Acetamide

Distribution by Scientific Domains
Distribution within Chemistry

Kinds of Acetamide

  • dimethyl acetamide


  • Selected Abstracts


    ChemInform Abstract: Novel Antitumor Acetamide, Pyrrole, Pyrrolopyrimidine, Thiocyanate, Hydrazone, Pyrazole, Isothiocyanate and Thiophene Derivatives Containing a Biologically Active Pyrazole Moiety.

    CHEMINFORM, Issue 16 2010
    Saleh I. Alqasoumi
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    3-Amino-4-sulfonylpyridinone Acetamide and Related Pyridothiadiazine Thrombin Inhibitors.

    CHEMINFORM, Issue 29 2003
    Philip E. J. Sanderson
    Abstract For Abstract see ChemInform Abstract in Full Text. [source]


    The Titanocene-Catalyzed Reduction of Acetamides to Tertiary Amines by PhMeSiH2.

    CHEMINFORM, Issue 18 2005
    Kumaravel Selvakumar
    No abstract is available for this article. [source]


    ChemInform Abstract: DBU, a Highly Efficient Reagent for the Facile Regeneration of (Hetero)arylamines from Their Acetamides and Benzamides: Influence of Solvent, Temperature, and Microwave Irradiation.

    CHEMINFORM, Issue 25 2002
    Manas Chakrabarty
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]


    Discovery of Indolone Acetamides as Novel SV2A Ligands with Improved Potency Toward Seizure Suppression

    CHEMMEDCHEM, Issue 2 2010
    Anne Frycia
    Capitalizing on the proven clinical efficacy of levetiracetam as an antiepileptic drug, a drug discovery program lead to the identification of a new generation of SV2A ligands with equal or better tolerability profiles than levetiracetam, and improved potency toward seizure suppression in animal models. [source]


    Palatal tremor in childhood: clinical and therapeutic considerations

    DEVELOPMENTAL MEDICINE & CHILD NEUROLOGY, Issue 12 2006
    J Campistol-Plana PhD
    Palatal tremor (PT) is a rhythmic movement of the soft palate that often causes an ear click. PT can be symptomatic (SPT) or essential (EPT). The symptomatic form usually occurs in adults and the essential form mainly occurs in children. Several different treatments for EPT in children appear in the literature with variable reported efficacy. This report details four paediatric patients with EPT (three males, one female; mean age 6y 4mo [SD 6mo]; age at onset 6,7y) treated with piracetam (2-oxo-1-pyrrolidine acetamide). Piracetam was used to treat EPT because of its antimyoclonic properties. All children showed a good response to doses of 100 to 300mg/kg/day. EPT relapsed on withdrawal of piracetam and remitted on reintroduction. Piracetam's effect on EPT was sustained. It is concluded that piracetam is an effective drug for the treatment of EPT in children. [source]


    New Anthraquinone Derivatives as Electrochemical Redox Indicators for the Visualization of the DNA Hybridization Process

    ELECTROANALYSIS, Issue 1 2010
    Agata Kowalczyk
    Abstract Interactions of dsDNA and ssDNA, at the surface of gold and silver electrodes, with three novel anthraquinone derivatives: 3-(9,,10,-dioxo-9,,10,-dihydro-anthracen-1-yl)-7,11-di(carboxymethyl)-3,7,11-triazatridecanedioic acid, (AQ-1); 1-(9,,10,-dioxo-9,,10,-dihydro-anthracen-1yl)-9-carboxymethyl-5-methyl-1,5,9-triazaundecanoicacid, (AQ-2); and N -(2-(9,10-dioxo-9,10-dihydro-anthracen-1-ylamino)ethyl)-2-(1,4,10,13-tetraoxa-7,16-diazacyclooctadecan-7-yl)acetamide, (AQ-3) are studied. These derivatives are well soluble in water and phosphate buffer solutions. The square wave voltammetric behavior of these redox indicators is described and the parameters of interactions with DNA are reported. It is also pointed out that these compounds can be employed as the hybridization indicators. The difference in the binding ability of the particular redox indicator to single and double stranded DNA can be used for the detection of the complementary nucleic acids. [source]


    Voltammetric Detection of Lead(II) Using Amide-Cyclam- Functionalized Silica-Modified Carbon Paste Electrodes

