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

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: cis-[Cu(2-RIm)₂(acr)₂]·xH₂O ((1): R = ⁻CH₃, x = 2; (4): R = ⁻CH₂⁻CH₃, x = 0), trans-[Cu(2-RIm)₂(acr)₂] ((2): R = ⁻CH₃; (5): R = ⁻CH₂⁻CH₃) and trans-[Cu(5-RIm)₂(acr)₂] ((3): 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 (2) and (5) 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 trans positions. For complex (4) 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 cis positions. These results indicate the fact that complexes (4) and (5) are the geometric isomers of the same compound bis(acrylate)-bis(2-ethylimidazole)-copper(II). Complexes (1) and (2), as well as (4) and (5), 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 trans isomers (2) and (5), followed by (4) have shown the broadest range of antimicrobial activity. In case of (1) and (2) isomers, the trans isomer (2) was significantly more active than cis (1), while the cis isomer (4) proved to be more active than trans (5). Taken together, the biological evaluation results indicate that the trans (2) 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.

Keywords: X-ray structure; antimicrobial activity; copper(II) complex; geometric isomerism; imidazole derivative.

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Antifungal Agents / pharmacology
  • Bacteria / drug effects
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry*
  • Carboxylic Acids / pharmacology*
  • Copper / chemistry*
  • Copper / pharmacology*
  • Crystallography, X-Ray
  • Fungi / drug effects
  • Hydrogen Bonding
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Imidazoles / pharmacology*
  • Isomerism
  • Ligands
  • Microbial Sensitivity Tests
  • Molecular Conformation

Substances

  • Anti-Infective Agents
  • Antifungal Agents
  • Carboxylic Acids
  • Imidazoles
  • Ligands
  • Copper