研究论文

含亚磺酸酯或亚磺酰胺基团的香豆素衍生物的合成及生物活性研究

  • 刘明 ,
  • 刘阳 ,
  • 刘艾林 ,
  • 张冬凯 ,
  • 陈明桂 ,
  • 吴长春 ,
  • 华学文 ,
  • 周莎 ,
  • 李正名
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  • a. 南开大学元素有机化学研究所 元素有机化学国家重点实验室 天津化学化工协同创新中心 天津 300071;
    b. 北京协和医学院 中国医学科学院药物研究所 北京 100050

收稿日期: 2016-01-11

  修回日期: 2016-02-22

  网络出版日期: 2016-03-11

基金资助

高等学校学科创新引智计划(No.B06005)、元素有机化学国家重点实验室和天津化学化工协同创新中心资助项目.

Synthesis and Bioactivities of Novel Coumarin Derivatives Containing Sulfinic Esters or Sulfinamide Moiety

  • Liu Ming ,
  • Liu Yang ,
  • Liu Ailin ,
  • Zhang Dongkai ,
  • Chen Minggui ,
  • Wu Changchun ,
  • Hua Xuewen ,
  • Zhou Sha ,
  • Li Zhengming
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  • a. State Key Laboratory of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
    b. Institute of Materia Medica, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100050

Received date: 2016-01-11

  Revised date: 2016-02-22

  Online published: 2016-03-11

Supported by

Project supported by the “111” Project of Ministry of Education of China (No. B06005), and the State Key Laboratory of Elemento-organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin).

摘要

采用活性基团拼接的方法,以二氯亚砜为硫源,设计合成了23个含有亚磺酸酯或亚磺酰胺结构的新型香豆素类衍生物,其结构经核磁共振氢谱、碳谱和元素分析确证. 抗肿瘤活性测试结果表明,在5.0 mg/L的浓度下部分化合物对人结肠癌细胞(HCT-8)、人肺腺癌细胞(A549)和人肝癌细胞(Bel7402)表现出较好的抑制效果. 离体抑菌活性测试结果表明,在50 mg/L的浓度下部分化合物对苹果轮纹病菌显示出不错的抑菌活性. 另外,初步探讨了此类化合物的构效关系.

本文引用格式

刘明 , 刘阳 , 刘艾林 , 张冬凯 , 陈明桂 , 吴长春 , 华学文 , 周莎 , 李正名 . 含亚磺酸酯或亚磺酰胺基团的香豆素衍生物的合成及生物活性研究[J]. 有机化学, 2016 , 36(7) : 1653 -1661 . DOI: 10.6023/cjoc201601011

Abstract

A series of novel coumarin derivatives containing sulfinic esters or sulfonamide were designed and synthesized. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays indicated that several target compounds exhibited good in vitro antitumor activities on A549 (up to 67.82%), Bel7402 (up to 58.47%) and HCT-8 (up to 74.80%) at 5.0 mg/L and moderate antifungal activities on Physalospora piricola (up to 82.0 %) at 50 mg/L. The structure-activity relationship of these target compounds was discussed accordingly.

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