Comprehensive study on the stereoselective epoxidation of aromatic atlantone: mechanism, ADME analysis, and potential as COVID-19 drug

Authors

  • Houria Raji
  • Abdellah Zeroual
  • Ahmed Chekroun
  • Haydar Mohammad-Salim
  • Asad Syed
  • Abdallah M. Elgorban
  • Islem Abid
  • Meenakshi Verma
  • Jesús Vicente de Julián-Ortiz
  • Ahmed Benharref

Keywords:

atlantone, COVID-19, molecular electron density theory, stereoselective reaction, in silico study

Abstract

This work presents a theoretical investigation of the epoxidation reaction of 2-methyl-6-(4-methylphenyl)hept-2-en-4-one using hydrogen peroxide in the presence of sodium hydroxide and ethanol as a solvent. The study was conducted using density functional theory (DFT) with the 6-311G(d,p) basis set. Calculations of activation energies for the transition states revealed the stereoselectivity of the reaction, with theoretical results closely matching experimental data. Additionally, an electronic localization function (ELF) analysis was performed to clarify the reaction mechanism. A docking study was also conducted to predict potential drug candidates against COVID-19.

 

Author Biographies

Houria Raji

Natural Substances Chemistry Laboratory,
Semlalia Faculty of Sciences, Cadi Ayyad University,
Marrakech, Morocco

Molecular Modelling and Spectroscopy Research Team,
Faculty of Science, Chouaïb Doukkali University,
P. O. Box 20, 24000 El Jadida, Morocco;

 

Abdellah Zeroual

Molecular Modelling and Spectroscopy Research Team,
Faculty of Science, Chouaïb Doukkali University,
P. O. Box 20, 24000 El Jadida, Morocco

Ahmed Chekroun

Natural Substances Chemistry Laboratory,
Semlalia Faculty of Sciences, Cadi Ayyad University,
Marrakech, Morocco

Haydar Mohammad-Salim

Molecular Topology and Drug Design Research Unit,
Department of Physical Chemistry, Pharmacy Faculty,
University of Valencia,
Burjassot 46100, Valencia, Spain

Department of Chemistry, Faculty of Science,
University of Zakho,
Zakho 42002, Duhok, Kurdistan Region, Iraq

 

Asad Syed

Department of Botany and Microbiology, College of Science, King Saud University,
P. O. Box 2455, Riyadh 11451, Saudi Arabia

 

Abdallah M. Elgorban

Centre of Excellence in Biotechnology Research (CEBR),
King Saud University,
Riyadh, Saudi Arabia

Islem Abid

Centre of Excellence in Biotechnology Research (CEBR),
King Saud University,
Riyadh, Saudi Arabia

Meenakshi Verma

University Centre for Research & Development,
Department of Chemistry,
Chandigarh University,
Gharuan, Mohali, India

Jesús Vicente de Julián-Ortiz

Molecular Topology and Drug Design Research Unit,
Department of Physical Chemistry, Pharmacy Faculty,
University of Valencia,
Burjassot 46100, Valencia, Spain

Ahmed Benharref

Natural Substances Chemistry Laboratory,
Semlalia Faculty of Sciences, Cadi Ayyad University,
Marrakech, Morocco

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Published

2025-02-13

Issue

Vol. 60 No. 11/12 (2024): Synthesis and properties of heterocyclic compounds in the light of the quantum-chemical studies

Section

Original Papers