Optimization of gefitinib analogues with potent anticancer activity

Kai Hao Yin, Yi Han Hsieh, Rohidas S. Sulake, Su Pei Wang, Jui-I Chao*, Chinpiao Chen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.

Original languageEnglish
Pages (from-to)5247-5250
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number22
DOIs
StatePublished - 15 Nov 2014

Keywords

  • A549
  • Anti-cancer
  • EGFR
  • Gefitinib
  • Iressa

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