Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: parallel synthesis, bioactivity, and in vitro pharmacokinetics

J Med Chem. 2007 Jan 11;50(1):65-73. doi: 10.1021/jm061045z.

Abstract

2-Aminopyridine-3,5-dicarbonitrile compounds were previously identified as mimetics of dominant-negative prion protein mutants and inhibit prion replication in cultured cells. Here, we report findings from a comprehensive structure-activity relationship study of the 6-aminopyridine-3,5-dicarbonitrile scaffold. We identify compounds with significantly improved bioactivity (approximately 40-fold) against replication of the infectious prion isoform (PrPSc) and suitable pharmacokinetic profiles to warrant evaluation in animal models of prion disease.

Publication types

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

MeSH terms

  • Aminopyridines / chemical synthesis*
  • Aminopyridines / chemistry
  • Aminopyridines / pharmacology
  • Animals
  • Cell Line, Tumor
  • Combinatorial Chemistry Techniques
  • Membranes, Artificial
  • Mice
  • Models, Molecular
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / pharmacology
  • Permeability
  • PrPSc Proteins / antagonists & inhibitors*
  • Solubility
  • Structure-Activity Relationship

Substances

  • Aminopyridines
  • Membranes, Artificial
  • Nitriles
  • PrPSc Proteins