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Synthesis and Biological Evaluation of New Ibuprofen‐1,3,4‐oxadiazole‐1,2,3‐triazole Hybrids
Author(s) -
Rayam Parsharamulu,
Polkam Naveen,
Kummari Bhaskar,
Banothu Venkanna,
Gandamalla Durgaiah,
Yellu Narsimha Reddy,
Anireddy Jaya Shree
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3409
Subject(s) - oxadiazole , chemistry , thio , thioether , 1,2,3 triazole , hela , antibacterial activity , click chemistry , stereochemistry , combinatorial chemistry , triazole , organic chemistry , in vitro , bacteria , biochemistry , biology , genetics
A new hybrid polydentate template comprising distinctive pharmacophoric groups, namely, ibuprofen, 1,3,4‐oxadiazole, and 1,2,3‐triazole linked through a thioether bridge was achieved by one‐pot synthesis by exploring multicomponent Cu‐catalyzed “click chemistry” approach. The target structures were characterized by NMR, IR, and LC‐Mass. The X‐ray analysis of 2‐(1‐(4‐isobutylphenyl)ethyl)‐5‐(((1‐(3‐nitrophenyl)‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)thio)‐1,3,4‐oxadiazole ( 8a ) confirmed the assigned structure. The in vitro antibacterial and anticancer activity of these compounds revealed that 2‐(1‐(4‐isobutylphenyl)ethyl)‐5‐(((1‐phenyl‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)thio)‐1,3,4‐oxadiazole ( 8b ) demonstrated more potent antibacterial activity against Gram‐negative strains ( Escherichia coli and Pseudomonas aeruginosa ) and 2‐(((1‐(2,4‐dimethylphenyl)‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)thio)‐5‐(1‐(4 isobutylphenyl)ethyl)‐1,3,4‐oxadiazole ( 8e ) exhibited anticancer activity with IC 50 of 27.50 and 31.03 μg/mL against HeLa and MCF‐7 cell lines, respectively.