Synthesis and biological evaluation of a triazole-based library of pyrido[2,3-d]pyrimidines as FGFR3 tyrosine kinase inhibitors

Org Biomol Chem. 2010 May 7;8(9):2164-73. doi: 10.1039/b923882d. Epub 2010 Mar 11.

Abstract

A library of pyrido[2,3-d]pyrimidines was designed as inhibitors of FGFR3 tyrosine kinase allowing possible interactions with an unexploited region of the ATP binding-site. This library was built-up with an efficient step of click-chemistry giving easy access to triazole-based compounds bearing a large panel of substituents. Among the 27 analogues synthesized, more than half exhibited 55-89% inhibition of in vitro FGFR3 kinase activity at 2 microM and one (19g) was able to inhibit auto-phosphorylation of mutant FGFR3-K650M in transfected HEK cells.

MeSH terms

  • Binding Sites
  • Cell Line
  • Drug Design*
  • Humans
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / pharmacology*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology*
  • Recombinant Proteins / antagonists & inhibitors
  • Small Molecule Libraries
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triazoles / chemistry*

Substances

  • 1-tert-butyl-3-(6-(3,5-dimethoxyphenyl)-2-((1-((1-methylpiperidin-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methylamino)pyrido(2,3-d)pyrimidin-7-yl)urea
  • Protein Kinase Inhibitors
  • Pyridines
  • Pyrimidines
  • Recombinant Proteins
  • Small Molecule Libraries
  • Triazoles
  • Protein-Tyrosine Kinases