3β-methyl-5α-androstane-3α,17β-diol | 2233-69-4

• 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-methyl-5α-androstane-3α,17β-diol
• 英文别名: 3β-Methyl-5α-androstandiol-(3α,17β)；3β-Methyl-androstandiol-(3α,17β)；3-methyl-5α-androstane-3α,17β-diol；3-Methyl-5α-androstan-3α,17β-diol；(3R,5S,8R,9S,10S,13S,14S,17S)-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 2233-69-4
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: OOFYVIQRILOIKE-UXGBMSEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-methyl-5α-androstane-3α,17β-diol 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 3α-hydroxy-3β-methyl-5α-androstan-17-one
  参考文献：
  名称：

  DE881945

  摘要：

  公开号：
• 作为产物：
  描述：

  17β-acetoxy-3-methyl-5α-androstan-3α-ol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 3β-methyl-5α-androstane-3α,17β-diol
  参考文献：
  名称：

  Pelc,B., Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 1624 - 1631

  摘要：

  DOI：

文献信息

• [EN] C17, C20, AND C21 SUBSTITUTED NEUROACTIVE STEROIDS AND THEIR METHODS OF USE<br/>[FR] STÉROÏDES NEUROACTIFS SUBSTITUÉS EN C17, C20 ET C21 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018013613A1

  公开（公告）日：2018-01-18

  Described herein are neuroactive steroids or a pharmaceutically acceptable salt thereof. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. Also provided are pharmaceutical compositions comprising a compound described herein and methods of use and treatment, e.g., such as for inducing sedation and/or anesthesia.

  本文描述了神经活性类固醇或其药用可接受盐。在某些实施例中，这些化合物被设想为GABA调节剂。还提供了包括本文描述的化合物的药物组合物以及使用和治疗方法，例如用于诱导镇静和/或麻醉。
• Androsterone 3α-Ether-3β-Substituted and Androsterone 3β-Substituted Derivatives as Inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase:  Chemical Synthesis and Structure−Activity Relationship
  作者：Béatrice Tchédam Ngatcha、Van Luu-The、Fernand Labrie、Donald Poirier

  DOI：10.1021/jm058179h

  日期：2005.8.1

  Type 3 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) is involved in the biosynthesis of androgen testosterone. To produce potent inhibitors of this key steroidogenic enzyme, we prepared a series of androsterone (ADT) derivatives by adding a variety of substituents at position 3. The 3 beta-substituted ADT derivatives proved to be good inhibitors (IC50 = 57-147 nM) with better inhibitory activities obtained for compounds bearing a propyl, s-butyl, cyclohexylalkyl, or phenylalkyl group. With an IC50 value of 57 nM, the 3 beta-phenylmethyl-ADT was 6-fold more potent than ADT, the lead compound, and 13-fold more potent than 4-androstene-3,17-dione, the natural enzyme substrate used itself as inhibitor. The 3 alpha-ether-3 beta-substituted ADT derivatives had a lower inhibitory activity compared to the 3 beta-substituted ADT analogues except for the 3 beta-phenylethyl-3 alpha-methl-O-ADT (IC50 = 73 nM), which proved to be a more potent inhibitor than 3 beta-phenylethyl-ADT (IC50 = 99 nM). The results of our study identified potent type 3 17 beta-HSD inhibitors for potential use in the treatment of androgen-sensitive diseases.
• Androsterone 3β-substituted derivatives as inhibitors of type 3 17β-hydroxysteroid dehydrogenase
  作者：Béatrice Tchédam Ngatcha、Van Luu-The、Donald Poirier

  DOI：10.1016/s0960-894x(00)00517-5

  日期：2000.11

  Androsterone derivatives substituted at position 3 were synthesized starting from dihydrotestosterone in a short sequence of reactions. They proved to be potent inhibitors (IC50 = 57-147 nM) of type 3 17beta-hydroxysteroid dehydrogenase, a key enzyme of steroidogenesis, which catalyzes the transformation of androstenedione to steroid active androgen testosterone.
• 3-methyl androstanes
  申请人：SCHERING AG

  公开号：US02713061A1

  公开（公告）日：1955-07-12