3α-azido-5α-pregnan-2-one | 440368-41-2

• 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-azido-5α-pregnan-2-one
• 英文别名: 3alpha-Azido-5alpha-pregnan-20-one；1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-azido-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 440368-41-2
• 化学式: C₂₁H₃₃N₃O
• 分子量: 343.513
• InChiKey: HBKDHWKTLARXMJ-SYBPFIFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-azido-5α-pregnan-2-one 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以30%的产率得到丝胶树碱
  参考文献：
  名称：

  Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity

  摘要：

  3α-羟基功能被认为是神经类固醇在GABA_A受体上的生物活性所必需的。研究发现，3α-氨基-5α-孕酮-20-酮（3）增加了在大脑皮层神经元原代培养中GABA_A受体上[³H]flunitrazepam的结合。这种衍生物在相关的神经活性浓度下没有显示细胞毒性，其结构使我们能够进一步了解可能在3α位置进行的功能基团修饰。为寻找最适合的合成方法，研究了各种合成方法。

  DOI：

  10.1135/cccc20041506
• 作为产物：
  描述：

  3β-O-(methanesulfonyl)-5α-pregnan-20-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以47%的产率得到3α-azido-5α-pregnan-2-one
  参考文献：
  名称：

  Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity

  摘要：

  3α-羟基功能被认为是神经类固醇在GABA_A受体上的生物活性所必需的。研究发现，3α-氨基-5α-孕酮-20-酮（3）增加了在大脑皮层神经元原代培养中GABA_A受体上[³H]flunitrazepam的结合。这种衍生物在相关的神经活性浓度下没有显示细胞毒性，其结构使我们能够进一步了解可能在3α位置进行的功能基团修饰。为寻找最适合的合成方法，研究了各种合成方法。

  DOI：

  10.1135/cccc20041506

文献信息

• Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity
  作者：Libor Matyáš、Alexander Kasal、Zoila Babot Riera、Cristina E. Sunol

  DOI：10.1135/cccc20041506

  日期：——

  The 3α-hydroxy function has been considered essential for the biological activity of neurosteroids at the GABA_A receptor. It was found that 3α-amino-5α-pregnan-20-one (3) increased the binding of [³H]flunitrazepam at the GABA_A receptor in the primary culture of cortical neurons. This derivative did not display cytotoxicity at relevant neuroactive concentrations, and its structure enabled us to gain further insight into possible functional group modifications in position 3α. Various synthetic methods were investigated in search for the most suitable synthetic approach.

  3α-羟基功能被认为是神经类固醇在GABA_A受体上的生物活性所必需的。研究发现，3α-氨基-5α-孕酮-20-酮（3）增加了在大脑皮层神经元原代培养中GABA_A受体上[³H]flunitrazepam的结合。这种衍生物在相关的神经活性浓度下没有显示细胞毒性，其结构使我们能够进一步了解可能在3α位置进行的功能基团修饰。为寻找最适合的合成方法，研究了各种合成方法。
• GABA a modulating neurosteroids
  申请人：Calogeropoulou Theodora

  公开号：US20050176976A1

  公开（公告）日：2005-08-11

  The present invention relates to novel steroid derivatives that ace on the gamma-aminobutyric acid receptor-chloride ionophore (GR) complex as well as methods for making the same and their applications to induce anesthesia, in the treatment of stress, anxiety, PMS, PND, and seizures such as those caused by epilepsy, to ameliorate or prevent the attacks of anxiety, muscle tension, and depression common with patients suffering from central nervous system abnormalities. The present invention comprises a compound represented by Formula (I): wherein, R, R 1 , R 2 , R 3 , R 4 , R 5 are defined in the description of the invention. The present invention also includes formulations which consist of one or more of the compounds of Formula (I).

  本发明涉及新型类固醇衍生物，其作用于γ-氨基丁酸受体-氯离子载体（GR）复合物，以及制备它们的方法和在诱导麻醉、治疗压力、焦虑、月经前综合征（PMS）、产后抑郁症（PND）以及癫痫引起的惊厥等方面的应用，以改善或预防中枢神经系统异常患者普遍出现的焦虑、肌肉紧张和抑郁症状。本发明包括由式（I）表示的化合物：其中，R、R1、R2、R3、R4、R5在本发明的描述中有定义。本发明还包括由式（I）中的一个或多个化合物组成的制剂。
• GABAA modulating neurosteroids
  申请人：——

  公开号：US07064116B2

  公开（公告）日：2006-06-20

  The present invention relates to novel steroid derivatives that ace on the gamma-aminobutyric acid receptor-chloride ionophore (GR) complex as well as methods for making the same and their applications to induce anesthesia, in the treatment of stress, anxiety, PMS, PND, and seizures such as those caused by epilepsy, to ameliorate or prevent the attacks of anxiety, muscle tension, and depression common with patients suffering from central nervous system abnormalities. The present invention comprises a compound represented by Formula (I): wherein, R, R1, R2, R3, R4, R5 are defined in the description of the invention. The present invention also includes formulations which consist of one or more of the compounds of Formula (I).

  本发明涉及新型类固醇衍生物，其作用于γ- 氨基丁酸受体-氯离子载体（GR）复合物，以及制备该类固醇衍生物的方法及其在诱导麻醉、治疗压力、焦虑、经前综合征（PMS）、产后抑郁症（PND）以及癫痫引起的癫痫发作等方面的应用，以缓解或预防患有中枢神经系统异常的患者常见的焦虑、肌肉紧张和抑郁症状。本发明包括由式（I）表示的化合物，其中，R、R1、R2、R3、R4、R5在发明说明书中有定义。本发明还包括由式（I）中的一种或多种化合物组成的制剂。
• US7064116B2
  申请人：——

  公开号：US7064116B2

  公开（公告）日：2006-06-20
• [EN] GABAA MODULATING NEUROSTEROIDS<br/>[FR] NEUROSTEROIDES MODULANT GABAA
  申请人：ELPEN S A

  公开号：WO2002053577A2

  公开（公告）日：2002-07-11

  The present invention relates to novel steroid derivatives that ace on the gamma-aminobutyric acid receptor-chloride ionophore (GR) complex as well as methods for making the same and their applications to induce anesthesia, in the treatment of stress, anxiety, PMS, PND, and seizures such as those caused by epilepsy, to ameliorate or prevent the attacks of anxiety, muscle tension, and depression common with patients suffering from central nervous system abnormalities. The present invention comprises a compound represented by Formula (I): wherein, R, R1, R2, R3, R4, R5 are defined in the description of the invention. The present invention also includes formulations which consist of one or more of the compounds of Formula (I).