The synthesis, antimicrobial activity and theoretical calculations of 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline

Abstract

Aim. To synthesize 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline, as well as make theoretical calculations of its structure and study its antimicrobial properties. Materials and methods. The synthesis procedures were performed in the presence of ionic liquid catalysts and under microwave conditions. The catalysts included 1-butyl-3-methylimidazolehydrosulfate, N-methylpyrrolidone perchlorate, and 1,4-dimethylpiperazinedihydrosulfate ionic liquids. Benzyl, ammonium acetate, p-aminoazobenzene and 4-(dimethylamino)benzaldehyde were taken as reagents. Ethanol was used as a solvent. Results. The results of the conditions were compared and it was determined that the 1,4-dimethylpiperazinedihydrosulfate catalyst reacted under microwave conditions in a shorter time (19 min) with a higher yield (78.1 %). The structure of the compound synthesized was analyzed by 1H, 13C NMR and IR spectroscopy. The theoretical calculations of the compound were determined using the density functional theory (DFT/B3LYP) method with a basic set of 6-31G(d,p). The geometry of the structure was optimized, bond lengths, angle degrees were given, and important quantum chemical parameters, such as HOMO, LUMO orbitals, reactivity, stability, electrophilicity, electronegativity, chemical softness, chemical hardness were calculated. It was found that the compound had a high stability (∆E = 2.359 eV) and a high biological activity (ω = 5.754 eV). The antimicrobial activity of the sample against bacteria of S. aureus, E. coli, P. aeruginosa, K. pneumoniae, B. anthracoides and C. albicans fungus was studied. Conclusions. In this work, 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline has been synthesized from benzyl, ammonium acetate, p-aminoazobenzene and 4-(dimethylamino)benzaldehyde in the presence of microwave and ionic liquid catalysts. It has been determined that 1,4-dimethylpiperazinedihydrosulfate catalyst reacts under microwave conditions in a shorter time (19 min) with a higher yield (78.1 %). The compound has been tested as an antimicrobial agent against bacteria of S. aureus, E. coli, P. aeruginosa, K. pneumoniae, B. anthracoides and C. albicans fungus, showing moderate and higher activity.