STUDIES OF VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .39. AROCALCIFEROLS - SYNTHESIS AND BIOLOGICAL EVALUATION OF AROMATIC SIDE-CHAIN ANALOGS OF 1-ALPHA,25-DIHYDROXYVITAMIN-D3

被引：72

作者：

FIGADERE, B

NORMAN, AW

HENRY, HL

KOEFFLER, HP

ZHOU, JY

OKAMURA, WH

机构：

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

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

[3] UNIV CALIF LOS ANGELES, CEDARS SINAI MED CTR, DEPT MED, DIV HEMATOL ONCOL, LOS ANGELES, CA 90048 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1991年 / 34卷 / 08期

关键词：

D O I：

10.1021/jm00112a021

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Aromatic side-chain analogues (arocalciferols 6-9) of the steroid hormone 1-alpha,25-dihydroxyvitamin D3 (1) were synthesized and biologically evaluated. The analogues were prepared by coupling the vitamin D A-ring enyne 14 with the appropriate enol triflate of a modified CD steroid fragment of the type 22. The resulting dienyne 23 was then transformed in three steps to the vitamin D analogues 6-9. Biological evaluation of these analogues have provided information concerning side-chain topographical effects on in vivo and in vitro activity.

引用

页码：2452 / 2463

页数：12

共 62 条

[1] DIFFERENTIATION OF MOUSE MYELOID-LEUKEMIA CELLS INDUCED BY 1-ALPHA,25-DIHYDROXYVITAMIN-D3
ABE, E
MIYAURA, C
SAKAGAMI, H
TAKEDA, M
KONNO, K
YAMAZAKI, T
YOSHIKI, S
SUDA, T
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (08): : 4990 - 4994
[2] SYNTHETIC ANALOGS OF VITAMIN-D3 WITH AN OXYGEN ATOM IN THE SIDE-CHAIN SKELETON - A TRAIL OF THE DEVELOPMENT OF VITAMIN-D COMPOUNDS WHICH EXHIBIT POTENT DIFFERENTIATION-INDUCING ACTIVITY WITHOUT INDUCING HYPERCALCEMIA
ABE, J
MORIKAWA, M
MIYAMOTO, K
KAIHO, SI
FUKUSHIMA, M
MIYAURA, C
ABE, E
SUDA, T
NISHII, Y
[J]. FEBS LETTERS, 1987, 226 (01) : 58 - 62
[3] STEREOSPECIFIC SYNTHESIS OF THE LYTHGOE RING A ALDEHYDE FOR THE PREPARATION OF 1-ALPHA-HYDROXYLATED TACHYSTEROLS AND CALCIFEROLS
BAGGIOLINI, EG
HENNESSY, BM
IACOBELLI, JA
USKOKOVIC, MR
[J]. TETRAHEDRON LETTERS, 1987, 28 (19) : 2095 - 2098
[4] STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL
BAGGIOLINI, EG
IACOBELLI, JA
HENNESSY, BM
BATCHO, AD
SERENO, JF
USKOKOVIC, MR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) : 3098 - 3108
[5] CLONING AND EXPRESSION OF FULL-LENGTH CDNA-ENCODING HUMAN VITAMIN-D RECEPTOR
BAKER, AR
MCDONNELL, DP
HUGHES, M
CRISP, TM
MANGELSDORF, DJ
HAUSSLER, MR
PIKE, JW
SHINE, J
OMALLEY, BW
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (10) : 3294 - 3298
[6] STUDIES OF VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .34. POTENTIAL INHIBITORS OF VITAMIN-D METABOLISM - AN OXA ANALOG OF VITAMIN-D
BARRACK, SA
GIBBS, RA
OKAMURA, WH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) : 1790 - 1796
[7] BLIGH EG, 1959, CAN J BIOCHEM PHYS, V37, P911
[8] BOLLAG W, 1981, CANCER CHEMOTH PHARM, V7, P27
[9] CACCHI S, 1986, SYNTHESIS-STUTTGART, P320
[10] SYNTHESIS OF MC-903, A BIOLOGICALLY-ACTIVE VITAMIN-D METABOLITE ANALOG
CALVERLEY, MJ
[J]. TETRAHEDRON, 1987, 43 (20) : 4609 - 4619

← 1 2 3 4 5 6 7 →