染料木素衍生物的合成及其对乳腺癌和肝癌细胞活性的分析-synthesis of genistein derivatives and analysis of their activities on breast cancer and liver cancer cells.docxVIP

万方数据 万方数据 The Synthesis and Anticancer Activities Against MCF-7 and HepG2 of Genistein Derivatives Abstract Objective: In order to search for the anticancer substances with high efficacy, low toxicity and provide a theoretical basis for the rational design of anticancer compounds, we introduced the alkane and trifluoromethyl into the structure of genistein, then we explore these compound’s anticancer activities and structure-activity relationships. Methods: Condensation of resorcinol with m-trihydroxybenzene catalyzed by ZnCl2 and followed by hydrolysis with HCl gas provided genistein and 4′-trifluoromethylated flavone. The reaction of 2 with RX in the presence of K2CO3 at reflux temperature gave genistein and 4′-trifluoromethylated flavone derivatives. We tested their anticancer activities against MCF-7(human breast cancer) and HepG2(human hepatocellular carcinoma) cells lines by MTT-Based Assay. We also summarized the general SAR(structure-activity relationship) of those compounds to MCF-7 and HepG2 cells. Results: We have synthesized and confirmed a series of genistein derivatives, and the derivatives were tested for their anti-cancer activities in vitro against MCF-7 (human breast cancer) and HepG2 (human hepatocellular carcinoma) cell lines by MTT-Based Assay. It appeared that these closely related molecules displayed remarkable differences in the inhibition of MCF-7 and HepG2 cell’s proliferation. Conclusion: We got 25 new genistein derivatives and the result indicated that compounds 4e and 4o had strongest activities against MCF-7 and HepG2 tumor cells. Key words: genistein; derivatives; anticancer activities Hui Wang Directed by Prof. Yusheng Zhou and Xing Zheng Institute of Pharmacy and Pharmacology University of South China Hengyang, 421001 - 2 - 引 言 染料木素（genistein, GEN）又名染料木黄酮、金雀异黄酮、5,7,4′-三羟基异 黄酮，其主要是从染料木(金雀花) 、槐角、大豆、葛根和广豆根等豆科植物中 提取出来的活性成分。它是 1931 年第一个从大豆中分离出的异黄酮，但是直到 320 世纪 50 年代，染料木素的雌激素活性才被发现[1]。从化学结构上分，染料木 素属于植物雌激素(phytoestrogens)中异黄酮(isof