3α-toluene-p-sulphonyloxy-5α-pregnan-20-one

• 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: 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one
• 英文别名: 3alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one；[(3R,5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 4-methylbenzenesulfonate
• 化学式: C₂₈H₄₀O₄S
• 分子量: 472.689
• InChiKey: HMQZDUPWUUCPPF-BNOLYSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α-toluene-p-sulphonyloxy-5α-pregnan-20-one 在 吡啶 、 盐酸 、 三氟化硼乙醚 、 sodium nitrite 作用下， 以 甲醇 、 六甲基磷酰三胺 、 水 、 苯 为溶剂， 反应 47.0h， 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：

  5alpha-孕甾-3alpha-醇-20-酮 、 对甲苯磺酰氯 、 盐酸 在 氯仿 、 盐酸 、 水 、 magnesium sulfate 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以gave 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one as a white solid的产率得到3α-toluene-p-sulphonyloxy-5α-pregnan-20-one
  参考文献：
  名称：

  Methods, compositions, and compounds for allosteric modulation of the

  摘要：

  使用某些类固醇衍生物在伽马-氨基丁酸受体-氯离子复合物的新发现位点上起作用，来调节大脑兴奋性以缓解压力、焦虑、失眠和癫痫活动的方法、组合物和化合物。

  公开号：

  US05232917A1

文献信息

• GABA RECEPTOR MODULATORS
  申请人：Euro-Celtique S.A.

  公开号：EP0554436B1

  公开（公告）日：2000-07-05
• US5232917A
  申请人：——

  公开号：US5232917A

  公开（公告）日：1993-08-03
• US5591733A
  申请人：——

  公开号：US5591733A

  公开（公告）日：1997-01-07
• Methods, compositions, and compounds for allosteric modulation of the
  申请人：University of Southern California

  公开号：US05232917A1

  公开（公告）日：1993-08-03

  Method, compositions, and compounds for modulating brain excitability to alleviate stress, anxiety, insomnia and seizure activity using certain steroid derivatives that act at a newly identified site on the gamma-aminobutyric acid receptor-chloride ionophore (GR) complex.

  使用某些类固醇衍生物在伽马氨基丁酸受体-氯离子载体（GR）复合物上的新识别位点，调节大脑兴奋性以缓解压力、焦虑、失眠和癫痫活动的方法、组合物和化合物。
• 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.