(20S)-3β,21-dihydroxy-17β,20-epoxy-5-androstene | 1094211-40-1

• 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: (20S)-3β,21-dihydroxy-17β,20-epoxy-5-androstene
• 英文别名: (20S)-3β,21-dihydroxy-17β,20-epoxy-5-pregnane；(20S)-3β,21-dihydroxy-17β,20-epoxy-5-pregnene；(3S,3'S,8R,9S,10R,13S,14S,17S)-3'-(hydroxymethyl)-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-oxirane]-3-ol
• CAS: 1094211-40-1
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: FMOHTQBFGJULLE-OCHQKFOUSA-N

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：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3β,17β-dihydroxy-20,21-epoxy-5-androstene 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到(20S)-3β,21-dihydroxy-17β,20-epoxy-5-androstene
  参考文献：
  名称：

  NEUROSTEROID COMPOUNDS

  摘要：

  本发明涉及具有抗凋亡、神经保护和神经生成特性的新型神经类固醇衍生物，其作用于神经系统，以及制备这些衍生物的方法以及它们在治疗和/或预防或改善与神经元凋亡或神经元损伤相关的神经退行性疾病或与凋亡相关或由凋亡导致的疾病，包括但不限于阿尔茨海默病、帕金森病、亨廷顿病、多发性硬化症和肌萎缩侧索硬化症（ALS）、视网膜变性和脱离、由遗传异常引起的周围神经病变、糖尿病、小儿麻痹症、疱疹、艾滋病和化疗、脑外伤、缺血和中风。活性化合物由式（I）表示：其中R1、R2、R3、R4、R5、R6、R7、A、B、X、Y和Z在本发明描述中有定义。本发明还包括包含式（I）中的一个或多个化合物的组合物。

  公开号：

  US20100234335A1

文献信息

• NEUROSTEROID COMPOUNDS
  申请人：Gravanis Achilleas

  公开号：US20100234335A1

  公开（公告）日：2010-09-16

  The present invention relates to novel neurosteroid derivatives with anti-apoptotic, neuroprotective and neurogenic properties that act on the nervous system as well as methods for making the same and their applications in the treatment and/or prevention or amelioration of neurodegenerative diseases related to neuronal apoptosis or neuronal injury, or conditions related to or resulting from apoptosis, including but not limited to Alzheimer's disease, Parkinson's disease, Huntington's disease, multiple sclerosis and amyotrophic lateral sclerosis (ALS), retinal degeneration and detachment, peripheral neuropathy caused by genetic abnormalities, diabetes, polio, herpes, AIDS and chemotherapy, brain trauma, or ischemia and stroke. The active compounds are represented by Formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, B, X, Y and Z are defined in the description of the invention. The present invention also includes compositions which comprise one or more of the compounds of Formula (I).

  本发明涉及具有抗凋亡、神经保护和神经生成特性的新型神经类固醇衍生物，其作用于神经系统，以及制备这些衍生物的方法以及它们在治疗和/或预防或改善与神经元凋亡或神经元损伤相关的神经退行性疾病或与凋亡相关或由凋亡导致的疾病，包括但不限于阿尔茨海默病、帕金森病、亨廷顿病、多发性硬化症和肌萎缩侧索硬化症（ALS）、视网膜变性和脱离、由遗传异常引起的周围神经病变、糖尿病、小儿麻痹症、疱疹、艾滋病和化疗、脑外伤、缺血和中风。活性化合物由式（I）表示：其中R1、R2、R3、R4、R5、R6、R7、A、B、X、Y和Z在本发明描述中有定义。本发明还包括包含式（I）中的一个或多个化合物的组合物。
• USE OF STEROID COMPOUNDS
  申请人：Panoutsakopoulou Vasiliki

  公开号：US20120225852A1

  公开（公告）日：2012-09-06

  This invention pertains to the use of steroid compounds including spirosteroid analogues in treating, preventing or ameliorating the symptoms of inflammatory conditions. The steroid compounds are useful for treating a range of inflammatory conditions, including, but not limited to asthma, lung inflammation, retinal inflammatory conditions, autoimmune diseases such as rheumatoid arthritis, diabetes type I, systemic lupus erythematosus, ulcerative colitis and inflammatory bowel diseases and myopathies, as well as multiple sclerosis. The active compounds are represented by Formula I: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, B, X, Y and Z are defined in the description of the invention.
• US9777037B2
  申请人：——

