A new pyrimidine-derived ligand, N-pyrimidine oxalamic acid, and its Cu(II), Co(II), Mn(II), Ni(II), Zn(II), Cd(II), and Pd(II) complexes: synthesis, characterization, electrochemical properties, and biological activity

Abstract

A new heterocyclic compound N-(5-benzoyl-2-oxo-4-phenyl-2H-pyrimidin-1-yl)-oxalamic acid has been synthesized from N-amino pyrimidine-2-one and oxalylchloride. Bis-chelate complexes of the ligand were prepared from acetate/chloride salts of Cu(II), Co(II), Mn(II), Ni(II), Zn(II), Cd(II), and Pd(II) in methanol. The structures of the ligand and its metal complexes were characterized by microanalyses, IR, AAS, NMR, API-ES, UV-Vis spectroscopy, magnetic susceptibility, and thermogravimetric analyses. An octahedral geometry has been suggested for all the complexes, except for Pd(II) complex, in which the metal center is square planar. Each ligand binds using C(2)=O, HN, and carboxylate. The cyclic voltammograms of the ligand and the complexes are also discussed. The new synthesized compounds were evaluated for antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi using the microdilution procedure. The Cu(II) complex displayed selective and effective antibacterial activity against one Gram-positive spore-forming bacterium (Bacillus cereus ATCC 7064), two Gram-positive bacteria (Staphylococcus aureus ATCC 6538 and S. aureus ATCC 25923) at 40–80 µg mL⁻¹, but poor activity against Candida species. The Cu(II) complex might be a new antibacterial agent against Gram-positive bacteria.

Keywords:

• N-aminopyrimidine
• Metal complexes
• Cyclic voltammetry
• Biological activity

Acknowledgment

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