4-amino-8-(2,5-dimethoxy-phenyl)-N-methyl-7-fluoro-cinnoline-3-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-amino-8-(2,5-dimethoxy-phenyl)-N-methyl-7-fluoro-cinnoline-3-carboxamide
• 英文别名: 4-amino-8-(2,5-dimethoxyphenyl)-N-ethyl-7-fluoro-cinnoline-3-carboxamide；4-amino-8-(2,5-dimethoxyphenyl)-N-ethyl-7-fluorocinnoline-3-carboxamide
• 化学式: C₁₉H₁₉FN₄O₃
• 分子量: 370.383
• InChiKey: BGGCZORPGAXQJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氰基-N-乙基乙酰胺 在 盐酸 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 甲苯 为溶剂， 生成 4-amino-8-(2,5-dimethoxy-phenyl)-N-methyl-7-fluoro-cinnoline-3-carboxamide
  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 - 849
  申请人：Arriza Jeffery Louis

  公开号：US20080318925A1

  公开（公告）日：2008-12-25

  This invention relates to the use of compounds having the structural formula I below: and their pharmaceutically acceptable salts, tautomers or in vivo-hydrolysable precursors, compositions in treating schizophrenia.

  本发明涉及使用具有以下结构式I的化合物及其药用可接受的盐、互变异构体或体内可水解的前体，在治疗精神分裂症方面的组合物。
• Compounds and Uses Thereof
  申请人：Chapdelaine J. Marc

  公开号：US20070142328A1

  公开（公告）日：2007-06-21

  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. These novel compounds provide a treatment or prophylaxis of anxiety disorders, cognitive disorders, and/or mood disorders.

  该发明涉及具有如下结构式I的新化合物及其药用盐、互变异构体或体内可水解前体，以及其使用的组合物和方法。这些新化合物可用于治疗或预防焦虑障碍、认知障碍和/或情绪障碍。
• Uses of cinnoline compounds to treat schizophrenia
  申请人：Arriza Jeffery Louis

  公开号：US20100184738A1

  公开（公告）日：2010-07-22

  This invention relates to the use of compounds having the structural formula I below: and their pharmaceutically acceptable salts, tautomers or in vivo-hydrolysable precursors, compositions in treating schizophrenia.

  本发明涉及使用具有以下结构式I的化合物及其药学上可接受的盐、互变异构体或体内水解前体，用于治疗精神分裂症的组合物。
• Cinnoline Compounds for the Treatment of Anxiety, Cognitive and Mood Disorders
  申请人：Chapdelaine Marc J.

  公开号：US20110144331A1

  公开（公告）日：2011-06-16

  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. These novel compounds provide a treatment or prophylaxis of anxiety disorders, cognitive disorders, and/or mood disorders.

  本发明涉及下面结构式I的新化合物及其药学上可接受的盐、互变异构体或体内可水解的前体物、组合物和使用方法。这些新化合物提供了治疗或预防焦虑症、认知障碍和/或情绪障碍的方法。
• SUBSTITUTED CINNOLINE DERIVATIVES AS GABAA-RECEPTOR MODULATORS AND METHOD FOR THEIR SYNTHESIS
  申请人：AstraZeneca AB

  公开号：EP1966158A1

  公开（公告）日：2008-09-10