Synthesis and in vitro biological evaluation of novel quinazoline derivatives

Bioorg Med Chem Lett. 2017 Apr 1;27(7):1584-1587. doi: 10.1016/j.bmcl.2017.02.027. Epub 2017 Feb 16.

Abstract

A series of novel 4-arylamino-6-(5-substituted furan-2-yl)quinazoline derivatives were designed, synthesized and evaluated on biological activities in vitro. Compound 2a, 3a and 3c exhibited highly anti-proliferation activities on all tested tumor cell lines including SW480, A549, A431 and NCI-H1975 cells. Especially, compound 2a not only exhibited strong anti-proliferation activities against the tumor cell lines which expressed wild type or mutant EGFRL858R/T790M, but also showed the most potent inhibitory activity toward wild type EGFR (IC50=5.06nM). The result of docking with EGFR suggested the binding mode of 2a was similar to that of lapatinib. While Western-blot analyses showed 2a obviously inhibited the activation of EGFR, Akt and Erk1/2 in lung cancer cells at indicated concentration. It is believed that this work would be very useful for developing a new series of TKIs targeting EGFR.

Keywords: 4-Arylamino-6-(5-substituted furan-2-yl)quinazoline; Anti-proliferation; EGFR; Tyrosine kinase inhibitors.

MeSH terms

  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • ErbB Receptors / antagonists & inhibitors
  • ErbB Receptors / genetics
  • Gefitinib
  • Humans
  • Lapatinib
  • Molecular Docking Simulation
  • Mutation
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / pharmacology*
  • Quinazolines / chemical synthesis
  • Quinazolines / pharmacology*
  • Signal Transduction

Substances

  • 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(5-hydroxymethylfuran-2-yl)quinazoline
  • Aniline Compounds
  • Antineoplastic Agents
  • Protein Kinase Inhibitors
  • Quinazolines
  • Lapatinib
  • EGFR protein, human
  • ErbB Receptors
  • Gefitinib