Articles

Synthesis and Antitumor Activities of 3'-Substituted Propanolursolates

  • Li Xia ,
  • Bai Xue ,
  • Wu Ke ,
  • Wang Yujun ,
  • Shi Wangqi ,
  • Li Ying ,
  • Yin Shufan
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  • a Collage of Chemistry, Sichuan University, Chengdu 610064;
    b Sichuan Guokang Pharmaceutical Co., Ltd, Chengdu 610041

Received date: 2011-09-25

  Revised date: 2011-11-29

  Online published: 2012-04-24

Abstract

3'-Substituted propanolursolates (1) were obtained by a reaction of ursolic acid with trimethylene bromide. This intermediate reacted with several N-containing compounds to afford a series of new derivatives 2a~2j. The structures of new products were characterized by means of 1H NMR, 13C NMR, IR and MS techniques. The preliminary bioassay test shows that several compounds give a good antitumor activity, and most of them are better than that of parent ursolic acid. Among them, compound 2e shows the best activity.

Cite this article

Li Xia , Bai Xue , Wu Ke , Wang Yujun , Shi Wangqi , Li Ying , Yin Shufan . Synthesis and Antitumor Activities of 3'-Substituted Propanolursolates[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 703 -708 . DOI: 10.6023/cjoc1109251

References

[1] Song, X.-K.; Wu, L.-J. Textbook of Natural Medicinal Chemistry, Chemical Industry Press, Beijing, 2004, pp. 198~200 (in Chinese). (宋晓凯, 吴立军, 天然药物化学, 化学工业出版社, 北京, 2004, pp. 198~200.)  

[2] Yang, D.-J.; Li, Y.; Yin, S.-F. Chin. J. Org. Chem. 2008, 28, 1055 (in Chinese). (杨定菊, 李颖, 尹述凡, 有机化学, 2008, 28, 1055.)

[3] Huang, J.; Sun, Y.; Lu, S.-X.; Su, T.; Jiao, S.-C. Chin. J. Integr. Trad. Western Med. 1999, 19, 296 (in Chinese). (黄镜, 孙燕, 陆士新, 苏涛, 焦顺昌, 中国中西医结合杂志, 1999, 19, 296.)

[4] Barry, M. A.; Behnek, C. A.; Eastman, A. Biochem. Pharmacol. 1990, 40, 2353.  

[5] Zhang, Q.-P.; Xie, L.-K.; Deng, T.; Hu, Z.-F.; Chen, H.-M.; Tan, J.-Q. Basic Clinics Med. 2004, 24, 414 (in Chinese). (张秋萍, 谢路琨, 邓涛, 胡志芳, 陈会敏, 谭锦泉, 基础医学与 临床, 2004, 24, 414.)

[6] Li, J.; Xu, L.-Z.; Zhu, W.-P.; Zhang, T.-M.; Li, X.-M.; Jin, A.-P.; Huang, K.-M.; Li, D.-L.; Yang, Q.-Y. China Oncol. 1999, 9, 395 (in Chinese). (李杰, 许良中, 朱伟萍, 张太明, 李小妹, 金爱萍, 黄抗美, 李 栋良, 杨庆尧, 中国癌症杂志, 1999, 9, 395.)

[7] Knighton, D. R.; Silver, I. A.; Hunt, T. K. Surgery 1981, 90.261.

[8] Wu, Q.-N.; Huang, W.; Huang, M.-S. J. Oncol. 2004, 10, 145 (in Chinese). (吴其年, 黄炜, 黄敏珊, 肿瘤学杂志, 2004, 10, 145.)
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