Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions

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Eşme A.

organics, vol.2, pp.1-16, 2021 (Peer-Reviewed Journal)

  • Publication Type: Article / Article
  • Volume: 2
  • Publication Date: 2021
  • Doi Number: 10.3390/org2010001
  • Journal Name: organics
  • Journal Indexes: Other Indexes
  • Page Numbers: pp.1-16
  • Kocaeli University Affiliated: Yes


Abstract: The regioselectvity and the mechanism of the (32CA) cycloadditions reactions of 1-bromo4-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 SARSCoV-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.