期刊
ARABIAN JOURNAL OF CHEMISTRY
卷 12, 期 8, 页码 3890-3901出版社
ELSEVIER
DOI: 10.1016/j.arabjc.2016.02.013
关键词
Claisen-Schmidt condensation; Crystal structure; X-ray diffraction; Cytotoxic activity; Antitumor compounds
资金
- Brazilian Research Council CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico) [472623/2011-7, 478336/2013-2]
- CNPq
- FAPEG (Fundacao de Amparo a Pesquisa do Estado de Goias) [201410267000635]
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 alpha- or beta-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 alpha-ionone-derived chalcone with quaternary carbon at the flap, while twist puckering was observed in beta-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. (C) 2016 The Authors. Published by Elsevier B.V. on behalf of King Saud University.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据