Synthesis, characterization, and investigation of the anticancer properties of some trifluoromethyl substituted chalcones

Objective: Chalcone compounds possess a 1,3-diaryl-2-propen-1-one structure and exhibit various biological activities, particularly anticancer activity. This thesis aimed to synthesize nine fluorine, chlorine, and bromine-substituted 2'-trifluoromethyl chalcone compounds, characterize them, and evaluate their anticancer activities on A549 and Hep3B cell lines using in-vitro activity methods. Materials and Methods: In this thesis study, starting from 2-trifluoromethylacetophenone in a basic medium, the corresponding chalcone compounds were synthesized via the Claisen-Schmidt condensation reaction using benzaldehyde derivatives substituted with fluorine, chlorine, and bromine at the 2, 3, and 4 positions. The anticancer activities of the synthesized chalcone derivatives were investigated on A549 and Hep3B cell lines using in vitro activity methods at different concentrations. Results: Based on the obtained results, among the nine synthesized chalcone derivatives containing a 2-trifluoromethyl group, the compound (15) bearing a chlorine atom at the 3′-position exhibited the strongest antiproliferative activity against both A549 and Hep3B cancer cell lines. Overall, chlorine-containing compounds were found to be more effective compared to their fluorine- and bromine-substituted counterparts; furthermore, the position of the halogen was observed to play a significant role in the cytotoxic effect. Conclusion: Among the synthesized chalcone derivatives, the compound containing a 3′-chloro substituent showed a significant antiproliferative effect, demonstrating that the type and position of halogen play an important role in biological activity. It is also considered that structural modifications should be taken into account in targeted anticancer drugdesign.