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

摘要

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)Cl-2 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 H-1 NMR, C-13 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.