Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2663-2670.DOI: 10.6023/cjoc201901041 Previous Articles     Next Articles

NOTE

C(3)-1,2,4-三氮唑取代的1,5-苯并硫氮杂(艹卓)的合成及抑菌活性

王岩a, 孔令满a, 王冉冉a, 田克情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 河北化工医药职业技术学院化学与环境工程系 石家庄 050026
  • 收稿日期:2019-01-25 修回日期:2019-04-01 出版日期:2019-09-25 发布日期:2019-05-06
  • 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)及河北师范大学研究生创新基金(No.CXZZSS201804)资助项目.

Synthesis and Antimicrobial Activity of C(3)-1,2,4-Triazolyl-1,5-benzothiazepines

Wang Yana, Kong Lingmana, Wang Ranrana, Tian Keqingb, Zhang Pinga   

  1. a College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024;
    b Environment and Chemical Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026
  • Received:2019-01-25 Revised:2019-04-01 Online:2019-09-25 Published:2019-05-06
  • Contact: 10.6023/cjoc201901041 E-mail:zhangpingp@sina.com
  • Supported by:

    Project supported by the Natural Science Foundation of Hebei Province (No. B2017205100) and the Graduate Student Innovation Fundation of Hebei Normal University (No. CXZZSS201804).

Three kinds of C(3)-1,2,4-triazolyl-1,5-benzothiazepines, 2,3-dihydro/2,5-dihydro/2,3,4,5-tetrahydro-3-(1,2,4-tria-zolyl)-4-aryl-1,5-benzothiazepines, were designed and synthesized. The synthesis conditions of intermediates and target products were studied, and the structures of two by-products were determined. The antimicrobial activity test of the target products showed that 2,3-dihydro/2,5-dihydro-3-(1,2,4-triazolyl)-4-aryl-1,5-benzothiazepines exhibited high inhibitory effects on C. neoformans and C. albicans. At concentration of 200 μg/disc, the inhibitory effects of four compounds on C. neoformans were stronger than that of fluconazol, and the inhibitory effects of three compounds on C. albicans were stronger than that of fluconazol. The preliminary study on the structure-activity relationship of antifungal revealed that 1,2,4-triazolyl and C=N double bond were the key function groups in the antifungal activity of 2,3-dihydro-3-(1,2,4-triazolyl)-4-aryl-1,5-benzothiazepines.

Key words: 1,5-benzothiazepine, 1,2,4-triazole, antimicrobical activity, structure-activity relationship