Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (05): 698-702. Previous Articles     Next Articles

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6-N-烷基-6-氮杂-2-氧代-3-氧杂-4-甲氧基-双环[3.1.0]己烷的合成、立体化学及抗癌活性研究

裴强*,孙俊永,金春雪,牛满丽,黄克靖   

  1. (信阳师范学院化学化工学院 信阳 464000)
  • 收稿日期:2009-06-03 修回日期:2009-09-08 发布日期:2009-12-15
  • 通讯作者: 裴强 E-mail:peiqiang_6@163.com
  • 基金资助:

    国家级.国家自然科学基金

Synthesis, Stereochemistry and Anti-cancer Activity of 6-N-Alkyl-4-methoxy-3-oxa-6-aza-bicyclo[3.1.0]hexan-2-one

PEI Qiang, SUN Jun-Yong, JIN Chun-Xue, NIU Man-Li, HUANG Ke-Jing   

  1. (Department of Chemistry, Xinyang Normal University, Xinyang 464000)
  • Received:2009-06-03 Revised:2009-09-08 Published:2009-12-15
  • Contact: Pei Qiang E-mail:peiqiang_6@163.com

Pairs of racemic diastereoisomeric aziridine derivatives (4 and 5) were obtained in good yields by Michael addition followed by internal nucleophilic substitution of 3-bromo-5-methoxy-2(5H)-furanone and primary amines. The resulting aziridines were elucidated by IR, 1H NMR, 13C NMR and EIMS, and tested for human cancer cell lines including colon cancer (HCT-8), liver cancer (BEL-7402), gastric cancer (BGC-823), pulmonary gland cancer (A549), and ovary cancer (A2780), wherein 5c and 5d display good activities against HCT-8, BGC-823, A549 and A2780. This result not only enriches the theoretical basis in this field, but also has a certain guidable significance for the manufacture of some new drugs.

Key words: 3-bromo-5-methoxy-2(5H)-furanone, aziridine derivate, stereochemistry, anti-tumor activity

CLC Number: