Synthesis, Characterizations, and Quantum Chemical Investigations on Imidazo[1,2- a]pyrimidine-Schiff Base Derivative: (E)-2-Phenyl- N-(thiophen-2-ylmethylene)imidazo[1,2- a]pyrimidin-3-amine

Mohamed Azzouzi; Omar Azougagh; Abderrahim Ait Ouchaoui; Salah Eddine El Hadad; Stéphane Mazières; Soufian El Barkany; Mohamed Abboud; Adyl Oussaid

doi:10.1021/acsomega.3c06841

Synthesis, Characterizations, and Quantum Chemical Investigations on Imidazo[1,2- a]pyrimidine-Schiff Base Derivative: (E)-2-Phenyl- N-(thiophen-2-ylmethylene)imidazo[1,2- a]pyrimidin-3-amine

ACS Omega. 2023 Dec 15;9(1):837-857. doi: 10.1021/acsomega.3c06841. eCollection 2024 Jan 9.

Authors

Mohamed Azzouzi¹, Omar Azougagh¹, Abderrahim Ait Ouchaoui², Salah Eddine El Hadad², Stéphane Mazières³, Soufian El Barkany¹, Mohamed Abboud⁴, Adyl Oussaid¹

Affiliations

¹ Laboratory of Molecular Chemistry, Materials and Environment (LCM2E), Department of Chemistry, Multidisciplinary Faculty of Nador, University Mohamed I, Nador 60700, Morocco.
² Laboratory of Medical Biotechnology (MedBiotech), Bionova Research Center, Medical and Pharmacy School, Mohammed V University, Agdal, Rabat B.P 8007, Morocco.
³ Laboratory of IMRCP, University Paul Sabatier, CNRS UMR 5623, 118 route de Narbonne, Toulouse 31062, France.
⁴ Catalysis Research Group (CRG), Department of Chemistry, College of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia.

Abstract

In this study, (E)-2-phenyl-N-(thiophen-2-ylmethylene)imidazo[1,2-a]pyrimidin-3-amine (3) is synthesized, and detailed spectral characterizations using ¹H NMR, ¹³C NMR, mass, and Fourier transform infrared (FT-IR) spectroscopy were performed. The optimized geometry was computed using the density functional theory method at the B3LYP/6-311++G(d,p) basis set. The theoretical FT-IR and NMR (¹H and ¹³C) analysis are agreed to validate the structural assignment made for (3). Frontier molecular orbitals, molecular electrostatic potential, Mulliken atomic charge, electron localization function, localized orbital locator, natural bond orbital, nonlinear optical, Fukui functions, and quantum theory of atoms in molecules analyses are undertaken and meticulously interpreted, providing profound insights into the molecular nature and behaviors. In addition, ADMET and drug-likeness studies were carried out and investigated. Furthermore, molecular docking and molecular dynamics simulations have been studied, indicating that this is an ideal molecule to develop as a potential vascular endothelial growth factor receptor-2 inhibitor.