Next Article in Journal
In Situ Investigation of a Self-Accelerated Cocrystal Formation by Grinding Pyrazinamide with Oxalic Acid
Next Article in Special Issue
Hybrid Molecules Containing a 7-Chloro-4-aminoquinoline Nucleus and a Substituted 2-Pyrazoline with Antiproliferative and Antifungal Activity
Previous Article in Journal
Differential Effects of Viscum album Preparations on the Maturation and Activation of Human Dendritic Cells and CD4+ T Cell Responses
Previous Article in Special Issue
Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(7), 916; doi:10.3390/molecules21070916

Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety

1
School of Chemistry, The University of New South Wales Australia, Sydney, NSW 2052, Australia
2
Children’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2031, Australia
3
ACRF Drug Discovery Centre for Childhood Cancer, Children’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2052, Australia
4
Kids Cancer Centre, Sydney Children’s Hospital, Randwick, NSW 2031, Australia
*
Authors to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 24 May 2016 / Revised: 5 July 2016 / Accepted: 8 July 2016 / Published: 14 July 2016
View Full-Text   |   Download PDF [2236 KB, uploaded 14 July 2016]   |  

Abstract

Identification of the novel (E)-N′-((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 1926 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. View Full-Text
Keywords: quinoline; hydrazide-hydrazone; anticancer; neuroblastoma; breast cancer quinoline; hydrazide-hydrazone; anticancer; neuroblastoma; breast cancer
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Bingul, M.; Tan, O.; Gardner, C.R.; Sutton, S.K.; Arndt, G.M.; Marshall, G.M.; Cheung, B.B.; Kumar, N.; Black, D.S. Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety. Molecules 2016, 21, 916.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top