3β-hydroxy-20-oxo-5α-pregnan-21-yl acetate | 96611-83-5

• 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-20-oxo-5α-pregnan-21-yl acetate
• 英文别名: 21-acetoxy-3α-hydroxy-5α-pregnan-20-one；[2-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 96611-83-5
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: LNQFXEKUXJUUMN-PGFPPNSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-20-oxo-5α-pregnan-21-yl acetate 在 吡啶 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 42.0h， 生成 3α-hydroxy-20-oxo-5α-pregnan-21-yl hemisuccinate
  参考文献：
  名称：

  Suppressing aggressive behavior with analogs of allopregnanolone (epalon)

  摘要：

  3 alpha -Hydroxy-20-oxo-5 alpha -pregnan-21-yl hemisuccinate (8) was produced by partial acylation of 3 alpha ,21-dihydroxy-5 alpha -pregnan-20-one (14). 3 alpha -Fluoro-5 alpha -pregnan-20-one (9) was prepared by treatment of 3 beta -hydroxy-5 alpha -pregnan-20-one (11) with DAST and by solvolysis of tosylate 12 with tetrabutylammonium fluoride. A behavioral test on mice was performed using 3 alpha -hydroxy-5 alpha -pregnan-20-one (1) and compounds 8 and 9. Compound 8 was found to be inactive, while the fluoro derivative 9 selectively reduced aggressive behavior in mice more than the corresponding 3 alpha -hydroxy compound 1; locomotion and other behavioral features were not affected. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00215-4
• 作为产物：
  描述：

  3α-toluene-p-sulphonyloxy-5α-pregnan-20-one 在 三氟化硼乙醚 、 sodium nitrite 作用下， 以 六甲基磷酰三胺 、 苯 为溶剂， 反应 5.0h， 生成 3β-hydroxy-20-oxo-5α-pregnan-21-yl acetate
  参考文献：
  名称：

  Suppressing aggressive behavior with analogs of allopregnanolone (epalon)

  摘要：

  3 alpha -Hydroxy-20-oxo-5 alpha -pregnan-21-yl hemisuccinate (8) was produced by partial acylation of 3 alpha ,21-dihydroxy-5 alpha -pregnan-20-one (14). 3 alpha -Fluoro-5 alpha -pregnan-20-one (9) was prepared by treatment of 3 beta -hydroxy-5 alpha -pregnan-20-one (11) with DAST and by solvolysis of tosylate 12 with tetrabutylammonium fluoride. A behavioral test on mice was performed using 3 alpha -hydroxy-5 alpha -pregnan-20-one (1) and compounds 8 and 9. Compound 8 was found to be inactive, while the fluoro derivative 9 selectively reduced aggressive behavior in mice more than the corresponding 3 alpha -hydroxy compound 1; locomotion and other behavioral features were not affected. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00215-4

文献信息

• Synthesis, metabolism, and pharmacological activity of 3.alpha.-hydroxy steroids which potentiate GABA-receptor-mediated chloride ion uptake in rat cerebral cortical synaptoneurosomes
  作者：Robert H. Purdy、A. Leslie Morrow、James R. Blinn、Steven M. Paul

  DOI：10.1021/jm00168a008

  日期：1990.6

  Certain 3 alpha-hydroxy steroids have recently been shown to bind to the gamma-aminobutyric acid (GABA) receptor gated chloride ion channel with high affinity and to potentiate the inhibitory effects of GABA when measured both in vitro and in vivo. In the present study, a series of natural and synthetic 3 alpha-hydroxy steroids were tested for their ability to potentiate GABA-receptor-mediated chloride

  最近已显示某些3α-羟基类固醇以高亲和力与γ-氨基丁酸（GABA）受体门控的氯离子通道结合，并在体外和体内测量时均能增强GABA的抑制作用。在本研究中，测试了一系列天然和合成的3α-羟基类固醇增强GABA受体介导的氯离子（Cl-）摄入大脑皮层突触神经小体的能力。天然代谢产物3α-羟基-5α-pregnan-20-one（allopregnanolone）和3 alpha，21-dihydroxy-5α-pregnan-20-one（allotetrahydroDOC）被发现在增加GABAA-中最活跃。受体介导的Cl摄取。具有5β-孕烷构型的相应异构体的药理活性降低，部分但不是全部降低，侧链的修饰。这些类固醇增强muscimol刺激的Cl吸收的能力由于在C3处乙酰化，在C9（11）处引入不饱和度，转化为3β-羟基异构体或在C17处构型转化而丧失。据报道，一种简便的方法可以合成未标记和tri标
• ANDROSTANE AND PREGNANE SERIES FOR ALLOSTERIC MODULATION OF GABA RECEPTOR
  申请人：COCENSYS, INC.

  公开号：EP0808325B1

  公开（公告）日：2001-01-17
• METHODS AND COMPOSITIONS FOR INDUCING SLEEP
  申请人：Purdue Pharma Ltd.

  公开号：EP0701444B1

  公开（公告）日：2010-04-07
• [EN] USE OF GABA AND NMDA RECEPTOR LIGANDS FOR THE TREATMENT OF MIGRAINE HEADACHE<br/>[FR] UTILISATION DE LIGANDS DE RECEPTEURS GABA ET NMDA POUR LE TRAITEMENT DES CEPHALEES DE LA MIGRAINE
  申请人：COCENSYS, INC.

  公开号：WO1998005337A1

  公开（公告）日：1998-02-12

  (EN) Methods of treating or preventing migraine headache are disclosed by administering to an animal a GABA receptor agonist and/or an NMDA receptor antagonist. Also disclosed are pharmaceutical compositions and kits for the treatment or prevention of migraine headache.(FR) Procédés de traitement ou de prévention des céphalées de la migraine, qui consistent à administrer à un animal un agoniste de récepteur GABA et un antagoniste de récepteur NMDA. Des compositions pharmaceutiques et des kits de traitement ou de prévention des céphalées de la migraine sont également décrits.
• Suppressing aggressive behavior with analogs of allopregnanolone (epalon)
  作者：Barbora Slavı́ková、Alexander Kasal、Leona Uhlı́řová、Miloslav Kršiak、Hana Chodounská、Ladislav Kohout

  DOI：10.1016/s0039-128x(00)00215-4

  日期：2001.1

  3 alpha -Hydroxy-20-oxo-5 alpha -pregnan-21-yl hemisuccinate (8) was produced by partial acylation of 3 alpha ,21-dihydroxy-5 alpha -pregnan-20-one (14). 3 alpha -Fluoro-5 alpha -pregnan-20-one (9) was prepared by treatment of 3 beta -hydroxy-5 alpha -pregnan-20-one (11) with DAST and by solvolysis of tosylate 12 with tetrabutylammonium fluoride. A behavioral test on mice was performed using 3 alpha -hydroxy-5 alpha -pregnan-20-one (1) and compounds 8 and 9. Compound 8 was found to be inactive, while the fluoro derivative 9 selectively reduced aggressive behavior in mice more than the corresponding 3 alpha -hydroxy compound 1; locomotion and other behavioral features were not affected. (C) 2001 Elsevier Science Inc. All rights reserved.