Halo-bridged Cu(II) complexes with pyridine–pyrazole ligands: Influence of halogen and ligand lipophilicity on antimicrobial activity

Abstract

A series of five coordinated, doubly halo bridged Cu(II) complexes [Cu2(μ-X)2(Ln)2×2] (X=Cl and Br; n = 1, 2 and 3), CuL1Cl, CuL1Br, CuL2Cl, CuL2Br, CuL3Cl and CuL3Br (where L1 = 2-((1H-pyrazol-1-yl)methyl)pyridine, L2 = 2-((3-methyl-1H-pyrazol-1-yl)methyl)pyridine, L3 = 2-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)pyridine) have been synthesized and structurally characterized using FT-IR and UV–Vis spectroscopy analysis. Moreover, CuL1Cl, CuL1Br and CuL3Cl structures have also been confirmed by single crystal X-ray structural analysis. Copper ion in CuL1Cl, CuL1Br and CuL3Cl displayed distorted squared pyramidal geometry and formed dimers via bridged μ‑chloro/μ‑bromo coordination in the crystal lattice. The intermolecular C–H···Cl hydrogen bonding interaction further connected the dimers of CuL1Cl and CuL3Cl with four neighboring dinuclear complex units. Copper complexes were evaluated for their antimicrobial activity against Gram-negative and Gram-positive bacteria. Interestingly, copper complexes exhibited selective antimicrobial activity against Gram-positive bacteria. Further the increasing ligand lipophilicity showed the increase of antibacterial activity of copper complexes. The lipophilicity of ligands was regulated by number of methyl substituents on the ligands. The chloro bridged copper complexes exhibited relatively higher antibacterial activity compared to the bromo bridged copper complexes. Thus, the present structure-activity of simple copper complexes might provide insight on the structural design of new antimicrobial agents based on coordination complexes.