Design and synthesis of novel Gefitinib analogues with improved anti-tumor activity

Bioorg Med Chem. 2010 Jun 1;18(11):3812-22. doi: 10.1016/j.bmc.2010.04.046. Epub 2010 Apr 21.

Abstract

There is an urgent need to design and develop new and more potent EGFR inhibitors with improved anti-tumor activity. Here we describe the design and synthesis of two series of 4-benzothienyl amino quinazolines as new analogues of the EGFR inhibitor Gefitinib. The anti-tumor activity of these novel Gefitinib analogues in 6 human cancer cell lines was examined. Compared with the parental Gefitinib, most of the new compounds show a markedly increased cytotoxicity to cancer cells. Furthermore, several of the series B compounds that side chains at position 7 contain either a methyl or ethyl group are potent pan-RTK inhibitors. Two representative compounds in this class, 15 and 17, have an enhanced capability to inhibit cancer cell growth and induce apoptosis in vitro and inhibit tumor formation in vivo in human cancer cells with high HER-2, as compared with the parental Gefitinib. Thus they may be promising lead compounds to be developed as an alternative for current Gefitinib therapy or for Gefitinb-resistant patients, potentially via simultaneously blocking multiple RTK signaling pathways.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design
  • ErbB Receptors
  • Gefitinib
  • Humans
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Quinazolines / therapeutic use
  • Receptor, ErbB-2

Substances

  • Antineoplastic Agents
  • Quinazolines
  • ErbB Receptors
  • Receptor, ErbB-2
  • Gefitinib