Discovery and evaluation of 7-alkyl-1,5-bis-aryl-pyrazolopyridinones as highly potent, selective, and orally efficacious inhibitors of p38alpha mitogen-activated protein kinase

J Med Chem. 2010 Apr 8;53(7):2973-85. doi: 10.1021/jm100095x.

Abstract

The p38alpha mitogen-activated protein (MAP) kinase is a central signaling molecule in many proinflammatory pathways, regulating the cellular response to a multitude of external stimuli including heat, ultraviolet radiation, osmotic shock, and a variety of cytokines especially interleukin-1beta and tumor necrosis factor alpha. Thus, inhibitors of this enzyme are postulated to have significant therapeutic potential for the treatment of rheumatoid arthritis, inflammatory bowel disease, and Crohn's disease, as well as other diseases where aberrant cytokine signaling is the driver of disease. In this communication, we describe a novel class of 7-alkyl-1,5-bis-aryl-pyrazolopyridinone-based p38alpha inhibitors. In particular, compound 3f is highly potent in the enzyme and cell-based assays, selective in an Ambit kinase screen, and efficacious (ED(50) < or = 0.01 mg/kg) in the rat collagen induced arthritis (CIA) model.

MeSH terms

  • Administration, Oral
  • Animals
  • Arthritis / chemically induced
  • Arthritis / drug therapy
  • Collagen / pharmacology
  • Drug Discovery*
  • Humans
  • Male
  • Mitogen-Activated Protein Kinase 14 / antagonists & inhibitors*
  • Mitogen-Activated Protein Kinase 14 / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Protein Kinase Inhibitors / administration & dosage*
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Pyridones / administration & dosage*
  • Pyridones / chemical synthesis
  • Pyridones / pharmacokinetics
  • Pyridones / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Protein Kinase Inhibitors
  • Pyridones
  • Collagen
  • Mitogen-Activated Protein Kinase 14

Associated data

  • PDB/3LHJ