    ELECTROANALYSIS, Issue 15 2009
    Stéphanie Goubert-Renaudin
    Abstract 2-(4,8,11-Triscarbamoylmethyl-1,4,8,11-tetraazacyclotetradec-1-yl)acetamide (TETAM) derivatives bearing 1, 2, or 4 silylated arms have been synthesized and grafted to the surface of silica gel and ordered mesoporous silica samples. The resulting organic-inorganic hybrids have been incorporated into carbon paste electrodes and applied to the preconcentration electroanalysis of Pb(II). The attractive recognition properties of these cyclam derivatives functionalized with amide pendent groups toward Pb(II) species and the highly porous structure of the adsorbents can be exploited for the selective and sensitive detection of the target analyte. Various parameters affecting the preconcentration and detection steps have been discussed with respect to the composition and pH of both accumulation and detection media, the nature of the adsorbent (number of silylated groups linking the macrocycle to silica, texture of materials), the accumulation time, and the presence of interfering cations. Under optimal conditions and for 2,min accumulation at open-circuit, the voltammetric response increased linearly with the Pb(II) concentration in a range extending from 2×10,7 to 10,5,M, while a longer accumulation time of 15,min afforded a linear calibration curve between 10,8 and 10,7,M with a detection limit of 2.7×10,9,M which is well below the European regulatory limit of lead in consumption water. [source]


    Pharmacokinetics of Levetiracetam and Its Enantiomer (R)-,-ethyl-2-oxo-pyrrolidine acetamide in Dogs

    EPILEPSIA, Issue 7 2001
    Nina Isoherranen
    Summary: ,Purpose: The new antiepileptic drug, levetiracetam (LEV, ucb LO59), is a chiral molecule with one asymmetric carbon atom whose anticonvulsant activity is highly enantioselective. The purpose of this study was to evaluate and compare the pharmacokinetics (PK) of LEV [(S)-,-ethyl-2-oxo-pyrrolidine acetamide] and its enantiomer (R)-,-ethyl-2-oxo-pyrrolidine acetamide (REV) after i.v. administration to dogs. This is the first time that the pharmacokinetics of both enantiomers has been evaluated. Methods: Optically pure LEV and REV were synthesized, and 20 mg/kg of individual enantiomers was administered intravenously to six dogs. Plasma and urine samples were collected until 24 h, and the concentrations of LEV and REV were determined by an enantioselective assay. The levels of 2-pyrrolidone- N -butyric acid, an acid metabolite of LEV and REV, were determined by high-performance liquid chromatography (HPLC). The data were used for PK analysis of LEV and REV. Results: LEV and REV had similar mean ± SD values for clearance; 1.5 ± 0.3 ml/min/kg and volume of distribution; 0.5 ± 0.1 L/kg. The half-life (t1/2) and mean residence time (MRT) of REV (t1/2, 4.3 ± 0.8 h, and MRT, 6.0 ± 1.1 h) were, however, significantly longer than those of LEV (t1/2, 3.6 ± 0.8 h, and MRT, 5.0 ± 1.2 h). The renal clearance and fraction excreted unchanged for LEV and REV were significantly different. Conclusions: In addition to the enantioselective pharmacodynamics, ,-ethyl-2-oxo-pyrrolidine acetamide has enantioselective PK. The enantioselectivity was observed in renal clearance. Because REV has more favorable PK in dogs than LEV, the higher antiepileptic potency of LEV is more likely due to intrinsic pharmacodynamic activity rather than to enantioselective PK. [source]


    o -Amine-Assisted Cannizzaro Reaction of Glyoxal with New 2,6-Diaminoanilines

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 14 2009
    Yuhki Irie
    Abstract The preparation of several new o -amine-substituted anilines was achieved according to a new bifunctional molecular design, and their reactions with glyoxal were conducted. Cannizzaro reactions of glyoxal proceeded using specifically designed anilines, such as 2,6-dipyrrolidinyl-, 2,6-dipiperidinyl-, 2,6-dimorpholinyl-, and 2-pyrrolidinyl-aniline, which are new and can easily be synthesized by substitution of halogen-substituted nitrobenzene with amines and subsequent reduction with hydrogen, to form ,-hydroxy acetamide and ,-amino acetamide derivatives, as a result of the Cannizzaro reaction. In comparison with the reaction of glyoxal with p -pyrrolidinylaniline to form a common diimine product, the reaction with o -pyrrolidinylaniline leads only to ,-hydroxy amides, strongly suggesting that the abnormal Cannizzaro reactions are attributed to the existence of basic nitrogen atoms at the o -positions, which suppress diimine formation and assist the generation of acetamides.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]


    Mannich and O -Alkylation Reactions of Tetraalkoxyresorcin[4]arenes , The Use of Some Products in Ligand-Assisted Reactions

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 22 2006
    Benjamin R. Buckley
    Abstract The measurement of the pKa of racemic tetramethoxyresorcin[4]arenes explains the failure to obtain good yields in attempted Mannich reactions of these substrates under classical reaction conditions. The failure is related to the lack of adequate concentrations of the iminium ions that results from the reduced acid strength of tetraalkoxyresorcin[4]arenes compared with that of the parent octahydroxyresorcin[4]arenes. However, the preparation of a series of Mannich bases derived from racemic tetraalkoxyresorcin[4]arenes was accomplished under microwave-assisted aprotic reaction conditions and the use of preformed iminium ion intermediates. When the reactions were carried out with the use of chiral bis(aminol) ethers, mixtures of diastereomers were obtained that could be separated by flash chromatography. The absolute configurations of the enantiomerically pure tetrabenzoxazine derivatives were established in some cases by X-ray crystallographic analysis and by a comparison of the nuclear magnetic resonance spectroscopic data. The alkylation of racemic tetramethoxyresorcin[4]arenes was achieved with the use of an excess of 2-bromo- N -[(R)-(+)-(,-methylbenzyl)]acetamide in acetonitrile containing potassium carbonate. Enantioselective ligand-assisted reactions of aromatic aldehydes are also reported with the use of dialkylzinc reagents both in the absence and in the presence of terminal alkynes.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]


