有机化学 ›› 2013, Vol. 33 ›› Issue (10): 2237-2243.DOI: 10.6023/cjoc201305039 上一篇    下一篇

研究简报

4-甲基-2-杂环-2,3-二氢苯并[f]-1,5-硫氮杂(艹卓)-3-羧酸乙酯及其还原产物的合成、晶体结构及抑菌活性的研究

田克情a, 刘晓欣b, 薛子桥b, 杨田b, 杜星琼c, 张萍b   

  1. a 河北化工医药职业技术学院化学与环境工程系 石家庄 050026;
    b 河北师范大学化学与材料科学学院 石家庄 050024;
    c 河北师范大学生命科学学院 石家庄 050024
  • 收稿日期:2013-05-24 修回日期:2013-06-10 出版日期:2013-10-25 发布日期:2013-06-21
  • 通讯作者: 张萍 E-mail:zhangpingp@sina.com
  • 基金资助:

    国家自然科学基金(No. 20972040)资助项目

Studies on the Synthesis, Crystal Structure and Antimicrobial Activities of 4-Methyl-2-heterocylic-2,3-dihydro-benzo[f]-1,5-thiazepine-3-carboxylic Acid Ethyl Ester and Its Reduction Products

Tian Keqinga, Liu Xiaoxinb, Xue Ziqiaob, Yang Tianb, Du Xingqiongc, Zhang Pingb   

  1. a Environment and Chemical Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026;
    b College of Chemistry, Hebei Normal University, Shijiazhuang 050024;
    c College of Life Science, Hebei Normal University, Shijiazhuang 050024
  • Received:2013-05-24 Revised:2013-06-10 Online:2013-10-25 Published:2013-06-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20972040).

以乙酰乙酸乙酯和含不同取代基的杂环醛为原料, 经两步反应合成了一系列新颖的4-甲基-2-杂环-2,3-二氢苯并[f]-1,5-硫氮杂(艹卓)-3-羧酸乙酯(2a2l), 并对其中的5个化合物进行了还原, 2a2l及还原产物的结构经1H NMR IR, MS, 元素分析确证. 同时采用X射线衍射法测定了2a的晶体结构, 2a属三斜晶系, P-1空间群. 采用滤纸片法测试所合成目标化合物对枯草芽孢杆菌、白色念珠菌、标准新生隐球菌和临床新生隐球菌的抑菌活性, 结果表明大部分化合物都有一定的抑菌效果, 其中2a的抑菌效果尤其突出.

关键词: 1,5-苯并硫氮杂(艹卓), 杂环, 还原, 晶体结构, 抑菌活性

Starting from ethyl acetoacetate and substituted heterocyclic aldehyde, a series of new 4-methyl-2-heterocyclic-2,3-dihydro-benzo[f]-1,5-thiazepine-3-carboxylic acid ethyl esters (2a2l) were synthesized through 2-step reactions, and of which five compounds were reduced. The structures of the compounds were characterized by 1H NMR, IR, MS, elemental analysis and X-ray diffraction study. The crystal of compound 2a belongs to triclinic system, space group P-1. The antibacterical activities of the new compounds against B. subtilis, C. albicans and C. neoformans were evaluated by filter paper approach, and the results indicated that most of them showed antibacterical activities, especially the compound 2a prominent.

Key words: 1,5-benzothiazepine, heterocyclic, reduction, crystal structure, antibacterical activity