Ethyl 1-[(2-ethoxy-2-oxoethyl)carbamoyl]-3-oxo-2,4-dihydroquinoxaline-2-carboxylate | 350795-76-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 1-[(2-ethoxy-2-oxoethyl)carbamoyl]-3-oxo-2,4-dihydroquinoxaline-2-carboxylate
• CAS: 350795-76-5
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 349.343
• InChiKey: XBFOGAYIEKXSQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 1-[(2-ethoxy-2-oxoethyl)carbamoyl]-3-oxo-2,4-dihydroquinoxaline-2-carboxylate 反应 0.5h， 以50%的产率得到Ethyl 2-(1,3,4-trioxo-3a,5-dihydroimidazo[1,5-a]quinoxalin-2-yl)acetate
  参考文献：
  名称：

  Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists

  摘要：

  The synthesis and glycine/NMDA and AMPA receptor affinities of a set of ethyl (+/-) 1-N-carbamoyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylates 1-11 and those of their constrained analogue (+/-) 1,2,3,3a,4,5-hexahydroimidazo[1,5-a]quinoxaline 1,3,4-triones 12-24 are reported. Compounds 1-11 bear a side-chain at position 1 which has been spatially constrained in compounds 12-24. Most of the reported tricyclic derivatives 12-24 showed glycine/NMDA binding activity comparable to that of their corresponding bicyclic analogues 1-11 providing further evidence that the spatial orientation of the side-chain is an important structural requirement for glycine/NMDA receptor antagonists. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01203-4
• 作为产物：
  描述：

  3-羟基-1,2-二氢喹喔啉-2-甲酸乙酯 、 异氰酰乙酸乙酯 以 苯 为溶剂， 以80%的产率得到Ethyl 1-[(2-ethoxy-2-oxoethyl)carbamoyl]-3-oxo-2,4-dihydroquinoxaline-2-carboxylate
  参考文献：
  名称：

  Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists

  摘要：

  The synthesis and glycine/NMDA and AMPA receptor affinities of a set of ethyl (+/-) 1-N-carbamoyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylates 1-11 and those of their constrained analogue (+/-) 1,2,3,3a,4,5-hexahydroimidazo[1,5-a]quinoxaline 1,3,4-triones 12-24 are reported. Compounds 1-11 bear a side-chain at position 1 which has been spatially constrained in compounds 12-24. Most of the reported tricyclic derivatives 12-24 showed glycine/NMDA binding activity comparable to that of their corresponding bicyclic analogues 1-11 providing further evidence that the spatial orientation of the side-chain is an important structural requirement for glycine/NMDA receptor antagonists. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01203-4

文献信息

• Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists
  作者：Flavia Varano、Daniela Catarzi、Vittoria Colotta、Lucia Cecchi、Guido Filacchioni、Alessandro Galli、Chiara Costagli

  DOI：10.1016/s0223-5234(00)01203-4

  日期：2001.2

  The synthesis and glycine/NMDA and AMPA receptor affinities of a set of ethyl (+/-) 1-N-carbamoyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylates 1-11 and those of their constrained analogue (+/-) 1,2,3,3a,4,5-hexahydroimidazo[1,5-a]quinoxaline 1,3,4-triones 12-24 are reported. Compounds 1-11 bear a side-chain at position 1 which has been spatially constrained in compounds 12-24. Most of the reported tricyclic derivatives 12-24 showed glycine/NMDA binding activity comparable to that of their corresponding bicyclic analogues 1-11 providing further evidence that the spatial orientation of the side-chain is an important structural requirement for glycine/NMDA receptor antagonists. (C) 2001 Editions scientifiques et medicales Elsevier SAS.