3α-hydroxy-3β-phenylethyl-5α-androstan-17-one

• 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: 3α-hydroxy-3β-phenylethyl-5α-androstan-17-one
• 英文别名: (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-3-(2-phenylethyl)-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• 化学式: C₂₇H₃₈O₂
• 分子量: 394.598
• InChiKey: MCYXBOSZDNUXSI-KGURPWLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  雄诺龙 在 咪唑 、 盐酸 、 甲醇 、 Jones reagent (2.7 M) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3α-hydroxy-3β-phenylethyl-5α-androstan-17-one
  参考文献：
  名称：

  Androsterone 3β-substituted derivatives as inhibitors of type 3 17β-hydroxysteroid dehydrogenase

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00517-5

文献信息

• Inhibitors of type 5 and 3 17beta-hydroxysteroid dehydrogenase and methods for their use
  申请人：Endorecherche Inc.

  公开号：EP1321146A2

  公开（公告）日：2003-06-25

  Novel methods of medical treatment and/or inhibition of development of diseases are disclosed for diseases that are sensitive to androgenic or estrogenic activity. The treatments utilize inhibitors of type 5 and/or type 3 17β-hydroxysteroid dehydrogenase. Novel inhibitors of type 5 17β-hydroxysteroid dehydrogenase are also disclosed, as are novel inhibitors of type 3 17β-hydroxysteroid dehydrogenase.

  针对对雄激素或雌激素活性敏感的疾病，公开了新的医疗和/或抑制疾病发展的方法。这些治疗方法利用了 5 型和/或 3 型 17β- 羟类固醇脱氢酶的抑制剂。还公开了 5 型 17β- 羟类固醇脱氢酶的新型抑制剂，以及 3 型 17β- 羟类固醇脱氢酶的新型抑制剂。
• 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.
• INHIBITORS OF TYPE 5 AND TYPE 3 17beta-HYDROXYSTEROID DEHYDROGENASE AND METHODS FOR THEIR USE
  申请人：Endorecherche Inc.

  公开号：EP1094798A2

  公开（公告）日：2001-05-02
• INHIBITORS OF TYPE 3 3ALPHA-HYDROXYSTEROID DEHYDROGENASE
  申请人：Endorecherche Inc.

  公开号：EP1102582A2

  公开（公告）日：2001-05-30
• US6541463B1
  申请人：——

  公开号：US6541463B1

  公开（公告）日：2003-04-01