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[目的]合成一系列二苯乙烯双键结构上含有氰基的白藜芦醇衍生物,并测定其体外抗癌活性.[方法]以3,5-二羟基苯甲酸为原料,经甲基化、还原、取代、Abozove重排、Wittig-Hornor反应和Knoevenegal反应合成白藜芦醇及其衍生物,利用1 H-NMR确认其结构,采用MTT法观察每种化合物对HCT116人结肠癌细胞的增殖抑制作用.[结果]二苯乙烯双键结构上含有氰基的白藜芦醇B环4′位引入甲氧基、乙氧基时其IC50值均小于0.20μmol/L,引入正丙氧基时IC50值小于15.00μmol/L,此3种化合物对HCT116人结肠癌细胞的增殖抑制作用均强于白藜芦醇(IC50=64.46μmol/L),当碳数超过3个时其IC50值均大于白藜芦醇的IC50值.[结论]二苯乙烯双键上含有氰基的白藜芦醇B环4′位引入甲氧基、乙氧基或正丙氧基时对HCT116人结肠癌细胞有增殖抑制作用,但正丁氧基等侧链碳数超过3个的羟基烷基化产物的增殖抑制作用较弱.
[Objective] The research aimed to synthesize a series of resveratrol derivatives containing cyano groups on the double bond structure of stilbene and to determine its anticancer activity in vitro. [Method] 3,5-dihydroxybenzoic acid The structures of resveratrol and its derivatives were synthesized by reduction, substitution, Abozove rearrangement, Wittig-Hornor reaction and Knoevenegal reaction. The structures of the resveratrol and its derivatives were confirmed by 1 H-NMR. The inhibitory effect of each compound on HCT116 human colon cancer cells [Result] The IC50 values of resveratrol B ring containing silanol groups on stilbene double bond were less than 0.20μmol / L when methoxy and ethoxy groups were introduced into the 4 ’ The IC50 value was less than 15.00μmol / L. The inhibitory effects of these three compounds on the proliferation of HCT116 human colon cancer cells were stronger than that of resveratrol (IC50 = 64.46μmol / L). When the carbon number was more than 3, the IC50 value Were greater than that of resveratrol. [Conclusion] The introduction of methoxy, ethoxy or n-propoxy at the 4 ’position of the resveratrol B ring containing a cyano group on the stilbene double bond resulted in a significant increase in HCT116 human colon The inhibition of proliferation of cancer cells, but n-butoxy side chain carbon number of more than three hydroxyl alkylation products of the proliferation inhibition is weak.