3α-hydroxy-5α-pregn-16-en-11,20-dione | 32226-03-2

• 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-hydroxy-5α-pregn-16-en-11,20-dione
• 英文别名: Δ¹⁶-alphaxalone；alphaxalone-16-ene；3α-hydroxy-5α-pregn-16-ene-11,20-dione；delta16-Alphaxalone；(3R,5S,8S,9S,10S,13S,14S)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15-dodecahydrocyclopenta[a]phenanthren-11-one
• CAS: 32226-03-2
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: BAIJWZQSAKPKNT-CQMXKPHISA-N

物化性质

• 沸点：
  483.2±45.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-5α-pregn-16-en-11,20-dione 在 重水 、 sodium methylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以95%的产率得到
  参考文献：
  名称：

  Anesthetic steroid mobility in model membrane preparations examined by high-resolution proton and deuterium NMR spectroscopy

  摘要：

  A series of structurally related pregnane analogues which exhibit a wide range of anesthetic potencies were incorporated into unilamellar egg lecithin vesicles and their relative mobilities examined with H-1 and H-2 high-resolution NMR spectroscopy. The data from this study reveal a trend suggesting a relationship between the motional properties of a steroid and its anesthetic potency. The data are congruent with the idea that anesthetic activity is associated with perturbation of the membrane bilayer by the steroid molecule; the degree to which the membrane is perturbed is apparently dependent upon the specific structural and stereochemical features of the steroid. This study supports the hypothesis that lipid bilayers are capable of a high degree of structural discrimination.

  DOI：

  10.1021/jm00109a024
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 以24 mg的产率得到3α-hydroxy-5α-pregn-16-en-11,20-dione
  参考文献：
  名称：

  Neurosteroid analogues. 15. A comparative study of the anesthetic and GABAergic actions of alphaxalone, Δ16-alphaxalone and their corresponding 17-carbonitrile analogues

  摘要：

  Alphaxalone, a neuroactive steroid containing a 17 beta-acetyl group, has potent anesthetic activity in humans. This pharmacological activity is attributed to this steroid's enhancement of gamma-amino butyric acid-mediated chloride currents at gamma-amino butyric acid type A receptors. The conversion of alphaxalone into Delta(16)-alphaxalone produces an analogue that lacks anesthetic activity in humans and that has greatly diminished receptor actions. By contrast, the corresponding 17 beta-carbonitrile analogue of alphaxalone and the Delta(16)-17-carbonitrile analogue both have potent anesthetic and receptor actions. The differential effect of the Delta(16)-double bond on the actions of alphaxalone and the 17 beta-carbonitrile analogue is accounted for by a differential effect on the orientation of the 17-acetyl and 17-carbonitrile substituents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.008

文献信息

• Anaesthetic composition containing a steroid of the 5.alpha.-pregnane
  申请人：Glaxo Laboratories Limited

  公开号：US03952031A1

  公开（公告）日：1976-04-20

  This invention relates to steroids of the pregnane and 19-norpregnane series having anaesthetic properties and compositions containing them. More particularly the present invention relates to such steroids having a variety of substituents in the 2.beta.-position, a 3.alpha.-hydroxy group and a 5.alpha.-hydrogen atom and esters and 20-ketals thereof. At the 11-position of such steroids is preferably either two hydrogen atoms or an oxo group. The compounds according to the invention may conveniently be prepared by reaction of an appropriate 2.alpha.,3.alpha.-epoxy-pregnane or 19-norpregnane with a reagent which introduces the desired 2.beta.-substituent and various modifications of the compound produced are described to produce compounds within the scope of the invention. The present invention provides compositions containing certain steroids of the pregnane and 19-norpregnane series and such compositions generally may be administered intravenously to induce anaesthesia, the invention providing methods of inducing anaesthesia.

