Characterization and structure-activity relationship study of iminodipyridinopyrimidines as novel hepatitis C virus inhibitor

Eur J Med Chem. 2017 Nov 10:140:65-73. doi: 10.1016/j.ejmech.2017.09.010. Epub 2017 Sep 6.

Abstract

Upon high-throughput screening of synthetic small molecule libraries with the infectious hepatitis C virus (HCV) cell culture system, we identified an iminodipyridinopyrimidine (IDPP) scaffold. IDPP did not inhibit HCV replication, but exhibited very potent inhibitory activity on early and late steps of HCV life cycle. Applying an intensive structure-activity relationship (SAR) study, a promising IDPP Lead compound (12c) with excellent potency (EC50 = 10 nM), high safety margin (SI > 2000), and an acceptable stability in human and rat liver microsomes (t1/2 >60 min) was identified. Overall, our results suggest that the IDPP scaffold could be used for the development of novel HCV interventions.

Keywords: Antiviral; HCV; Iminodipyridinopyrimidine.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cells, Cultured
  • Dose-Response Relationship, Drug
  • Female
  • Hepacivirus / drug effects*
  • Heterocyclic Compounds, 3-Ring / chemical synthesis
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Heterocyclic Compounds, 3-Ring / pharmacology*
  • Humans
  • Male
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Rats
  • Structure-Activity Relationship
  • Virus Replication / drug effects

Substances

  • 4-(trifluoromethyl)benzyl 2-imino-8-methyl-5-oxo-1-(4-(trifluoromethoxy)benzyl)-1,5-dihydro-2H-dipyrido(1,2-a-2',3'-d)pyrimidine-3-carboxylate
  • Antiviral Agents
  • Heterocyclic Compounds, 3-Ring