Ethyl 16-methyl-7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaene-4-carboxylate | 177417-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 16-methyl-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: 177417-75-3
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: HXYHBQBOQAUWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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 16-methyl-7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaene-4-carboxylate 在 盐酸 、 sodium hydroxide 、 三甲基氯硅烷 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 16-(4-Carboxybutyl)-16-methyl-7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaene-4-carboxylic acid
  参考文献：
  名称：

  Synthesis of anticonvulsive AMPA antagonists

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00180-9
• 作为产物：
  描述：

  diethyl imidazole-2,4-dicarboxylate 在 palladium on activated charcoal ammonium acetate 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 15.0~20.0 ℃ 、101.35 kPa 条件下， 反应 70.75h， 生成 Ethyl 16-methyl-7-oxo-2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaene-4-carboxylate
  参考文献：
  名称：

  Synthesis of anticonvulsive AMPA antagonists

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00180-9