Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety

Murat Bingul, Owen Tan, Christopher R. Gardner, Selina K. Sutton, Greg M. Arndt, Glenn M. Marshall, Belamy B. Cheung*, Naresh Kumar, David St C. Black

*Corresponding author for this work

Research output: Contribution to journalArticle

34 Citations (Scopus)
5 Downloads (Pure)

Abstract

Identification of the novel (E)-N1-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio) propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19-26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved by replacement of the quinoline moiety with other aromatic systems. All the newly synthesized compounds were evaluated for their anti-cancer activity against the SH-SY5Y and Kelly neuroblastoma cell lines, as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Analogues 19 and 22 significantly reduced the cell viability of neuroblastoma cancer cells with micromolar potency and significant selectivity over normal cells. The quinoline hydrazide 22 also induced G1 cell cycle arrest, as well as upregulation of the p27kip1 cell cycle regulating protein.

Original languageEnglish
Article number916
Number of pages19
JournalMolecules
Volume21
Issue number7
DOIs
Publication statusPublished - 1 Jul 2016
Externally publishedYes

Bibliographical note

Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • Anticancer
  • Breast cancer
  • Hydrazide-hydrazone
  • Neuroblastoma
  • Quinoline

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