    Biochemical characterization and inhibitor discovery of shikimate dehydrogenase from Helicobacter pylori

    FEBS JOURNAL, Issue 20 2006
    Cong Han
    Shikimate dehydrogenase (SDH) is the fourth enzyme involved in the shikimate pathway. It catalyzes the NADPH-dependent reduction of 3-dehydroshikimate to shikimate, and has been developed as a promising target for the discovery of antimicrobial agent. In this report, we identified a new aroE gene encoding SDH from Helicobacter pylori strain SS1. The recombinant H. pylori shikimate dehydrogenase (HpSDH) was cloned, expressed, and purified in Escherichia coli system. The enzymatic characterization of HpSDH demonstrates its activity with kcat of 7.7 s,1 and Km of 0.148 mm toward shikimate, kcat of 7.1 s,1 and Km of 0.182 mm toward NADP, kcat of 5.2 s,1 and Km of 2.9 mm toward NAD. The optimum pH of the enzyme activity is between 8.0 and 9.0, and the optimum temperature is around 60 °C. Using high throughput screening against our laboratory chemical library, five compounds, curcumin (1), 3-(2-naphthyloxy)-4-oxo-2-(trifluoromethyl)-4H -chromen-7-yl 3-chlorobenzoate (2), butyl 2-{[3-(2-naphthyloxy)-4-oxo-2-(trifluoromethyl)-4H -chromen-7-yl]oxy}propanoate (3), 2-({2-[(2-{[2-(2,3-dimethylanilino)-2-oxoethyl]sulfanyl}-1,3-benzothiazol-6-yl)amino]-2-oxoethyl}sulfanyl)- N -(2-naphthyl)acetamide (4), and maesaquinone diacetate (5) were discovered as HpSDH inhibitors with IC50 values of 15.4, 3.9, 13.4, 2.9, and 3.5 µm, respectively. Further investigation indicates that compounds 1, 2, 3, and 5 demonstrate noncompetitive inhibition pattern, and compound 4 displays competitive inhibition pattern with respect to shikimate. Compounds 1, 4, and 5 display noncompetitive inhibition mode, and compounds 2 and 3 show competitive inhibition mode with respect to NADP. Antibacterial assays demonstrate that compounds 1, 2, and 5 can inhibit the growth of H. pylori with MIC of 16, 16, and 32 µg·mL,1, respectively. This current work is expected to favor better understanding the features of SDH and provide useful information for the development of novel antibiotics to treat H. pylori -associated infection. [source]


    N -[4-(dicyanomethylazo)phenyl]-2-saccharin-2-ylacetamide in the synthesis of pyridazine and pyrimidine derivatives

    HETEROATOM CHEMISTRY, Issue 1 2004
    A. A. Aly
    N -[4-(Dicyanomethylazo)phenyl]-2-saccharin-2-ylacetamide (2) proved to be a convenient precursor for the synthesis of a variety of pyridazine and pyrimidine derivatives 4a,b,6, and 7. Also a series of substituted pyrimidines 10,16 were prepared from the reaction of N -[4-(2-amino-1-cyano-2-substitutedvinylazo)phenyl]-2-(saccharin-2-yl)acetamide 9a,b with different reagents via initial addition to either the cyano or amino group, followed by cyclization. Some of the synthesized heterocycles were screened for their biological activity. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 15:2,8, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10194 [source]


    Reaction of ,-carbonyl substituted 1,3,3-trimethyl-2-methyleneindolines with phosphorus(III) halides

    HETEROATOM CHEMISTRY, Issue 1 2003
    Alexej A. Chekotylo
    The phosphorylation of N -benzoyl-2-(1,3,3-trimethyl-2-methyleneindoline)acetamide (2) and ,-(3-dimethylamino)benzoyl-1,3,3-trimethyl-2-methyleneindoline (6) with phosphorus(III) halides resulted in the formation of 2,3-dihydro-4H -1,5,2-oxazaphosphinin-4-one and 1,2-dihydro-3H -phosphindol-3-one systems, respectively. The properties of the obtained compounds were studied. Further cyclization of 1,2-dihydro-3H -phosphindol-3-one into dihydrophosphindolo[3,2- c]pyrazole was carried out. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:23,28, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10060 [source]


    5-Chloro-3-methylthio-1,2,4-thiadiazol-2-ium chlorides as useful synthetic precursors to a variety of 6a,4 -thiapentalene systems

