有机化学 ›› 2020, Vol. 40 ›› Issue (2): 398-407.DOI: 10.6023/cjoc201907056 上一篇    下一篇

研究论文

含1,2,3-三氮唑结构的1,5-苯并硫氮杂(艹卓)的合成及其抑真菌活性

王冉冉a, 王岩a, 边彦青b, 张萍a   

  1. a 河北师范大学化学与材料科学学院 石家庄 050024;
    b 河北师范大学生命科学学院 石家庄 050024
  • 收稿日期:2019-07-31 修回日期:2019-10-05 发布日期:2019-10-25
  • 通讯作者: 张萍 E-mail:zhangpingp@sina.com
  • 基金资助:
    河北省自然科学基金(No.B2017205100)资助项目.

Synthesis and Antifungal Activity of 1,5-Benzothiazepines Containing 1,2,3-Triazole

Wang Ranrana, Wang Yana, Bian Yanqingb, Zhang Pinga   

  1. a College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024;
    b College of Life Science, Hebei Normal University, Shijiazhuang 050024
  • Received:2019-07-31 Revised:2019-10-05 Published:2019-10-25
  • Supported by:
    Project supported by the Natural Science Foundation of Hebei Province (No. B2017205100).

设计合成了三类含1,2,3-三氮唑结构的1,5-苯并硫氮杂(艹卓)化合物3-(1H-1,2,3-三氮唑)-4-芳基-2,5-二氢-1,5-苯并硫氮杂(艹卓)(5a~5f)、3-(2H-1,2,3-三氮唑)-4-芳基-2,3-二氢-1,5-苯并硫氮杂(艹卓)(6a~6f)和3-(1H-1,2,3-三氮唑)-4-芳基-2,3,4,5-四氢-1,5-苯并硫氮杂(艹卓)(7a~7f).研究了中间体及目标产物的合成条件,分离出其中两个副产物并进行了结构确定.目标产物的抑真菌活性测试表明,化合物5a~5f对真菌具有良好的抑制作用,对新生隐球菌的抑制效果尤为突出.初步抑真菌构效关系研究表明,1H-1,2,3-三氮唑环和C=C双键是化合物5a~5f抑真菌活性的关键官能团.

关键词: 1,5-苯并硫氮杂, 1,2,3-三氮唑, 抑真菌活性, 构效关系

Three kinds of 1,5-benzothiazepines containing 1,2,3-triazole, 3-(1H-1,2,3-triazolyl)-4-aryl-2,5-dihydro-1,5-benzo-thiazepines (5a~5f), 3-(2H-1,2,3-triazolyl)-4-aryl-2,3-dihydro-1,5-benzothiazepines (6a~6f) and 3-(1H-1,2,3-triazolyl)-4-aryl-2,3,4,5-tetrahydro-1,5-benzothiazepines (7a~7f), were designed and synthesized. The synthesis conditions of intermediates and target products were studied. Two by-products were separated and their structures were determined. The antifungal activity test of the target products showed that compounds 5a~5f exhibited high inhibitory effects against fungi especially for Cryptococcus neoformans. The preliminary study on the structure-activity relationship of antifungal activity reveled that 1H-1,2,3-triazolyl and C=C double bond were the key function groups in the antifungal activity of 5a~5f.

Key words: 1,5-benzothiazepine, 1,2,3-triazole, antifungal activity, structure-activity relationship