Synthesis, physico‐chemical characterization and theoretical exploration of some 2,4,5‐triaryl imidazole derivatives

• Published in: Journal of heterocyclic chemistry 2023-08, Vol.60 (8), p.1394-1415
• Main Authors: Chettri, Sailesh, Tamang, Sumiran, Rai, Prasansha, Rai, Yachna, Singha, Uttam Kumar, Pradhan, Kiran, Brahman, Dhiraj, Sinha, Biswajit
• Format: Article
• Language: English
• Subjects: Benzil; Chemical synthesis; Imidazole; Molecular docking; Molecular orbitals; Molecular structure; Optimization; Proteins; Solid phases; Vapor phases
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.4670

A series of six 2, 4, 5‐triarylimidazole (IM‐1 to IM‐6) have been prepared by the multi‐component condensation reaction involving benzil, substituted salicylaldehyde and NH4OAc under solvent free condition by using unconventional CuB4O7 catalyst. The compounds were characterized using various analytical and spectroscopic techniques. Furthermore, DFT studies such as optimization of gas phase structure, HOMO‐LUMO energies, Molecular electrostatic potential, NLO properties of these compounds have been investigated. In‐silico molecular docking study of 2, 4, 5‐triarylimidazole derivatives (IM‐1 to IM‐6) have been carried out to ascertain the inhibitory potential of these molecules against a diabetic protein (PDB ID 1IR3). The study showed that the these compounds have remarkable inhibitory potential against the protein 1IR3 with binding energy (ΔG) values for the compounds (IM‐1 to IM‐6) −8.7, −8.4, −8.8, −8.0, −8.9 and −7.8 kcal/mol respectively. In addition, the pharmacokinetic properties (ADMET) of the compounds (IM‐1 to IM‐6) have also been studied. In this research work, we have synthesized a series of six 2,4,5‐triarylimidazole derivatives utilizing a multi component, solvent free and green approach involving benzil, substituted salicyldehyde and NH4OAc using a cheap and unconventional Copper Borate(CuB4O7) catalyst. The prepared triarylimidazoles have been characterized by various spectroscopic and analytical techniques. Moreover, DFT studies involving geometry optimisation of gas phase structure, HOMO‐LUMO energies, Molecular Electrostatic Potential, Non‐linear optical properties of these compounds have also been studied along with the molecular docking study of the compounds against a diabetic protein (PDB 1IR3). The molecular docking study of the compounds have shown promising inhibitory potential against the protein 1IR3 and the binding energy values of the compounds against the target receptor protein are found to be in the range of −7.8 to −8.9 kcal/mol.