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Click Chemistry Approach for Bis‐Chromenyl Triazole Hybrids and Their Antitubercular Activity
Author(s) -
Naik Reshma J.,
Kulkarni Manohar V.,
Sreedhara Ranganath Pai K.,
Nayak Pawan G.
Publication year - 2012
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2012.01441.x
Subject(s) - chemistry , cycloaddition , click chemistry , agarose gel electrophoresis , regioselectivity , 1,2,3 triazole , triazole , stereochemistry , 1,3 dipolar cycloaddition , agarose , cleavage (geology) , mtt assay , gram , combinatorial chemistry , dna , organic chemistry , bacteria , chromatography , biochemistry , in vitro , biology , catalysis , genetics , paleontology , fracture (geology)
1,4‐Disubstituted bis‐chromenyl triazole hybrids 5a – m have been synthesized in a three‐step reaction sequence from 4‐(bromomethyl)‐2 H ‐chromen‐2‐ones 3a – m . The intermediate azides 4a – m underwent a regioselective 1,3‐dipolar cycloaddition with a 2 H ‐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.