9-amino-5-bromo-2-ethyl-2,3-dihydro-pyrrolo[3,4-b]quinolin-1-one | 1093951-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-amino-5-bromo-2-ethyl-2,3-dihydro-pyrrolo[3,4-b]quinolin-1-one
• 英文别名: 9-Amino-5-bromo-2-ethyl-2,3-dihydropyrrolo[3,4-b]quinolin-1-one；9-amino-5-bromo-2-ethyl-3H-pyrrolo[3,4-b]quinolin-1-one
• CAS: 1093951-31-5
• 化学式: C₁₃H₁₂BrN₃O
• 分子量: 306.162
• InChiKey: YBJLPMNVISUOFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-amino-5-bromo-2-ethyl-2,3-dihydro-pyrrolo[3,4-b]quinolin-1-one 、 2,5-二甲氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 生成 9-amino-5-(2,5-dimethoxyphenyl)-2-ethyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  Development and SAR of functionally selective allosteric modulators of GABAA receptors

  摘要：

  Positive modulators at the benzodiazepine site of alpha 2- and alpha 3-containing GABA(A) receptors are believed to be anxiolytic. Through oocyte voltage clamp studies, we have discovered two series of compounds that are positive modulators at alpha 2-/alpha 3-containing GABA(A) receptors and that show no functional activity at alpha 1-containing GABAA receptors. We report studies to improve this functional selectivity and ultimately deliver clinical candidates. The functional SAR of cinnolines and quinolines that are positive allosteric modulators of the alpha 2- and alpha 3-containing GABA(A) receptors, while simultaneously neutral antagonists at alpha 1-containing GABAA receptors, is described. Such functionally selective modulators of GABA(A) receptors are expected to be useful in the treatment of anxiety and other psychiatric illnesses. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.035
• 作为产物：
  描述：

  3-bromo-2-(1-ethyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl-amino)benzonitrile 在 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 生成 9-amino-5-bromo-2-ethyl-2,3-dihydro-pyrrolo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  Development and SAR of functionally selective allosteric modulators of GABAA receptors

  摘要：

  Positive modulators at the benzodiazepine site of alpha 2- and alpha 3-containing GABA(A) receptors are believed to be anxiolytic. Through oocyte voltage clamp studies, we have discovered two series of compounds that are positive modulators at alpha 2-/alpha 3-containing GABA(A) receptors and that show no functional activity at alpha 1-containing GABAA receptors. We report studies to improve this functional selectivity and ultimately deliver clinical candidates. The functional SAR of cinnolines and quinolines that are positive allosteric modulators of the alpha 2- and alpha 3-containing GABA(A) receptors, while simultaneously neutral antagonists at alpha 1-containing GABAA receptors, is described. Such functionally selective modulators of GABA(A) receptors are expected to be useful in the treatment of anxiety and other psychiatric illnesses. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.035

文献信息

• Compounds and Uses Thereof - 848
  申请人：Chang Hui-Fang

  公开号：US20080318943A1

  公开（公告）日：2008-12-25

  This invention relates to novel compounds having the structural formula I below: and their pharmaceutically acceptable salts, tautomers or in vivo-hydrolysable precursors, compositions and methods of use thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined in the specification. These novel compounds provide a treatment or prophylaxis of anxiety disorders, schizophrenia, cognitive disorders, and/or mood disorders.

  本发明涉及具有下面结构式I的新化合物：及其药用盐、互变异构体或体内水解前体，其组合物和使用方法，其中R1、R2、R3、R4、R5和R6在规范中定义。这些新化合物提供了治疗或预防焦虑症、精神分裂症、认知障碍和/或情绪障碍的方法。
• FUSED QUINOLINE DERIVATIVES USEFUL AS GABA MODULATORS
  申请人：AstraZeneca AB

  公开号：EP2176263A2

  公开（公告）日：2010-04-21
• [EN] COMPOUNDS AND USES THEREOF-848<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2008155572A2

  公开（公告）日：2008-12-24

  [EN] This invention relates to novel compounds having the structural formula (I) below: and their pharmaceutically acceptable salts, tautomers or in vivo-hydrolysable precursors, compositions and methods of use thereof, wherein R1, R2, R3, R4, R5, and R6 are defined in the specification. These novel compounds provide a treatment or prophylaxis of anxiety disorders, schizophrenia, cognitive disorders, and/or mood disorders.
  [FR] Cette invention porte sur de nouveaux composés présentant la formule structurale (I) ci-après : et sur leurs sels, tautomères ou précurseurs hydrolysable in-vivo, pharmaceutiquement acceptables, et sur des compositions et des procédés pour leur utilisation. Dans la formule (I), R1, R2, R3, R4, R5, et R6 sont définis dans la description. Ces nouveaux composés fournissent un traitement ou une prophylaxie de troubles de l'anxiété, de la schizophrénie, de troubles cognitifs et/ou de troubles de l'humeur.