A novel series of 1,4-disubstituted-1,2,3-triazole derivatives 3a-l and 5a-i were one-pot synthesized via CuAAC-alkyne click chemistry and evaluated for their antibacterial activity against four organisms and screened for their anticancer activity against human colon cancer cell line HT-29 and human lung cancer cell line HTB-29. These hybrid molecules structure elucidation has been performed by IR, 1 H-NMR, 13 C-NMR, and mass spectral analysis. Synthesized nonsteroidal anti-inflammatory drugs-triazoles evaluated for their antibacterial activities against bacterial microorganisms Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Klebsiella pneumonia. Final compounds 3i, 3c, and 5b showed magnificent broad spectrum activity against P. aeruginosa, K. pneumonia, E. coli, and S. aureus with zone of inhibition values of 20, 15, 17, and 16 mm, respectively. Among the series of compound, 3j showed the best antibacterial activity against all the strains. Further, the compounds 3i and 5a were more cytotoxic than cisplatin against all tested two human cancer cell lines, with 50.8%, and 52.3% and 73.4% and 75.3% of growth, respectively. The synthesized compounds were tested for kinase inhibitory activity against glycogen synthase kinase-3 protein kinases, in addition, for cytotoxic activity against two different human cancer cell lines.(1-((5-Chloro-2,3-dihydrobenzo[b]oxepin-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl-2-(6-methoxynaphthalen-2-yl) propanoate (3j). Off white solid. M.P.: 78-80°C. R f : 0.4 (4:1 petroleum ether: ethyl acetate). IR (KBr) ν max /cm