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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (9): 1358-1365. 上一篇    下一篇

研究论文

1-对氯苯基-3-苯基-4-苯甲酰基-吡唑啉酮-5缩胺类席夫碱铜配合物的合成与抑菌活性

俞志刚*，丁为民，纪红蕊，竹学友   

  1. (哈尔滨理工大学化学与环境工程学院 哈尔滨 150040)
  • 收稿日期:2009-09-01 修回日期:2010-02-28 发布日期:2010-04-25
  • 通讯作者: 俞志刚 E-mail:yzgyh@126.com
  • 基金资助:

    国家级.国家自然科学基金

Synthesis and Antibacterial Activity of the Schiff Bases Derived from 1-(p-Chlorophenyl)-3-phenyl-4-benzoyl-pyrazolone-5 and Amine Compounds and Their Transitional Metallic Copper Com-plexes

YU Zhi-Gang, DING Wei-Min, JI Hong-Rui, ZHU Xue-You   

  1. (Schoof of Chemistry and Environmental Engineering College, Harbin University of Science and Technol-ogy, Harbin 150040)
  • Received:2009-09-01 Revised:2010-02-28 Published:2010-04-25
  • Contact: YU Zhi-Gang E-mail:yzgyh@126.com

PDF

1430

被引次数

13 | 2

合成了7种新型酰基吡唑啉酮席夫碱过渡金属铜配合物. 7种席夫碱分别为: 1-对氯苯基-3-苯基-4-苯甲酰基-吡唑啉酮-5缩苯胺(HS1)、对氯苯胺(HS2)、对溴苯胺(HS3)、糠胺(HS4)、对甲氧苯胺(HS5)、对乙氧苯胺(HS6)和萘胺(HS7)席夫碱. 由元素分析、络合滴定法、质谱和摩尔电导值确定配合物的组成通式为[Cu(S)2] (S＝S1, S2, S3, S4, S5, S6, S7), 通过红外光谱、热重谱、核磁共振氢谱和液相色谱-质谱联用技术对配体及配合物的结构进行了表征, 同时对7个席夫碱配体及其7个铜配合物的抑菌活性进行了初步研究. 表征结果表明: 在不同的测试条件下, 7个配体的异构体存在方式不同. 配位时酮式结构可能转化为烯醇式结构, 按去质子方式以烯醇氧负离子和亚胺基氮原子双齿形式与铜中心离子成键. 抑菌实验结果显示: 所有化合物对受试的4个菌种均有不同程度的抑菌活性, 其中配合物普遍强于配体. 抑菌能力呈现浓度效应, 在浓度为3.0 mg•mL－1时最大直径可达16.0 mm.

关键词: 席夫碱, 铜配合物, 合成, 抑菌活性

Seven novel transitional metallic copper complexes of seven new acyl pyrazolone Schiff bases have been synthesized in the nonaqueous solvent. These seven Schiff bases were derived from 1-(p-chlorophenyl)-3-phenyl-4-benzoyl-pyrazolone-5 and aniline (HS1), parachloroani-line (HS2), parabromoaniline (HS3), furfuryl amine (HS4), p-methoxy aniline (HS5), p-ethoxyaniline (HS6) and naphthyl-amine (HS7), respectively. The general formula of complexes was confirmed to be [Cu(S)2] (S＝S1, S2, S3, S4, S5, S6, S7) based on elemental analysis, complexometric titration, mass spectra and molar conductance value. Their molecular structures were characterized by IR, TG, 1HNMR and liquid chromatography coupled with mass spectrometry, and the antibacterial ac-tivities of these seven Schiff bases and their complexes were also investigated with the oxford cup plate as-say method. The characterization results showed that the isomers of seven ligands existed differently under different testing conditions. The ketoform structure might change into the enolform structure after coordina-tion and bonded with copper central ion by enolic oxygen negative ion losing one proton and nitrogen atom of imine group in bis-cog form. The results of antibacterial activity experiment indicated that all compounds were all resistant to four different bacteria with various degrees under different concentrations. The antibac-terial action of the complexes was generally stronger than that of the ligands. The varying trend of antibacte-rial capability followed the concentration effect, the maximal diameter could be 16.0 mm under the concen-tration of 3.0 mg•mL－1.

Key words: Schiff base, copper complex, synthesis, antibacterial activity