白藜芦醇类似物的合成

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.

Synthesis of Rseveratrol Analogues

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.