Structure-Activity Relationships of Benzamides and Isoindolines Designed as SARS-CoV Protease Inhibitors Effective against SARS-CoV-2

ChemMedChem. 2021 Jan 19;16(2):340-354. doi: 10.1002/cmdc.202000548. Epub 2020 Oct 16.

Abstract

Inhibition of coronavirus (CoV)-encoded papain-like cysteine proteases (PLpro ) represents an attractive strategy to treat infections by these important human pathogens. Herein we report on structure-activity relationships (SAR) of the noncovalent active-site directed inhibitor (R)-5-amino-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide (2 b), which is known to bind into the S3 and S4 pockets of the SARS-CoV PLpro . Moreover, we report the discovery of isoindolines as a new class of potent PLpro inhibitors. The studies also provide a deeper understanding of the binding modes of this inhibitor class. Importantly, the inhibitors were also confirmed to inhibit SARS-CoV-2 replication in cell culture suggesting that, due to the high structural similarities of the target proteases, inhibitors identified against SARS-CoV PLpro are valuable starting points for the development of new pan-coronaviral inhibitors.

Keywords: Antiviral agents; Computational chemistry; Drug design; Protease inhibitors; Structure-activity relationships.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / metabolism
  • Antiviral Agents / pharmacology*
  • Benzamides / chemical synthesis
  • Benzamides / metabolism
  • Benzamides / pharmacology*
  • Catalytic Domain
  • Chlorocebus aethiops
  • Coronavirus 3C Proteases / chemistry
  • Coronavirus 3C Proteases / metabolism*
  • Crystallography, X-Ray
  • Cysteine Proteinase Inhibitors / chemical synthesis
  • Cysteine Proteinase Inhibitors / metabolism
  • Cysteine Proteinase Inhibitors / pharmacology*
  • Isoindoles / chemical synthesis
  • Isoindoles / metabolism
  • Isoindoles / pharmacology*
  • Molecular Docking Simulation
  • Molecular Structure
  • Protein Binding
  • SARS-CoV-2 / drug effects*
  • Structure-Activity Relationship
  • Vero Cells
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Benzamides
  • Cysteine Proteinase Inhibitors
  • Isoindoles
  • 3C-like proteinase, SARS-CoV-2
  • Coronavirus 3C Proteases