Preparation, characterization, biological activity, density functional theory calculations and molecular docking of chelates of diazo ligand derived from m-phenylenediamine and p-chlorophenol

A novel azo dye ligand, 2,2'-(1,3-phenylenebis(diazene-2,1-diyl))bis(4-chlorophenol), was synthesized from the diazotization of m-phenelyenediamine and coupling with p-chlorophenol in alkaline medium. Mononuclear Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes of the azo ligand (H2L) were prepared and characterized using elemental analyses, infrared spectroscopy, electron spin resonance, magnetic susceptibility, conductance measurements and thermal analyses. The UV-visible, H-1 NMR and mass spectra of the ligand and its chelates were also recorded. The analytical data showed that the metal-to-ligand ratio in the mononuclear azo complexes was 1:1. Diffuse reflectance and magnetic moment measurements revealed the complexes to have octahedral geometry. The infrared spectral data showed that the chelation behaviour of the ligand towards transition metal ions was through phenolic oxygen and azo nitrogen atoms. The electronic spectral results indicated the existence of pi ->pi* (phenyl rings) and n ->pi* (-N=N) and confirmed the mentioned structure. Molar conductivity revealed the non-electrolytic nature of all chelates. The presence of water molecules in all complexes was supported by thermal studies. Molecular docking was used to predict the binding between H2L and the receptors of breast cancer mutant 3hb5-oxidoreductase, crystal structure of Escherichia coli (3t88) and crystal structure of Staphylococcus aureus (3q8u). The molecular and electronic structure of H2L was optimized theoretically and the quantum chemical parameters were calculated. In addition, the effects of the H2L azo ligand and its complexes on the inhibition of bacterial or fungal growth were evaluated. The prepared complexes had enhanced activity against bacterial or fungal growth compared to the H2L azo ligand.