Design, synthesis and evaluation of novel anti-HCV molecules that deliver intracellularly three highly potent NS5A inhibitors

Bioorg Med Chem Lett. 2015 Sep 1;25(17):3711-5. doi: 10.1016/j.bmcl.2015.06.031. Epub 2015 Jun 15.

Abstract

The design and synthesis of new non-symmetrical NS5A inhibitors with sulfur containing amino acids is reported along with their ability to block HCV replication in an HCV 1b replicon system. These compounds display EC50 values in the picomolar range with a large therapeutic index (>10(6)). Moreover, cellular pharmacology studies show that our preferred compounds intracellularly deliver three potent NS5A inhibitors.

Keywords: Antiviral; HCV; NS5A.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antiviral Agents / administration & dosage
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Carbamates
  • Cell Line / drug effects
  • Cell Line / virology
  • Chemistry Techniques, Synthetic
  • Chlorocebus aethiops
  • Drug Design
  • Drug Evaluation, Preclinical / methods
  • Hepacivirus / drug effects*
  • Hepacivirus / genetics
  • Humans
  • Imidazoles / pharmacology
  • Molecular Targeted Therapy
  • Mutation
  • Pyrrolidines
  • Structure-Activity Relationship
  • Valine / analogs & derivatives
  • Vero Cells / drug effects
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / chemistry
  • Viral Nonstructural Proteins / genetics
  • Viral Nonstructural Proteins / metabolism
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Carbamates
  • Imidazoles
  • Pyrrolidines
  • Viral Nonstructural Proteins
  • NS-5 protein, hepatitis C virus
  • Valine
  • daclatasvir