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Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids

Senthilkumar, Palaniappan and Dinakaran, Murugesan and Yogeeswari, Perumal and Sriram, Dharmarajan and China, Arnab and Nagaraja, Valakunja (2009) Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids. In: European Journal of Medicinal Chemistry, 44 (1). pp. 345-358.

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Various 1-(substituted)-1,4-dihydro-6-nitro-4-oxo-7-(sub-secondary amino)-quinoline-3-carboxylic acids were synthesized from 2,4-dichlorobenzoic acid by six step synthesis. The compounds were evaluated for antimycobacterial in vitro and in vivo 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 48 synthesized compounds, 7-(4-((benzo[d][1,3]dioxol-5-yl)methyl)piperazin-1-yl)-1-cyclopropyl -1,4-dihydro-6-nitro-4-oxoquinotine-3-carboxylic acid (8c) was found to be the most active compound in vitro with MIC of 0.08 and 0.16 mu M against MTB and MDR-TB, respectively. In the in vivo animal model 8c decreased the bacterial load in lung and spleen tissues with 2.78 and 4.15-log 10 protections, respectively, at the dose of 50 mg/kg body weight.

Item Type: Journal Article
Publication: European Journal of Medicinal Chemistry
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Nitroquinolones;Quinolones;Antitubercular;Antimycobacterial;Tuberculosis.
Department/Centre: Division of Biological Sciences > Microbiology & Cell Biology
Date Deposited: 30 Oct 2009 10:17
Last Modified: 19 Sep 2010 05:26
URI: http://eprints.iisc.ac.in/id/eprint/19069

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