In this study, we synthesized novel benzimidazole-oxadiazole derivatives and assessed their potential as anticancer, antioxidant, antimicrobial activities, and carbonic anhydrase I-II and IX inhibition. Thorough characterization of these compounds was achieved using various spectroscopic techniques such as 1H NMR, 13C NMR, and HRMS. Our findings highlighted the potent anticancer effects of these compounds against glial, colon, and breast cancers while demonstrating low cytotoxicity against normal cells. Compounds 6c, 6d, 6e, and 6f showed promising anticancer activity. According to these results, the compounds potentially with the highest inhibitory is compound 6d for hCA I, and compound 6c for hCA II. The results of hCA IX inhibition with compounds 6h and 6i also showed significant inhibition. According to the antioxidant test, compounds 6c and 6d have an antioxidant power as active as vitamin E. Additionally, our investigation included an analysis of the inhibitory properties of these compounds against various microorganisms. According to the MIC values, no antimicrobial activity was observed in any of these compounds. Compounds 6c and 6d are promising in terms of anticancer, antioxidant, and carbonic anhydrase I, II inhibition when all activities are evaluated. Compounds 6c and 6d exhibited moderate activity in carbonic anhydrase IX. Potential inhibitory compounds were also subjected to in silico screening for molecular docking study, and their ADME properties were examined.