    HETEROATOM CHEMISTRY, Issue 1 2003
    Georges Morel
    Title salts 3 were easily obtained by treatment of formimidoyl isothiocyanates 1 with a twofold excess of methanesulfenyl chloride. They showed interesting chemical behavior toward several nitrogen and carbon nucleophiles. Substitution reactions with isothioureas and acetamide in the presence of triethylamine gave the 1H, 6H -6a,4 -thia-1,3,4,6-tetraazapentalenes 7 and 6H -6a,4 -thia-1-oxa-3,4,6-triazapentalene 9, respectively. Addition of p -toluidine furnished the 5-imino-thiadiazole derivatives 10, which reacted further with diverse heterocumulenes to yield the corresponding thiatriaza- and tetraazapentalene species 11. The N,N,-bis(1,2,4-thiadiazol-5-ylidene)diaminobenzenes 13 were also prepared and reacted with phenyl isothiocyanate. Two stable rotational isomers were separated for the 1,2-phenylene product 14b. Other ,-hypervalent sulfur compounds 16 were synthesized under similar conditions from salts 3 and methyl cyanoacetate or dimethyl malonate. The structural assignments were discussed on the basis of IR and NMR spectroscopic data and received additional support from X-ray analysis of substrate 16a. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:95,105, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10106 [source]


    Synthesis of N -Acetyl-,-aminobutyric Acid via Amidocarbonylation: A Case Study

    ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 4 2003
    Dirk Gördes
    Abstract The synthesis of N -acetyl-,-aminobutyric acid by amidocarbonylation of propionaldehyde with acetamide in the presence of palladium catalysts is studied in detail. The influence of various reaction conditions and compositions (e.g., the co-catalysts acid and bromide) on the yield of N -acetyl-,-aminobutyric acid is shown. For the first time it is demonstrated that the palladium-catalyzed amidocarbonylations of aldehydes can be run with significantly lower halide concentrations (<30 mol,%) without a major yield decrease. While phosphine-free catalyst systems give best yields at low CO pressure, phosphine-ligated palladium catalysts lead to better yields at higher CO pressure. At low palladium loadings (<0.1 mol,%), unwanted condensation reactions of propionaldehyde become increasingly competitive. [source]


    Compatibility studies with blends based on poly(n -butyl methacrylate) and polyacrylonitrile

    JOURNAL OF APPLIED POLYMER SCIENCE, Issue 6 2010
    Zhaogang Ge
    Abstract In this study, poly(n -butyl methacrylate) (PBMA) was prepared by a suspension polymerization process, and blending with polyacrylonitrile (PAN) in N,N -dimethyl acetamide to prepare PAN/PBMA blends in various proportions. Hansen's three dimensional solubility parameters of PAN and PBMA were calculated approximately through the contributions of the structural groups. The compatibility in these blend systems was studied with theoretical calculations as well as experimental measurements. Viscometric methods, Fourier transform infrared spectroscopy, dynamic mechanical analysis, scanning electron microscopy, and thermogravimetric analysis were used for this investigation. All the results showed that a partial compatibility existed in PAN/PBMA blend system, which may be due to the intermolecular interactions between the two polymers. And, the adsorption experiment results showed that the addition of PBMA contributed to the enhancing adsorptive properties of blend fibers, which lays the foundation for further studying PAN/PBMA blend fibers with adsorptive function. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010 [source]


    Electrospinning of cellulose-based nanofibers

    JOURNAL OF APPLIED POLYMER SCIENCE, Issue 3 2007
    Audrey Frenot
    Abstract Cellulose derivatives of carboxymethyl cellulose sodium salt (CMC), hydroxypropyl methylcellulose (HPMC), methylcellulose (MC), and enzymatically treated cellulose have been electrospun, and the microstructure of the resulting nanofibers has been analyzed by scanning electron microscopy (SEM). Before electrospinning, the solutions were characterized by viscometry and surface tension measurements, and the results were correlated with spinnability. Four different CMC derivatives, varying in molecular weight (Mw), degree of substitution (DS), and substitution pattern, have been electrospun in mixtures with poly(ethylene oxide) (PEO), and nanofibers of various characteristics have formed. The CMC-based nanostructures, i.e., the nonwoven sheet and individual nanofibers, proved to be independent of Mw and DS but largely dependent on the substitution pattern. The nonwoven sheets varied in homogeneity, and beads appeared on the individual fibers. Depending on the chemical nature of the CMC, the extraction of PEO resulted in pure CMC nanostructures of varying appearance, indicating that the distribution of PEO and CMC in the nanofibers also varied. Two different HPMC derivatives, varying in DS, were electrospun into nanofibers. Homogeneous nonwoven sheets based on nanofibers of similar appearance are formed, independent of the substitution content of the HPMC sample. Preliminary fibers were obtained from enzymatically treated cellulose in a solvent system based on lithium chloride dissolved in dimethyl acetamide (LiCl: DMAc). © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 1473,1482, 2007 [source]


