应用化学 ›› 2009, Vol. 26 ›› Issue (11): 1282-1286.

• 研究论文 • 上一篇    下一篇

N,N′-二(-2-羟苄基)取代咪唑烷的合成、表征及抑菌活性研究

张明,卢俊瑞*,辛春伟,刘芳,高惠涵,鲍秀荣,陈丽然   

  1. (天津理工大学化学化工学院 天津 300384)
  • 收稿日期:2008-11-03 修回日期:2009-01-08 出版日期:2009-11-10 发布日期:2009-11-10
  • 通讯作者: 卢俊瑞,男,博士,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)天津市高校科技发展基金重点(2006ZD33)资助项目

Synthesis, Characterization and Antibacterial Activities of N,N′-bis(-2-hydroxybenzyl) substitute imidazolidine derivative

ZHANG Ming, LEI Jun-Rui* XIN Chun-Wei, LIU Fang, GAO Hui-Han, BAO Xiu-Rong, CHEN Li-Ran   

  1. (College of Chemistry and Chemical Engineering,Tianjin University of Technology,Tianjin 300384)
  • Received:2008-11-03 Revised:2009-01-08 Published:2009-11-10 Online:2009-11-10

摘要:

利用生物活性叠加原理,将“邻羟苯基”和“咪唑烷”分子片断有机结合,合成了6种N,N′-二(-2-羟苄基)取代咪唑烷类化合物(3a-3f).以水杨醛和乙二胺为起始原料,经缩合、NaBH4还原制得N,N′-二邻羟苄基乙二胺(2),进而与芳醛类化合物缩合关环制得目标化合物. 化合物的结构经1H NMR、IR、MS和元素分析等表征确认.结果表明,水杨醛与乙二胺的缩合反应,可专一性地生成对称双缩席夫碱化合物(1);芳醛上的取代基对缩合关环反应有显著影响,邻、对位吸电基可使芳醛的羰基活化,有利于缩合关环反应的进行,邻、对位供电基可使芳醛的羰基钝化,不利于缩合关环反应进行.抑菌测试表明,质量浓度为0.1%时,N,N′-二(-2-羟苄基)取代咪唑烷化合物对不同菌株的抑菌活性具有明显的特异性,对白色念珠菌、大肠杆菌的抑菌率高达100%,是一类极具潜力的抗真菌、抗革兰氏阴性菌的化合物.

关键词: N,N′-二(-2-羟苄基)取代咪唑烷, 合成, 表征, 抑菌活性

Abstract:

A series of N,N′-bis(-2-hydroxy benzyl) substituted imidazolidine derivatives (3a-3f) were designd by means of combining segments o-hydroxy phenyl and imidazolidine compounds, according to realize reinforcement of biological activities. The N,N′-bis-o-hydroxy benzyl diaminoethane(2) by synthesized by using salicylaldehyd and 1,2-Diaminoethane as material, through condensation reactions and reducted by NaBH4, then reacted with aromatic aldehydes to obtain the target compound. The structures of all the compounds have been confirmed by 1H NMR、IR、mass spectra and element analysis. The result shows that the reaction of salicylaldehyde and 1,2-Diaminoethane singled to obtain the symmetric Schiff base(1); The condensation of Aromatic Aldehyde with N,N′-bis(o-hydroxy benzyl) diaminoethane(2) were noticeably different for different substituents: o-,p-substituted electron-withdrawing groups can active aromatic aldehyde and result in higher yield of ring closing reaction, but o-,p-substitute electron-donating groups have opposite effects. The result of preliminary bioassay shows that target compounds have obvious specificity to different classificatory bacterium at 0.1%(mass concentration), and have 100% inhibitory ratio on Monilia albican and Escherichia coli. They will be a series of finer potential antibacterial compounds in fungus and Gram-negative bacteria.

Key words: N,N′-bis(-2-hydroxybenzyl)substitute imidazolidine, synthesis, characterization, antibacterial activity

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