Studies on some new hydrazone compounds

In this thesis, totally 16 hybrid compounds which all of are new including substituted-1,2,3-triazole-arylidenehydrazide (51a-h) and substituted-1,2,3-triazole-4-thiazolidinone (52a-h) derivatives were synthesized starting from 4-hydroxybenzoic acid. Also hydrazide and ester compounds, which are starting molecules for the synthesis of the hybrid compounds, were synthesized for the first time in this thesis. For the synthesis of arylidenehydrazide compounds, the related hydrazide compound was reacted with 8 different aromatic aldehydes. The imine groups in the arylidenehydrazide compounds were converted to 4-thiazolidinone ring through the reaction with thioglycolic acid. Structure determinations of the compounds were performed by NMR, HRMS, IR and UV analyzes. The cytotoxic effects of the synthesized compounds on the human healthy breast epithelial cells MCF10A and human breast cancer cells MCF7 were determined by in vitro MTT assays. The biological activity results of the hybrid compounds were compared with the standard anticancer drug doxorubicin. The IC50 values for the cytotoxic effect of doxorubicin on MCF7 and MCF10A cells are 8.01 and 32.32 µM, respectively, while these values are 10.10 and 96.88 µM for 51d and 8.48 and 114.80 µM for 51g, respectively. For 52g, the IC50 values against the same cell lines are 4.38 and 170.60 µM, respectively. According to the biological activity results, it was determined that the OH and OCH3 substituted compounds 51d, 51g and 52g showed much higher selectivity than doxorubicin against MCF7 and MCF10A cell lines. As a result, 51d, 51g and 52g are promising candidate compounds as new potential anticancer drugs.