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
Author(s)
이응석라다깔끼박찬미[박찬미]전규연[전규연]타라만카다얏권영주[권영주]
Keywords
DNA TOPOISOMERASES; INHIBITORY-ACTIVITIES; CANCER-CHEMOTHERAPY; GREEN TEA; IN-VITRO; CYTOTOXICITY; DERIVATIVES; ALPHA; PYRIDINES; CELLS
Issue Date
201501
Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Citation
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v.90, pp.360 - 378
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.
URI
http://hdl.handle.net/YU.REPOSITORY/33748http://dx.doi.org/10.1016/j.ejmech.2014.11.045
ISSN
0223-5234
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약학대학 > 약학부 > Articles
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