文献类型：期刊文献

中文题名：白藜芦醇类似物的合成

英文题名：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[5]

机构：[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

年份：2006

卷号：26

期号：7

起止页码：958

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000238905100013)】；北大核心:【北大核心2004】；CSCD:【CSCD2011_2012】；

基金：江苏省卫生厅重点(No.K200412)资助项目.

语种：中文

中文关键词：白藜芦醇类似物;3,4’;5-三羟基-反式-二苯乙烯;生理活性

外文关键词：resveratrol analogues; 3,4＇,5-trihydroxy-trans-stilben; biological evaluation

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.