Divulging the regioselectivity of epoxides in the ring-opening reaction, and potential himachalene derivatives pre dicte d to target the antibacterial activities and SARS-CoV-2 spike protein with docking study


Aitouna A. O. , Belghiti M. E. , EŞME A. , Aitouna A. O. , Salah M., Chekroun A., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1244, 2021 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1244
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2021.130864
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Keywords: Opening epoxide, LiAlH4, B3LYP/6-31(d), MEDT, SARS-CoV-2, ESSENTIAL OILS, ANTIMICROBIAL ACTIVITY, AUTOMATED DOCKING, OPTIMIZATION, EPOXIDATION, PLANTS

Abstract

The ring-opening reaction of epoxides 1b and 1c utilizing LiAlH4, have been studied within the Molecular Electron Density Theory (MEDT) at the B3LYP/6-31(d) computational level. The regioisomeric reaction paths including the two oxiranes cycles of epoxides 1b and 1c have been explored. DFT calculations show that the attack of the hydride ion H- is favorable on the carbon C-3 for the epoxide 1b, while this action is realized on carbon C-2 for the epoxide 1c in the highest conformity with the experimental outcomes. Furthermore, we have operated a docking calculation to examine the antibacterial activities of the products 1a-1f, further more we have performed a docking calculation to scrutinize the products 1-9 against SARS-CoV-2. Indeed, the docking results showed that alpha-himachalene (2) possess a higher affinity to the main protease. (C) 2021 Published by Elsevier B.V.