New acridone-4-carboxylic acid derivatives as potential inhibitors of hepatitis C virus infection

Bioorg Med Chem. 2008 Oct 1;16(19):8846-52. doi: 10.1016/j.bmc.2008.08.074. Epub 2008 Aug 31.

Abstract

A new class of compounds--acridone derivatives--was tested using the direct fluorometric helicase activity assay to determine the inhibitory properties of the derivatives towards the NS3 helicase of Hepatitis C virus (HCV). The compounds were also tested as putative transcription inhibitors of in vitro transcription based on the DNA-dependent T7 RNA polymerase. Most of the acridone derivatives tested were transcription inhibitors; however, only four of them inhibited the NS3 helicase at low concentrations (IC(50) from 3 microM to 20 microM) and were therefore selected for further studies on the mechanism of inhibition. The acridone derivatives probably act via intercalation into double-stranded nucleic acids but they may also interact directly with viral enzymes. Selected carboxamides were tested in the subgenomic HCV replicon system. Two of the compounds: N-(pyridin-4-yl)-amide and N-(pyridin-2-yl)-amide of acridone-4-carboxylic acid are efficient RNA replication inhibitors with selectivity indexes of 19.4 and 40.5, respectively, proving that the acridone derivatives may be regarded as potential antiviral agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridones / chemical synthesis
  • Acridones / pharmacology*
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / pharmacology*
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / pharmacology*
  • DNA-Directed RNA Polymerases / antagonists & inhibitors
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Fluorometry
  • Hepacivirus / drug effects*
  • Hepacivirus / enzymology
  • Inhibitory Concentration 50
  • RNA Helicases / antagonists & inhibitors
  • RNA Helicases / metabolism
  • RNA Viruses / drug effects*
  • Structure-Activity Relationship
  • Virus Replication / drug effects*

Substances

  • Acridones
  • Antiviral Agents
  • Carboxylic Acids
  • Enzyme Inhibitors
  • DNA-Directed RNA Polymerases
  • RNA Helicases