The fight against the influenza A virus H1N1: synthesis, molecular modeling, and biological evaluation of benzofurazan derivatives as viral RNA polymerase inhibitors

ChemMedChem. 2014 Jan;9(1):129-50. doi: 10.1002/cmdc.201300378. Epub 2013 Nov 27.

Abstract

The influenza RNA polymerase complex, which consists of the three subunits PA, PB1, and PB2, is a promising target for the development of new antiviral drugs. A large library of benzofurazan compounds was synthesized and assayed against influenza virus A/WSN/33 (H1N1). Most of the new derivatives were found to act by inhibiting the viral RNA polymerase complex through disruption of the complex formed between subunits PA and PB1. Docking studies were also performed to elucidate the binding mode of benzofurazans within the PB1 binding site in PA and to identify amino acids involved in their mechanism of action. The predicted binding pose is fully consistent with the biological data and lays the foundation for the rational development of more effective PA-PB1 inhibitors.

Keywords: H1N1; RNA polymerase; antiviral agents; benzofurazans; influenza A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Benzoxazoles / chemistry*
  • Benzoxazoles / pharmacology
  • Binding Sites
  • DNA-Directed RNA Polymerases / antagonists & inhibitors*
  • DNA-Directed RNA Polymerases / metabolism
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • HEK293 Cells
  • Humans
  • Influenza A Virus, H1N1 Subtype / enzymology*
  • Molecular Dynamics Simulation
  • Protein Binding
  • Protein Interaction Maps / drug effects
  • Protein Structure, Tertiary
  • Protein Subunits / antagonists & inhibitors
  • Protein Subunits / metabolism
  • Viral Proteins / antagonists & inhibitors*
  • Viral Proteins / metabolism
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Benzoxazoles
  • Enzyme Inhibitors
  • Protein Subunits
  • Viral Proteins
  • benzofurazan
  • DNA-Directed RNA Polymerases