2-Benzimidazolyl-9-(chroman-4-yl)-purinone derivatives as JAK3 inhibitors

Bioorg Med Chem Lett. 2009 Dec 1;19(23):6788-92. doi: 10.1016/j.bmcl.2009.09.080. Epub 2009 Sep 25.

Abstract

A novel class of Janus tyrosine kinase 3 (JAK3) inhibitors based on a 2-benzimidazoylpurinone core structure is described. Through substitution of the benzimidazoyl moiety and optimization of the N-9 substituent of the purinone, compound 24 was identified incorporating a chroman-based functional group. Compound 24 shows excellent kinase activity, good oral bioavailability and demonstrates efficacy in an acute mechanistic mouse model through inhibition of interleukin-2 (IL-2) induced interferon-gamma (INF-gamma) production.

MeSH terms

  • Animals
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Interferon-gamma / biosynthesis
  • Interleukin-2 / antagonists & inhibitors
  • Janus Kinase 3 / antagonists & inhibitors*
  • Mice
  • Models, Animal
  • Models, Molecular
  • Molecular Structure
  • Purines / chemical synthesis
  • Purines / chemistry
  • Purines / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Benzimidazoles
  • Enzyme Inhibitors
  • Interleukin-2
  • Purines
  • Interferon-gamma
  • Janus Kinase 3