    A Kirkwood-Buff derived force field for amides

    JOURNAL OF COMPUTATIONAL CHEMISTRY, Issue 13 2006
    Myungshim Kang
    Abstract A force field for the computer simulation of aqueous solutions of amides is presented. The force field is designed to reproduce the experimentally observed density and Kirkwood,Buff integrals for N -methylacetamide (NMA), allowing for an accurate description of the NMA activity. Other properties such as the translational diffusion constant and heat of mixing are also well reproduced. The force field is then extended to include N,N,-dimethylacetamide and acetamide with good success. Analysis of the simulations of low concentrations of NMA in water indicates a high degree of solvation with only 15% of the NMA molecules involved in solute,solute hydrogen bonding. There is only a weak angular dependence of the solute,solute hydrogen bonding interaction with a minimum at an angle of 65° for the NH and CO dipole vectors. The models presented here provide a basis for an accurate force field for peptides and proteins. © 2006 Wiley Periodicals, Inc. J Comput Chem 27: 1477,1485, 2006 [source]


    Rational determination of charge distributions for free energy calculations

    JOURNAL OF COMPUTATIONAL CHEMISTRY, Issue 4 2003
    Christophe Chipot
    Abstract Point charges derived from RHF/6-31G* electrostatic potentials are attractive because they tend to exaggerate the polarity of solvated molecules, thereby compensating in an average fashion missing induction effects. In the context of free energy calculations, wherein the molecule is transferred from a polar environment to a nonpolar one, we propose a more rational approach based on a self-consistent reaction field computation at a higher level of theory, supplemented by an estimation of the corresponding distortion energy to account for the change of polarity of the surroundings. Application of this method to the test cases acetamide, acetic acid, methyl acetate and phenol, using multinanosecond molecular dynamics/"umbrella sampling" simulations, yields consistent hydration free energies in reasonably good agreement with experiment. © 2003 Wiley Periodicals, Inc. J Comput Chem 24: 409,415, 2003 [source]


    A computationally inexpensive modification of the point dipole electrostatic polarization model for molecular simulations

    JOURNAL OF COMPUTATIONAL CHEMISTRY, Issue 3 2003
    George A. Kaminski
    Abstract We present an approximation, which allows reduction of computational resources needed to explicitly incorporate electrostatic polarization into molecular simulations utilizing empirical force fields. The proposed method is employed to compute three-body energies of molecular complexes with dipolar electrostatic probes, gas-phase dimerization energies, and pure liquid properties for five systems that are important in biophysical and organic simulations,water, methanol, methylamine, methanethiol, and acetamide. In all the cases, the three-body energies agreed with high level ab initio data within 0.07 kcal/mol, dimerization energies,within 0.43 kcal/mol (except for the special case of the CH3SH), and computed heats of vaporization and densities differed from the experimental results by less than 2%. Moreover, because the presented method allows a significant reduction in computational cost, we were able to carry out the liquid-state calculations with Monte Carlo technique. Comparison with the full-scale point dipole method showed that the computational time was reduced by 3.5 to more than 20 times, depending on the system in hand and on the desired level of the full-scale model accuracy, while the difference in energetic results between the full-scale and the presented approximate model was not great in the most cases. Comparison with the nonpolarizable OPLS-AA force field for all the substances involved and with the polarizable POL3 and q90 models for water and methanol, respectively, demonstrates that the presented technique allows reduction of computational cost with no sacrifice of accuracy. We hope that the proposed method will be of benefit to research employing molecular modeling technique in the biophysical and physical organic chemistry areas. © 2003 Wiley Periodicals, Inc. J Comput Chem 24: 267,276, 2003 [source]


    Synthesis of some thiazolyl and thiadiazolyl derivatives of substituted furan and pyrrole

    JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 1 2007
    Seham Y. Hassan
    Four series of substituted furan and pyrrole have been synthesized. The first series was prepared by cyclization of the key intermediates ethyl 5-[(4-substituted thiosemicarbazido)methyl]-2-methylfuran-3-carboxylates 2a-2d and 1-[(4-acetyl-5-methyl-1H -pyrrol-2-yl)methylene]-4-substituted thiosemicarbazides 8a-8d with chloroacetic acid or (ethyl bromoacetate) to afford the corresponding 4-oxo-3-substituted thiazolidin-2-ylidene 3a-3d or 3-substituted thiazolidin-4-one 9a-9d. On the other hand, heating of the intermediates 2a-2d or 8a-8d with acetic anhydride afforded the corresponding (N -substituted acetylamino)-2,3-dihydro-[1,3,4]thiadiazol-2-yl derivatives 4a-4d and [1,3,4]thiadiazol-2-yl- N -substituted acetamide 10a-10d respectively, while cyclization with p -bromophenacyl bromide gave rise to the corresponding 3-substituted thiazol-2-yl-ylidene 5a-5d and 11a-11d respectively. Furthermore, 4-oxo-3-substituted thioureido-thiazolidin-2-yl 6a-6d or 4-oxo-thiazolidin-3-yl-3-substituted thiourea 12a-12d were obtained by reaction of the intermediates 2a-2d or 8a-8d with thioglycolic acid. Some of the synthesized compounds showed promising antimicrobial activities. [source]


