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Antimycobacterial and phototoxic evaluation of novel 6-fluoro/nitro-4-oxo-7-(sub)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

Murugesan, Dinakaran and Palaniappana, Senthilkumar and Peruma, Yogeeswari and Arnab, China and Valakunja, Nagaraja and Sriram, Dharmarajan (2008) Antimycobacterial and phototoxic evaluation of novel 6-fluoro/nitro-4-oxo-7-(sub)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid. In: International Journal of Antimicrobial Agents, 31 (4). pp. 337-344.

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Several newer 6-fluoro/nitro-4-oxo-7-(sub)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acids (10–11a–q) were synthesised from 3,4-difluoro aniline and 3-fluoro-4-nitro aniline by nine-step synthesis. The compounds were evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multidrug-resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis $(MC^2)$ as well as being tested for their ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the synthesised compounds, 7-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-6-nitro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (11l) was found to be the most active compound in vitro, with minimum inhibitory concentrations (MICs) of 0.09 μM and <0.09 \mu M against MTB and MTR-TB, respectively. Compound 11l was found to be 4 times and >506 times more potent than isoniazid against MTB and MDR-TB, respectively. In the in vivo animal model, 11l decreased the bacterial load in lung and spleen tissues by 30 \% and 42 \%, respectively, at a dose of 50 mg/kg body weight.

Item Type: Journal Article
Publication: International Journal of Antimicrobial Agents
Publisher: Elsevier B.V.
Additional Information: Copyright of this article belongs to Elsevier B.V.
Keywords: Antimycobacterial activity;Antitubercular activity; Tuberculosis;Thiazetoquinolone.
Department/Centre: Division of Biological Sciences > Microbiology & Cell Biology
Date Deposited: 17 Apr 2008
Last Modified: 22 Feb 2012 05:58
URI: http://eprints.iisc.ac.in/id/eprint/13747

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