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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (9): 1516-1521. 上一篇    下一篇

研究简报

氨基酸席夫碱的合成及性质研究

赵小菁*，张丽影，金黎明，范圣第   

  1. (大连民族学院化学工程系 国家民委-教育部重点实验室 大连 116605)
  • 收稿日期:2011-01-05 修回日期:2011-03-15 发布日期:2011-04-27
  • 通讯作者: 赵小菁 E-mail:qingxj@126.com

Synthesis and Properties of the Amino Acid Schiff Base

ZHAO Xiao-Jing, ZHANG Li-Ying, JIN Li-Ming, FAN Sheng-Di   

  1. (Key Laboratory of the State Ethnic Affairs Commission, Ministry of Education, Department of Chemical Engineering, Dalian Nationalities University, Dalian 116605)
  • Received:2011-01-05 Revised:2011-03-15 Published:2011-04-27

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3255

被引次数

49

合成了5种氨基酸席夫碱Sal-Gly(甘氨酸席夫碱)、Sal-Glu(谷氨酸席夫碱)、Sal-Met(甲硫氨酸席夫碱)、Sal-Tyr(酪氨酸席夫碱)、Sal-Arg(精氨酸席夫碱)及其金属锌离子配合物共10种化合物. 用元素分析、核磁共振、红外光谱、紫 外-可见光谱等手段对其组成的结构进行表征. 以Sal-Tyr-Zn为主体, 咪唑(1), 1-甲基-咪唑(2), 2-乙基-4-甲基咪唑(3), 吡唑(4), 4-碘苯胺(5), DABCO (1,4-重氮双环[2,2,2]辛烷)(6), 邻苯二胺(7)和1,2-环己二胺(8)为客体, 进行配位相互作用研究. 选取大肠杆菌作为抑菌菌种, 研究了氨基酸席夫碱的抑菌能力. 结果表明, 氨基酸席夫碱配体及金属锌配合物对大肠杆菌均有抑菌活性, 配体的抗菌活性随氨基酸残基的增大而减小. 金属锌配合物的抑菌活性大于其所对应的氨基酸席夫碱配体的抑菌活性, 活性最大的则为Sal-Arg-Zn.

关键词: 氨基酸席夫碱, 合成, 表征, 抑菌活性

Five amino acid Schiff bases: Sal-Gly (glycine acid Schiff base), Sal-Glu (glutamic acid Schiff base), Sal-Met (methionine acid Schiff base), Sal-Tyr (tyrosine acid Schiff base), Sal-Arg (arginine acid Schiff base), and its zinc complexes were synthesized and characterized by elemental analysis, 1H NMR, IR and UV-vis techniques. The association behavior between Sal-Tyr-Zn and the nitrogen-containing compounds including imidazole (1), 1-methyl imidazole (2), 2-ethyl-4-methyl-imidazole (3), pyrazole (4), 4-iodoaniline (5), DABCO (1,4-diazobycyclo[2,2,2]octane) (6), 1,2-diaminobenzene (7) and 1,2-diaminocyclohexane (8) was studied. Amino acid Schiff bases and their zinc complexes have antibacterial activity to some fungus, so the antibacterial activity of the compounds to Escherichia coli was studied. The results show that both the amino acid Schiff base and their zinc complexes have the bacteriostatic activity to Escherichia coli. The antibacterial activity of the ligands decreased when the size of amino-acid residue R-group increased. The activity of the zinc complexes is more powerful than that of the ligands, and Sal-Arg-Zn shows the strongest inhibitory activity.

Key words: amino acid Schiff base, synthesis, characterization, antibacterial activity

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