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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (07): 958-962. 上一篇    下一篇

研究论文

白藜芦醇类似物的合成

朱玉松1,2，罗世能2,3，沈永嘉*,1，俞惠新2，陈波2，张来国3   

  1. (1华东理工大学精细化工研究所 上海 200237)
    (2江苏省原子医学研究所 无锡 214063)
    (3江南大学化学与材料工程学院 无锡 214036)
  • 收稿日期:2005-06-08 修回日期:2006-01-20 发布日期:2006-07-01
  • 通讯作者: 沈永嘉

Synthesis of Rseveratrol Analogues

ZHU Yu-Song1,2,LUO Shi-Neng2,3,SHEN Yong-Jia*,1,YU Hui-Xin2
CHEN Bo2,ZHANG Lai-Guo3   

  1. (1 Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237)
    (2 Jiangsu Institute of Nuclear Medicine, Wuxi 214063)
    (3 School of Chemical and Material Engineering, Southern Yangtze Univer-sity, Wuxi 214036)
  • Received:2005-06-08 Revised:2006-01-20 Published:2006-07-01
  • Contact: SHEN Yong-Jia

PDF

1344

被引次数

59

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, 1H NMR, 13C NMR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.

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

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 deriva-tives 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.

Key words: 3,4',5-trihydroxy-trans-stilben, biological evaluation, resveratrol analogues