6533b860fe1ef96bd12c3b5a
RESEARCH PRODUCT
Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions
Abdellah ZeroualMar Ríos-gutiérrezMohammed SalahHabib El Alaoui El AbdallaouiMohammed El IdrissiAslı EşmeNoureddine MazoirMohamed El GhozlaniLuis R. DomingoAnas Ouled Aitounasubject
2019-20 coronavirus outbreakCoronavirus disease 2019 (COVID-19)010405 organic chemistryChemistrySARS-CoV-2Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2)OxideMEDTRegioselectivity010402 general chemistry01 natural sciencesMedicinal chemistryDFTCycloaddition3. Good health0104 chemical scienceschemistry.chemical_compoundBenzonitrileELFDocking (molecular)regioselectivity2-isoxazolinedescription
The regioselectvity and the mechanism of the (32CA) cycloadditions reactions of 1-bromo-4-vinylbenzene 1 and 1-chloro-4-vinylbenzene 2 with benzonitrile oxide 3 were investigated under the molecular electron density theory (MEDT) at the B3LYP/6-311++G(d,p) computational level. Evaluation of the ELF reveals that these zwitterionic type (zw-type) 32CA reactions take place in a two-stage one-step mechanism. This MEDT study shows that the meta isoxazolines are kinetically and thermodynamically favored over the ortho ones, these 32CA reactions being completely regioselective, in agreement with experimental outcomes. In addition, the efficiency of isoxazolines against SARS-CoV-2 have been also investigated. According to the docking analysis, the present study concludes that 5-(p-bromophenyl)-3-phenyl-2-isoxazoline (B-m) shows better interactions for the inhibition of SARS-CoV-2 in comparison to chloroquine.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-01-04 | Organics |