Design, synthesis, and mechanism of action of 2-(3-hydroxy-5-methoxyphenyl) -6-pyrrolidinylquinolin-4-one as a potent anticancer lead

Yung Yi Cheng, Chin Yu Liu, Meng Tung Tsai, Hui Yi Lin, Jai Sing Yang, Tian Shung Wu, Sheng Chu Kuo, Li Jiau Huang, Kuo Hsiung Lee

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

New 6- (or 6,7-) substituted 2-(hydroxyl substituted phenyl)quinolin-4-one derivatives were synthesized and screened for antiproliferative effects against cancer cell lines. Structure-activity relationship correlations were established and the most promising compound 2-(3-hydroxy-5-methoxyphenyl)-6-pyrrolidin-1- ylquinolin-4-one (6h) exhibited strong inhibitory activity against various human cancer cell lines, particularly non-small cell lung cancer NCI-H522. Additional studies suggested a mechanism of action resembling that of the antimitotic drug vincristine. The presence of a C-ring OH group in 6h will allow this compound to be converted readily to a water soluble and physicochemically stable hydrophilic prodrug. Compound 6h is proposed as a new anticancer lead compound.

Original languageEnglish
Pages (from-to)5223-5227
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number18
DOIs
Publication statusPublished - 2013 Sep 15

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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