  这项发明涉及具有麻醉特性的孕烷和19-去甲孕烷系列类固醇以及含有它们的组合物。更具体地，本发明涉及具有2.beta.-位上各种取代基、3.alpha.-羟基和5.alpha.-氢原子以及其酯和20-酮缩醛的类固醇。在这种类固醇的11位上最好是两个氢原子或一个酮基团。根据本发明的化合物可以通过将适当的2.alpha.,3.alpha.-环氧孕烷或19-去甲孕烷与引入所需的2.beta.-取代基的试剂反应来方便地制备，并描述了所产生化合物的各种修饰以制备属于本发明范围内的化合物。本发明提供了含有孕烷和19-去甲孕烷系列某些类固醇的组合物，这些组合物通常可通过静脉注射来诱导麻醉，本发明提供了诱导麻醉的方法。
• Chemical compounds
  申请人：——

  公开号：US03943124A1

  公开（公告）日：1976-03-09

  Steroids of the androstane series having a 3.alpha.-hydroxy group, a 3.beta.-hydrogen or methyl group; a 10-hydrogen atom or methyl group, an 11-oxo group or two hydrogen atoms at the 11-position, a 17.alpha.-hydrogen atom, and a group at the 17.beta.-position which is esterified carboxyl group, an N-mono or di-substituted carbamoyl group, a cyano group, a formyl group or an acetalised formyl group; and the 3.alpha.-esters thereof. The steroids possess anaesthetic properties.

  雄烯烷系列类固醇具有3.alpha.-羟基、3.beta.-氢或甲基基团；10-氢原子或甲基基团，11-位置处的11-酮基团或两个氢原子，17.alpha.-氢原子，以及17.beta.-位置上的羧酰化羧基团，N-单或双取代的氨基甲酰基团，氰基团，甲酰基团或乙缩甲酰基团；以及其3.alpha.-酯。这些类固醇具有麻醉性能。
• NEUROACTIVE 13, 17-SUBSTITUTED STEROIDS AS MODULATORS FOR GABA TYPE-A RECEPTORS
  申请人：WASHINGTON UNIVERSITY

  公开号：US20140249120A1

  公开（公告）日：2014-09-04

  The present disclosure is generally directed to neuroactive 13,17-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13,17-取代类固醇，以及其药用盐，例如作为麻醉剂使用，和/或用于治疗与GABA功能和活性相关的疾病。本公开还涉及包含这些化合物的药物组合物。
• NEUROACTIVE 17(20)-Z-VINYLCYANO-SUBSTITUTED STEROIDS, PRODRUGS THEREOF, AND METHODS OF TREATMENT USING SAME
  申请人：Covey Douglas

  公开号：US20140309443A1

  公开（公告）日：2014-10-16

  The present disclosure is generally directed to neuroactive 17(20)-Z-vinylcyano-substituted compound of Formula (I) and (II), 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.

  本公开涉及一般指向化合物的神经活性17(20)-Z-乙烯基氰基取代物，其化学式为(I)和(II)，并且其药学上可接受的盐，例如用作麻醉剂，和/或用于治疗与GABA功能和活性相关的疾病。本公开还涉及包含这种化合物的药物组合物。
• Anaesthetic steroids of the androstance and pregnane series
  申请人：Glaxo Laboratories Limited

  公开号：US03953429A1

  公开（公告）日：1976-04-27

  Steroids of the androstane and pregnane series possessing a 2.alpha.-hydrogen or halogen or an alkyl group; a 3.alpha.-hydroxy or acyloxy group, a 3.beta.-hydrogen or alkyl group; an 11.beta.-hydrogen or hydroxy group or an epoxy group linked also to the 9-position; an 11.alpha.-hydrogen or alkyl or allyl group; or an 11-oxo group; a 16 hydrogen or halogen or a methyl or dimethyl group; a 20-oxo or ethylenedioxy group; and a 20-methyl or alkoxy group. The compounds may be unsaturated at the 1(2), 8(9) or 9(11) positions. The compounds possess anaesthetic properties.

  具有2.alpha.-氢或卤素或烷基；3.alpha.-羟基或酰氧基，3.beta.-氢或烷基；11.beta.-氢或羟基或环氧基，也与9位点连接；11.alpha.-氢或烷基或烯丙基；或11-酮基；16氢或卤素或甲基或二甲基基团；20-酮基或乙二氧基基团；和20-甲基或烷氧基团的雄甾烷和孕甾烷系列类固醇。这些化合物在1(2)、8(9)或9(11)位点可能不饱和。这些化合物具有麻醉特性。