Structure and cytotoxic activity of terpenoid-like chalcones

Resumo

Compounds with either ionone or chalcone skeletons present many biological properties including anticancer activity. Here we have prepared eight terpenoid-like chalcones in order to assess whether hybrid compounds with both structural frameworks could exhibit enhanced pharmacological profile. The terpenoid-like chalcones were synthesized by means of Claisen–Schmidt condensation reaction, using either α- or β-ionone with substituted benzaldehydes. The structure of six derivatives was elucidated by single crystal X-ray diffraction technique for the first time. Cyclohexene ring adopts half-chair conformation in α-ionone-derived chalcone with quaternary carbon at the flap, while twist puckering was observed in β-ionone terpenoid-like chalcones. All prepared compounds were tested for their cytotoxic activity against three cancer cell lines, namely SF-295, HCT-116 and OVCAR-8, which allowed us to establish some structure–activity relationships. Terpenoid-like chalcones with nitro substituted phenyl rings, regardless of its position and ionone type, were the most active chalcones among all that tested. The IC50 values do also reveal a trend of decrease in cytotoxic activity with weak electron-withdrawing groups at phenyl ring.

Descrição

Palavras-chave

Claisen–Schmidt condensation, Crystal structure, X-ray diffraction, Cytotoxic activity, Antitumor compounds

Citação

LIMA, Rosa S. et al. Structure and cytotoxic activity of terpenoid-like chalcones. Arabian Journal of Chemistry, Amsterdam, v. 12, n. 8, p. 3890-3901, 2019. DOI: 10.1016/j.arabjc.2016.02.013. Disponível em: https://www.sciencedirect.com/science/article/pii/S1878535216000381?via%3Dihub. Acesso em: 24 ago. 2023.