Synthesis of Some New N-Substituted Imidazole Derivatives and Their In Vitro Antibacterial Investigation

Here we reported the synthesis of N-substituted imidazole derivatives (VIa–o) that involves Suzuki coupling reaction between 1-(2-((4-bromobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole (V) and various aryl boronic acids using Pd(dppf)Cl2 with DCM as the catalyst in 1,4-dioxane/H2O (2 : 1) solvent and using potassium carbonate as base. All the newly synthesized compounds were characterized by 1H NMR, 13C NMR and mass spectral data. They were screened for their antibacterial activity against gram-positive bacterial strains, Bacillus subtilis and Staphylococcus aureus where the compounds 4-(4-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)phenyl)pyridine (VIc), 1-(2-(2,4-dichlorophenyl)-2-((3'-fluoro-4'-methoxy-[1,1'-biphenyl]-4-yl)methoxy)ethyl)-1H-imidazole (VIe), 4'-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)-[1,1'-biphenyl]-3-carbonitrile (VIi), 1-(2-(2,4-dichlorophenyl)-2-((3'-fluoro-[1,1'-biphenyl]-4-yl)methoxy)ethyl)-1H-imidazole (VIj), 1-(2-(2,4-dichlorophenyl)-2-((4'-fluoro-3'-methyl-[1,1'-biphenyl]-4-yl)methoxy)ethyl)-1H-imidazole (VIn) and 4-(4-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)phenyl)-1H-pyrazole (VIo) exhibited remarkable activity compared to the reference streptomycin.