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Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics

Authors
Gim, Hyo JinLi, HuaJung, So RaPark, Yong JooRyu, Jae-HaChung, Kyu HyuckJeon, Raok
Issue Date
Oct-2014
Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Keywords
Estrogen receptor; ER agonist; Azaisoflavones; Proliferation
Citation
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v.85, pp 107 - 118
Pages
12
Journal Title
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume
85
Start Page
107
End Page
118
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/10784
DOI
10.1016/j.ejmech.2014.07.030
ISSN
0223-5234
1768-3254
Abstract
A series of azaisoflavone analogs were designed and synthesized and their transactivation activities and binding affinities for ER alpha and ER beta were investigated. Among these compounds, 2b and 3a were the most potent with 6.5 and 1.1 mu M of EC50, respectively. Molecular modeling study showed putative binding modes of the compound 3a in the active site of ER alpha and ER beta, which were similar with that of genistein and provided insight of the effect of N-alkyl substitution of azaisoflavones on ER beta activity. Also, a biphasic effect of azaisoflavone analogs on MCF-7 cell growth depending on their concentrations was investigated. (C) 2014 Elsevier Masson SAS. All rights reserved.
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