高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (3): 505-510.doi: 10.7503/cjcu20140588

• 有机化学 • 上一篇    下一篇

4-取代苯基-1,5-苯并硫氮杂䓬-2-甲酸的合成及抑菌活性

王娇1, 田克情2, 薛子桥1, 武云云1, 杨田1, 赵惠敏1, 张萍1()   

  1. 1. 河北师范大学化学与材料科学学院, 石家庄050024
    2. 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:2014-06-27 出版日期:2015-03-10 发布日期:2015-01-23
  • 作者简介:联系人简介: 张 萍, 女, 副教授, 主要从事有机化合物合成及抑菌活性研究. E-mail: zhangpingp@sina.com

Syntheses and Antimicrobial Activities of 4-Substituted Phenyl 1,5-Benzothiazepines-2-carboxylic Acids

WANG Jiao1, TIAN Keqing2, XUE Ziqiao1, WU Yunyun1, YANG Tian1, ZHAO Huimin1, ZHANG Ping1,*()   

  1. 1. College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024, China
    2. Environment and Chemical Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026, China
  • Received:2014-06-27 Online:2015-03-10 Published:2015-01-23
  • Contact: ZHANG Ping E-mail:zhangpingp@sina.com

摘要:

合成了七元环的杂?化合物2a~2k, 并发现化合物2a~2k会向其同分异构体六元环内酰胺3a~3k转化. 化合物2a~2k的结构通过红外光谱(IR)、 核磁共振波谱(NMR)、 质谱(MS)和元素分析确证. 初步的抑菌活性测试结果表明, 化合物2a~2k对白色念珠菌、 标准新生隐球菌、 临床新生隐球菌、 大肠杆菌和枯草牙孢杆菌均有较好的抑菌活性, 而六元环内酰胺3a~3k对所测菌种没有活性. 实验还测定了部分混合物(2a~2e和3a~3e)的抑菌活性, 结果表明化合物2a~2e和3a~3e混合物的抑真菌效果比单一的化合物2a~2e要好, 化合物3a~3e的存在增强了化合物2a~2e的抑菌活性.

关键词: α,β,-不饱和羧酸, 1,5-苯并硫氮杂?, 抑菌活性

Abstract:

It was reported the products of α,β-unsaturated carboxylic acid and o-aminothiophenol with acid catalyst were seven-membered ring benzothiazepins containing a carboxyl group. Subsequent literature suggested that the structure of the reaction product was a six-membered ring lactam structure. According to the reported method we carried out the reaction and the products obtained were not the reported seven-membered ring benzothiazepin structure, but the six-membered ring lactam structures 3a—3k, which structures were confirmed by mapping and crystal structure analysis. Under the different experimental conditions, we obtained seven-membered ring benzothiazepins 2a—2k, and found that compounds 2a—2k could converted to its isomers six-membered ring lactam 3a—3k. The structures of compounds 2a—2k were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. Antibacterial activity tests showed that compounds 2a—2k had good antibacterial activity against Candida albicans, Cryptococcus neoformans(standard and clinical), E. coli and B. subtilis. While compounds 3a—3k had no activities of the measured strains. It was noteworthy that the mixtures of compounds 2a—2e and 3a—3e had better antifungal effects than those of compounds 2a—2e single, the presence of compound 3a—3e enhanced the antibacterial activities of compounds 2a—2e.

Key words: α,β,-Unsaturated carboxylic acid, 1,5-Benzothiazepine, Antibacterical activity

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