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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (9): 1335-1341. 上一篇    下一篇

研究论文

微波辐射下6-烷氧基大黄酸的合成及抑菌活性研究

朱小康1，叶小利2，袁吕江1，朱家颖1，丁阳平1，李学刚*,1   

  1. (1西南大学药学院 重庆 400716)
    (2西南大学生命科学院 重庆 400716)
  • 收稿日期:2009-10-23 修回日期:2010-02-02 发布日期:2010-04-21
  • 通讯作者: 朱小康 E-mail:xiaokangzhu1982@yahoo.com.cn
  • 基金资助:

    国家级.国家自然科学基金

Microwave-Assisted Synthesis and Antibacterial Activity of 6-Alkoxy Rheins

Zhu Xiaokang1 Ye Xiaoli2 Yuan Luji-ang1 Zhu Jiaying1 Ding Yangping1 Li Xuegang*,1   

  1. (1 School of Pharmaceutical Science, Southwest University, Chongqing 400716)
    (2 School of Life Science, Southwest University, Chongqing 400716)
  • Received:2009-10-23 Revised:2010-02-02 Published:2010-04-21
  • Contact: ZHU Xiao-Ming E-mail:xiaokangzhu1982@yahoo.com.cn

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被引次数

4 | 2

以大黄素为起始原料经过Williamson醚合成, 乙酰基保护, 氧化, 脱乙酰保护合成5个新型的6-烷氧基大黄酸4a～4e. 对比研究了微波反应和常规反应对中间体3-烷氧基大黄素合成产率的影响. 比较了在合成关键中间产物3a～3e时不同氧化体系对反应产率的影响, 找到了最佳的氧化条件. 所有目标化合物的结构都通过IR, 1H NMR, MS和HRMS进行了表征. 对目标化合物4a～4e进行了抑菌活性测试, 结果表明随着取代烷氧基链的增长, 抑菌活性呈规律性变化.

关键词: 大黄素, 6-烷氧基大黄酸, 微波, 氧化, 抑菌

Five new 6-alkoxy rheins have been designed and synthesized through Williamson reaction, acetyl protection, oxidation reaction and deprotection. The effects of microwave and conventional method on the yield of 3-alkyl emodin derivatives were compared. The effects of different oxidants in the synthesis of 3a～3e were studied and the best oxidation conditions were found. All the structures have been confirmed by IR, 1H NMR, MS and HRMS techniques. The minimal inhibitory concentration (MIC) assay indicated that antibacterial activity changes regularly, as the alkyl chain growth.

Key words: emodin, 6-alkoxy rhein, microwave, oxidation, antibacterial activity