A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3:: Remarkably high affinity to vitamin D receptor

被引：86

作者：

Kittaka, A

Suhara, Y

Takayanagi, H

Fujishima, T

Kurihara, M

Takayama, H ^{[1
]}

机构：

[1] Teikyo Univ, Fac Pharmaceut Sci, Kanagawa 1990195, Japan

[2] Natl Inst Hlth Sci, Setagaya Ku, Tokyo 1588501, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 17期

关键词：

D O I：

10.1021/ol006222j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A convenient and potentially valuable synthetic approach to the novel 2 alpha-functionalized 1 alpha,25-dihydroxyvitamin D-3 [1 alpha,25(OH)(2)D-3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2 alpha-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25(OH)(2)D-3 derivatives, la and Ib showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

引用

页码：2619 / 2622

页数：4

共 29 条

[1] TOTAL SYNTHESIS OF (+)-METHYL PSEUDOMONATE-C FROM CARBOHYDRATES [J].