Synthesis of New Organoselenium-Based Succinanilic and Maleanilic Derivatives and In Silico Studies as Possible SARS-CoV-2 Main Protease Inhibitors

Herein we report the synthesis of organic selenide-based maleanilic and succinanilic acids in good yields (up to 95%). Their structural identities were elucidated by spectroscopic techniques (e.g., IR, 1H- & 13C-NMR, and MS). The ADMET analysis, molecule electrostatic potential map, DFT, and fro...

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Published inInorganics Vol. 11; no. 8; p. 321
Main Authors Shaaban, Saad, Al-Faiyz, Yasair S, Alsulaim, Ghayah M, Alaasar, Mohamed, Amri, Nasser, Ba-Ghazal, Hussein, Al-Karmalawy, Ahmed A, Abdou, Aly
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.07.2023
Subjects
Acids
Analysis
Binding
Chemical synthesis
Chemistry
COVID-19
Crystallization
Electrostatic properties
in silico
Infections
maleic
Methods
Molecular docking
Molecular dynamics
Molecular orbitals
NMR
Nuclear magnetic resonance
organic selenides
Organoselenium compounds
Pharmacokinetics
Properties
Protease inhibitors
Proteinase inhibitors
SARS-CoV-2
Selenide
Selenides
Selenium
Selenium compounds
Severe acute respiratory syndrome coronavirus 2
Structure
succinic
Succinic acid
Synthesis
Viral infections
Viruses
Egypt
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Summary:Herein we report the synthesis of organic selenide-based maleanilic and succinanilic acids in good yields (up to 95%). Their structural identities were elucidated by spectroscopic techniques (e.g., IR, 1H- & 13C-NMR, and MS). The ADMET analysis, molecule electrostatic potential map, DFT, and frontier molecular orbital were used to study the organoselenium compounds’ pharmacokinetics, drug-likeness characteristics, geometries, and chemical and electronic properties. Moreover, a molecular docking tool was employed to investigate the organic selenides’ ability to inhibit the SARS-CoV-2 Mpro target (PDB: 7BFB). Within this context, organic selenides exhibited promising binding affinities to the SARS-CoV-2 Mpro receptor in the following order (12 > 11 > 10 > 9 > 7 > 8). Furthermore, molecular dynamics simulations were also carried out for 200 ns to evaluate the exact behavior of the most active compound (12) within the Mpro binding pocket of SARS-CoV-2 compared with its co-crystallized inhibitor (Co).
ISSN:2304-6740
2304-6740
DOI:10.3390/inorganics11080321