme, Christine; Poli, Rinaldo

    2012-10-01

    This work reveals the preponderance of an intramolecular metal chelation phenomenon in a controlled radical polymerization system involving the reversible trapping of the radical chains by a cobalt complex bis(acetylacetonato)cobalt(II). The cobalt-mediated radical polymerization (CMRP) of a series of N-vinyl amides was considered with the aim of studying the effect of the cobalt chelation by the amide moiety of the last monomer unit of the chain. The latter reinforces the cobalt-polymer bond in the order N-vinylpyrrolidoneacetamide, and is responsible for the optimal control of the polymerizations observed for the last two monomers. Such a double linkage between the controlling agent and the polymer, through a covalent bond and a dative bond, is unique in the field of controlled radical polymerization and represents a powerful opportunity to fine tune the equilibrium between latent and free radicals. Possible hydrogen bond formation is also taken into account in the case of N-vinyl acetamide and N-vinyl formamide. These results are essential for understanding the factors influencing Co-C bond strength in general, and the CMRP mechanism in particular, but also for developing a powerful platform for the synthesis of new precision poly(N-vinyl amide) materials, which are an important class of polymers that sustain numerous applications today. PMID:22907863

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

    NASA Astrophysics Data System (ADS)

    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.

  16. Synthesis, antitumor activity and molecular docking study of some novel 3-benzyl-4(3H)quinazolinone analogues.

    PubMed

    Al-Suwaidan, Ibrahim A; Abdel-Aziz, Alaa A-M; Shawer, Taghreed Z; Ayyad, Rezk R; Alanazi, Amer M; El-Morsy, Ahmad M; Mohamed, Menshawy A; Abdel-Aziz, Naglaa I; El-Sayed, Magda A-A; El-Azab, Adel S

    2016-01-01

    A novel series of 3-benzyl-substituted-4(3H)-quinazolinones were designed, synthesized and evaluated for their in vitro antitumor activity. The results of this study demonstrated that 2-(3-benzyl-6-methyl-4-oxo-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)acetamide, 2-(3-benzyl-6,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)acetamide and 3-(3-benzyl-6-methyl-4-oxo-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)-propanamide have shown amazing broad spectrum antitumor activity with mean GI(50) (10.47, 7.24 and 14.12 µM. respectively), and are nearly 1.5-3.0-fold more potent compared with the positive control 5-FU with mean GI50, 22.60 µM. On the other hand, compounds 6 and 10 yielded selective activities toward CNS, renal and breast cancer cell lines, whereas compound 9 showed selective activities towards leukemia cell lines. Molecular docking methodology was performed for compounds 7 and 8 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib, while compound 11 into ATP binding site of B-RAF kinase inhibited the growth of melanoma cell lines through inhibition of B-RAF kinase, similar to PLX4032. PMID:25815668

  17. Achromobacter insolitus sp. nov. and Achromobacter spanius sp. nov., from human clinical samples.

    PubMed

    Coenye, Tom; Vancanneyt, Marc; Falsen, Enevold; Swings, Jean; Vandamme, Peter

    2003-11-01

    A polyphasic taxonomic study (employing whole-cell protein and fatty acid analyses, 16S rDNA sequencing, DNA-DNA hybridization, determination of DNA G+C content, antibiotic susceptibility testing and extensive phenotypic characterization) was performed on 10 isolates that appeared to be related to Alcaligenes faecalis. The isolates were recovered from diverse environments that included human clinical samples. 16S rDNA sequence analysis indicated that these isolates belonged to the genus ACHROMOBACTER: Whole-cell protein analysis distinguished two groups, which were confirmed by DNA-DNA hybridization. Based on the results of this study, the organisms were classified as two novel Achromobacter species, Achromobacter insolitus sp. nov. (type strain, LMG 6003(T)) and Achromobacter spanius sp. nov. (type strain, LMG 5911(T)). Achromobacter insolitus can be distinguished from Achromobacter spanius by its ability to grow on acetamide and to assimilate mesaconate and aconitate, and by its inability to assimilate diaminobutane. Various tests allow the differentiation of both novel species from other Achromobacter species, including growth on acetamide, denitrification and assimilation of D-glucose, D-xylose, mesaconate, aconitate and diaminobutane. PMID:14657110

