Synthesis, characterization, cyclic voltammetry, and antimicrobial properties of N-(5-benzoyl-2-oxo-4-phenyl-2H-pyrimidine-1-yl)-malonamic acid and its metal complexes

Abstract

A new heterocyclic compound, N-(5-benzoyl-2-oxo-4-phenyl-2H-pyrimidin-1-yl)-malonamic acid, was synthesized from N-aminopyrimidine-2-one and malonyldichloride. Bis-chelate complexes of the ligand were prepared from acetate/chloride salts of Cu(II), Co(II), Ni(II), Mn(II), Zn(II), Cd(II), Fe(III), Cr(III), and Ru(III) in methanol. The structures of the ligand and its metal complexes were characterized by microanalyses, IR, NMR, API-ES, UV-Vis spectroscopy, magnetic susceptibility, and conductometric analyses. Octahedral geometry was suggested for all the complexes, in which the metal center coordinates to ONO donors of the ligand. Each ligand binds the metal using C=O, HN, and carboxylate. The cyclic voltammograms of the ligand and the complexes were also discussed. The compounds were evaluated for their antimicrobial activities against Gram-positive and Gram-negative bacteria, and fungi using microdilution procedure. The antimicrobial studies showed that Cu(II), Fe(III), and Ru(III) complexes exhibited good antibacterial activity against Gram-positive bacteria with minimum inhibitory concentrations between 20 and 80 µg mL⁻¹. However, the ligand and the complexes possess weak efficacy against Gram-negative bacterium and Candida strains. As a result, we suggest that these complexes containing pyrimidine might be a new group of antibacterial agents against Gram-positive bacteria.

Keywords:

• N-aminopyrimidine complexes
• Cyclic voltammetry
• Biological activity

Acknowledgments

We are grateful to Scientific and Research Council of Turkey (TBAG 105T145) for the support of this research.