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

被引：13

作者：

El Idrissi, Mohammed ^{[1
,2
]}

El Ghozlani, Mohamed ^{[3
]}

Esme, Asli ^{[4
]}

Rios-Gutierrez, Mar ^{[5
]}

Aitouna, Anas Ouled ^{[1
]}

Salah, Mohammed ^{[1
]}

El Abdallaoui, Habib El Alaoui ^{[1
]}

Zeroual, Abdellah ^{[1
]}

Mazoir, Noureddine ^{[6
]}

Domingo, Luis R. ^{[5
]}

机构：

[1] Chouaib Doukkali Univ, Fac Sci, Mol Modeling & Spect Res Team, El Jadida 24000, Morocco

[2] Sultan Moulay Slimane Univ, Polydisciplinary Fac, Lab Chem Proc & Appl Mat, Beni Mellal 23000, Morocco

[3] Sultan Moulay Slimane Univ, Fac Sci & Technol, Organ & Analyt Chem Lab, Beni Mellal 23000, Morocco

[4] Kocaeli Univ, Fac Educ, Dept Elementary Sci Educ, Kocaeli, Turkey

[5] Univ Valencia, Dept Organ Chem, Dr Moliner 50, Valencia 46100, Spain

[6] Chouaib Doukkali Univ, Fac Sci, Dept Organ Chem, El Jadida 24000, Morocco

来源：

ORGANICS | 2021年 / 2卷 / 01期

关键词：

2-isoxazoline; MEDT; regioselectivity; SARS-CoV-2; DFT; ELF; 1,3-DIPOLAR CYCLOADDITIONS; ELECTRON LOCALIZATION; AUTOMATED DOCKING; FLUORINE; PHARMACEUTICALS; PARTICIPATION; OPTIMIZATION; DERIVATIVES; GENERATION; MECHANISM;

D O I：

10.3390/org2010001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1 / 16

页数：16

共 89 条

[1] Synthesis and biological evaluations of novel isoxazoles and furoxan derivative as anti-inflammatory agents [J].