  18. Structural and Spectroscopic Characterizations of Amide-AlCl3-Based Ionic Liquid Analogues.

    PubMed

    Hu, Pengcheng; Zhang, Rui; Meng, Xianghai; Liu, Haiyan; Xu, Chunming; Liu, Zhichang

    2016-03-01

    Several amide-AlCl3-based ionic liquid (IL) analogues were synthesized through a one-step method using three different structure amides as donor molecules. The effects of the steric and inductive effects of the methyl group substituted on the N atom on the asymmetric splitting of AlCl3 and the coordination site of the amide were investigated by (27)Al NMR, Raman, in situ IR, and UV-vis spectra for these IL analogues. Bidentate coordination through both the O and N atoms was dominant in the N-methylacetamide-AlCl3- and N,N-dimethylacetamide-AlCl3-based IL analogues because of the inductive effect of the methyl group. By contrast, the acetamide-AlCl3-based IL analogue presented mainly in the form of monodentate coordination via the O atom. Compared with monodentate coordination, bidentate coordination was favorable to the asymmetric splitting of AlCl3 with the same amide-AlCl3 molar ratio. Under the influence of the steric and inductive effects of the methyl group, the ionic species percentages in these IL analogues ranked in the following order: N-methylacetamide > N,N-dimethylacetamide > acetamide. PMID:26848508

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

    PubMed

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

    2016-01-01

    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 presence of anhydrous potassium carbonate. With very few exceptions, all of the synthesized compounds showed varying antiprolific activities against HepG2, MCF-7, and A549 cell lines. Compound 5a was very similar in potency to doxorubicin as an anticancer drug, with IC50 values 4.1 ± 0.5, 4.1 ± 0.5, and 5.0 ± 0.6 µg/mL versus 4.2 ± 0.5, 4.9 ± 0.6, and 6.1 ± 0.6 µg/mL against HepG2, MCF-7, and A549 cell lines, respectively. In contrast, none of the compounds showed activity against human prostate PC3 cancer cells. Additionally, the sulfoxide derivatives were more potent than the corresponding sulfides. PMID:27110495

  20. Inhibition of metastasis by HEXIM1 through effects on cell invasion and angiogenesis

    PubMed Central

    Ketchart, Wannarasmi; Smith, Kerri M.; Krupka, Tianyi; Wittmann, Bryan M.; Hu, Yanduan; Rayman, Patricia A.; Doughman, Yong Qiu; Albert, Jeffrey M.; Bai, Xiadong; Finke, James H.; Xu, Yan; Exner, Agata A.; Montano, Monica M.

    2012-01-01

    We report on the role of Hexamethylene-bis-acetamide-inducible protein 1 (HEXIM1) as an inhibitor of metastasis. HEXIM1 expression is decreased in human metastatic breast cancers when compared to matched primary breast tumors. Similarly we observed decreased expression of HEXIM1 in lung metastasis when compared to primary mammary tumors in a mouse model of metastatic breast cancer, the Polyoma Middle-T antigen (PyMT) transgenic mouse. Re-expression of HEXIM1 (through transgene expression or localized delivery of a small molecule inducer of HEXIM1 expression, Hexamethylene-bis-acetamide) in PyMT mice resulted in inhibition of metastasis to the lung. Our present studies indicate that HEXIM1 downregulation of HIF-1α protein allows not only for inhibition of VEGF-regulated angiogenesis, but also inhibition of compensatory pro-angiogenic pathways and recruitment of bone marrow derived cells (BMDCs). Another novel finding is that HEXIM1 inhibits cell migration and invasion, that can be partly attributed to decreased membrane localization of the 67kDa laminin receptor, 67LR, and inhibition of the functional interaction of 67LR with laminin. Thus HEXIM1 re-expression in breast cancer has therapeutic advantages by simultaneously targeting more than one pathway involved in angiogenesis and metastasis. Our results also support the potential for HEXIM1 to indirectly act on multiple cell types to suppress metastatic cancer. PMID:22964639

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

    PubMed Central

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

    2016-01-01

    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 presence of anhydrous potassium carbonate. With very few exceptions, all of the synthesized compounds showed varying antiprolific activities against HepG2, MCF-7, and A549 cell lines. Compound 5a was very similar in potency to doxorubicin as an anticancer drug, with IC50 values 4.1 ± 0.5, 4.1 ± 0.5, and 5.0 ± 0.6 µg/mL versus 4.2 ± 0.5, 4.9 ± 0.6, and 6.1 ± 0.6 µg/mL against HepG2, MCF-7, and A549 cell lines, respectively. In contrast, none of the compounds showed activity against human prostate PC3 cancer cells. Additionally, the sulfoxide derivatives were more potent than the corresponding sulfides. PMID:27110495

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

    PubMed

    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. Urine metabolomics in rats after administration of ketamine

    PubMed Central

    Wen, Congcong; Zhang, Meiling; Ma, Jianshe; Hu, Lufeng; Wang, Xianqin; Lin, Guanyang

    2015-01-01

    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. PMID:25678776

  4. Characterization of Two Novel Propachlor Degradation Pathways in Two Species of Soil Bacteria

    PubMed Central

    Martin, Margarita; Mengs, Gerardo; Allende, Jose Luis; Fernandez, Javier; Alonso, Ramon; Ferrer, Estrella

    1999-01-01

    Propachlor (2-chloro-N-isopropylacetanilide) is an acetamide herbicide used in preemergence. In this study, we isolated and characterized a soil bacterium, Acinetobacter strain BEM2, that was able to utilize this herbicide as the sole and limiting carbon source. Identification of the intermediates of propachlor degradation by this strain and characterization of new metabolites in the degradation of propachlor by a previously reported strain of Pseudomonas (PEM1) support two different propachlor degradation pathways. Washed-cell suspensions of strain PEM1 with propachlor accumulated N-isopropylacetanilide, acetanilide, acetamide, and catechol. Pseudomonas strain PEM1 grew on propachlor with a generation time of 3.4 h and a Ks of 0.17 ± 0.04 mM. Acinetobacter strain BEM2 grew on propachlor with a generation time of 3.1 h and a Ks of 0.3 ± 0.07 mM. Incubations with strain BEM2 resulted in accumulation of N-isopropylacetanilide, N-isopropylaniline, isopropylamine, and catechol. Both degradative pathways were inducible, and the principal product of the carbon atoms in the propachlor ring was carbon dioxide. These results and biodegradation experiments with the identified metabolites indicate that metabolism of propachlor by Pseudomonas sp. strain PEM1 proceeds through a different pathway from metabolism by Acinetobacter sp. strain BEM2. PMID:9925619

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

    PubMed

    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 < 0.05). Moreover, N-carbamylglutamate significantly increased the urine levels of creatinine, ethanol, indoxyl sulfate, lactate, methymalonate, acetoacetate, m-hydroxyphenylacetate, and sarcosine, and decreased the urine levels of acetamide, acetate, citrulline, creatine, glycine, hippurate, homogentisate, N-acetylglutamate, phenylacetyglycine, acetone, and p-hydroxyphenylacetate (p < 0.05). Results suggested that 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

  6. Antifibrotic and anticancer action of 5-ene amino/iminothiazolidinones.

    PubMed

    Kaminskyy, Danylo; den Hartog, Gertjan J M; Wojtyra, Magdalena; Lelyukh, Maryan; Gzella, Andrzej; Bast, Aalt; Lesyk, Roman

    2016-04-13

    Here we describe the synthesis and the antifibrotic and anticancer activity determination of amino(imino)thiazolidinone derivatives. An efficient one-pot three-component reaction which involved [2 + 3]-cyclocondensation and Knoevenagel condensation was used for the synthesis of 5-ene-2-amino(imino)-4-thiazolidinones. Following amino-imino tautomerism, the compound structures were confirmed by X-ray analysis. Comparison of SRB assays on fibroblasts and cancer cells revealed that compounds which significantly reduced the viability of fibroblasts did not possess an anticancer effect. A series of thiazolidinone derivatives as interesting candidates for further testing has been identified. Among the tested compounds 2-{3-furan-2-ylmethyl-2-[(2-methyl-3-phenylallylidene)hydrazono]-thiazolidin-4-one-5-yl}-N-(3-trifluoromethylphenyl)-acetamide (5), N-(2-methoxyphenyl)-2-[5-(4-oxothiazolidin-2-ylideneamino)-[1,3,4]thiadiazol-2-ylsulfanyl]-acetamide (12), 3-[3-allyl-4-oxo-2-(thiazol-2-ylimino)thiazolidin-5-ylidene]-1,3-dihydroindol-2-one (33), and 5(Z)-(thiophen-2-ylmethylene)-4-(4-chlorophenylamino)thiazol-2(5H)-one (34) possessed high antifibrotic activity levels, had a similar effect as Pirfenidone, and did not scavenge superoxide radicals. Their antifibrotic potential was confirmed using the xCelligence system. PMID:26896707

