19-methylandrost-4-en-3,17-dione | 6030-28-0

• 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: 19-methylandrost-4-en-3,17-dione
• 英文别名: 10-ethylestr-4-ene-3,17-dione；19-Methyl-androst-4-en-3,17-dion；10beta-Ethyl-estra-4-ene-3,17-dione；(8R,9S,10R,13S,14S)-10-ethyl-13-methyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 6030-28-0
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: YBQJZPUCIDDTLT-TXTPUJOMSA-N

物化性质

• 熔点：
  109-111 °C
• 沸点：
  443.9±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  19-methylandrost-4-en-3,17-dione 生成 10-acetylestr-4-ene-3,17-dione
  参考文献：
  名称：

  Metabolism of 19-methyl substituted steroids and a proposal for the third aromatase monooxygenation

  摘要：

  The article summarizes the results of recent studies on the metabolism of 10-ethylestr-4-ene-3,17-dione, 10-[(1R)-1-hydroxyethyl]-, and 10-[(1S)-1-hydroxyethyl]estr-4-ene-3,17-dione, in placenta. These compounds are the 19-methyl analogs of androstenedione, 19-hydroxyandrostenedione, and 19-oxoandrostenedione, respectively. No conversion of 10-ethylestr-4-ene-3,17-dione to either estrogens or oxygenated metabolites was detected. Both 10-[(1R)-1-hydroxyethyl]- and 10-[(1S)-1-hydroxyethyl]estr-4-ene-3,17-dione were oxygenated to 10-(1,1-dihydroxyethyl)estr-4-ene-3,17-dione and isolated following in situ dehydration as 10-acetylestr-4-ene-3,17-dione. Evidence for the involvement of aromatase in these conversions is discussed. No conversion of 10-acetylestr-4-ene-3,17-dione to either estrogens or other oxygenated products was detected. These results lead us to propose a new mechanism for the third aromatase monooxygenation. We propose that the third oxygenation is initiated by 1 beta-hydrogen abstraction at C1 of 19,19-dihydroxyandrostenedione, followed by homolytic cleavage of the C10-C19 bond with concurrent formation of a delta 1(10),4-3-ketosteroid and a C19 carbon radical, and terminated by oxygen rebound at C19.

  DOI：

  10.1016/0039-128x(87)90025-0
• 作为产物：
  描述：

  3,17-bis(ethylenedioxy)-androst-5-en-19-al 在 palladium on activated charcoal 2-甲基苯磺酸 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 73.0h， 生成 19-methylandrost-4-en-3,17-dione
  参考文献：
  名称：

  Novel silylated steroids as aromatase inhibitors

  摘要：

  Androst-4-en-3-one analogs incorporating a trimethylsilyl or a trimethylsilylmethyl group at C-1, C-2 or C-19 were prepared and evaluated as inhibitors of aromatase. Only 10-[1-hydroxy-2-(trimethylsilyl)ethyl]estr-4-ene-3,17-dione inhibited human placental aromatase. Enzyme kinetic analysis revealed competitive inhibition [apparent dissociation constant (Ki) of 562 +/- 12 nM] associated with marginal time-dependent inhibition.

  DOI：

  10.1016/0039-128x(85)90084-4

文献信息

• Estrogen synthesis inhibitors
  申请人：The Rockefeller University

  公开号：US04546098A1

  公开（公告）日：1985-10-08

  Invention relates to 3-methylene substituted androst-4-ene-17-oxygenated compounds substituted with various substituents at the 10.beta.-position which are useful as inhibitors of estrogen biosynthesis.

  本发明涉及3-亚甲基取代的雄甾-4-烯-17-氧化化合物，其在10-beta-位置上具有各种取代基，可用作雌激素生物合成抑制剂。
• NEUROACTIVE 19-ALKOXY-17-SUBSTITUTED STEROIDS, PRODRUGS THEREOF, AND METHODS OF TREATMENT USING SAME
  申请人：Sage Therapeutics, Inc.

  公开号：US20140235600A1

  公开（公告）日：2014-08-21

  The present disclosure is generally directed to neuroactive 19-alkoxy-17-substituted steroids as referenced herein, and pharmaceutically acceptable salts thereof, for use as, for example, an anesthetic, and/or in the treatment of disorders relating to GABA function and activity. The present disclosure is further directed to pharmaceutical compositions comprising such compounds.

  本公开涉及神经活性的19-烷氧基-17-取代类固醇，以及其药学上可接受的盐，例如用作麻醉剂和/或治疗与GABA功能和活性有关的疾病。本公开还涉及包含这些化合物的制药组合物。
• NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
  申请人：SAGE THERAPEUTICS, INC.

  公开号：US20160229887A1

  公开（公告）日：2016-08-11

  Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein -------, R 1 , R 2 , R 5 , A and L are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

  本文描述了式(I)的神经活性类固醇或其药学上可接受的盐；其中-------，R1，R2，R5，A和L的定义如下。在某些实施方式中，这些化合物被认为是GABA调节剂。本发明还提供了包含本发明化合物的制药组合物以及使用和治疗方法，例如用于诱导镇静和/或麻醉。
• METALLO-OXIDOREDUCTASE INHIBITORS USING METAL BINDING MOIETIES IN COMBINATION WITH TARGETING MOIETIES
  申请人：Viamet Pharmaceuticals, Inc.

  公开号：EP2086546A2

  公开（公告）日：2009-08-12
• US4546098A
  申请人：——

  公开号：US4546098A

  公开（公告）日：1985-10-08