L-proline-catalysed facile green protocol for the synthesis and antimycobacterial evaluation of [1,4]-thiazines.
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.
Indumathi
Sethuraman
S
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai-625021, Tamil Nadu, India.
Perumal
Subbu
S
Banerjee
Debjani
D
Yogeeswari
Perumal
P
Sriram
Dharmarajan
D
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D024901:Drug Resistance, Multiple, Bacterial; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000187:drug effects*; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D011392:Proline / Q000494:pharmacology*; D013843:Thiazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000995:Antitubercular Agents; D013843:Thiazines; D011392:Proline