应用化学 ›› 2009, Vol. 26 ›› Issue (10): 1165-1168.

• 研究论文 • 上一篇    下一篇

卤代邻羟苄基谷氨酸(酯)的合成、表征及抑菌活性

刘芳,卢俊瑞,辛春伟,陈丽然,张明,鲍秀荣,张海涛   

  1. (天津理工大学化学化工学院 天津 300384)
  • 收稿日期:2008-10-06 修回日期:2008-11-25 出版日期:2009-10-10 发布日期:2009-10-10
  • 通讯作者: 卢俊瑞,男,教授,博士生导师; E-mail:lujunrui@tjut.edu.cn; 研究方向:新型精细化学品
  • 基金资助:
    国家自然科学基金(20576103;20776114)天津市高校科技发展基金(2006ZD33;20050712)天津市自然科学基金(05YFJIYJC14000)资助项目

Synthesis, Characterization and Antibacterial Property of Halogenated o-hydroxybenzyl-glutamates and there esters

LIU Fang, LU Jun-Rui, XIN Chun-Wei, CHEN Li-Ran, ZHANG Ming, BAO Xiu-Rong, ZHANG Hai-Tao   

  1. (College of Chemistry and Chemical Engineering,Tianjin University of Technology,Tianjin 300384)
  • Received:2008-10-06 Revised:2008-11-25 Published:2009-10-10 Online:2009-10-10

摘要:

分别用氯代水杨醛、溴代水杨醛与L-谷氨酸及其酯反应,首先制得水杨醛缩谷氨酸类席夫碱(2),再经硼氢化钠还原制得邻羟苄基取代谷氨酸及其酯(3),化合物的结构经IR、1H NMR、MS与元素分析表征确认. 测试表明,在质量浓度为0.05%时,卤代邻羟苄基谷氨酸对大肠杆菌具有高的抑菌活性,抑菌率高达97%,对白色念珠菌、金黄色葡萄球菌的抑菌效果较差,但其甲酯化产物卤代邻羟苄基谷氨酸甲酯对白色念珠菌具有高的抑菌活性,抑菌率高达100%,对大肠杆菌、金黄色葡萄球菌的抑菌效果较差,说明该类衍生物对菌株的抑杀作用具有明显的专一性和特异性,氯代邻羟苄基谷氨酸甲酯、溴代邻羟苄基谷氨酸甲酯是白色念珠菌的优良抗菌化合物。

关键词: 卤代邻羟苄基谷氨酸, 卤代邻羟苄基谷氨酸酯, 合成, 表征, 抑菌活性

Abstract:

The Salicylaldehyde-type glutamate Schiff bases (2) were obtained first by the reactions of Chlorinated salicylaldehyde、bromide salicylaldehyde and L-glutamates and there esters, then the schiff bases were reduced by NaBH4 to produce halogenated o-hydroxybenzyl-glutamates and there esters (3), The structures of the products were confirmed by 1H NMR、IR、MS and element analysis. The results of preliminary bioassay shows that at the mass concentration of 0.05%, p-halo-o-hydroxybenzyl-glutamates have obvious antimicrobial activity against E. coli, inhibition rate was as high as 97 %, but have less effective to M.albicans or S.aureus. The methyl esters, such as p-halo-o-hydroxybenzyl-glutamate methylesters, have obvious antimicrobial avtivity against M.albicans, inhibition rate was as high as 100 %, but have less effective to E. coli or S.aureus. It shows that the antibacterial property of title compounds have obvious selectivity and specificity. p-Chloride-o-hydroxybenzyl-glutamate methylester, p-bromide-o-hydroxybenzyl-glutamate methylester are fine M.aureus antibacterial compounds.

Key words: halo-o-hydroxybenzyl-glutamate, halo-o-hydroxybenzyl-glutamate methylester, synthesis, characterization, antibacterial property

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