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新型含咪唑衍生物的铜(II)羧酸配合物的 X 射线晶体结构、几何异构和抗菌活性。

X-ray Crystal Structure, Geometric Isomerism, and Antimicrobial Activity of New Copper(II) Carboxylate Complexes with Imidazole Derivatives.

机构信息

National Institute of Materials Physics, 405A Atomistilor, 077125 Magurele-Bucharest, Romania.

National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donat Avenue, 400293 Cluj-Napoca, Romania.

出版信息

Molecules. 2018 Dec 9;23(12):3253. doi: 10.3390/molecules23123253.

Abstract

Five new copper(II) acrylate complexes (acr is the acrylate anion: C₃H₃O₂) with imidazole derivatives (2-methylimidazole/2-MeIm, 5-methylimidazole/5-MeIm, 2-ethylimidazole/2-EtIm) of type: -[Cu(2-RIm)₂(acr)₂]·xH₂O ((): R = ⁻CH₃, x = 2; (): R = ⁻CH₂⁻CH₃, x = 0), -[Cu(2-RIm)₂(acr)₂] ((): R = ⁻CH₃; (): R = ⁻CH₂⁻CH₃) and -[Cu(5-RIm)₂(acr)₂] ((): R = ⁻CH₃) have been prepared and characterized by elemental analysis, Fourier Transform Infrared spectrometry (FTIR), Electron Paramagnetic Resonance (EPR), electronic reflectance spectroscopy, scanning electron microscopy, and mass spectrometry. The single crystal X-ray diffraction study of complexes () and () reveals that the copper(II) ion is located on an inversion center and show elongated octahedral geometry completed by two coplanar bidentate acrylates and two unidentate imidazole derivatives displayed in positions. For complex () the single crystal X-ray diffraction shows that the copper(II) ion is in a distorted octahedral environment which can be easily confused with a trigonal prism completed by two bidentate acrylates and two unidentate imidazole derivatives displayed in positions. These results indicate the fact that complexes () and () are the geometric isomers of the same compound bis(acrylate)-bis(2-ethylimidazole)-copper(II). Complexes () and (), as well as () and (), were produced simultaneously in the reaction of the corresponding copper(II) acrylate with imidazole derivatives in methanol solution. Furthermore, in order to be able to formulate potential applications of the obtained compounds, our next goal was to investigate the in vitro antimicrobial activity of the synthesized complexes against Gram-positive and Gram-negative bacteria, as well as fungal strains, of both clinical and ecological importance (biodeterioration of historical buildings). The isomers () and (), followed by () have shown the broadest range of antimicrobial activity. In case of () and () isomers, the trans isomer () was significantly more active than cis (), while the cis isomer () proved to be more active than trans (). Taken together, the biological evaluation results indicate that the trans () was the most active complex, demonstrating its potential for the development of novel antimicrobial agents, with potential applications in the biomedical and restoration of architectural monuments fields.

摘要

已制备并通过元素分析、傅里叶变换红外光谱 (FTIR)、电子顺磁共振 (EPR)、电子反射光谱、扫描电子显微镜和质谱对五种新的铜 (II) 丙烯酸盐配合物(acr 是丙烯酸盐阴离子:C₃H₃O₂)与咪唑衍生物(2-甲基咪唑/2-MeIm、5-甲基咪唑/5-MeIm、2-乙基咪唑/2-EtIm)进行了表征:-[Cu(2-RIm)₂(acr)₂]·xH₂O(():R = ⁻CH₃,x = 2;():R = ⁻CH₂⁻CH₃,x = 0),-[Cu(2-RIm)₂(acr)₂](():R = ⁻CH₃;():R = ⁻CH₂⁻CH₃)和 -[Cu(5-RIm)₂(acr)₂](():R = ⁻CH₃)。单晶 X 射线衍射研究配合物()和()表明,铜 (II) 离子位于反演中心,呈现出由两个共面的双齿丙烯酸盐和两个显示在 位置的单齿咪唑衍生物组成的拉长八面体几何形状。对于配合物(),单晶 X 射线衍射表明,铜 (II) 离子处于扭曲的八面体环境中,很容易与由两个双齿丙烯酸盐和两个显示在 位置的单齿咪唑衍生物组成的三角棱柱体相混淆。这些结果表明配合物()和()是同一化合物双(丙烯酸盐)-双(2-乙基咪唑)-铜 (II) 的几何异构体。配合物()和()以及()和()同时在甲醇溶液中相应的铜 (II) 丙烯酸盐与咪唑衍生物反应中生成。此外,为了能够制定所合成配合物的潜在应用,我们的下一个目标是研究它们对临床和生态重要性(历史建筑的生物降解)的革兰氏阳性和革兰氏阴性细菌以及真菌菌株的体外抗菌活性。立体异构体()和(),其次是(),表现出最广泛的抗菌活性。对于()和()异构体,反式异构体()比顺式异构体()显著更具活性,而顺式异构体()比反式异构体()更具活性。总的来说,生物评价结果表明,反式()是最活跃的配合物,显示出其作为新型抗菌剂的发展潜力,在生物医学和建筑纪念碑修复领域具有潜在应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a9c/6321156/519843b3e496/molecules-23-03253-g001.jpg

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