1. Click chemistry approach for bis-chromenyl triazole hybrids and their antitubercular activity.
- Author
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Naik RJ, Kulkarni MV, Sreedhara Ranganath Pai K, and Nayak PG
- Subjects
- Anti-Bacterial Agents chemical synthesis, Anti-Bacterial Agents chemistry, Anti-Bacterial Agents pharmacology, Antifungal Agents chemical synthesis, Antifungal Agents chemistry, Antifungal Agents pharmacology, Antitubercular Agents chemical synthesis, Bacteria drug effects, Cell Line, Chromones chemical synthesis, Click Chemistry, Fungi drug effects, Humans, Microbial Sensitivity Tests, Structure-Activity Relationship, Triazoles chemical synthesis, Tuberculosis drug therapy, Antitubercular Agents chemistry, Antitubercular Agents pharmacology, Chromones chemistry, Chromones pharmacology, Mycobacterium tuberculosis drug effects, Triazoles chemistry, Triazoles pharmacology
- Abstract
1,4-Disubstituted bis-chromenyl triazole hybrids 5a-m have been synthesized in a three-step reaction sequence from 4-(bromomethyl)-2H-chromen-2-ones 3a-m. The intermediate azides 4a-m underwent a regioselective 1,3-dipolar cycloaddition with a 2H-chromen-2-one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n-butanol reaction medium. Three compounds 5h-j exhibited 6.25 μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram-positive and Gram-negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay., (© 2012 John Wiley & Sons A/S.)
- Published
- 2012
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