Ring fusion strategy for the synthesis of anthra[2,3-d ]oxazole-2-thione-5,10-dione homologues as DNA topoisomerase inhibitors and as antitumor agents

Chun Liang Chen, Fei Lan Liu, Chia Chung Lee, Tsung Chih Chen, Wen Wei Chang, Jih Hwa Guh, Ahmed Atef Ahmed Ali, Deh Ming Chang, Hsu Shan Huang

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The efficient synthesis of mono-substituted anthraquinones and ring fusion into anthra[2,3-d]oxazole-2-thione-5,10-dione derivatives were developed, and all the compounds were tested for their cytotoxicity against PC-3 cancer cell lines. Compounds 8, 14, 17 and 23 were selected by the NCI and 12, 17 and 19 were evaluated for topoisomerase I-mediated DNA relaxation. Among them, 17 appeared to be the most active compound of this series and not only showed higher inhibition when indicated from the low IC50values against PC-3 cancer cell line but also attenuated the in vitro topoisomerase I-mediated DNA relaxation at low micromolar concentrations. All test compounds exhibited different cytostatic and cytotoxic activities for further developing potential anticancer drugs.

Original languageEnglish
Pages (from-to)30-38
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume87
DOIs
Publication statusPublished - Nov 24 2014

Fingerprint

Topoisomerase Inhibitors
Oxazoles
Thiones
Type I DNA Topoisomerase
Antineoplastic Agents
Fusion reactions
Cells
Cell Line
Anthraquinones
DNA
Cytostatic Agents
Cytotoxicity
Neoplasms
Derivatives
Pharmaceutical Preparations
heparinized hydrophilic polymer

Keywords

  • cell panel assay
  • mediated DNA relaxation NCI 60
  • Topoisomerase I

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology
  • Medicine(all)

Cite this

Ring fusion strategy for the synthesis of anthra[2,3-d ]oxazole-2-thione-5,10-dione homologues as DNA topoisomerase inhibitors and as antitumor agents. / Chen, Chun Liang; Liu, Fei Lan; Lee, Chia Chung; Chen, Tsung Chih; Chang, Wen Wei; Guh, Jih Hwa; Ahmed Ali, Ahmed Atef; Chang, Deh Ming; Huang, Hsu Shan.

In: European Journal of Medicinal Chemistry, Vol. 87, 24.11.2014, p. 30-38.

Research output: Contribution to journalArticle

Chen, Chun Liang ; Liu, Fei Lan ; Lee, Chia Chung ; Chen, Tsung Chih ; Chang, Wen Wei ; Guh, Jih Hwa ; Ahmed Ali, Ahmed Atef ; Chang, Deh Ming ; Huang, Hsu Shan. / Ring fusion strategy for the synthesis of anthra[2,3-d ]oxazole-2-thione-5,10-dione homologues as DNA topoisomerase inhibitors and as antitumor agents. In: European Journal of Medicinal Chemistry. 2014 ; Vol. 87. pp. 30-38.
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AU - Liu, Fei Lan

AU - Lee, Chia Chung

AU - Chen, Tsung Chih

AU - Chang, Wen Wei

AU - Guh, Jih Hwa

AU - Ahmed Ali, Ahmed Atef

AU - Chang, Deh Ming

AU - Huang, Hsu Shan

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