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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (05): 698-702. 上一篇    下一篇

研究论文

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

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以3-溴-5-甲氧基-2(5H)-呋喃酮和伯胺为原料, 在均相中用三乙胺作碱性催化剂, 可以得到一对非对映异构体(1Z,4E,5Z)-6-N-烷基-6-氮杂-2-氧代-3-氧杂-4-甲氧基-双环[3.1.0]己烷(4)和(1Z,4Z,5Z)-6-N-烷基-6-氮杂-2-氧代-3-氧杂-4-甲氧基-双环[3.1.0]己烷(5). 目标分子4和5经IR, 1H NMR, 13C NMR, EIMS进行了表征, 并做了结肠癌细胞(HCT-8)、肝癌细胞(BEL-7402)、人胃癌细胞(BGC-823)、肺腺癌细胞(A549)和人卵巢癌细胞(A2780)的抗癌活性实验, 其中5c和5d对HCT-8, BGC-823, A549和A2780等癌细胞有一定的抑制作用. 此研究结果不仅丰富了该领域研究的理论基础, 而且对某些新型药物的研制具有一定的指导意义.

关键词: 3-溴-5-甲氧基-2(5H)-呋喃酮, 氮杂环丙烷衍生物, 立体化学, 抗癌活性

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

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