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

    PubMed Central

    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 < 0.05). Moreover, N-carbamylglutamate significantly increased the urine levels of creatinine, ethanol, indoxyl sulfate, lactate, methymalonate, acetoacetate, m-hydroxyphenylacetate, and sarcosine, and decreased the urine levels of acetamide, acetate, citrulline, creatine, glycine, hippurate, homogentisate, N-acetylglutamate, phenylacetyglycine, acetone, and p-hydroxyphenylacetate (p < 0.05). Results suggested that 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

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

    PubMed Central

    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) on the thickness of the solvent-filled region of the bilayer was assessed in these bilayers to determine the contribution of this region to the overall barrier. The flux of acetamide was found to vary linearly with bilayer area with Pm = (2.9 +/- 0.3) x 10(-4) cm s-1, after correcting for diffusion through unstirred water layers. The ratio between the overall membrane permeability coefficient and that calculated for diffusion through the hydrocarbon core in membranes having maximum thickness was 0.24, suggesting that the solvent domain contributes only slightly to the overall barrier properties. Consistent with these results, the permeability of acetamide was found to be independent of bilayer thickness. The relative contributions of the bilayer interface and ordered hydrocarbon regions to the transport barrier may be evaluated qualitatively by exploring the effective chemical nature of the barrier microenvironment. This may be probed by comparing functional group contributions to transport with those obtained for partitioning between water and various model bulk solvents ranging in polarity or hydrogen-bonding potential. A novel approach is described for obtaining group contributions to transport using ionizable permeants and pH adjustment. Using this approach, bilayer permeability coefficients of p-toluic acid and p-hydroxymethyl benzoic acid were determined to be 1.1 +/- 0.2 cm s-1 and (1.6 +/- 0.4) x 10(-3) cm s-1, respectively. From these values, the -OH group contribution

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

    PubMed

    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

  10. Herbicides in ground water beneath Nebraska's Management Systems Evaluation Area.

    PubMed

    Spalding, Roy F; Exner, Mary E; Snow, Daniel D; Cassada, David A; Burbach, Mark E; Monson, Stephen J

    2003-01-01

    Profiles of ground water pesticide concentrations beneath the Nebraska Management Systems Evaluation Area (MSEA) describe the effect of 20 yr of pesticide usage on ground water in the central Platte Valley of Nebraska. During the 6-yr (1991-1996) study, 14 pesticides and their transformation products were detected in 7848 ground water samples from the unconfined water table aquifer. Triazine and acetamide herbicides applied on the site and their transformation products had the highest frequencies of detection. Atrazine [6-chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4,-diamine] concentrations decreased with depth and ground water age determined with 3H/3He dating techniques. Assuming equivalent atrazine input during the past 20 yr, the measured average changes in concentration with depth (age) suggest an estimated half-life of >10 yr. Hydrolysis of atrazine and deethylatrazine (DEA; 2-chloro-4-amino-6-isopropylamino-s-triazine) to hydroxyatrazine [6-hydroxy-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine] appeared to be the major degradation route. Aqueous hydroxyatrazine concentrations are governed by sorption on the saturated sediments. Atrazine was detected in the confined Ogallala aquifer in ultra-trace concentrations (0.003 microg L(-1)); however, the possibility of introduction during reverse circulation drilling of these deep wells cannot be eliminated. In fall 1997 sampling, metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] was detected in 57% of the 230 samples. Metolachlor oxanilic acid [(2-ethyl-6-methylphenyl)(2-methoxy-1-methylethyl) amino]oxo-acetic acid] was detected in most samples. In ground water profiles, concentrations of metolachlor ethane sulfonic acid [2-[(ethyl-6-methylphenyl)(2-methoxy-1-methylethyl)amino]-2-oxo-ethanesulfonic acid] exceeded those of deethylatrazine. Alachlor [2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide] was detected in <1% of the samples; however, alachlor