Optimization of 4-Aminopiperidines as Inhibitors of Influenza A Viral Entry That Are Synergistic with Oseltamivir

J Med Chem. 2020 Mar 26;63(6):3120-3130. doi: 10.1021/acs.jmedchem.9b01900. Epub 2020 Mar 2.

Abstract

Vaccination is the most prevalent prophylactic means for controlling seasonal influenza infections. However, an effective vaccine usually takes at least 6 months to develop for the circulating strains. Therefore, new therapeutic options are needed for the acute treatment of influenza infections to control this virus and prevent epidemics/pandemics from developing. We have discovered fast-acting, orally bioavailable acylated 4-aminopiperidines with an effective mechanism of action targeting viral hemagglutinin (HA). Our data show that these compounds are potent entry inhibitors of influenza A viruses. We present docking studies that suggest an HA binding site for these inhibitors on H5N1. Compound 16 displayed a significant decrease of viral titer when evaluated in the infectious assays with influenza virus H1N1 (A/Puerto Rico/8/1934) or H5N1 (A/Vietnam/1203/2004) strains and the oseltamivir-resistant strain with the most common H274Y mutation. In addition, compound 16 showed significant synergistic activity with oseltamivir in vitro.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / metabolism
  • Antiviral Agents / pharmacology*
  • Binding Sites
  • Dogs
  • Drug Synergism
  • Hemagglutinins, Viral / chemistry
  • Hemagglutinins, Viral / metabolism
  • Humans
  • Influenza A Virus, H1N1 Subtype / chemistry
  • Influenza A Virus, H1N1 Subtype / drug effects*
  • Influenza A Virus, H5N1 Subtype / chemistry
  • Influenza A Virus, H5N1 Subtype / drug effects*
  • Madin Darby Canine Kidney Cells
  • Mice
  • Microbial Sensitivity Tests
  • Microsomes, Liver / metabolism
  • Molecular Docking Simulation
  • Molecular Structure
  • Oseltamivir / pharmacology*
  • Piperidines / chemical synthesis
  • Piperidines / metabolism
  • Piperidines / pharmacology*
  • Protein Binding
  • Small Molecule Libraries / chemical synthesis
  • Small Molecule Libraries / pharmacology
  • Structure-Activity Relationship
  • Virus Internalization / drug effects*

Substances

  • Antiviral Agents
  • Hemagglutinins, Viral
  • Piperidines
  • Small Molecule Libraries
  • Oseltamivir