Identification of novel N-(morpholine-4-carbonyloxy) amidine compounds as potent inhibitors against hepatitis C virus replication

Antimicrob Agents Chemother. 2012 Mar;56(3):1315-23. doi: 10.1128/AAC.05764-11. Epub 2011 Dec 27.

Abstract

To identify novel compounds that possess antiviral activity against hepatitis C virus (HCV), we screened a library of small molecules with various amounts of structural diversity using an HCV replicon-expressing cell line and performed additional validations using the HCV-JFH1 infectious-virus cell culture. Of 4,004 chemical compounds, we identified 4 novel compounds that suppressed HCV replication with 50% effective concentrations of ranging from 0.36 to 4.81 μM. N'-(Morpholine-4-carbonyloxy)-2-(naphthalen-1-yl) acetimidamide (MCNA) was the most potent and also produced a small synergistic effect when used in combination with alpha interferon. Structure-activity relationship (SAR) analyses revealed 4 derivative compounds with antiviral activity. Further SAR analyses revealed that the N-(morpholine-4-carbonyloxy) amidine moiety was a key structural element for antiviral activity. Treatment of cells with MCNA activated nuclear factor κB and downstream gene expression. In conclusion, N-(morpholine-4-carbonyloxy) amidine and other related morpholine compounds specifically suppressed HCV replication and may have potential as novel chemotherapeutic agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / chemistry
  • Amidines / pharmacology*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Blotting, Western
  • Cell Line, Tumor
  • Drug Synergism
  • Gene Expression / drug effects
  • Genes, Reporter
  • Hepacivirus / drug effects*
  • Hepacivirus / physiology
  • Hepatitis C, Chronic / virology
  • Humans
  • Inhibitory Concentration 50
  • Interferon alpha-2
  • Interferon-alpha / pharmacology
  • Luciferases
  • Morpholines / chemistry
  • Morpholines / pharmacology*
  • NF-kappa B / genetics
  • NF-kappa B / metabolism
  • Recombinant Proteins / pharmacology
  • Signal Transduction / drug effects
  • Small Molecule Libraries
  • Structure-Activity Relationship
  • Virus Replication / drug effects

Substances

  • Amidines
  • Antiviral Agents
  • Interferon alpha-2
  • Interferon-alpha
  • Morpholines
  • NF-kappa B
  • Recombinant Proteins
  • Small Molecule Libraries
  • Luciferases