    Synthesis and reactions of 3-amino-2-methyl-3H -[1,2,4]triazolo[5,1- b]-quinazolin-9-one and 2-hydrazino-3-phenylamino-3H -quinazolin-4-one

    JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 6 2003
    Mohamed A. Saleh
    The reaction of 3- N -(2-mercapto-4-oxo-4H -quinazolin-3-yl)acetamide (1) with hydrazine hydrate yielded 3-amino-2-methyl-3H -[1,2,4]triazolo[5,1- b]quinazolin-9-one (2). The reaction of 2 with o -chlorobenzaldehyde and 2-hydroxy-naphthaldehyde gave the corresponding 3-arylidene amino derivatives 3 and 4, respectively. Condensation of 2 with 1-nitroso-2-naphthol afforded the corresponding 3-(2-hydroxy-naphthalen-1-yl-diazenyl)-2-methyl-3H -[1,2,4]triazolo[5,1- b]quinazolin-9-one (5), which on subsequent reduction by SnCl2 and HCl gave the hydrazino derivative 6. Reaction of 2 with phenyl isothiocyanate in refluxing ethanol yielded thiourea derivative 7. Ring closure of 7 subsequently cyclized on refluxing with phencyl bromide, oxalyl dichloride and chloroacetic acid afforded the corresponding thiazolidine derivatives 8, 9 and 10, respectively. Reaction of 2-mercapto-3-phenylamino-3H -quinazolin-4-one (11) with hydrazine hydrate afforded 2-hydrazino-3-phenylamino-3H -quinazolin-4-one (12). The reactivity 12 towards carbon disulphide, acetyl acetone and ethyl acetoacetate gave 13, 14 and 15, respectively. Condensation of 12 with isatin afforded 2-[N -(2-oxo-1,2-dihydroindol-3-ylidene)hydrazino]-3-phenylamino-3H -quinazolin-4-one (16). 2-(4-Oxo-3-phenylamino-3,4-dihydroquinazolin-2-ylamino)isoindole-1,3-dione (17) was synthesized by the reaction of 12 with phthalic anhydride. All isolated products were confirmed by their ir, 1H nmr, 13C nmr and mass spectra. [source]


    Synthesis of 2-amino-7,8-dihydro-6(5H)-quinazolinone, 2,4-diamino-7,8-dihydro-6(5H)-quinazolinone, 5,6,7,8-tetrahydro-2,6-quinazoline-diamine and 5,6,7,8-tetrahydro-2,4,6-quinazolinetriamine derivatives

    JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 2 2000
    Petra Marinko
    N -(2-Amino-5,6,7,8-tetrahydro-6-quinazolinyl)acetamide (9) and N -(2,4-diamino-5,6,7,8-tetrahydro-6-quinazolinyl)acetamide (6) were synthesized from N -(4-oxocyclohexyl)acetamide (5) as novel peptidomimetic building blocks. With similar purpose, N -(6-oxo-5,6,7,8-tetrahydro-2-quinazolinyl)acetamide (18) and N -[2-(acetylamino)-6-oxo-5,6,7,8-tetrahydro-4-quinazolinyl]acetamide (14) were prepared from cyclohexane-1,4-dione monoethylene ketal (11). [source]


    Design, synthesis and properties of novel iron(III)-specific fluorescent probes

    JOURNAL OF PHARMACY AND PHARMACOLOGY: AN INTERNATI ONAL JOURNAL OF PHARMACEUTICAL SCIENCE, Issue 4 2004
    Wei Luo
    ABSTRACT Bidentate chelators such as hydroxypyridinones and hydroxypyranones are highly iron selective. The synthesis of two novel fluorescent probes N -[2-(3-hydroxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl]-2-(7-methoxy-2-oxo-2H -chromen-4-yl)acetamide (CP600) and N -[(3-hydroxy-6-methyl-4-oxo-4H -pyran-2-yl)methyl]-2-(7-methoxy-2-oxo-2H -chromen-4-yl)acetamide (CP610) is reported. The method involves coupling the bidentate ligands, 3-hydroxypyridin-4-one and 3-hydroxypyran-4-one, with the well-characterised fluorescent probe methoxycoumarin. Fluorescence emission of both probes at 380 nm is readily quenched by Fe3+. The fluorescence was quenched to a greater extent by Fe3+ than by Mn2+, Co2+, Zn2+, Ca2+, Mg2+, Na+ and K+ and to approximately the same extent as Cu2+. Comparison of the fluorescence-quenching ability by a range of metal ions on CP600 and CP610 and the hexadentate chelator, calcein, under in-vitro conditions, demonstrated advantages of the two novel fluorescent probes with respect to both iron(III) sensitivity and selectivity. Chelation of iron(III) by CP600 and CP610 leads to the formation of a complex with a metal-to-ligand ratio of 1:3. Fluorescence is quenched on formation of such complexes. These probes possess a molecular weight less than 400 and thus they are predicted to permeate biological membranes by passive diffusion, and have potential for reporting intracellular organelle labile iron levels. [source]


    Reactions of 1,2,5-thiadiazole 1,1-dioxide derivatives with nitrogenated nucleophiles.

