(3beta,5alpha,6beta)-雄甾烷-3,5,6-三醇 | 4725-51-3

• 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
• 中文名称: (3beta,5alpha,6beta)-雄甾烷-3,5,6-三醇
• 中文别名: 安脑三醇
• 英文名称: 5α-androst-3β,5,6β-triol
• 英文别名: androst-3β,5α,6β-triol；5α-androst-3β,5α,6β-triol；(3S,5R,6R,8S,9S,10R,13S,14S)-10,13-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,5,6-triol；(3S,5R,6R,8S,9S,10R,13S,14S)-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol
• CAS: 4725-51-3
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: IFRIPYPBJCUNAG-OTMXHXQLSA-N

物化性质

• 熔点：
  208-213 °C(Solv: acetone (67-64-1); ligroine (8032-32-4))
• 沸点：
  430.1±35.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3beta,5alpha,6beta)-雄甾烷-3,5,6-三醇 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 3β-p-toluensulfonyloxy-5α-hydroxy-androst-6-one
  参考文献：
  名称：

  2ß,3a,5a-TRIHYDROXY-ANDROST-6-ONE AND PREPARATION METHODS AND USE THEREOF

  摘要：

  本发明公开了具有式(I)结构的化合物2β,3α,5α-三羟基-雄甾-6-酮。本发明还公开了制备该化合物的多种方法和该化合物的用途。

  公开号：

  US20160039862A1
• 作为产物：
  描述：

  3β,6β-diformyloxy-5α-androst-5-ol 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以49.6 g的产率得到(3beta,5alpha,6beta)-雄甾烷-3,5,6-三醇
  参考文献：
  名称：

  2ß,3a,5a-TRIHYDROXY-ANDROST-6-ONE AND PREPARATION METHODS AND USE THEREOF

  摘要：

  本发明公开了具有式(I)结构的化合物2β,3α,5α-三羟基-雄甾-6-酮。本发明还公开了制备该化合物的多种方法和该化合物的用途。

  公开号：

  US20160039862A1

文献信息

• The reaction of lead tetraacetate with 3.BETA.-hydroxy steroids.
  作者：RIKIO OHUCHI、KENYU SHIBATA、NOBUAKI YAMAKOSHI、HIROMU MORI

  DOI：10.1248/cpb.29.43

  日期：——

  It was found that the reaction of lead tetraacetate with 3β-hydroxy steroids of the 5α-series gave the corresponding 3β, 19-oxido steroids. Only poor yields were obtained in the cases of 3β-hydroxy steroids having no substituent at C-5 (5α-H). Substitution at the 5α-position by an electronegative group such as halogen or acetoxyl enhanced the yield of the 3β, 19-oxido compound. The best result was obtained when a steroid was heated with lead tetraacetate in benzene in the presence of calcium carbonate and a trace of benzoyl peroxide.

  发现四乙酸铅与5α系列3β-羟基甾体化合物的反应产生了相应的3β, 19-氧代甾体化合物。在没有C-5（5α-H）取代基的3β-羟基甾体化合物的情况下，仅得到了较低的产率。通过在5α位引入电负性基团如卤素或乙酰氧基能提高3β, 19-氧代化合物的产率。当甾体化合物在碳酸钙和微量过氧化苯甲酰存在下，与四乙酸铅在苯中加热时，得到了最佳结果。
• 2β,3α,5α-트리하이드록시-안드로스트-6-원 및 이의 제조 방법 및 이의 용도
  申请人：GUANGZHOU CELLPROTEK PHARMACEUTICAL CO., LTD. 광저우 셀프로텍 파마슈티컬 컴퍼니 리미티드(520140496337)

  公开号：KR20160021083A

  公开（公告）日：2016-02-24

  본 발명은 화학식 I의 구조를 갖는 2β,3α,5α-트리하이드록시-안드로스트-6-원 (2β,3α,5α-trihydroxy-androst-6-one) 화합물을 개시한다. 본 발명은 또한 상기 화합물의 제조를 위한 복수 개의 방법 및 상기 화합물의 용도를 개시한다. 화학식 (I).

  本发明公开了具有化学式I结构的2β,3α,5α-三羟基-雄甾-6-酮（2β,3α,5α-trihydroxy-androst-6-one）化合物。本发明还公开了用于制备上述化合物的多种方法以及上述化合物的用途。化学式（I）。
• Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking
  作者：Wenli Chen、Xinying Chen、Shujia Zhou、Hong Zhang、Ling Wang、Jun Xu、Xiaopeng Hu、Wei Yin、Guangmei Yan、Jingxia Zhang

  DOI：10.1016/j.steroids.2016.03.004

  日期：2016.6

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.
• A synthetic steroid 5α-androst-3β,5,6β-triol blocks hypoxia/reoxygenation-induced neuronal injuries via protection of mitochondrial function
  作者：Jiesi Chen、Tiandong Leng、Wenli Chen、Min Yan、Wei Yin、Yijun Huang、Suizhen Lin、Dayue Duan、Jun Lin、Gongxiong Wu、Jingxia Zhang、Guangmei Yan

  DOI：10.1016/j.steroids.2013.06.004

  日期：2013.10

  Ischemic stroke is a leading cause of death worldwide, yet therapies are limited. During periods of ischemia following reperfusion in ischemic stroke, not only loss of energy supply, but a few other factors including mitochondrial dysfunction and oxidative stress also make vital contribution to neuronal injury. Here we synthesized a steroid compound 5 alpha-androst-3 beta,5,6 beta-triol by 3 steps starting from dehydroepiandrosterone and examined its effect on mitochondrial function and oxidative stress in primary cultured cortical neurons exposed to hypoxia followed by reoxygenation. 5 alpha-Androst-3 beta,5,6 beta-triol dose-dependently protected cortical neurons from hypoxia/reoxygenation exposure. Rates of reduction in neuronal viability, loss of mitochondrial membrane potential, disruption of ATP production and oxidative stress were ameliorated in 5 alpha-androst-3 beta,5,6 beta-triol pretreated cultures. In summary, these results suggest that 5 alpha-androst-3 beta,5,6 beta-triol is neuroprotective against hypoxia/reoxygenation induced neuronal injuries through mediation of mitochondrial function and oxidative stress. (C) 2013 The Authors. Published by Elsevier Inc. All rights reserved.
• Sulfuric acid hydrolysis of 3β-hydroxy-5α, 6α-epoxyandrostane
  作者：Jacqueline Weinman、Serge Weinman

  DOI：10.1016/0039-128x(65)90094-2

  日期：1965.12