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化学学报
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化学学报 ›› 1992, Vol. 50 ›› Issue (7): 698-701. 上一篇    下一篇

研究论文

4-巯基-4-脱氧-4'-去甲表鬼臼毒素的立体控制合成

王志光;马维勇;张椿年   

  1. 国家医药管理局上海医药工业研究院
  • 发布日期:1992-07-15

Stereocontrolled synthesis of 4-mercapto-4-deoxy-4'-demethylepipodophyllotoxin

WANG ZHIGUANG;MA WEIYONG;ZHANG CHUNNIAN   

  • Published:1992-07-15

PDF

510

被引次数

26

4-巯基-4-脱氧-4'-去甲表鬼臼毒素是合成4位硫取代的4'-去甲表鬼臼毒素的关键中间体,由4'-去甲表鬼臼毒素与硫化氢在BF~3·Et~2O存在下立体控制制备,也可通过以NH~3/CH~CN选择性 地水解4-乙酰硫基-4-脱氧-4'-去甲表鬼臼毒素而制备.

关键词: 巯基, 立体选择性, 抗癌活性, 鬼臼毒素

4-Mercapto-4-deoxy-4'-demethylepipodophyllotoxin (I), a key intermediate for 4S-substituted-4-deoxy-4'-demethylepipodophyllotoxins, was prepared with high stereospecificity by the reaction of 4'-demethylepipodophyllotoxin and H2S in the presence of BF3譋t2O. I can also be obtained by reaction of 4'-demethylepipodophyllotoxin and thioacetic acid, followed by S-deacetylation with NH3/MeCN. I had an ID50 of 1.92 mg/mL against leukemia cell L1210.

Key words: MERCAPTO GROUP, STEREOSELECTIVITY, ANTINEOPLASTIC ACTIVITY

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