In the present study, some isoxazole-(benz)azole derivatives (3a-3j) were synthesized by considering antimicrobial and anticancer potencies of azole compounds. Chemical structures of obtained compounds (3a-3j) were confirmed by the data of spectral and elemental analyses. Anticancer activity evaluation was performed at two steps. Initially, cytotoxic effects of the compounds (3a-3j) on HT-29 (colon carcinoma) and C-6 (melanoma) cell lines were determined by MTT assay. Secondly, the compounds 3g-3i, which indicated significant cytotoxicity were selected and analysed for their inhibitory activity on DNA synthesis of carcinogenic cells. The compounds 3g and 3h showed notable DNA synthesis inhibition on both cancer cell lines. Antibacterial and antifungal activities of the synthesized compounds (3a-3j) were also examined. All of the compounds exhibited very poor antibacterial activity against gram negative and gram positive bacterial strains, whereas antifungal activity of the compounds 3a-3f was equal to that of Ketoconazole.