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., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1244, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1244
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molstruc.2021.130864
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Opening epoxide, LiAlH4, B3LYP/6-31(d), MEDT, SARS-CoV-2, ESSENTIAL OILS, ANTIMICROBIAL ACTIVITY, AUTOMATED DOCKING, OPTIMIZATION, EPOXIDATION, PLANTS
  • Kocaeli Üniversitesi Adresli: Evet

Özet

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.