SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 10: 2237 - 2243

DOI: https://doi.org/10.6023/cjoc201305039

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 ,
  • 刘晓欣 ,
  • 薛子桥 ,
  • 杨田 ,
  • 杜星琼 ,
  • 张萍
展开
  • 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

  网络出版日期: 2013-06-21

基金资助

国家自然科学基金(No. 20972040)资助项目

收起

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 Keqing ,
  • Liu Xiaoxin ,
  • Xue Ziqiao ,
  • Yang Tian ,
  • Du Xingqiong ,
  • Zhang Ping
Expand
  • 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 date: 2013-05-24

  Revised date: 2013-06-10

  Online published: 2013-06-21

Supported by

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

Fold

摘要

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(2a～2l), 并对其中的5个化合物进行了还原, 2a～2l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

本文引用格式

田克情 , 刘晓欣 , 薛子桥 , 杨田 , 杜星琼 , 张萍 . 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[J]. 有机化学, 2013 , 33(10) : 2237 -2243 . DOI: 10.6023/cjoc201305039

Abstract

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 (2a～2l) 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

参考文献

[1] Prakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S. P.; Claramunt, R. M.; Sanz, D.; Alkorta, I.; Elguero, J. Tetrahedron 2005, 61, 6642.
[2] Nagao, T.; Sato, M.; Iwasawa, Y.; Takada, T.; Ishida, R. Jpn. J. Pharmacol. 1972, 22, 467.
[3] Fabrizio, M.; Fabio, D.; Aldo, F.; Merlo, G. J. Comb. Chem. 2001, 67, 224.
[4] Nagao, T.; Sato, M.; Nakajima, H.; Kiyomoto, A. Chem. Pharm. Bull. 1973, 21, 92.
[5] Yamada, K.; Shimamura, T.; Nakajima, H. Jpn. J. Pharmacol. 1973, 23, 321.
[6] Bariwal, J. B.; Upadhyay, K. D.; Manvar, A. T.; Trivedi, J. C.; Singh, J. S.; Jain, K. S.; Shah, A. K. Eur. J. Med. Chem. 2008, 43, 2279.
[7] Grandolini, G.; Perioli, L.; Ambrogi, V. Eur. J. Med. Chem. 1999, 34, 701.
[8] Bajaj, K.; Archana; Kumar, A. Eur. J. Med. Chem. 2004, 39, 369.
[9] Ambrogi, V.; Furlani, A.; Grandolini, G.; Papaioannou, A.; Perioli, L.; Scarcia, V.; Tuttobello, L. Eur. J. Med. Chem. 1993, 28, 659.
[10] Desai, M. D.; Desai, K. K. Asian J. Chem. 2002, 14, 974.
[11] Zhang, P.; Wang, L.-Z.; Wu, H.-S.; Lan, J.-M.; Li, Y.; Wang, Y.-X. Chin. Chem. Lett. 2009, 20, 660
[12] Li, W.-H.; Lan, J.-M.; Li, C.; Cao, Y.-T.; Wang, H.-B.; Wang, L.-Z.; Zhang, P.; Wang, Y.-X.; Li, Y. Acta Chim. Sinica 2009, 67, 2732 (in Chinese). (李文红, 兰佳明, 李成, 曹云涛, 王海波, 王兰芝, 张萍, 王永祥, 李媛, 化学学报, 2009, 67, 2732.)
[13] Zhang, P.; Xuan, Y.; Liu, W.; Li. Y. Chin. J. Org. Chem. 2011, 31, 1240 (in Chinese). (张萍, 宣烨, 刘薇, 李媛, 有机化学, 2011, 31, 1240.)
[14] Zhang, P.; Huang, J. H.; Wang, L.-Z.; Liu, W.; Li. Y. Chin. J. Org. Chem. 2010, 30, 1939 (in Chinese). (张萍, 黄金华, 王兰芝, 刘薇, 李媛, 有机化学, 2010, 30, 1939.)
[15] Liu, Q.; Zhao, L.-F.; Li, W.-H.; Li, Y. Chin. J. Org. Chem. 2012, 32, 2122 (in Chinese). (刘倩, 赵利飞, 李文红, 李媛, 有机化学, 2012, 32, 2122.)
[16] Li, W.-H.; Zhang, L. F.; Liu, W.; Du, X. Q.; Li, Y. Chin. J. Org. Chem. 2011, 31, 1252 (in Chinese). (李文红, 张玲芬, 刘薇, 杜星琼, 李媛, 有机化学, 2011, 31, 1252.)
[17] Wang, L.-Z.; Zhang, P.; Zhang, X.-M.; Zhang, Y.-H.; Wang, Y.-X.; Li, Y. Eur. J. Med. Chem. 2009, 44, 2815.
[18] Qiu, S. L.; Wang, L.-Z.; Li, W.-H.; Li, Y. Acta Chim. Sinica 2011, 69, 1217 (in Chinese). (邱召来, 王兰芝, 李文红, 李媛, 化学学报, 2011, 69, 1217.)
[19] Hooton T. M. Infect. Dis. Clin. North. Am. 2003, 17, 303.
[20] Liu, M.; Zhang, W.-J.; Gao, N. Chem. Reag. 2009, 31, 795 (in Chinese). (刘敏, 章文军, 高宁, 化学试剂, 2009, 31, 795.)
[21] Nishiyama, Y.; Makino, Y.; Hamanaka, S.; Ogawa, A.; Sonoda, N. Bull. Chem. Soc. Jpn. 1989, 62, 1683.
[22] Houghten, R. A. Perspect. Drug Discovery Des. 1995, 2, 287.
[23] Xing, Y.; Xie, Z.-F.; Liu, F.-M. Chem. J. Chin. Univ. 2008, 29, 533 (in Chinese). (邢烨, 解正峰, 刘方明, 高等学校化学学报, 2008, 29, 533.)
[24] Yang, D. B.; Liu, F. M.; Shen, S. W.; Chen, S. Q. Chin. J. Org. Chem. 2010, 30, 244 (in Chinese). (杨德保, 刘方明, 沈松伟, 陈盛钦, 有机化学, 2010, 30, 244.)
[25] Zhang, X. M. M.S. Thesis, Hebei Normal University, Shijiazhuang, 2007 (in Chinese).(张学梅, 硕士论文, 河北师范大学, 石家庄, 2007.)
Options
文章导航

/

〈 〉