Indian Journal of Chemistry: Sec B- Organic Chemistry including Medicinal Chemistry

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Published by: NISCAIR (CSIR)

Subjects: Chemistry

Indian Journal of Chemistry (Section B) is published by the National Institute of Science Communication and Information Resources (NISCAIR)-CSIR, New Delhi. This journal publishes articles in Organic and Medicinal Chemistry. It includes full length papers, notes and communications and short reviews. The monthly issues covers articles in organic reaction mechanism, theoretical organic chemistry, structure-activity relationships, medicinal chemistry, synthesis of chiral compounds, bio-organic chemistry, enzymes in organic synthesis, reagents in organic synthesis, heterocyclic compounds, phytochemistry (natural products), amino acids, peptides and proteins, spectroscopy in characterization of organic compounds, chemoenzymatic and enantioselective synthesis of organic compounds, synthesis of fullerenes, metal-catalyzed asymmetric reactions, bioactive plant products and combinatorial chemistry.

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Editor,
Dr. P Paravatharajan
email: prema@niscair.res.in


ISSN No. :    0376-4699
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A facile synthesis of 3-hydroxy-N-(4-oxo-2-arylthiazolidin-3-yl)quinoxaline-2-carboxamides and N-(3-chloro-2-oxo-4-arylazetidin-1-yl)-3-hydroxyquinoxaline-2-carboxamides
Title: A facile synthesis of 3-hydroxy-N-(4-oxo-2-arylthiazolidin-3-yl)quinoxaline-2-carboxamides and N-(3-chloro-2-oxo-4-arylazetidin-1-yl)-3-hydroxyquinoxaline-2-carboxamides

Authors: Haripriya, V; Laxminarayana, E; Chary, M Thirumala

Abstract: o-Phenylenediamine reacts with diethylbromo malonate to form ethyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylate 2, which reacts with hydrazinehydrate to form 3-hydroxy-quinoxaline-2-carbohydrazide 3. Compound 3 on condensation with different aromatic aldehydes gives N'-arylidene-3-hydroxyquinoxaline-2-carbohydrazides 4 which is cyclised with chloroacetyl chloride and thioglycolic acid to obtain N-(3-chloro-2-oxo-4-arylazetidin-1-yl)-3-hydroxyquinoxaline-2-carboxamides 5 and 3-hydroxy-N-(4-oxo-2-phenylthiazolidin-3-yl)quinoxaline-2-carboxamides 6 respectively. The structures of these compounds are confirmed by 1H NMR and LC-MS data.

Page(s): 1222-1225

An asymmetric synthesis of Levetiracetam
Title: An asymmetric synthesis of Levetiracetam

Authors: Raju, Veeramalla; Somaiah, Sripathi; Sashikanth, Suthrapu; Laxminarayana, Eppakayala; Mukkanti, Kagga

Abstract: An asymmetric synthesis of (S)-levetiracetam has been developed through application of a Strecker reaction using [(1S)-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of propanaldehyde to a solution of sodium cyanide and [(1S)-1-(4-methoxyphenyl)ethyl]amine hydrochloride in the mixture of methanol and water at 25-30°C afforded diastereomerically pure 2-[2-(4-methoxyphenyl)-(S)-methylethyl-amino]-(S)-butyronitrile hydrochloride compound 4. In this reaction cyanide group attack at less hindered side that is re-face of the imine intermediate gave the diastereomerically pure nitrile 4. Which upon hydrolysis in the presence of 6 M aqueous hydrochloride solution obtained enantiomerically pure (S)-2-aminobutyric acid hydrochloride 5, is a key intermediate for the (S)-levetiracetam. This intermediate further react with SOCl2 in presence of methanol formed S-2-amino methyl butyrate as in situ intermediate which on further ammonalysis in the presence of methnaolic ammonia as a solvent under ammonia pressure provided S-2-amino butyramide hydrochloride 6 which further condensed with 4-chlorobutyryl chloride 7 and followed by cyclization in the presence of potassium hydroxide, dichloromethane solvent used catalytic amount of tetra butyl ammonium bromide afforded crude (S)-levetiracetam 1, further recrystalization in the presence of ethyl acetate obtained pure (S)-levetiracetam 1

Page(s): 1218-1221

Development and validation of LC-MS/MS method for simultaneous quantitation of testosterone, trenbolone, salbutamol and taleranol in chicken muscle
Title: Development and validation of LC-MS/MS method for simultaneous quantitation of testosterone, trenbolone, salbutamol and taleranol in chicken muscle

Authors: Dahiya, Meenakshi; Dubey, Nidhi; Singh, G N

Abstract: A comparatively simple, sensitive and rapid analytical method has been developed and validated to determine the residues of testosterone, trenbolone, salbutamol and taleranol in chicken muscle using LC-MS/MS in positive ionization mode. Two main parameters that are focused for the identification of target compound is retention time and ion ratio. m/z at 289 > 97, 270 > 198, 240 > 148 and 322 > 304 have been taken as quantifier ion and m/z at 289 >109, 270 >226, 240 > 166 and 322 > 286 have been taken as qualifier ion for testosterone, trenbolone, salbutamol and taleranol, respectively. The LOD and LOQ are found to be 0.2 ng/kg and 0.4 ng/kg for testosterone and 0.1μg/kg and 0.2 μg/kg trenbolone, salbutamol, taleranol, respectively which is below the MRL value fixed by Export Inspection Council, Ministry of Commerce and Industry, Govt. of India. Considering the risk of misuse of veterinary drugs and importance of their monitoring, the present method has advantages, such as simple and robust extraction procedure, lesser consumption of organic solvent, shorter run time of 5.0 min, high throughput analysis, precise, the ability to quantify residues at low detection limits in complex matrix and screening of multiple drug residues in a single run with high selectivity and accuracy.

Page(s): 1211-1217

A practical synthetic approach to a trans-cyclohexane-bearing C-glucoside as potent SGLT2 inhibitor
Title: A practical synthetic approach to a trans-cyclohexane-bearing C-glucoside as potent SGLT2 inhibitor

Authors: Zhang, Shuo; Yu, Xiu Ling; Wang, Wen Jin; Wang, Jian Wu; Zhao, Gui Long

Abstract: An improved synthetic approach to a potent SGLT2 inhibitor, 1-deoxy-1-{4-methoxy-3-[(trans-4-n-propylcyclohexyl)methyl]-phenyl}-β-D-glucose 1 has been developed. This facile approach is highlighted by practicality, reproducibility and high yield. Several alternative routes are also investigated and discussed.

Page(s): 1205-1210

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