Potent non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase complex

J Med Chem. 2008 Jul 10;51(13):3731-41. doi: 10.1021/jm701239a. Epub 2008 Jun 5.

Abstract

Measles virus (MV) is one of the most infectious pathogens known. In spite of the existence of a vaccine, approximately 350000 deaths/year result from MV or associated complications. Antimeasles compounds could conceivably diminish these statistics and provide a therapy that complements vaccine treatment. We recently described a high-throughput screening hit compound 1 (16677) against MV-infected cells with the capacity to eliminate viral reproduction at 250 nM by inhibiting the action of the virus's RNA-dependent RNA polymerase complex (RdRp). The compound, 1-methyl-3-(trifluoromethyl)- N-[4-sulfonylphenyl]-1 H-pyrazole-5-carboxamide, 1 carries a critical CF 3 moiety on the 1,2-pyrazole ring. Elaborating on the preliminary structure-activity (SAR) study, the present work presents the synthesis and SAR of a much broader range of low nanomolar nonpeptidic MV inhibitors and speculates on the role of the CF 3 functionality.

Publication types

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

MeSH terms

  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Ligands
  • Measles virus / drug effects*
  • Measles virus / enzymology*
  • Models, Molecular
  • Molecular Structure
  • Nucleosides / chemistry
  • Nucleosides / pharmacology
  • Piperidines / chemical synthesis
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Protein Binding
  • Pyrazoles / chemistry
  • Quantitative Structure-Activity Relationship
  • RNA-Dependent RNA Polymerase / antagonists & inhibitors*
  • RNA-Dependent RNA Polymerase / chemistry
  • RNA-Dependent RNA Polymerase / metabolism
  • Virus Internalization / drug effects

Substances

  • Enzyme Inhibitors
  • Imidazoles
  • Ligands
  • Nucleosides
  • Piperidines
  • Pyrazoles
  • pyrazole
  • RNA-Dependent RNA Polymerase