Design and discovery of 4-anilinoquinazoline-urea derivatives as dual TK inhibitors of EGFR and VEGFR-2

Eur J Med Chem. 2017 Jan 5:125:245-254. doi: 10.1016/j.ejmech.2016.09.039. Epub 2016 Sep 14.

Abstract

EGFR and VEGFR-2 are involved in pathological disorders and the progression of different kinds of tumors, the combined blockade of EGFR and VEGFR signaling pathways appears to be an attractive approach to cancer therapy. In this work, a series of 4-anilinoquinazoline derivatives containing substituted diaryl urea or glycine methyl ester moiety were designed and identified as EGFR and VEGFR-2 dual inhibitors. Compounds 19i, 19j and 19l exhibited the most potent inhibitory activities against EGFR (IC50 = 1 nM, 78 nM and 51 nM, respectively) and VEGFR-2 (IC50 = 79 nM, 14 nM and 14 nM, respectively), they showed good antiproliferative activities as well. Molecular docking established the interaction of 19i with the DFG-out conformation of VEGFR-2, suggesting that they might be type II kinase inhibitors.

Keywords: 4-Anilinoquinazoline-urea; Antitumor; EGFR; Tyrosine kinase inhibitor; VEGFR-2.

MeSH terms

  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacokinetics
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • ErbB Receptors / antagonists & inhibitors*
  • Humans
  • Molecular Docking Simulation
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacology
  • Quinazolines / chemical synthesis
  • Quinazolines / pharmacology*
  • Urea / analogs & derivatives*
  • Urea / pharmacology
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*

Substances

  • Aniline Compounds
  • Antineoplastic Agents
  • Protein Kinase Inhibitors
  • Quinazolines
  • Urea
  • ErbB Receptors
  • Vascular Endothelial Growth Factor Receptor-2