Synthesis and Selective Estrogen Receptor Binding Affinity of 7-Hydroxylisoflavones

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1245-1251. Previous Articles Next Articles

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7-羟基异黄酮及其衍生物的合成与选择性雌激素受体结合的构效关系研究

王星^1,2，吕广颖³，杨利娟⁴，王飞¹，王淳*^,1

(¹中国科学院成都生物研究所成都610041)
(²中国科学院研究生院北京 100049)
(³西南科技大学材料科学与工程学院绵阳 621010)
(⁴成都中医药大学药学院成都 611137)

收稿日期:2010-12-17 修回日期:2011-02-17 发布日期:2011-03-30
通讯作者: 王淳 E-mail:wangchun@cib.ac.cn

Synthesis and Selective Estrogen Receptor Binding Affinity of 7-Hydroxylisoflavones

Wang Xing^1,2 Lü Guangying³ Yang Li-juan⁴ Wang Fei¹ Wang Chun*^,1

(¹ Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041)
(² Graduate University of Chinese Academy of Sciences, Beijing 100049)
(³ School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010)
(⁴ School of Pharmaceutical Sciences, Chengdu University of Traditional Chinese Medicine, Chengdu 611137)

Received:2010-12-17 Revised:2011-02-17 Published:2011-03-30
Contact: Chun Wang E-mail:wangchun@cib.ac.cn

Twenty six 7-hydroxylisoflavones, including four new compounds 3r, 3s, 3u and 3v, were successfully synthesized. Among which twenty four, 3a～3x, were directly given by “One-Pot” strategy from polyphenolic compounds and substituted phenylacetic acids. 2-Hydroxylisoflavones 4a and 4b were further developed from 2-methoxylisoflvones 3d and 3g by demethylation. Nine out of twenty-six synthesized compounds exhibited higher selectivity for estrogen receptor ERβ than genistein|7,8-dihydroxylisoflavones showed better binding affinities for ERβ than 7-hydroxylisoflavones|4-substituents of isoflavones influenced relative binding affinities (RBA) of ERβ/ERα in the order: H＞Cl＞F＞OH|2, 3 and 5-substituents reduced the binding affinity to both ERα and ERβ.

Key words: 7-hydroIsoflavone, estrogen receptor, binding affinity, structure-activity relationship (SAR)

CLC Number:

914.5

Cite this article

WANG Xing, LV Guang-Ying, YANG Li-Juan, WANG Fei, WANG Chun. Synthesis and Selective Estrogen Receptor Binding Affinity of 7-Hydroxylisoflavones[J]. Chin. J. Org. Chem., 2011, 31(08): 1245-1251.

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7-羟基异黄酮及其衍生物的合成与选择性雌激素受体结合的构效关系研究

Synthesis and Selective Estrogen Receptor Binding Affinity of 7-Hydroxylisoflavones

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