Synthesis, Thermal, DFT Calculations, HOMO-LUMO, MEP, and Molecular Docking Analysis of New Derivatives of Imidazolin-4-Ones

Khedidja Merdja (Laboratory of Applied Organic Synthesis, Faculty of Exact and Applied Sciences, University Oran1 Ahmed Ben Bella, El M’Naouer, Oran 31000, Algeria Laboratory of Synthesis and Catalysis (LSCT), Faculty of Materials Sciences, University Ibn Khaldoun-T)
Choukry Kamel Bendeddouche (Laboratory of Applied Organic Synthesis, Faculty of Exact and Applied Sciences, University Oran1 Ahmed Ben Bella, El M’Naouer, Oran 31000, Algeria)
Mokhtaria Drissi (Laboratory of Synthesis and Catalysis (LSCT), Faculty of Materials Sciences, University Ibn Khaldoun-Tiaret, Tiaret 14000, Algeria)
Farah Chafika Kaouche (Laboratory of Synthesis and Catalysis (LSCT), Faculty of Materials Sciences, University Ibn Khaldoun-Tiaret, Tiaret 14000, Algeria)
Nassima Medjahed (Laboratoire de Catalyse et Synthèse en Chimie Organique, Faculté des Sciences, Université de Tlemcen, Tlemcen 13000, Algeria Faculté des Sciences et de la Technologie, Université d’Ain Témouchent, Ain Témouchent 46000, Algeria)
José Manuel Padrón (BioLab, Instituto Universitario de Bio-Organica “Antonio González”, Universidad de La Laguna, La Laguna 38200, Spain)
Mansour Debdab (Laboratory of Synthesis and Catalysis (LSCT), Faculty of Materials Sciences, University Ibn Khaldoun-Tiaret, Tiaret 14000, Algeria)
Mustapha Rahmouni (Laboratory of Synthesis and Catalysis (LSCT), Faculty of Materials Sciences, University Ibn Khaldoun-Tiaret, Tiaret 14000, Algeria)
El Habib Belarbi (Laboratory of Synthesis and Catalysis (LSCT), Faculty of Materials Sciences, University Ibn Khaldoun-Tiaret, Tiaret 14000, Algeria)

Indonesian Journal of Chemistry
Vol 23, No 6 (2023)

This work focuses on synthesizing new imidazolin-4-one derivatives (2a-c), akin to leucettamine B analogs, via microwave-assisted transamination reactions. This reaction was carried out between 3-alkyl-5-dimethylamino-2-thioxo-imidazolidin-4-one (1a-c) and aniline. The structural integrity of the synthesized compounds was confirmed using NMR and MS spectroscopy, and their configurations were validated through DFT calculations. Analyses encompassed molecular electrostatic potential, frontier molecular orbitals, HOMO-LUMO energies, energy band gap, and global chemical reactivity descriptors, providing comprehensive insights into their characteristics. The investigation extended to the biological domain, employing substance activity spectra prediction (PASS) and molecular docking with Autodock Vina4 program. Notably, this holistic assessment aimed to gauge the potential regulatory effect of the compounds on cholesterol. This integrated approach contributes to compound design understanding and potential applications, spanning drug design and broader biomedical contexts.