Triazole-containing 1,5,6,7-tetrahydro-4H-indazol-4-ones and 6,7-dihydrobenzo[d]isoxazol-4(5H)-ones were synthesized by cyclocondensation of 2-[(1H-1,2,3-triazol-1-yl)acetyl]cyclohexane-1,3-diones with phenylhydrazine (4-fluorophenylhydrazine) or hydroxylamine, respectively. Structure and composition of the obtained compounds were confirmed by 1H, 13C, 19F NMR spectroscopy methods and by data of elemental analysis. Cytotoxic and cytostatic activities of the series of obtained compounds were investigated in vitro against human hepatocellular carcinoma cells HepG2, mammary adenocarcinoma cells MCF-7, and laryngeal cancer cells Hep2.