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SYNTHESIS AND ACTIVITY INVITRO OF 25-MASKED-1-ALPHA-HYDROXYLATED VITAMIN-D3 ANALOGS
被引:19
作者
:
NAPOLI, JL
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NAPOLI, JL
[
1
]
FIVIZZANI, MA
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
FIVIZZANI, MA
[
1
]
HAMSTRA, AH
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
HAMSTRA, AH
[
1
]
SCHNOES, HK
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
SCHNOES, HK
[
1
]
DELUCA, HF
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
DELUCA, HF
[
1
]
STERN, PH
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
STERN, PH
[
1
]
机构
:
[1]
NORTHWESTERN UNIV,DEPT PHARMACOL,CHICAGO,IL 60611
来源
:
STEROIDS
|
1978年
/ 32卷
/ 04期
基金
:
美国国家卫生研究院;
关键词
:
D O I
:
10.1016/0039-128X(78)90058-2
中图分类号
:
Q5 [生物化学];
Q7 [分子生物学];
学科分类号
:
071010 ;
081704 ;
摘要
:
1α-Hydroxylated-25-masked-vitainin D3 analogs were synthesized as probes to help evaluate the role of 25-hydroxyl group in hormone-receptor Interactions of 1α,25-dihydroxyvitamin D3 (13a). Synthetic work on model systems showed that the steroidal 25-hydroxyl group could be easily fluorinated in high yield with diethylaminosulfur trifluoride. Treatment of 25-fluoro compound with acetic acid resulted in both elimination and displacement of fluorine by acetate. The desired 1α-hydroxy-25-fluoro-vitamin D3 (14b) was obtained efficiently by fluorination and subsequent deacecylation of 1α,25-dihydroxyvitamin D3 1,3-diacetate (13b). Also obtained was a mixture of 1α-hydroxyvitamin D3-24- and 25-enes (15b). Both 14b and 15b were 300-400 times less active than 13a in the chick intestinal cytosol protein binding assay, making these analogs similar in potency to 1α-hydroxyvitamin D3 in vitro. The essentially equivalent activity of 14b and 15b with 1α-hydroxyvitamin D3 indicates that in the absence of a 25-hydroxyl group some alterations to the side chain carbons of 13a may be tolerated without further weakening analog-protein interactions. The fluoroanalog 14b was also about 250 times less potent than 13a in stimulating bone resorption in vitro. These compounds should prove to be valuable tools in aiding understanding of the salient structural features of the vitamin D3 metabolites. © 1978.
引用
收藏
页码:453 / 466
页数:14
相关论文
共 26 条
[21]
CALCIUM-MOBILIZING EFFECT OF LARGE DOSES OF 25-HYDROXYCHOLECALCIFEROL IN ANEPHRIC RATS
PAVLOVITCH, H
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, LAB TISSUS CALCIFIES, PARIS, FRANCE
PAVLOVITCH, H
GARABEDIAN, M
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, LAB TISSUS CALCIFIES, PARIS, FRANCE
GARABEDIAN, M
BALSAN, S
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, LAB TISSUS CALCIFIES, PARIS, FRANCE
BALSAN, S
[J].
JOURNAL OF CLINICAL INVESTIGATION,
1973,
52
(10)
: 2656
-
2659
[22]
PETERS RA, 1957, ADV ENZYMOL REL S BI, V18, P113
[23]
BONE RESORPTION IN TISSUE CULTURE . FACTORS INFLUENCING RESPONSE TO PARATHYROID HORMONE
RAISZ, LG
论文数:
0
引用数:
0
h-index:
0
RAISZ, LG
[J].
JOURNAL OF CLINICAL INVESTIGATION,
1965,
44
(01)
: 103
-
&
[24]
1,25-DIHYDROXYCHOLECALCIFEROL - POTENT STIMULATOR OF BONE RESORPTION IN TISSUE-CULTURE
RAISZ, LG
论文数:
0
引用数:
0
h-index:
0
RAISZ, LG
TRUMMEL, CL
论文数:
0
引用数:
0
h-index:
0
TRUMMEL, CL
HOLICK, MF
论文数:
0
引用数:
0
h-index:
0
HOLICK, MF
DELUCA, HF
论文数:
0
引用数:
0
h-index:
0
DELUCA, HF
[J].
SCIENCE,
1972,
175
(4023)
: 768
-
+
[25]
BONE RESORBING ACTIVITY OF VITAMIN-D METABOLITES AND CONGENERS INVITRO - INFLUENCE OF HYDROXYL SUBSTITUENTS IN A-RING
STERN, PH
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
STERN, PH
TRUMMEL, CL
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
TRUMMEL, CL
SCHNOES, HK
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
SCHNOES, HK
DELUCA, HF
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
DELUCA, HF
[J].
ENDOCRINOLOGY,
1975,
97
(06)
: 1552
-
1558
[26]
TANAKA Y, 1977, J BIOL CHEM, V252, P1421
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1
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3
→
共 26 条
[21]
CALCIUM-MOBILIZING EFFECT OF LARGE DOSES OF 25-HYDROXYCHOLECALCIFEROL IN ANEPHRIC RATS
PAVLOVITCH, H
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, LAB TISSUS CALCIFIES, PARIS, FRANCE
PAVLOVITCH, H
GARABEDIAN, M
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, LAB TISSUS CALCIFIES, PARIS, FRANCE
GARABEDIAN, M
BALSAN, S
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, LAB TISSUS CALCIFIES, PARIS, FRANCE
BALSAN, S
[J].
JOURNAL OF CLINICAL INVESTIGATION,
1973,
52
(10)
: 2656
-
2659
[22]
PETERS RA, 1957, ADV ENZYMOL REL S BI, V18, P113
[23]
BONE RESORPTION IN TISSUE CULTURE . FACTORS INFLUENCING RESPONSE TO PARATHYROID HORMONE
RAISZ, LG
论文数:
0
引用数:
0
h-index:
0
RAISZ, LG
[J].
JOURNAL OF CLINICAL INVESTIGATION,
1965,
44
(01)
: 103
-
&
[24]
1,25-DIHYDROXYCHOLECALCIFEROL - POTENT STIMULATOR OF BONE RESORPTION IN TISSUE-CULTURE
RAISZ, LG
论文数:
0
引用数:
0
h-index:
0
RAISZ, LG
TRUMMEL, CL
论文数:
0
引用数:
0
h-index:
0
TRUMMEL, CL
HOLICK, MF
论文数:
0
引用数:
0
h-index:
0
HOLICK, MF
DELUCA, HF
论文数:
0
引用数:
0
h-index:
0
DELUCA, HF
[J].
SCIENCE,
1972,
175
(4023)
: 768
-
+
[25]
BONE RESORBING ACTIVITY OF VITAMIN-D METABOLITES AND CONGENERS INVITRO - INFLUENCE OF HYDROXYL SUBSTITUENTS IN A-RING
STERN, PH
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
STERN, PH
TRUMMEL, CL
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
TRUMMEL, CL
SCHNOES, HK
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
SCHNOES, HK
DELUCA, HF
论文数:
0
引用数:
0
h-index:
0
机构:
NORTHWESTERN UNIV,MED SCH,DEPT PHARMACOL,CHICAGO,IL 60611
DELUCA, HF
[J].
ENDOCRINOLOGY,
1975,
97
(06)
: 1552
-
1558
[26]
TANAKA Y, 1977, J BIOL CHEM, V252, P1421
←
1
2
3
→