(8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 22204-44-0

• 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: (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
• 英文别名: 11β,17β-dhydroxy-17α-methylandrost-1,4-dien-3-one；11β,17β-dihydroxy-17α-methyl-androsta-1,4-dien-3-one；11β,17β-Dihydroxy-17α-methyl-androsta-1,4-dien-3-on；11β,17β-Dihydroxy-17α-methyl-1,4-androstadien-3-on；11beta,17beta-Dihydroxy-17alpha-methylandrosta-1,4-dien-3-one；(8S,9S,10R,11S,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: 22204-44-0
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: JYSKGJQTRZNVIX-OWLVHUDESA-N

物化性质

• 熔点：
  262-265 °C(Solv: acetone (67-64-1))
• 沸点：
  478.4±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

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：

  (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-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：

  (8S,9S,10R,11S,13S,14S,17S)-11,17-二羟基-10,13,17-三甲基-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊并[a]菲-3-酮 生成 (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  11beta-hydroxy-17alpha-methyl-1-dehydrotes-tosterone, and the 11beta, 17beta-diacylates thereof

  摘要：

  公开号：

  US02864832A1

文献信息

• HYDROXYSTEROID COMPOUNDS, THEIR INTERMEDIATES, PROCESS OF PREPARATION, COMPOSITION AND USES THEREOF
  申请人：Sphaera Pharma Pvt. Ltd.

  公开号：EP3795578A2

  公开（公告）日：2021-03-24

  The present invention relates to novel steroidal compounds of formula (I), process for preparation of the same and composition comprising these compounds.

  本发明涉及新型的式 (I) 类固醇化合物、制备方法和包含这些化合物的组合物。
• Hydroxysteroid compounds, their intermediates, process of preparation, composition and uses thereof
  申请人：Epirium Bio Inc.

  公开号：US10618933B2

  公开（公告）日：2020-04-14

  The present invention relates to novel steroidal compounds of formula (I), process for preparation of the same and composition comprising these compounds.

  本发明涉及新型的式 (I) 类固醇化合物、制备方法和包含这些化合物的组合物。
• 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.
• 11.BETA.-HYDROXYSTEROID-4-AZA-COMPOUNDS, COMPOSITIONS AND USES THEREOF
  申请人：Sphaera Pharma Pvt. Ltd.

  公开号：EP3171855B1

  公开（公告）日：2020-08-26
• A Phosphorylation of Steroids and a Dienone-Phenol Rearrangement leading to a Secosteroidal Aldehyde Which has a Strong Toxicity
  作者：TAKUICHI MIKI、KENTARO HIRAGA、HIROTOMO MASUYA、TSUNEHIKO ASAKO、SHOICHIRO FUJII、KIYOHISA KAWAI、KENZO KIKUCHI、SHIGERU SHINTANI、MINORU YAMAZAKI

  DOI：10.1248/cpb.22.1439

  日期：——

  By the use of pyrophosphoryl chloride, 21-hydroxy-20-oxosteroids were phosphorylated in one step in quantitative yield. When the reaction was carried out on prednisolone at a higher temperature, a dienonephenol rearrangement and a simultaneous pinacolic shift took place resulting in the formation of 3, 21-diphosphate of C-nor-9, 10-secosteroidal aldehyde (A) as a by-product. This compound showed a cardioinhibitory and vasoconstricting activity and a strong toxicity to rabbits.

  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。