2005•Academic Journal of Second Military Medical UniversityRequires access
Design and synthesis of genistein derivatives 5-hydroxy-4’-nitro-7-substituted-acyloxo-isoflavone and their antitumor effects
Yongsheng Jin
Open publisher page 1 citations
Abstract
Objective:To design and synthesize genistein derivatives 5-hydroxy -4’-nitro-7-sustituted-acyloxo-isoflavones and to evaluate their antitumor effects. Methods: Benzyl chloride was used as the raw material to obtain the title compounds by multi-step reaction: substitution, nitration, Friedel-Crafts reaction, cyclation reaction and acylation or alkylation. Results: Synthesized compounds were confirmed by 1HNMR and element analysis. Of them 5B(5-hydroxy-4’-nitro-7-propionyloxy isoflavone) had the most potent inhibitory effects on MDA-MB-435 breast cancer cells line in vitro and vivo. Conclusion: Propanoylation of 7-OH and substitution of OH by NO 2 can enhance the antitumor activity of genistein.