Synthesis and structure-activity relationship of cytotoxic 5,2′,5′-trihydroxy-7,8-dimethoxyflavanone analogues

Abstract

Analogues of 2(S)-5,2′,5′-trihydroxy-7,8-dimethoxyflavanone, a naturally-occurring compound, which had been reported to have potent antitumor activity, were synthesized and examined for the cytotoxicity against three cancer cell lines. Among the intermediate chalcones and synthetic 5-hydroxy-7,8-dimethoxyflavanone analogues, (±)2′,5′-dibenzyloxy-5,7,8-trimethoxyflavanone exhibited about 2–8 times stronger activity than 2(S)-5,2′,5′-trihydroxy-7,8-dimethoxyflavanone against L1210, K562 and A549 cancer cell lines. In the structure-activity relationship, it is suggested that among analogues of 5-hydroxy-7,8-dimethoxyflavanone, the existence of two oxygenated groups ofpara-relation at C-2′ and C-5′ positions on flavanone Bring, may be necessary to exhibit effective cytotoxic activity.