Synthesis and biological evaluation of steroidal derivatives bearing a small ring as vitamin D receptor agonists

被引：2

作者：

Arichi, Norihito ^{[1
]}

Fujiwara, Shinichi ^{[1
]}

Ishizawa, Michiyasu ^{[2
]}

Makishima, Makoto ^{[2
]}

Hua, Duy H. ^{[3
]}

Yamada, Ken-ichi ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Takasu, Kiyosei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Nihon Univ, Sch Med, Dept Biomed Sci, Div Biochem,Itabashi Ku, Tokyo 1738610, Japan

[3] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 15期

关键词：

Steroids; Vitamin D receptor; Cyclopropanes; Cyclobutanes; 2+2] cycloaddition; SILYL ENOL ETHERS; ALPHA; BETA-UNSATURATED ESTERS; CONFORMATIONAL RESTRICTION; 2+2 CYCLOADDITION; CYCLOBUTANES; CYCLOPROPANATION; STEREOCHEMISTRY; CONTRACTION; INHIBITORS;

D O I：

10.1016/j.bmcl.2017.05.089

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel series of 3-ketolithocholic acid derivatives as well as estrone derivatives bearing a small ring for the conformational fixation of the side chain were synthesized by using a catalytic [2+2] cycloaddition and a ring-contraction rearrangement. The steroidal derivatives were evaluated for transcriptional activation of vitamin D receptor by luciferase reporter assays. Among them, two estrone derivatives showed a higher efficacy of the transactivation of vitamin D receptor than 3-ketolithocholic acid, and the small ring moieties were found to be important for the efficacy. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：3408 / 3411

页数：4

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