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Issue 10, 2014
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N-Arylalkylbenzo[d]thiazole-2-carboxamides as anti-mycobacterial agents: design, new methods of synthesis and biological evaluation

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Abstract

Benzothiazole-2-carboxyarylalkylamides are reported as a new class of potent anti-mycobacterial agents. Forty-one target compounds have been synthesized following a green synthetic strategy using water as the reaction medium to construct the benzothiazole scaffold followed by (i) microwave-assisted catalyst-free and (ii) ammonium chloride-catalyzed solvent-free amide coupling. The anti-mycobacterial potency of the compounds was determined against H37Rv strain. Twelve compounds exhibited promising anti-TB activity in the range of 0.78–6.25 μg mL−1 and were found to be non-toxic (<50% inhibition at 50 μg mL−1) to HEK 293T cell lines with therapeutic index (TI) of 8–64. The most promising anti-TB compound 5bf showed MIC of 0.78 μg mL−1 (TI > 64). The molecular docking studies of 5bf predict it to be a ligand for the M. tuberculosis HisG, the putative drug target for tuberculosis and could serve as a guiding principle for lead optimization.

Graphical abstract: N-Arylalkylbenzo[d]thiazole-2-carboxamides as anti-mycobacterial agents: design, new methods of synthesis and biological evaluation

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Publication details

The article was received on 28 May 2014, accepted on 29 Jun 2014 and first published on 30 Jun 2014


Article type: Concise Article
DOI: 10.1039/C4MD00224E
Citation: Med. Chem. Commun., 2014,5, 1489-1495
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    N-Arylalkylbenzo[d]thiazole-2-carboxamides as anti-mycobacterial agents: design, new methods of synthesis and biological evaluation

    P. Shah, T. M. Dhameliya, R. Bansal, M. Nautiyal, D. N. Kommi, P. S. Jadhavar, J. P. Sridevi, P. Yogeeswari, D. Sriram and A. K. Chakraborti, Med. Chem. Commun., 2014, 5, 1489
    DOI: 10.1039/C4MD00224E

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