Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (07): 958-962. Previous Articles     Next Articles

Original Articles

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

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 2a2d, which were all Z-isomers. The Perkin reaction between 6 and benzaldehyde or its derivatives afforded 3a3c, which were all E-isomers. 2a2d and 3a3c 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 2a2d and 3a3c 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