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Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison

Title
Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison
Authors
Karki, RadhaPark, ChanmiJun, Kyu-YeonKadayat, Tara ManLee, Eung-SeokKwon, Youngjoo
Ewha Authors
권영주
SCOPUS Author ID
권영주scopus
Issue Date
2015
Journal Title
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
ISSN
0223-5234JCR Link

1768-3254JCR Link
Citation
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY vol. 90, pp. 360 - 378
Keywords
Terpyridine bioisosteresTopoisomerase poisonAntitumor agentsDihydroxylated 2,4-dipheny1-6-aryl pyridineCytotoxicity
Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen Schmidt condensation reaction and modified Krohnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups at artho, meta or para position of 2- and 4-phenyl rings attached to the central pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines for the development of novel antitumor agents. Most of the prepared compounds exhibited significant antiproliferative activity on human cancer cell lines, HCT15 and K562, as well as potent topo II inhibitory activity comparable to or stronger than etoposide. The structure activity relationship demonstrated that compounds with hydroxyl group at meta or para position of 2-phenyl ring in combination with hydroxyl at ortho, meta or para position of 4-phenyl ring displayed the most potent topoisomerase II inhibitory activity and cytotoxicity. Positive correlation between topoisomerase II inhibition and cytotoxicity was obtained for several compounds (30, 35, 36, 40-45, 49, 54, 56). Compound 56 showed the most potent topoisomerase H inhibitory activity at low concentration and functioned as a topoisomerase poison like the mode of action of etoposide. (C) 2014 Elsevier Masson SAS. All rights reserved.
DOI
10.1016/j.ejmech.2014.11.045
Appears in Collections:
약학대학 > 약학과 > Journal papers
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