2-(4-hydroxyphenyl)-4-5-diphenylimidazole and Diabetes-Mellitus

A new and efficient solvent free synthesis of 2,4,5-trisubstituted imidazoles (3a-3j) was achieved by N-acetyl glycine (NAG) catalyzed three components condensation of aldehydes, benzil and ammonium acetate. Our synthetic methodology accommodated a range of various substituted alkyl and aryl aldehydes. Evaluation of α-glucosidase inhibitory activity of these imidazole derivatives revealed that most of them presented good α-glucosidase inhibition at low micro-molar concentrations. Among the synthesized compounds, compound 3c, bearing the ortho-hydroxy phenyl substituent at position 2 displayed the highest inhibitory activity with an IC50 value 74.32±0.59 μM. In silico molecular docking for all compounds and computational studies of the most active compound 3c were also performed.

Topics: Catalysis; Diabetes Mellitus; Glycoside Hydrolase Inhibitors; Humans; Imidazoles; Models, Molecular; Proton Magnetic Resonance Spectroscopy; Solvents; Spectrometry, Mass, Electrospray Ionization; Spectroscopy, Fourier Transform Infrared; Structure-Activity Relationship