    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, Issue 4 2003
    1-dioxide, 4-diphenyl-, 5-thiadiazole , Addition of amines, Part , amides to
    Abstract The addition reactions of some amides and aromatic amines to a CN double bond of 3,4-diphenyl-1,2,5-thiadiazole 1,1-dioxide (1) were studied in aprotic solvent solutions [N,N -dimethylformamide (DMF) and acetonitrile (MeCN)]. Equilibrium constants for the reactions of 1 with acetamide, 2-fluoroacetamide, butyramide, benzamide, aniline and 3-aminopyridine were measured using a previously reported cyclic voltammetric (CV) method. Aliphatic amines gave unstable solutions, probably owing to reactions of anionic species derived from 1. Other N nucleophiles tested (formamide, succinimide, thioacetamide and cyanamide) yielded different products that have not yet been characterized. DMF, N,N -dimethylacetamide (DMA) and N -methylacetamide did not react. The addition thiadiazoline produced in the reaction of acetamide with 1 was characterized by IR and 1H and 13C RMN NMR spectroscopy as a prototype compound. For this system, the equilibrium constant could also be measured by a standard UV,VIS method and was found to be in agreement with the value obtained by CV. The reaction of 1 with urea produced a bicyclic product, identified as 3a,6a-diphenyltetrahydroimidazo[4,5- c]-1,2,5-thiadiazol-5-one 2,2-dioxide. Copyright © 2003 John Wiley & Sons, Ltd. [source]


    Synthesis of soluble branched polyimides derived from an ABB, monomer

    JOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 13 2004
    Kun-Li Wang
    Abstract A novel ABB, monomer, an isomeric mixture of 4-[4-(2,4-diaminophenoxy)phenoxy]phthalic acid 2-methyl ester, was successfully prepared. The direct polycondensation of the ABB, monomer was carried out to form polyamic acid monomethyl ester as a precursor with an inherent viscosity of 0.30 dL/g and a number-average molecular weight of 12,000. The degree of branching of the precursor, determined by 1H NMR, was 0.07. The low degree of branching was caused by the differences in the reactivities of the amino groups. The shape factor was calculated to be 0.72. End-modified reactions with acetyl chloride, benzoyl chloride, and phthalic anhydride were carried out. After the chemical imidization of the end-modified precursors, end-modified polyimides were successfully prepared. The end-modified polyimides were soluble in dimethyl sulfoxide, dimethylformamide (DMF), and N -methyl-2-pyrrolidinone. On the basis of thermogravimetry and differential scanning calorimetry measurements of the polyimides, the 5 wt % thermal loss temperatures were determined to be 400,520 °C, and the glass-transition temperatures were determined to be 200,258 °C. According to the X-ray diffraction measurements, the end-modified polyimides were amorphous. A strong but brittle film was prepared from an acetamide end-modified polyimide solution, via casting from a DMF solution, with a tensile strength of 46 MPa, an elongation at break of 4%, and a modulus of 1.3 GPa. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3200,3211, 2004 [source]


    Metabolism of a novel antiangiogenic agent KR-31831 in rats using liquid chromatography-electrospray mass spectrometry

    JOURNAL OF SEPARATION SCIENCE, JSS, Issue 14 2005
    Hui-Hyun Kim
    Abstract KR-31831 ((2S,3R,4S)-4-(((1H-imidazol-2-yl)methyl)(4-chlorophenyl)amino)-6-amino-2-(dimethoxymethyl)-2-methyl-3,4-dihydro-2H-chromen-3-ol) is a novel antiangiogenic agent. In vitro and in vivo metabolism of KR-31831 in rats has been investigated using LC-MS and LC-MS/MS analysis. Incubation of rat liver microsomes and hepatocytes with KR-31831 produced three metabolites (M1,M3). M1, M2, and M3 were identified as N -((1H-imidazol-2-yl)methyl)-4-chlorobenzenamine, (2R,3R,4S)-4-(((1H-imidazol-2-yl)methyl)(4-chlorophenyl) amino)-6-amino-2-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-chromen-3-ol, and N -((2S,3R,4S)-4-(((1H-imidazol-2-yl)methyl)(4-chlorophenyl)amino)-2-(dimethoxymethyl)-3-hydroxy-2-methyl-3,4-dihydro-2H-chromen-6-yl)acetamide, respectively, by co-chromatography with the authentic standards and by comparison with product ion spectra of the authentic standards. Those in vitro metabolites were also detected in bile, plasma, or urine samples after an intravenous administration of KR-31831 to rats. The metabolic routes for KR-31381 included the metabolism of acetal group to hydroxymethyl group (M2), N -dealkylation to M1, and N -acetylation at the 6-amino group (M3). [source]


