5-Beta-雄甾-3-beta-醇 | 15360-52-8

• 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
• 中文名称: 5-Beta-雄甾-3-beta-醇
• 英文名称: 5β-androstan-3β-ol
• 英文别名: (5β)-androstan-3β-ol；(10S)-3c-Hydroxy-10r.13c-dimethyl-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β-Hydroxy-10.13-dimethyl-5β-gonan；5β-Androstanol-(3β)；3β-Hydroxy-5β-androstan；etiocholan-3β-ol；5beta-Androstan-3beta-ol；(3S,5R,8S,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 15360-52-8
• 化学式: C₁₉H₃₂O
• 分子量: 276.462
• InChiKey: DJTOLSNIKJIDFF-KYQPOWKGSA-N

物化性质

• 沸点：
  375.9±10.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Beta-雄甾-3-beta-醇 在 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 生成 3α-amino-5β-androstane hydrochloride
  参考文献：
  名称：

  Physicochemical and biological properties of novel amide-based steroidal inhibitors of NMDA receptors

  摘要：

  Herein, we report a new class of amide-based inhibitors (1-4) of N-methyl-o-aspartate receptors (NMDARs) that were prepared as analogues of pregnanolone sulfate (PAS) and pregnanolone glutamate (PAG) - the steroidal neuroprotective NMDAR inhibitors. A series of experiments were conducted to evaluate their physicochemical and biological properties: (i) the inhibitory effect of compounds 3 and 4 on NMDARs was significantly improved (IC50 = 1.0 and 1.4 mu M respectively) as compared with endogenous ihhibitor - pregnanolone sulfate (IC50 = 24.6 mu M) and pregnanolone glutamate (IC50 = 51.7 mu M); (ii) physicochemical properties (logP and logD) were calculated; (iii) Caco-2 assay revealed that the permeability properties of compounds 2 and 4 are comparable with pregnanolone glutamate; (iv) compounds 1-4 have minimal or no adverse hepatic effect; (v) compounds 1-4 cross blood-brain-barrier. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.08.010
• 作为产物：
  描述：

  17α-benzoyloxy-5β-androstanone-(3) 在 乙醇 、 aluminum isopropoxide 、 异丙醇 、 铂 作用下， 生成 5-Beta-雄甾-3-beta-醇
  参考文献：
  名称：

  类固醇和性激素。（第113部分）。类固醇的组成与气味关系的研究

  摘要：

  DOI：

  10.1002/hlca.660280185

文献信息

• Amphiphilic compounds with neuroprotective properties
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, v.v.i.

  公开号：US10017535B2

  公开（公告）日：2018-07-10

  Amphiphilic compounds with tetradecahydrophenanthrene skeleton and their enantiomers, exhibiting neuroprotective effects, their use in methods of treatment of neuropsychiatric disorders associated with an imbalance in glutamatergic neurotransmitter system, such as ischemic damage of CNS, neurodegenerative changes and disorders of CNS, affective disorders, depression, post-traumatic stress disorder and diseases related to stress, anxiety, schizophrenia and psychotic disorders, pain, addiction, multiple sclerosis, epilepsy, glioma, and a pharmaceutical composition containing compound.

  具有十四氢菲骨架的两性化合物及其对映体，具有神经保护作用，可用于治疗与谷氨酸能神经递质系统失衡有关的神经精神疾病，如中枢神经系统缺血性损伤、神经退行性变化和中枢神经系统紊乱、情感障碍、抑郁症、创伤后应激障碍和与应激有关的疾病、焦虑症、精神分裂症和精神病、疼痛、成瘾、多发性硬化症、癫痫、胶质瘤，以及含有化合物的药物组合物。
• A New Formylation Reagent:<i>N,N</i>-Diformylacetamide
  作者：J. C. Gramain、R. Rémuson

  DOI：10.1055/s-1982-29771

  日期：——
• LIPOSOME FORMULATIONS OF 5BETA STEROIDS
  申请人：SUPERGEN, INC.

  公开号：EP0801557B1

  公开（公告）日：2003-07-02
• AMPHIPHILIC COMPOUNDS WITH NEUROPROTECTIVE PROPERTIES
  申请人：Ustav Organicke Chemie a Biochemie AV CR, v.v.i.

  公开号：EP3186267B1

  公开（公告）日：2019-10-02