The development of monocyclic pyrazolone based cytokine synthesis inhibitors

Bioorg Med Chem Lett. 2005 May 2;15(9):2285-9. doi: 10.1016/j.bmcl.2005.03.007.

Abstract

4-Aryl-5-pyrimidyl based cytokine synthesis inhibitors that contain a novel monocyclic, pyrazolone heterocyclic core are described. Many of these inhibitors showed low nanomolar activity against LPS-induced TNF-alpha production. One of the compounds (6e) was found to be efficacious in the rat iodoacetate (RIA) in vivo model of osteoarthritis. The X-ray crystal structure of a pyrazolone inhibitor cocrystallized with mutated p38 (mp38) is presented.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Cytokines / antagonists & inhibitors*
  • Cytokines / biosynthesis*
  • Disease Models, Animal
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Kinetics
  • Lipopolysaccharides / pharmacology
  • Models, Molecular
  • Molecular Conformation
  • Osteoarthritis / prevention & control
  • Pyrazolones / chemical synthesis*
  • Pyrazolones / chemistry
  • Pyrazolones / pharmacology*
  • Rats
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / biosynthesis
  • p38 Mitogen-Activated Protein Kinases / antagonists & inhibitors

Substances

  • Cytokines
  • Enzyme Inhibitors
  • Lipopolysaccharides
  • Pyrazolones
  • Tumor Necrosis Factor-alpha
  • p38 Mitogen-Activated Protein Kinases