Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

https://doi.org/10.1016/j.molstruc.2022.132579Get rights and content

Highlights

  • 10 derivatives of novel sulfamoyloxy-oxazolidinones were designed and synthesized.

  • The structure of the new compounds was confirmed using spectroscopy and spectrometry methods (IR, LC-MS, NMR and EA).

  • Molecular docking study was performed in order to evaluate synthesized compounds as possible inhibitors of SARS-CoV-2.

  • The physicochemical properties of sulfamoyloxy-oxazolidinones has been optimized using bioinformatics studies (DFT, ADMET).

  • A single crystal of the studied compound 6C, were selected for single crystal X-ray diffraction analysis.

Abstract

A new series of sulfamoyloxyoxazolidinone (SOO) derivatives have been synthesized and characterized by single-crystal X-ray diffraction, NMR, IR, MS and EA. Chemical reactivity and geometrical characteristics of the target compounds were investigated using DFT method. The possible binding mode between SOO and Main protease (Mpro) of SARS-CoV-2 and their reactivity were studied using molecular docking simulation. Single crystal X-ray diffraction showed that SOO crystallizes in a monoclinic system with P 2 1 space group. The binding energy of the SARS-CoV-2/Mpro-SOO complex and the calculated inhibition constant using docking simulation showed that the active SOO molecule has the ability to inhibit SARS-CoV2. We studied the prediction of absorption, distribution, properties of metabolism, excretion and toxicity (ADMET) of the synthesized molecules.

Keywords

Sulfamoyloxy-oxazolidinone
SARS-CoV-2
In silico study
Crystal structure
Molecular docking
DFT study

Cited by (0)

View Abstract