3β-Hydroxy-5α-androstan-7,17-dion | 49643-99-4

• 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-Hydroxy-5α-androstan-7,17-dion
• 英文别名: 3beta-hydroxy-5alpha-Androstane-7,17-dione；(3S,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-7,17-dione
• CAS: 49643-99-4
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: ONVVZSHYQMOXLN-ZVMDJWLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-Hydroxy-5α-androstan-7,17-dion 生成 5α-androstane-3,7,17-trione
  参考文献：
  名称：

  Zur Lokalisierung仿射器Gruppen在类固醇激素治疗中，我酮类固醇

  摘要：

  在快速的AllenFällenübereine Oxydation zu Ste entsprechenden Ketonen中的Steroidskelett gelingt上的羟基化合物发生了反应。Sie erlauben可以用于A / B环系统。

  DOI：

  10.1002/cber.19701030521
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 palladium on activated charcoal sodium hydroxide 、 sodium chromate(VI) 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸酐 、 溶剂黄146 为溶剂， 生成 3β-Hydroxy-5α-androstan-7,17-dion
  参考文献：
  名称：

  Kagan,H.B.; Jacques,J., Bulletin de la Societe Chimique de France, 1960, p. 1551 - 1558

  摘要：

  DOI：

文献信息

• [EN] C7, C12, AND C16 SUBSTITUTED NEUROACTIVE STEROIDS AND THEIR METHODS OF USE<br/>[FR] STÉROÏDES NEUROACTIFS SUBSTITUÉS EN C7, C12 ET C16 ET MÉTHODES D'UTILISATION ASSOCIÉES
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018013615A1

  公开（公告）日：2018-01-18

  Described herein are neuroactive steroids of Formula (I), Formula (V), or Formula (IX) or a pharmaceutically acceptable salt thereof; wherein each instance of R2, R3, R4, R5, R6, R7, R11a, R11b,R12, R16, R17, R19, and ----- are as defined herein. 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.

  本文描述了化学式（I）、化学式（V）或化学式（IX）的神经活性类固醇或其药用盐；其中R2、R3、R4、R5、R6、R7、R11a、R11b、R12、R16、R17、R19和-----的每个实例如本文所定义。在某些实施例中，这些化合物被设想为GABA调节剂。还提供了包含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。
• Microbiological transformations. Part 4. Microbiological transformations of 5α-androstan-17-ones and of 17a-aza-<scp>D</scp>-homo-5α-androstan-17-ones with the fungus Cunninghamella elegans
  作者：Trevor A. Crabb、John A. Saul、Roger O. Williams

  DOI：10.1039/p19810001041

  日期：——

  The microbiological transformation of 5α-androstan-17-one, and the 3β-acetoxy- and 3α-hydroxy-derivatives, by Cunninghamella elegans is dominated by 1β,7-dihydroxylation or 7-monohydroxylation. 3α-Acetoxy-5α-androstan-17-one undergoes predominant 6β,11β-dihydroxylation. 17a-Aza-D-homo-5α-androstan-17-one and the 3α-acetoxy-derivative undergo predominant monohydroxylation at 6β or 7α, in contrast to

  秀丽隐杆线虫对5α-雄甾烷17-one，3β-乙酰氧基和3α-羟基衍生物的微生物转化主要由1β，7-二羟基化或7-单羟基化。3α-乙酰氧基-5α-雄烷-17-主要发生6β，11β-二羟基化。17a- Aza- D -homo-5α-androstan-17-one和3α-乙酰氧基衍生物在6β或7α处主要发生单羟基化反应，而3β-乙酰氧基衍生物虽然进行类似的单羟基化反应却得到良好的收率。 9α-单羟基化产物。
• Hexose-6-phosphate Dehydrogenase Modulates 11β-Hydroxysteroid Dehydrogenase Type 1-Dependent Metabolism of 7-keto- and 7β-hydroxy-neurosteroids
  作者：Lyubomir G. Nashev、Charlie Chandsawangbhuwana、Zoltan Balazs、Atanas G. Atanasov、Bernhard Dick、Felix J. Frey、Michael E. Baker、Alex Odermatt

  DOI：10.1371/journal.pone.0000561

  日期：——

  BackgroundThe role of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) in the regulation of energy metabolism and immune system by locally reactivating glucocorticoids has been extensively studied. Experiments determining initial rates of enzyme activity revealed that 11β-HSD1 can catalyze both the reductase and the dehydrogenase reaction in cell lysates, whereas it predominantly catalyzes the reduction of cortisone to cortisol in intact cells that also express hexose-6-phosphate dehydrogenase (H6PDH), which provides cofactor NADPH. Besides its role in glucocorticoid metabolism, there is evidence that 11β-HSD1 is involved in the metabolism of 7-keto- and 7-hydroxy-steroids; however the impact of H6PDH on this alternative function of 11β-HSD1 has not been assessed.MethodologyWe investigated the 11β-HSD1-dependent metabolism of the neurosteroids 7-keto-, 7α-hydroxy- and 7β-hydroxy-dehydroepiandrosterone (DHEA) and 7-keto- and 7β-hydroxy-pregnenolone, respectively, in the absence or presence of H6PDH in intact cells. 3D-structural modeling was applied to study the binding of ligands in 11β-HSD1.Principal FindingsWe demonstrated that 11β-HSD1 functions in a reversible way and efficiently catalyzed the interconversion of these 7-keto- and 7-hydroxy-neurosteroids in intact cells. In the presence of H6PDH, 11β-HSD1 predominantly converted 7-keto-DHEA and 7-ketopregnenolone into their corresponding 7β-hydroxy metabolites, indicating a role for H6PDH and 11β-HSD1 in the local generation of 7β-hydroxy-neurosteroids. 3D-structural modeling offered an explanation for the preferred formation of 7β-hydroxy-neurosteroids.ConclusionsOur results from experiments determining the steady state concentrations of glucocorticoids or 7-oxygenated neurosteroids suggested that the equilibrium between cortisone and cortisol and between 7-keto- and 7-hydroxy-neurosteroids is regulated by 11β-HSD1 and greatly depends on the coexpression with H6PDH. Thus, the impact of H6PDH on 11β-HSD1 activity has to be considered for understanding both glucocorticoid and neurosteroid action in different tissues.

  -hydroxy-neurosteroids。
• Bell,A.M. et al., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2131 - 2136
  作者：Bell,A.M. et al.

  DOI：——

  日期：——
• Joska,J. et al., Collection of Czechoslovak Chemical Communications, 1961, vol. 26, p. 1646 - 1657
  作者：Joska,J. et al.

  DOI：——

  日期：——