Discovery of novel 7-azaindole derivatives bearing dihydropyridazine moiety as c-Met kinase inhibitors

Eur J Med Chem. 2017 Jun 16:133:97-106. doi: 10.1016/j.ejmech.2017.03.045. Epub 2017 Mar 23.

Abstract

A series of 7-azaindole derivatives bearing the dihydropyridazine scaffold were synthesized and evaluated for their c-Met kinase inhibitory, and antiproliferative activity against 4 cancer cell lines (HT29, A549, H460, U87MG) were evaluated in vitro. Most compounds showed moderate to excellent potency. Compared to foretinib, the most promising analog 34 (c-Met IC50: 1.06 nM, a multitarget tyrosine kinase inhibitor) showed a 6.4-, 7.8-, and 3.2-fold increase in activity against HT29, A549, and H460 cell lines, respectively. Structure activity relationship studies indicated that mono-EWGs (such as R2 = F) at 4-position of moiety D was a key factor in improving the antitumor activity.

Keywords: 7-Azaindole derivatives; Anti-tumor; Dihydropyridazine; Receptor tyrosine kinase; c-Met.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology*
  • Molecular Docking Simulation
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacology*
  • Proto-Oncogene Proteins c-met / antagonists & inhibitors*
  • Proto-Oncogene Proteins c-met / metabolism
  • Pyridazines / chemistry
  • Pyridazines / pharmacology

Substances

  • 7-azaindole dimer
  • Antineoplastic Agents
  • Indoles
  • Protein Kinase Inhibitors
  • Pyridazines
  • MET protein, human
  • Proto-Oncogene Proteins c-met