白藜芦醇类似物的合成  

Synthesis of Rseveratrol Analogues

作　　者：朱玉松[1,2] 罗世能[3,4] 沈永嘉[1] 俞惠新[3] 陈波[3] 张来国 

机构地区：[1]华东理工大学精细化工研究所 [2]江苏省原子医学研究所无锡214063 [3]江苏省原子医学研究所 [4]江南大学化学与材料工程学院无锡214036 [5]江南大学化学与材料工程学院

出　　处：《有机化学》2006年第7期958-962,共5页Chinese Journal of Organic Chemistry

基　　金：江苏省卫生厅重点(No.K200412)资助项目.

摘　　要：3,5-二甲氧基苄溴(4)与NaCN反应生成3,5-二甲氧基苄腈(5),5经水解得到3,5-二甲氧基苯乙酸(6).5与苯甲醛或取代苯甲醛发生Knoevenagel反应生成化合物2a～2d,为Z式构型.6与苯甲醛或取代苯甲醛发生Perkin反应得到化合物3a～3c,为E式构型.2a～2d和3a～3c均为白藜芦醇类似物.给出了各步反应产物的IR,1HNMR,13CNMR和MS数据,讨论了影响反应的因素,并给出了化合物2a～2d和3a～3c对乳腺癌细胞MCF-7、肺癌细胞H446、乳腺癌细胞231的体外生理活性和对正常肝细胞L02体外毒性的半致死浓度.3,5-Dimethoxybenzyl bromide （4） reacted with sodium cyanide to form 3,5-dimethoxybenzyl nitrile （5）, which was transformed into 3,5-dimethoxyphenylacetic acid （6） via hydrolysis. The Knoevenagel reaction between 5 and benzaldehyde or its derivatives afforded 2a～2d, which were all Z-isomers. The Perkin reaction between 6 and benzaldehyde or its derivatives afforded 3a～3c, which were all E-isomers. 2a～2d and 3a～3c all are the analogues of resveratrol 1. The structures of the products of every step reaction were charaterized by IR, ^1H NMR, ^13C NMR and MS spectra. The factors of affecting the reactions were discussed. Compounds 2a～2d and 3a～3c were tested in vitro for their antitumor activity on breast tumor cells MCF-7, lung tumor cells H446, breast tumor cells 231 and their toxicity on normal liver cells L02. Their IC50 values were given.

关 键 词：白藜芦醇类似物 3 4’ 5-三羟基-反式-二苯乙烯 生理活性 

分 类 号：TQ463.2[化学工程—制药化工]