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
收稿日期: 2019-01-25
修回日期: 2019-04-01
网络出版日期: 2019-05-06
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
Received date: 2019-01-25
Revised date: 2019-04-01
Online published: 2019-05-06
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).
设计合成了3类C（3）-1，2，4-三氮唑取代的1，5-苯并硫氮杂（艹卓）化合物，2，3-二氢/2，5-二氢/2，3，4，5-四氢-3-（1，2，4-三氮唑）-4-芳基-1，5-苯并硫氮杂（艹卓）.研究了中间体及目标产物的合成条件，确定了其中2个副产物的结构.目标产物的抑菌活性测试表明，2，3-二氢/2，5-二氢-3-（1，2，4-三氮唑）-4-芳基-1，5-苯并硫氮杂（艹卓）对新生隐球菌和白色念珠菌表现出很高的抑制作用，在200 μg/disc的浓度下，有4个化合物对新生隐球菌的抑制作用高于对照药物氟康唑，有3个化合物对白色念珠菌的抑制活性高于对照药物氟康唑.初步抑真菌构效关系研究表明，1，2，4-三氮唑环和C=N双键是2，3-二氢-3-（1，2，4-三氮唑）-4-芳基-1，5-苯并硫氮杂（艹卓）抑真菌活性的关键药效团.
关键词： 1,5-苯并硫氮杂（艹卓）; 1,2,4-三氮唑; 抑菌活性; 构效关系
王岩 , 孔令满 , 王冉冉 , 田克情 , 张萍 . 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[J]. 有机化学, 2019 , 39(9) : 2663 -2670 . DOI: 10.6023/cjoc201901041
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.
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