  公开号：US9777037B2

  公开（公告）日：2017-10-03
• [EN] NEUROSTEROID COMPOUNDS<br/>[FR] COMPOSÉS NEUROSTÉROÏDES
  申请人：BIONATURE E A LTD

  公开号：WO2008155534A2

  公开（公告）日：2008-12-24

  (EN) The present invention relates to novel neurosteroid derivatives with anti-apoptotic, neuroprotective and neurogenic properties that act on the nervous system as well as methods for making the same and their applications in the treatment and/or prevention or amelioration of neurodegenerative diseases related to neuronal apoptosis or neuronal injury, or conditions related to or resulting from apoptosis, including but not limited to Alzheimer's disease, Parkinson's disease, Huntington's disease, multiple sclerosis and amyotrophic lateral sclerosis (ALS), retinal degeneration and detachment, peripheral neuropathy caused by genetic abnormalities, diabetes, polio, herpes, AIDS and chemotherapy, brain trauma, or ischemia and stroke. The active compounds are represented by Formula (I): wherein R1, R2, R3, R4, R5, R6, R7, A, B, X, Y and Z are defined in the description of the invention. The present invention also includes compositions which comprise one or more of the compounds of Formula (I).(FR) La présente invention porte sur de nouveaux dérivés neurostéroïdes, présentant des propriétés anti-apoptotiques, neuroprotectrices et neurogéniques qui agissent sur le système nerveux ainsi que sur des procédés de fabrication de ces dérivés et sur leurs applications dans le traitement et/ou la prévention ou l'amélioration de maladies neuro-dégénératives se rapportant à une apoptose neuronale ou à une lésion neuronale, ou d'états se rapportant à ou résultant d'une apoptose, comprenant mais sans y être limités la maladie d'Alzheimer, la maladie de Parkinson, la maladie de Huntington, la sclérose en plaques et la sclérose latérale amyotrophique (SLA), la dégénérescence rétinienne et le décollement de la rétine, la neuropathie périphérique provoquée par des anomalies génétiques, le diabète, la polio, l'herpès, le SIDA et la chimiothérapie, le traumatisme du cerveau ou l'ischémie et l'attaque. Les composés actifs sont représentés par la Formule (I) : dans laquelle R1, R2, R3, R4, R5, R6, R7, A, B, X, Y et Z sont définis dans la description de l'invention. La présente invention porte également sur des compositions qui comprennent un ou plusieurs des composés de Formule (I).
• Novel Dehydroepiandrosterone Derivatives with Antiapoptotic, Neuroprotective Activity
  作者：Theodora Calogeropoulou、Nicolaos Avlonitis、Vassilios Minas、Xanthippi Alexi、Athanasia Pantzou、Ioannis Charalampopoulos、Maria Zervou、Varvara Vergou、Efrosini S. Katsanou、Iakovos Lazaridis、Michael N. Alexis、Achille Gravanis

  DOI：10.1021/jm900468p

  日期：2009.11.12

  DHEA analogues with modifications at positions C3 or 07 were synthesized and evaluated for neuroprotective activity against the neural-crest-derived PC12 cell model of serum deprivation-induced apoptosis. The most potent compounds were the spiro-epoxy derivatives 17 beta-spiro[5-androstene-17, 2'-oxiran]-3 beta-ol (20), (20S)-3 beta,21-dihydroxy-17 beta,20-epoxy-5-pregnene (23), and (20R)-3 beta,21-dihydroxy-17 alpha,20-epoxy-5-pregnene (27) with IG(50) values of 0.19 +/- 0.01, 99.0 +/- 4.6, and 6.4 +/- 0.3 nM, respectively. Analogues 20, 23, and 27, up to the micromolar range of concentrations, were unable to activate estrogen receptor alpha and beta (ER alpha and ER beta) or to interfere with ER-dependent gene expression significantly. In addition, they were unable to stimulate the growth of Ishikawa, MCF-7, and LNCaP cells. Our results suggest that the spiro-epoxyneurosteroid derivatives 20, 23, and 27 may prove to be lead molecules for the synthesis of novel neuroprotective agents.