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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.

A series of regioisomeric (2,5‐dimethoxybenzoic acid, veratric acid) analogues were prepared by swapping the carboxylic motif to its oxadiazole bioisostere and have been screened for in vitro anticancer studies by using MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) colorimetric assay. All of them were well characterized by spectroscopic techniques. Among the screened compounds, 9 i (2‐(2,5‐dimethoxyphenyl)‐5‐(5‐phenylthiophen‐2‐yl)‐1,3,4‐oxadiazole) demonstrated superior activity against MDA231 cells. Products 9 i displayed excellent activity against DU145, HCT15 and 10 i (2‐(3,4‐dimethoxyphenyl)‐5‐(5‐phenylthiophen‐2‐yl)‐1,3,4‐oxadiazole) against MDA231 cells. Structure of 10 c (2‐(3,4‐dimethoxyphenyl)‐5‐(2,4,6‐trimethoxyphenyl)‐1,3,4‐oxadiazole) was further authenticated through single crystal X‐ray diffraction. Analogue 9 i have come out to be the best anticancer and antimycobacterial agent.