l-Proline-catalysed facile green protocol for the synthesis and antimycobacterial evaluation of [1,4]-thiazines

European Journal of Medicinal Chemistry
2009.0

Abstract

A series of ethyl 6-(4-chlorobenzoyl)-1,1-dioxo-3,5-diaryl-1,4-thiazinane-2-carboxylates was prepared in good yields (72-90%) from the reaction of ethyl 2-[(2-oxo-2-arylethyl)sulfonyl]acetate, substituted aromatic aldehydes and amines in presence of green catalyst, L-proline. These compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC(2)) using agar dilution method. Ethyl 6-(4-chlorobenzoyl)-3,5-di(4-nitrophenyl)-1,1-dioxo-1,4-thiazinane-2-carboxylate was found to be the most promising compound (MIC: 0.68 microM) active against MTB and MDR-TB.

Knowledge Graph

Similar Paper

l-Proline-catalysed facile green protocol for the synthesis and antimycobacterial evaluation of [1,4]-thiazines
European Journal of Medicinal Chemistry 2009.0
N-Arylalkylbenzo[d]thiazole-2-carboxamides as anti-mycobacterial agents: design, new methods of synthesis and biological evaluation
Med. Chem. Commun. 2014.0
Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents
Bioorganic & Medicinal Chemistry Letters 2016.0
An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles
Bioorganic & Medicinal Chemistry Letters 2007.0
Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio]propionates
Bioorganic & Medicinal Chemistry Letters 2006.0
A green expedient synthesis of pyridopyrimidine-2-thiones and their antitubercular activity
Bioorganic & Medicinal Chemistry Letters 2011.0
Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Part 2
European Journal of Medicinal Chemistry 2012.0
Synthesis and in vitro antimycobacterial activity of 2-methoxybenzanilides and their thioxo analogues
European Journal of Medicinal Chemistry 2012.0
Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents
European Journal of Medicinal Chemistry 2010.0
Antimycobacterial activities of novel 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid
Bioorganic & Medicinal Chemistry 2008.0