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Synthesis of 3 beta-hydroxy-5 alpha-cholest-8-en-7-one and 3 beta-hydroxy-5 alpha-cholest-8-en-11-one: evaluation as potential hypocholesterolemic agents.

作者信息

Parish E J, Nanduri V B, Seikel J M, Kohl H H, Nusbaum K E

机构信息

Department of Chemistry, Auburn University, Alabama 36849-3501.

出版信息

Steroids. 1986 Nov-Dec;48(5-6):407-18. doi: 10.1016/0039-128x(86)90027-9.

DOI:10.1016/0039-128x(86)90027-9
PMID:3445290
Abstract

An efficient procedure for the chemical synthesis of 3 beta-hydroxy-5 alpha-cholest-8-en-7-one and 3 beta-hydroxy-5 alpha-cholest-8-en-11-one is described. These ketosterols have been shown to have possible significant hypocholesterolemic effects when fed to normal rats at a level of 0.15% in a laboratory chow diet. The diets containing the steroids caused significant decreases in food consumption which were associated with decreases in the rate of gain in body weight.

摘要

相似文献

1
Synthesis of 3 beta-hydroxy-5 alpha-cholest-8-en-7-one and 3 beta-hydroxy-5 alpha-cholest-8-en-11-one: evaluation as potential hypocholesterolemic agents.
Steroids. 1986 Nov-Dec;48(5-6):407-18. doi: 10.1016/0039-128x(86)90027-9.
2
Crystal structure of 3 beta-benzoyloxy-6 alpha-chloro-5 alpha-cholest-7-ene, a key intermediate in the chemical synthesis of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one.3β-苯甲酰氧基-6α-氯-5α-胆甾-7-烯的晶体结构,5α-胆甾-8(14)-烯-3β-醇-15-酮化学合成中的关键中间体。
Chem Phys Lipids. 1988 Aug;47(4):283-9. doi: 10.1016/0009-3084(88)90051-5.
3
Inhibitors of sterol synthesis. Dietary administration of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one inhibits the intestinal absorption of cholesterol in lymph-cannulated rats.固醇合成抑制剂。给经淋巴管插管的大鼠经饮食给予5α-胆甾-8(14)-烯-3β-醇-15-酮可抑制胆固醇的肠道吸收。
Biochem Biophys Res Commun. 1987 Aug 14;146(3):1003-8. doi: 10.1016/0006-291x(87)90747-9.
4
Inhibitors of sterol synthesis. Metabolism-based design and construction of a new analog of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one and its effects in cultured mammalian cells and in rats.甾醇合成抑制剂。基于代谢的3β-羟基-5α-胆甾-8(14)-烯-15-酮新类似物的设计与构建及其在培养的哺乳动物细胞和大鼠中的作用。
J Lipid Res. 1995 Apr;36(4):767-86.
5
Chemical synthesis of 15-ketosterols and their inhibitions of cholesteryl ester transfer protein.
Bioorg Med Chem. 1995 Apr;3(4):367-74. doi: 10.1016/0968-0896(95)00025-c.
6
Inhibitors of sterol synthesis. The effects of dietary 5 alpha-cholest-8(14)-en-3 beta-ol-15-one on the fate of [4-14C]cholesterol and [2,4-3H]5 alpha-cholest-8(14)-en-3 beta-ol-15-one after intragastric administration to rats.固醇合成抑制剂。大鼠经胃内给予膳食5α-胆甾-8(14)-烯-3β-醇-15-酮后,其对[4-¹⁴C]胆固醇和[2,4-³H]5α-胆甾-8(14)-烯-3β-醇-15-酮代谢命运的影响。
Chem Phys Lipids. 1988 May;47(1):1-20. doi: 10.1016/0009-3084(88)90029-1.
7
Concerning the structure of 3 beta-benzoyloxy-5 beta-cholesta-8,14-diene, a major byproduct in the chemical synthesis of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one.关于3β-苯甲酰氧基-5β-胆甾-8,14-二烯的结构,它是5α-胆甾-8(14)-烯-3β-醇-15-酮化学合成中的一种主要副产物。
Chem Phys Lipids. 1988 Aug;47(4):273-82. doi: 10.1016/0009-3084(88)90050-3.
8
Concerning the chemical synthesis of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one, a novel regulator of cholesterol metabolism.
Chem Phys Lipids. 1988 Sep;48(1-2):7-17. doi: 10.1016/0009-3084(88)90129-6.
9
Inhibitors of sterol synthesis. Hypocholesterolemic action of dietary 9 alpha-fluoro-5 alpha-cholest-8(14)-en-3 beta-ol-15-one.固醇合成抑制剂。膳食中9α-氟-5α-胆甾-8(14)-烯-3β-醇-15-酮的降胆固醇作用。
Biochem Biophys Res Commun. 1980 Apr 14;93(3):813-8. doi: 10.1016/0006-291x(80)91149-3.
10
Enzymatic formation and chemical synthesis of an active metabolite of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one, a potent regulator of cholesterol metabolism.
Biochem Biophys Res Commun. 1988 Feb 29;151(1):130-6. doi: 10.1016/0006-291x(88)90568-2.

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