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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (10): 1606-1610. 上一篇    下一篇

研究论文

N1-烃基-3-肟基靛玉红的简便合成、晶体结构及抗肿瘤活性研究

王朝晖a   王 越a   冯明声b   谭 雪b  程景才c   华维一b   姚其正*,b   

  1. (a中国药科大学基础部 南京 210009) (b中国药科大学药学院 南京 210009) (c无锡杰西医药科技有限公司 无锡 214036)
  • 收稿日期:2009-02-28 修回日期:2009-04-27 发布日期:2009-05-18

Facile Synthesis, X-ray Structure and Anticancer Activity of N1-Alkylindirubin-3’-oxime

Wang, Zhaohuia   Wang, Yuea   Feng, Mingshengb   Tan, Xueb   Cheng, Jingcaic   Hua, Weiyib   Yao, Qizheng*,b   

  1. (a College of Basic Science, China Pharmaceutical University, Nanjing 210009) (b School of Pharmacy, China Pharmaceutical University, Nanjing 210009) (c Wuxi JC Pharmaceutical Technology Inc., Wuxi 214036)
  • Received:2009-02-28 Revised:2009-04-27 Published:2009-05-18

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研究了N1-烃基-3-肟基靛玉红的合成新方法. 以靛玉红为起始原料, 经N-烃基化、成肟反应选择性地得到单烃基化的 N1-烃基-3-肟靛玉红衍生物3a～3c. 晶体结构测定证明所合成的N1-乙基-3-肟基靛玉红(3b)以(3Z,3E)构型存在. 体外5种细胞株抗肿瘤活性筛选数据显示, 化合物3a～3c都有抗肿瘤作用, 其中, N1-乙基-3-肟基靛玉红(3b)具有较强的抗肿瘤活性和较低的毒性.

关键词: N1-烃基-3-肟基靛玉红, 合成, 晶体结构, 抗肿瘤活性

A novel synthetic method of N1-alkylindirubin-3-oxime (3a～3c) was explored using indirubin as the starting material, including N-alkylation and oximation. Crystal X-ray diffraction studies of N1-ethylindirubin-3-oxime (3b) gave good support for the (3Z,3E) structure. The anticancer activity of compounds 3a～3c was evaluated and compound 3b showed potent anticancer effect and low toxicity com-pared to other chemotherapy drugs .

Key words: N1-alkylindirubin-3-oxime, synthesis, crystal structure, anticancer activity