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Título: Structure and cytotoxic activity of terpenoid-like chalcones
Autor(es): Lima, Rosa S.
Perez, Caridad N.
Silva, Cameron C. da
Santana, Mabio J.
Queiroz Júnior, Luiz H. K.
Barreto, Stefânio
Moraes, Manoel O. de
Martins, Felipe T.
Palavras-chave: Chalconas
Raios X
Data do documento: Mar-2016
Editor: Arabian Journal of Chemistry
Citação: LIMA, R. S. et al. Structure and cytotoxic activity of terpenoid-like chalcones. Arabian Journal of Chemistry, p. 1-12, mar. 2016.
Abstract: 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.
ISSN: 1878-5352
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