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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (07): 983-987. 上一篇    下一篇

研究简报

2'-羟基查耳酮的Mannich反应及其产物的生物活性

刘滔，胡永洲*   

  1. (浙江大学药学院药物化学教研室 杭州 310031)
  • 收稿日期:2005-11-02 修回日期:2006-01-20 发布日期:2006-07-01
  • 通讯作者: 胡永洲

Mannich Reaction of 2'-Hydroxychalcone and Biological Activity ofIts Mannich Base

LIU Tao,HU Yong-Zhou*   

  1. (Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310031)
  • Received:2005-11-02 Revised:2006-01-20 Published:2006-07-01
  • Contact: HU Yong-Zhou

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1331

被引次数

81

研究了2'-羟基查耳酮的Mannich反应, 发现该反应区域选择性地发生在查耳酮B环C-3'位, 利用此法共合成了12个新的Mannich碱化合物, 其结构经元素分析、1H NMR和IR得到确证. 该反应制备步骤简单, 条件温和, 产物易纯化, 收率从中等到高(49～72%). 初步的生物活性测定表明其中部分化合物具强效的CDK1/cyclin B抑制活性, 多数化合物对肿瘤细胞具较强的抑制活性.

关键词: 2'-羟基查耳酮, 抗肿瘤活性, Mannich反应, CDK1/cyclin B抑制活性, Mannich碱

Twelve Mannich base derivatives of 2'-hydroxychalcone were synthesized through Mannich reaction, and the regioselectivity of the reaction occurred preferentially at C-3' position of B ring of chalcone backbone. All the target compounds have been identified by 1H NMR, IR spectra and elemental analyses, and further confirmed by X-ray analysis. The characteristic of this reaction was simple process, mild condi-tion, easy purification and middle to good yields (49%～72%). Some compounds showed potent CDK1/cyclin B inhibitory activities and most of compounds displayed a significant growth inhibitory action against various cancer cell lines.

Key words: Mannich reaction, growth inhibitory activity, Mannich base, CDK1/cyclin B inhibitory activity, 2'-hydroxychalcone