11α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one | 25356-68-7

• 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: 11α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one
• 英文别名: 17α-methyl-1,4-androstdien-11α,17β-diol-3-one；11α-hydroxymethandrostenolone；11α,17β-dihydroxy-17α-methyl-androsta-1,4-dien-3-one；11α,17β-Dihydroxy-17α-methyl-androsta-1,4-dien-3-on；11α,17β-Dihydroxy-17α-methyl-1,4-androstadien-3-on；11alpha-Hydroxy methandrostenolone；(8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 25356-68-7
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: JYSKGJQTRZNVIX-QMNUTNMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one 生成 Phosphoric acid mono-{3-[2-((1S,2S,3aS,4S,6aS)-2-formyl-4-hydroxy-3a,4-dimethyl-octahydro-pentalen-1-yl)-ethyl]-4-methyl-phenyl} ester
  参考文献：
  名称：

  类固醇的磷酸化和二烯酮-苯酚的重排导致具有强毒性的类固醇醛。

  摘要：

  通过使用焦磷酰氯，21-羟基-20-氧甾类化合物被一步磷酸化，并获得了定量产率。当在较高温度下对泼尼松龙进行反应时，会发生二壬酚重排并同时发生嚬哪醇转移，从而形成副产物 3，21-二磷酸 C-去甲-9，10-甾醛（A）。这种化合物具有抑制心脏和血管收缩的活性，对兔子有剧毒。

  DOI：

  10.1248/cpb.22.1439
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 11α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one
  参考文献：
  名称：

  11alpha-hydroxy-1-dehydromethyltestosterone and the esters thereof

  摘要：

  公开号：

  US02864831A1

文献信息

• Gas chromatography/chemical ionization triple quadrupole mass spectrometry analysis of anabolic steroids: ionization and collision-induced dissociation behavior
  作者：Michael Polet、Wim Van Gansbeke、Peter Van Eenoo、Koen Deventer

  DOI：10.1002/rcm.7472

  日期：2016.2.28

  detection of new anabolic steroid metabolites and new designer steroids is a challenging task in doping analysis. Switching from electron ionization gas chromatography triple quadrupole mass spectrometry (GC/EI‐MS/MS) to chemical ionization (CI) has proven to be an efficient way to increase the sensitivity of GC/MS/MS analyses and facilitate the detection of anabolic steroids. CI also extends the possibilities

  新的合成代谢类固醇代谢物和新设计的类固醇的检测在掺杂分析中是一项艰巨的任务。从电子电离气相色谱三重四极杆质谱（GC / EI-MS / MS）切换到化学电离（CI）是提高GC / MS / MS分析灵敏度并促进合成代谢类固醇检测的有效方法。CI还扩展了GC / MS / MS分析的可能性，因为分子离子由于较软的电离而保留为其质子化形式。在EI中，由于分子离子的丰度低或不存在以及广泛的（很大程度上是不可预测的）碎片，很难找到以前未知但预期的代谢物。这项工作的主要目的是研究大量合成代谢雄激素类固醇（AAS）作为其三甲基甲硅烷基衍生物的CI和碰撞诱导解离（CID）行为，以确定结构与CID片段化之间的相关性。需要澄清这些相关性，以阐明未知类固醇和新代谢产物的结构。
• Verfahren zur Herstellung von 11-alpha-Hydroxy-20-alpha-hydroxymethyl-1,4-pregnadien-3-on
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0028309A1

  公开（公告）日：1981-05-13

  11α-Hydroxy-3-oxo-Δ1,4-steroide der Androstan- oder Pregnanreihe werden hergestellt, indem man die entsprechenden in der 11-Position unsubstituierten 3-Oxo-Δ1,4 -steroide der Androstan- oder Pregnanreihe mit einer lebenden Kultur von Aspergillusocchraceus fermentiert.

  11α-羟基-3-酮基-Δ1,4-甾体（属于胆甾烷或孕甾烷系列）的合成方法为：将对应的、在11位不带取代基的3-酮基-Δ1,4-甾体（属于胆甾烷或孕甾烷系列），与活体的青霉菌属 ochraceus 菌株共同进行发酵。
• 11alpha-hydroxylation of steroids by sporotrichum
  申请人：UPJOHN CO

  公开号：US02877162A1

  公开（公告）日：1959-03-10
• Biotransformation of dianabol with the filamentous fungi and β-glucuronidase inhibitory activity of resulting metabolites
  作者：Naik T. Khan、Salman Zafar、Shagufta Noreen、Abdullah M. Al Majid、Zeid A. Al Othman、Saud Ibrahim Al-Resayes、Atta-ur-Rahman、M. Iqbal Choudhary

  DOI：10.1016/j.steroids.2014.04.004

  日期：2014.7

  Biotransformation of the anabolic steroid dianabol (1) by suspended-cell cultures of the filamentous fungi Cunninghamella elegans and IVIacrophomina phaseolina was studied. Incubation of 1 with C elegans yielded five hydroxylated metabolites 2-6, while M. phaseolina transformed compound 1 into polar metabolites 7-11. These metabolites were identified as 0,1 713-dihydroxy-1 7ct-methylandrost-1,4dien-3-one (2), 1 5 ct,1 70-dihydroxy-1 7ot-methylandrost-1,4-dien-3-one (3), 1 1 cx,1 7 p-dihydroxy-1 7amethylandrost- 1,4-dien-3-one (4), 613,120,1 7 p-trihydroxy-1 7a-methylandrost-1,4-dien-3 -one (5), 613,1 5 cc,1 70-trihydroxy-1 7ct-methylandrost-1,4-dien-3-one (6), 1713-hydroxy-1 7ct-methylandrost-1,4dien-3,6-dione (7), 713,1 70,-dihydroxy-1 7a-methylandros 1,4-dien-3-one (8), 1513,1 70-dihydroxy-1 7otmethylandrost-1,4-dien-3-one (9), 17 13-hydroxy-17a-methylandrost-1,4-dien-3,1 1 -dione (10), and 1 113,17p-dihydroxy-17a-methylandrost-1,4-dien-3-one (11). Metabolite 3 was also transformed chemically into diketone 12 and oximes 13, and 14. Compounds 6 and 12-14 were identified as new derivatives of dianabol (I). The structures of all transformed products were deduced on the basis of spectral analyses. Compounds 1-14 were evaluated for p-glucuronidase enzyme inhibitory activity. Compounds 7, 13, and 14 showed a strong inhibition of p-glucuronidase enzyme, with IC50 values between 49.0 and 84.9 [1.M. 0 2014 Elsevier Inc. All rights reserved.
• DE1048579
  申请人：——

  公开号：——

  公开（公告）日：——