3α-hydroxy-20-oxo-5β-pregnan-7α-yl nicotinate | 1177358-19-8

• 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
• 英文名称: 3α-hydroxy-20-oxo-5β-pregnan-7α-yl nicotinate
• 英文别名: [(3R,5S,7R,8R,9S,10S,13S,14S,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl] pyridine-3-carboxylate
• CAS: 1177358-19-8
• 化学式: C₂₇H₃₇NO₄
• 分子量: 439.595
• InChiKey: WGQDXTLVGDCOOF-FYAJOKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-20-oxo-5β-pregnan-7α-yl nicotinate 、 三氧化硫吡啶 以 氯仿 为溶剂， 以74%的产率得到20-oxo-5β-pregnane-3α,7α-diyl 3-sulfate 7-nicotinate pyridinium salt
  参考文献：
  名称：

  ANIONIC PREGNANE COMPOUNDS, METHOD FOR THEIR PRODUCING AND USE OF THEM

  摘要：

  公开号：

  EP2313424B1
• 作为产物：
  描述：

  3α-(tert-butyldimethylsilyloxy)-20-oxo-5β-pregnan-7α-yl acetate 在 吡啶 、 4-二甲氨基吡啶 、 乙醇 、 四丁基氟化铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 133.0h， 生成 3α-hydroxy-20-oxo-5β-pregnan-7α-yl nicotinate
  参考文献：
  名称：

  ANIONIC PREGNANE COMPOUNDS, METHOD FOR THEIR PRODUCING AND USE OF THEM

  摘要：

  公开号：

  EP2313424B1

文献信息

• Synthesis of C3, C5, and C7 pregnane derivatives and their effect on NMDA receptor responses in cultured rat hippocampal neurons
  作者：Eva Stastna、Hana Chodounska、Vladimir Pouzar、Vojtech Kapras、Jirina Borovska、Ondrej Cais、Ladislav Vyklicky

  DOI：10.1016/j.steroids.2008.11.011

  日期：2009.2

  The synthesis of several novel 5 alpha- and 5 beta-20-oxo-pegnane derivatives substituted in the position 3 and 7 of the steroid skeleton is described. Activity of synthesized compounds was studied in voltage-clamped cultured rat hippocampal neurons. Substituted derivatives inhibited NMDA-elicited neuronal activity. The relationship between biological activity and structure is discussed. (C) 2008 Published by Elsevier Inc.
• [EN] ANIONIC PREGNANE COMPOUNDS, METHOD FOR THEIR PRODUCING AND USE OF THEM<br/>[FR] COMPOSÉS ANIONIQUES DE PRÉGNANE, LEUR PROCÉDÉ DE FABRICATION ET LEUR UTILISATION
  申请人：USTAV ORSANICKE CHEMIE A BIOCH

  公开号：WO2010003391A2

  公开（公告）日：2010-01-14

  This invention relates to pregnane anionic compounds of general formula I in which R1 is ester group, which is able to form ion such as sulfate, pyridinium sulfate, hemisuccinate etc., R2 is hydrogen atom in alpha or beta configuration, and R3 is ester group, as is acetoxy group, nicotinoyloxy group etc., and their pharmaceutically acceptable salts. Compounds of general formula I are preferably produced from the diol of formula II or diol of formula VIII, which are converted according to described sequence of reactions, to compounds of general formula I, in which R1 is ester group, which is able to form ion such as sulfate, pyridinium sulfate, hemisuccinate etc., R2 is hydrogen atom in alpha or beta configuration, and R3 is ester group. The compounds of general formula I are useful as active ingredients for production of pharmaceuticals for the treatment of neurological and psychiatric diseases and conditions associated with excessive activation of NMDA receptors such as neuroprotective agents against excitotoxic damage of the central nervous system (CNS), conditions associated with excessive activation of NMDA-subtype glutamate receptors or, where this type of receptor is involved in the creation or during the certain mental and neurological diseases, in particular concerning the traumatic and hypoxic damage Io nervous tissue in the central nervous system diseases, such as Alzheimer's, Huntington's and Parkinson's disease, also in cognitive disorders in aging; the other indications could be tardive dyskinesia, amyotrophic lateral sclerosis, olivopontocerebellar degeneration, neurological problems1 associated with AIDS infection, allergic encephalomyelitis, and for medication of epilepsy, anxiety, depression, schizophrenia, chronic pain and drug addiction.