19-norepiandrosterone | 10002-93-4

• 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: 19-norepiandrosterone
• 英文别名: 3β-Hydroxyestran-17-one；19-nor-5α-androstan-3β-ol-17-one；(3β,5α)-3-hydroxyestran-17-one；(3β,5α)-hydroxyestran-17-one；3β-hydroxy-19-nor-5α-androstane-17-one；19-nor-5α-Androstan-3β-ol-17-on；3β-Hydroxy-5α-estran-17-one；(3S,5S,8R,9R,10S,13S,14S)-3-hydroxy-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 10002-93-4
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: UOUIARGWRPHDBX-LRMMUPRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  19-norepiandrosterone 在 lithium carbonate 、 对甲苯磺酸 、 lithium bromide 、 copper(ll) bromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 25.0 ℃ 、344.75 kPa 条件下， 反应 40.0h， 生成 (3S,5S,8R,9R,10S,13S,14R)-13-methylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-ol
  参考文献：
  名称：

  Neurosteroid analogues. Part 13: Synthetic methods for the preparation of 2β-hydroxygonane derivatives as structural mimics of ent-3α-hydroxysteroid modulators of GABAA receptors

  摘要：

  Many different 3 alpha-hydroxysteroids in the androstane and pregnane steroid series enhance the actions of gamma-aminobutyric acid (GABA) at GABA type-A (GABA(A)) receptors in the mammalian central nervous system. Recent studies have shown that (3 alpha,5 alpha)-3-hydroxy-androstan-17- one (androsterone) is less active at these receptors than its enantiomer ent-androsterone. Further structure-activity relationship (SAR) studies are needed to explore the structural features of ent-androsterone that are important for its enhanced action at these receptors. Molecular modeling shows that 2 beta-hydroxysteroids are similar in three-dimensional shape to the enantiomers of 3 alpha-hydroxysteroids. The development of synthetic methods to gain access to C-17-substituted analogues of 2 beta-hydroxygonanes for SAR studies is demonstrated with the synthesis of (2 beta,5 alpha,14 beta)-2-hydroxygonan-17-one. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.068
• 作为产物：
  描述：

  诺龙 在 lithium 、 lithium tri-t-butoxyaluminum hydride 、 叔丁醇 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 3.0h， 生成 19-norepiandrosterone
  参考文献：
  名称：

  Neurosteroid analogues. Part 13: Synthetic methods for the preparation of 2β-hydroxygonane derivatives as structural mimics of ent-3α-hydroxysteroid modulators of GABAA receptors

  摘要：

  Many different 3 alpha-hydroxysteroids in the androstane and pregnane steroid series enhance the actions of gamma-aminobutyric acid (GABA) at GABA type-A (GABA(A)) receptors in the mammalian central nervous system. Recent studies have shown that (3 alpha,5 alpha)-3-hydroxy-androstan-17- one (androsterone) is less active at these receptors than its enantiomer ent-androsterone. Further structure-activity relationship (SAR) studies are needed to explore the structural features of ent-androsterone that are important for its enhanced action at these receptors. Molecular modeling shows that 2 beta-hydroxysteroids are similar in three-dimensional shape to the enantiomers of 3 alpha-hydroxysteroids. The development of synthetic methods to gain access to C-17-substituted analogues of 2 beta-hydroxygonanes for SAR studies is demonstrated with the synthesis of (2 beta,5 alpha,14 beta)-2-hydroxygonan-17-one. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.068

文献信息

• [EN] C17, C20, AND C21 SUBSTITUTED NEUROACTIVE STEROIDS AND THEIR METHODS OF USE<br/>[FR] STÉROÏDES NEUROACTIFS SUBSTITUÉS EN C17, C20 ET C21 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018013613A1

  公开（公告）日：2018-01-18

  Described herein are neuroactive steroids or a pharmaceutically acceptable salt thereof. 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.

  本文描述了神经活性类固醇或其药用可接受盐。在某些实施例中，这些化合物被设想为GABA调节剂。还提供了包括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。
• Hydroxysteroid Dehydrogenase-Catalyzed Highly Regio-, Chemo-, and Enantioselective Hydrogenation of 3-Keto in Steroids
  作者：Chunling Zeng、Shitang Xu、Jie Shen、Saijie Zhao、Xinhua Xu、Lifen Peng

  DOI：10.1021/acs.orglett.3c03557

  日期：2024.1.12

  A highly selective hydrogenation of 3-keto in steroids to 3-hydroxyl steroids catalyzed by hydroxysteroid dehydrogenases (HSDHs) was demonstrated. The Ct3α-HSDH-catalyzed hydrogenation generated 3α-hydroxyl steroids as the main enantiopure isomers in high yields, while the Ss3β-HSDH catalytic system afforded 3β-hydroxyl steroids in excellent yields. In both catalytic systems, the hydrogenation proceeded

  证明了在羟基类固醇脱氢酶 (HSDH) 的催化下，类固醇中的 3-酮基可以高度选择性地氢化为 3-羟基类固醇。 Ct3α-HSDH催化的氢化反应以高产率产生了作为主要对映体纯异构体的3α-羟基类固醇，而Ss3β-HSDH催化体系则以优异的产率产生了3β-羟基类固醇。在两种催化体系中，氢化反应在 3-酮基上进行区域选择性，7-、11-、17-和 20-酮基几乎未反应，并且在 C=C 键和酯基未受攻击的情况下进行化学选择性氢化。我们的HSDH促进的氢化反应具有区域选择性、化学选择性和对映选择性高、收率好、条件温和、底物范围广、适合克级合成等优点。值得注意的是，通过我们的氢化方法，可以轻松、高产地获得脱氢表雄酮、布烯醇酮和阿法沙酮等生物活性分子。
• ——
  作者：Andrew R. McKinney、Damon D. Ridley

  DOI：10.1071/ch01158

  日期：——

  Reformatsky reactions involving ethyl bromoacetate/zinc are reported for 19-norandrosterone acetate and 19-norepiandrosterone acetate. In each case the major product was the 17beta-alcohol from alpha-attack, although a significant amount of the 17alpha-alcohol from beta-attack was also isolated. The ethyl 3-acetoxy-17beta-hydroxy-19-nor-5alpha,17alpha-pregnan-21-oates were then hydrolysed to 3,17beta-dihydroxy-19-nor-5alpha,17beta-pregnan-21-oic acids or reduced to 19-nor-5alpha,17alpha-pregnane-3,17beta,21-triols. Comparison of the synthetic products with compounds previously reported as metabolites of norethandrolone in the horse provided valuable information on the regio- and stereo-chemistry of equine steroid metabolism.
• Suginome, Hiroshi; Senboku, Hisanori; Yamada, Shinji, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2199 - 2205
  作者：Suginome, Hiroshi、Senboku, Hisanori、Yamada, Shinji

  DOI：——

  日期：——
• Dmochowska-Gladysz, Jadwiga; Tlomak, Elzbieta; Siewinski, Antoni, Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1980, vol. 28, # 1, p. 1 - 8
  作者：Dmochowska-Gladysz, Jadwiga、Tlomak, Elzbieta、Siewinski, Antoni

  DOI：——

  日期：——