    Pharmacokinetics of intravenous ceftiofur sodium and concentration in body fluids of foals

    JOURNAL OF VETERINARY PHARMACOLOGY & THERAPEUTICS, Issue 4 2009
    S. MEYER
    The objectives of this study were to determine pharmacokinetics of intravenous (i.v.) ceftiofur in foals, to compare ultra-high performance liquid chromatography tandem mass spectometry (UPLC-MS/MS) and microbiologic assay for the measurement of ceftiofur concentrations, and to determine the minimum inhibitory concentration (MIC) of ceftiofur against common equine bacterial pathogens. In a cross-over design, ceftiofur sodium was administered i.v. to six foals (1,2 days-of-age and 4,5 weeks-of-age) at dosages of 5 and 10 mg/kg. Subsequently, five doses of ceftiofur were administered i.v. to six additional foals between 1 and 5 days of age at a dose of 5 mg/kg q 12 h. Concentrations of desfuroylceftiofur acetamide (DCA), the acetamide derivative of ceftiofur and desfuroylceftiofur-related metabolites were measured in plasma, synovial fluid, urine, and CSF by use of UPLC-MS/MS. A microbiologic assay was used to measure ceftiofur activity for a subset of plasma samples. Following i.v. administration of ceftiofur at a dose of 5 mg/kg to 1,2 day-old foals, DCA had a t˝ of 7.8 ± 0.1 h, a body clearance of 74.4 ± 8.4 mL/h/kg, and an apparent volume of distribution of 0.83 ± 0.09 L/kg. After multiple i.v. doses at 5 mg/kg, DCA concentrations in CSF were significantly lower than concurrent plasma concentrations. Ceftiofur activity using a microbiologic assay significantly underestimated plasma concentrations of DCA. The MIC of ceftiofur required to inhibit growth of 90% of isolates of Escherichia coli, Pasteurella spp, Klebsiella spp, and ,-hemolytic streptococci was <0.5 ,g/mL. Intravenous administration of ceftiofur sodium at the rate of 5 mg/kg every 12 h would provide sufficient coverage for the treatment of susceptible bacterial isolates. [source]


    Comparison of plasma pharmacokinetics and bioequivalence of ceftiofur sodium in cattle after a single intramuscular or subcutaneous injection

    JOURNAL OF VETERINARY PHARMACOLOGY & THERAPEUTICS, Issue 5 2000
    S. A. Brown
    Ceftiofur sodium, a broad-spectrum cephalosporin, is active against gram-positive and gram-negative pathogens of veterinary importance. This study was designed to compare the bioequivalence of the sodium salt in cattle after a single intramuscular (i.m.) or subcutaneous dose (s.c.) of 2.2 mg ceftiofur equivalents/kg body weight. The criteria used to evaluate bioequivalence were (1) the area under the curve from time of injection to the limit of quantitation (LOQ) of the assay (AUC0-LOQ), and (2) time concentrations remained above 0.2 ,g/mL (t>0.2). Twelve crossbred beef cattle were enrolled in a three-period, two-treatment crossover trial, with a minimum 2-week washout period between doses of 2.2 mg ceftiofur equivalents/kg. Blood samples were collected serially for up to 72 h post-injection. Plasma samples were then analyzed using a validated assay that measures ceftiofur, and all desfuroylceftiofur-related metabolites, by high-performance liquid chromatography (HPLC) as the stable derivative, desfuroylceftiofur acetamide. A maximum plasma concentration (Cmax) of 13.9±3.55 ,g/mL was observed from 0.67,2.0 h after i.m. administration, whereas a Cmax of 13.6±3.85 ,g/mL was observed from 0.67,3.0 h after s.c. administration. The AUC0-LOQ was 108±35.0 ,g · h/mL after i.m. dosing, compared with 105±29.8 ,g · h/mL after s.c. dosing. The pre-established criterion for equivalence of the AUC0-LOQ for the i.m. and s.c. routes of administration was satisfied. The t>0.2 was 49.2±8.55 h after i.m. administration, compared with 47.0±9.40 h after s.c. administration. The pre-established criterion for equivalence of the t>0.2 for i.m. and s.c. administration was satisfied. The equivalence of AUC0-LOQ and t>0.2 for i.m. and s.c. administration of 2.2 mg ceftiofur equivalents (CE)/kg doses of ceftiofur sodium suggest similar therapeutic efficacy and systemic safety for the two routes of administration. [source]