Orally active anti-proliferation agents: novel diphenylamine derivatives as FGF-R2 autophosphorylation inhibitors

Bioorg Med Chem Lett. 2004 Feb 23;14(4):875-9. doi: 10.1016/j.bmcl.2003.12.019.

Abstract

(6,7-Disubstituted-quinolin-4-yloxy-phenyl)(4-substituted-phenyl)amine derivatives were synthesized and evaluated by a cellular autophosphorylation assay for FGF-R2 in the human scirrhous gastric carcinoma cell line, OCUM-2MD3. We also performed metabolic stability studies showing that substitutions at the 7-position of quinoline affect its biological stability. In this study, we achieved a remarkable improvement in the solubility and metabolic stability of the diphenylamine derivative. The most promising compound 15e showed a significant decrease in tumor volume when orally administered.

MeSH terms

  • Administration, Oral
  • Animals
  • Antineoplastic Agents / pharmacology*
  • Cell Division / drug effects
  • Cell Line, Tumor
  • Diphenylamine / analogs & derivatives
  • Diphenylamine / metabolism
  • Diphenylamine / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Phosphorylation
  • Rats
  • Receptor Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Receptor, Fibroblast Growth Factor, Type 2
  • Receptors, Fibroblast Growth Factor / antagonists & inhibitors*
  • Stomach Neoplasms / drug therapy

Substances

  • Antineoplastic Agents
  • Receptors, Fibroblast Growth Factor
  • Diphenylamine
  • FGFR2 protein, human
  • Fgfr2 protein, rat
  • Receptor Protein-Tyrosine Kinases
  • Receptor, Fibroblast Growth Factor, Type 2