ethyl 4,5-dihydro-4-oxo-10H-imidazol[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate | 177417-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]吡嗪-8-酮
• 英文名称: ethyl 4,5-dihydro-4-oxo-10H-imidazol[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate
• 英文别名: ethyl 4-oxo-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate；ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate；ethyl 7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaene-4-carboxylate
• CAS: 177417-38-8
• 化学式: C₁₆H₁₃N₃O₃
• 分子量: 295.298
• InChiKey: IIMLLMNKDACERY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4,5-dihydro-4-oxo-10H-imidazol[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate 在 potassium nitrate 作用下， 以 palladized charcoal 、 乙醇 、 二甲基亚砜 为溶剂， 生成 ethyl 8-amino-4,10-dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate
  参考文献：
  名称：

  Imidazo\x9b1,2-A!indeno\x9b1,2-E!pyrazine-2-carboxylic acid derivatives,

  摘要：

  公式（I）的化合物：##STR1##其中R、R.sub.1、R.sub.2和R.sub.3如申请中所定义，其盐、其制备方法及含有该化合物的药物。

  公开号：

  US05726175A1
• 作为产物：
  描述：

  丙炔酸乙酯 在 乙酸铵 、 三乙胺 作用下， 以 N-甲基乙酰胺 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 水 、 溶剂黄146 、 丁酮 为溶剂， 生成 ethyl 4,5-dihydro-4-oxo-10H-imidazol[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate
  参考文献：
  名称：

  Imidazo\x9b1,2-A!indeno\x9b1,2-E!pyrazine-2-carboxylic acid derivatives,

  摘要：

  公式（I）的化合物：##STR1##其中R、R.sub.1、R.sub.2和R.sub.3如申请中所定义，其盐、其制备方法及含有该化合物的药物。

  公开号：

  US05726175A1

文献信息

• Synthesis of anticonvulsive AMPA antagonists
  作者：Jean-Marie Stutzmann、Georg Andrees Bohme、Alain Boireau、Dominique Damour、Marc Williams Debono、Arielle Genevois-Borella、Patrick Jimonet、Jeremy Pratt、John C.R Randle、Yves Ribeill、Marc Vuilhorgne、Serge Mignani

  DOI：10.1016/s0960-894x(01)00180-9

  日期：2001.5

  The overstimulation of excitatory amino acid receptors such as the glutamate AMPA receptor has been implicated in the physiopathogenesis of egilepsy as well as ill acute and chronic neurodegenerative disorders. An original series of readily water soluble 4-oxo-10-substituted-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid derivatives was synthesized. The most potent derivative 6a exhibited nanomolar binding affinity (IC50=35nM) and antagonist activity (IC50-6nM) at ionotropic AMPA receptor. This compound also demonstrated potent anticonvulsant properties in MES in mice and rats with long durations of action with ED50 values in the 1-3 mg/kg dose range following ip and iv administration. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 4,10-Dihydro-4-oxo-4 H -imidazo[1,2- a ]indeno[1,2- e ]pyrazin-2-carboxylic acid derivatives
  作者：Jean-Marie Stutzmann、Georg Andrees Bohme、Alain Boireau、Dominique Damour、Marc Williams Debono、Arielle Genevois-Borella、Assunta Imperato、Patrick Jimonet、Jeremy Pratt、John C.R. Randle、Yves Ribeill、Marc Vuilhorgne、Serge Mignani

  DOI：10.1016/s0960-894x(00)00181-5

  日期：2000.5

  A novel series of 2-substituted-4,5-dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazine derivatives was synthesised. One of them, 4e-a highly water soluble compound - exhibited a nanomolar affinity and demonstrated competitive antagonist properties at the ionotropic AMPA receptors. This compound also displayed potent anticonvulsant properties against electrically or sound-induced convulsions in mice after systemic administration, thus suggesting adequate brain penetration. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Imidazo\x9b1,2-A!indeno\x9b1,2-E!pyrazine-2-carboxylic acid derivatives,
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05726175A1

  公开（公告）日：1998-03-10

  A compound of formula (I): ##STR1## wherein R, R.sub.1, R.sub.2, and R.sub.3 are as defined in the application, salts thereof, preparation thereof and drugs containing same.

  公式（I）的化合物：##STR1##其中R、R.sub.1、R.sub.2和R.sub.3如申请中所定义，其盐、其制备方法及含有该化合物的药物。