Synthesis and Biological Evaluation of New Ibuprofen‐1,3,4‐oxadiazole‐1,2,3‐triazole Hybrids

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...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2019-01, Vol.56 (1), p.296-305
Main Authors: Rayam, Parsharamulu, Polkam, Naveen, Kummari, Bhaskar, Banothu, Venkanna, Gandamalla, Durgaiah, Yellu, Narsimha Reddy, Anireddy, Jaya Shree
Format: Article
Language:English
Subjects:
Anticancer properties
Cancer
Chemical synthesis
E coli
Hybrids
Ibuprofen
Infrared radiation
NMR
Nonsteroidal anti-inflammatory drugs
Nuclear magnetic resonance
Organic chemistry
Oxadiazoles
Pharmacology
Pseudomonas aeruginosa
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Summary: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)‐1H‐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‐1H‐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)‐1H‐1,2,3‐triazol‐4‐yl)methyl)thio)‐5‐(1‐(4 isobutylphenyl)ethyl)‐1,3,4‐oxadiazole (8e) exhibited anticancer activity with IC50 of 27.50 and 31.03 μg/mL against HeLa and MCF‐7 cell lines, respectively.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3409