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Synthesis, antimycobacterial activities and phototoxic evaluation of 5H-thiazolo[3,2-a]quinoline-4-carboxylic acid derivatives

Dinakaran, Murugesan and Senthilkumar, Palaniappan and Yogeeswari, Perumal and China, Arnab and Nagaraja, Valakunja and Sriram, Dharmarajan (2008) Synthesis, antimycobacterial activities and phototoxic evaluation of 5H-thiazolo[3,2-a]quinoline-4-carboxylic acid derivatives. In: Medicinal Chemistry, 4 (5). pp. 482-491.

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Thirty four novel 7-fluoro/nitro-1,2-dihydro-5-oxo-8-(sub)-5H-thiazolo[3,2-a]quinoline-4 carboxylic acids were synthesized from 2,4-dichlorobenzoic acid and 2,4-dichloro-5 fluoroacetophenone by multi step reaction, evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the synthesized compounds, 8-[6-[[(1,1-dimethylethoxy) carbonyl]amino]-3-azabicyclo[3.1.0]hex-3 yl]-1,2-dihydro-7-nitro-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid (10q) was found to be the most active compound in vitro with MIC of 0.08 mu M and < 0.08 mu M against MTB and MDR-TB respectively. Compound 10q was found to be 4.5 and >570 times more potent than isoniazid against MTB and MDR-TB respectively. In the in vivo animal model 10q decreased the bacterial load in lung and spleen tissues with 2.51 and 3.71-log10 protections respectively at the dose of 50 mg/kg body weight.

Item Type: Journal Article
Publication: Medicinal Chemistry
Publisher: Bentham Science Publishers
Additional Information: copyright of this article belongs to publisher
Keywords: antimycobacterial activity; antitubercular activity; tuberculosis; thiazoloquinolone
Department/Centre: Division of Biological Sciences > Microbiology & Cell Biology
Date Deposited: 19 Dec 2008 18:27
Last Modified: 19 Dec 2008 18:27
URI: http://eprints.iisc.ac.in/id/eprint/16465

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