STUDIES OF VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .43. 2 NOVEL ALLENIC SIDE-CHAIN ANALOGS OF 1-ALPHA,25-DIHYDROXYVITAMIN-D(3)

被引：32

作者：

CRAIG, AS

NORMAN, AW

OKAMURA, WH

机构：

[1] UNIV CALIF RIVERSIDE, DEPT CHEM, RIVERSIDE, CA 92521 USA

[2] UNIV CALIF RIVERSIDE, DEPT BIOCHEM, RIVERSIDE, CA 92521 USA

[3] UNIV CALIF RIVERSIDE, DIV BIOMED SCI, RIVERSIDE, CA 92521 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 16期

关键词：

D O I：

10.1021/jo00042a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new analogues of the steroid hormone 1-alpha,25-dihydroxyvitamin D3 (1) in which allenic functionality has been incorporated into the side chain have been synthesized. Both the 22S and 22R allene analogues (2a and 2b) were each separately synthesized in nine steps from a common precursor 9. While both analogues exhibited significant binding to the 1-alpha,25-dihydroxyvitamin D3 chick intestinal receptor, they showed low in vivo activity in stimulating intestinal calcium absorption in the chick.

引用

收藏

页码：4374 / 4380

页数：7

相关论文

共 52 条

[1] STEREOSPECIFIC SYNTHESIS OF THE LYTHGOE RING A ALDEHYDE FOR THE PREPARATION OF 1-ALPHA-HYDROXYLATED TACHYSTEROLS AND CALCIFEROLS [J].

BAGGIOLINI, EG ;

HENNESSY, BM ;

IACOBELLI, JA ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1987, 28 (19) :2095-2098

[2] STUDIES OF VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .34. POTENTIAL INHIBITORS OF VITAMIN-D METABOLISM - AN OXA ANALOG OF VITAMIN-D [J].

BARRACK, SA ;

GIBBS, RA ;

OKAMURA, WH .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1790-1796

[3]

BRAVERMAN S, 1967, ISR J CHEM, V5, P125

[4]

CACCHI S, 1986, SYNTHESIS-STUTTGART, P320

[5] PALLADIUM-CATALYZED SYNTHESIS OF DIENYNES RELATED TO VITAMIN-D FROM ENOL TRIFLATES [J].

CASTEDO, L ;

MOURINO, A ;

SARANDESES, LA .

TETRAHEDRON LETTERS, 1986, 27 (13) :1523-1526

[6] PALLADIUM-CATALYZED SYNTHESIS OF DIENYNES RELATED TO 1-ALPHA,25-DIHYDROXYVITAMIN-D3 [J].

CASTEDO, L ;

MASCARENAS, JL ;

MOURINO, A ;

SARANDESES, LA .

TETRAHEDRON LETTERS, 1988, 29 (10) :1203-1206

[7] AN IMPROVED SYNTHESIS OF 1-ALPHA,25-DIHYDROXYVITAMIN D A SYNTHONS [J].

CASTEDO, L ;

MASCARENAS, JL ;

MOURINO, A .

TETRAHEDRON LETTERS, 1987, 28 (19) :2099-2102

[8] ASYMMETRIC INDUCTION AND RACEMIZATION IN ALLENIC SULFOXIDES [J].

CINQUINI, M ;

COLONNA, S ;

COZZI, F ;

STIRLING, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (19) :2061-2067

[9] STUDIES ON VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .40. 1-ALPHA,25-DIHYDROXYPREVITAMIN-D3 - SYNTHESIS OF THE 9,14,19,19,19-PENTADEUTERIO DERIVATIVE AND A KINETIC-STUDY OF ITS [1,7]-SIGMATROPIC SHIFT TO 1-ALPHA,25-DIHYDROXYVITAMIN-D3 [J].

CURTIN, ML ;

OKAMURA, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :6958-6966

[10] CALCIFEROL AND ITS RELATIVES .16. TOTAL SYNTHESIS OF PRECALCIFEROL [J].

DAWSON, TM ;

DIXON, J ;

LITTLEWOOD, PS ;

LYTHGOE, B ;

SAKSENA, AK .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (18) :2960-+

← 1 2 3 4 5 6 →