3β,7α,16α-trihydroxyandrost-5-ene-17-one | 95801-49-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β,7α,16α-trihydroxyandrost-5-ene-17-one
• 英文别名: 3beta,7alpha,16alpha-Trihydroxyandrost-5-en-17-one；(3S,7S,8R,9S,10R,13S,14S,16R)-3,7,16-trihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 95801-49-3
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: LNYAGDKBVMXDBL-BDWREFLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,7α,16α-trihydroxyandrost-5-ene-17-one 、 三甲基氯硅烷 、 甲氧基胺盐酸盐 在 N,O-双(三甲基硅烷基)三氟乙酰胺 作用下， 以 吡啶 为溶剂， 反应 1.75h， 生成
  参考文献：
  名称：

  Derivatives of 16α-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: Synthesis and gas chromatography/mass spectrometry analysis

  摘要：

  Derivatives of 16 alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3 beta, 16 alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by L-Selectride (R) or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7 alpha-hydroxy and 7 beta-hydroxy derivatives of 16 alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by H-1 and C-13 NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.002
• 作为产物：
  描述：

  3β,16α-dihydroxy-17,17-dimethoxyandrost-5-ene 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 氢氧化钾 、 对甲苯磺酸一水合物 、 L-Selectride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 57.5h， 生成 3β,7α,16α-trihydroxyandrost-5-ene-17-one
  参考文献：
  名称：

  Derivatives of 16α-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: Synthesis and gas chromatography/mass spectrometry analysis

  摘要：

  Derivatives of 16 alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3 beta, 16 alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by L-Selectride (R) or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7 alpha-hydroxy and 7 beta-hydroxy derivatives of 16 alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by H-1 and C-13 NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.002

文献信息

• Drug Screen and Treatment Method
  申请人：Flores-Riveros Jaime

  公开号：US20080221074A1

  公开（公告）日：2008-09-11

  The invention relates to methods identify or characterize compounds that can be used to treat specified clinical disorders such as hyperglycemia and type 2 diabetes. Compounds that can be used in these methods include 4α-fluoro-17α-ethynylandrost-5-ene-3β,7β,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3β,7α,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3α,7β,17β-triol and 4α-fluoro-17α-ethynylandrost-5-ene-3β,17β-triol-7-one.

  本发明涉及用于治疗特定临床疾病，如高血糖和2型糖尿病的化合物的鉴定或表征方法。可以在这些方法中使用的化合物包括4α-氟-17α-乙炔基雄烯-5-烯-3β，7β，17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3β，7α，17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3α，7β，17β-三醇和4α-氟-17α-乙炔基雄烯-5-烯-3β，17β-三醇-7-酮。
• Drug Screening and Treatment Methods
  申请人：Flores-Riveros Jaime

  公开号：US20080146532A1

  公开（公告）日：2008-06-19

  The invention relates to methods identify or characterize compounds that can be used to treat specified clinical disorders such as hyperglycemia and type 2 diabetes. Compounds that can be used in these methods include 4α-fluoro-17α-ethynylandrost-5-ene-3β, 7β,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3β,7α,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3α,7β,17β-triol and 4α-fluoro-17α-ethynylandrost-5-ene-3β,17β-triol-7-one.

  本发明涉及一种用于识别或表征可用于治疗特定临床疾病如高血糖和2型糖尿病的化合物的方法。可用于这些方法的化合物包括4α-氟-17α-乙炔基雄烯-5-烯-3β,7β,17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3β,7α,17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3α,7β,17β-三醇和4α-氟-17α-乙炔基雄烯-5-烯-3β,17β-三醇-7-酮。
• Drug Identification and Treatment Method
  申请人：Frincke James M.

  公开号：US20080153792A1

  公开（公告）日：2008-06-26

  The invention relates to methods to identify compounds that can treat autoimmune conditions and treat specified clinical disorders such as multiple sclerosis, ulcerative colitis or arthritis. Compounds include 17α-ethynylandrost-5-ene-3β,15β,7α,17β-tetrol, 4α-acetoxy-17α-ethynylandrost-5-ene-3β,7β,17β-triol, 17α-ethynylandrost-5-ene-3β,4β,7α,17β-tetrol, 17α-ethynylandrost-5-ene-3α,4β,7α,17β-tetrol and 17α-ethynylandrost-5-ene-3α,4β,17β-triol-7-one.

  本发明涉及一种识别能够治疗自身免疫疾病和治疗特定临床疾病（如多发性硬化症、溃疡性结肠炎或关节炎）的化合物的方法。这些化合物包括17α-乙炔基雄烯-5-烯-3β,15β,7α,17β-四醇，4α-乙酰氧基-17α-乙炔基雄烯-5-烯-3β,7β,17β-三醇，17α-乙炔基雄烯-5-烯-3β,4β,7α,17β-四醇，17α-乙炔基雄烯-5-烯-3α,4β,7α,17β-四醇和17α-乙炔基雄烯-5-烯-3α,4β,17β-三醇-7-酮。
• Drug Identification Method
  申请人：Harbor Therapeutics, Inc.

  公开号：US20130164780A1

  公开（公告）日：2013-06-27

  The invention relates to a method to identify compounds exert a transient effect(s) on one or more biological mediators of acute biological responses to acute stimuli or biological insult in subjects exposed to an acute stimulus or biological insult such as systemic exposure to bacterial LPS. The compounds are identified by measuring the effect of the test compound on the mediator of the acute stimulus or biological insult at times when an acute effect(s) to the stimulus or insult is occurring.

  该发明涉及一种方法，用于识别对急性刺激或生物损伤的急性生物反应的一个或多个生物介质产生短暂影响的化合物，这些化合物可以在接受细菌LPS的全身暴露等急性刺激或生物损伤的受试者中被识别。通过测量测试化合物对急性刺激或生物损伤介质的影响，可以在发生刺激或损伤的急性影响时识别化合物。
• Drugs and uses
  申请人：Harbor BioSciences, Inc.

  公开号：EP2486924A2

  公开（公告）日：2012-08-15

  The invention relates to methods to treat specified clinical disorders such as hyperglycemia, type 2 diabetes, arthritis and multiple sclerosis. The invention also provides methods to identify and characterize drugs, which are characterized in part by eliciting a variable biologic or therapeutic effect on a biomolecule at one time and relative normalization of the biomolecule at another time point. Compounds include 17α-ethynylandrost-5-ene-3β, 7β, 17β-triol or androst-5-ene-3β, 4β, 16α, 17β-tetrol, which can be used as reference standards to facilitate assessing and characterizing such candidate drugs.

  本发明涉及治疗特定临床疾病的方法，如高血糖、2 型糖尿病、关节炎和多发性硬化症。本发明还提供了鉴定和表征药物的方法，这些药物的部分特征是在一个时间点上对生物分子产生可变的生物或治疗作用，而在另一个时间点上生物分子相对正常化。化合物包括 17α-乙炔基雄甾烷-5-烯-3β，7β，17β-三醇或雄甾烷-5-烯-3β，4β，16α，17β-四醇，它们可用作参考标准，以便于评估和表征此类候选药物。