Synthesis and biological activity of 22-oxa CD-ring modified analogues of 1α,25-dihydroxyvitamin D3:: cis-perhydrindane CE-ring analogues

被引：9

作者：

Demin, S

Van Haver, D

Vandewalle, M

De Clercq, PJ

Bouillon, R

Verstuyf, A

机构：

[1] State Univ Ghent, Dept Organ Chem, B-9000 Ghent, Belgium

[2] Catholic Univ Louvain, Lab Expt Med & Endocrinol, B-3000 Louvain, Belgium

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 15期

关键词：

D O I：

10.1016/j.bmcl.2004.05.067

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis and biological activity of novel CD-ring modified analogues of 22-oxa-1alpha,25-dihydroxyvitamin D-3, lacking the D-ring and featuring a connection between C-12 and C-21 (cis-perhydrindane CE-ring analogues), is described. The synthesis of the CE-ring system follows Meyers' methodology for the preparation of enantiomerically pure hydrinden-2-ones. The analogues show a complete lack of binding affinity for the vitamin D receptor (pig nVDR) and of antiproliferative activity (MCF-7 cells), as compared to calcitriol. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3885 / 3888

页数：4

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