ethyl 8-nitro-4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate | 366804-02-6

• 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: ethyl 8-nitro-4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate
• CAS: 366804-02-6
• 化学式: C₁₂H₉N₅O₅
• 分子量: 303.234
• InChiKey: JIMCTXMCYBKBFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 8-nitro-4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以67%的产率得到8-Nitro-4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylic acid
  参考文献：
  名称：

  Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173

  摘要：

  A seires of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure-activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N-3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 muM AMPA or NMDA in mouse cortical wedge preparations.

  DOI：

  10.1021/jm010862q
• 作为产物：
  描述：

  [1,2,4]三唑并[1,5-a]喹喔啉-2-羧酸,4,5-二氢-4-羰基-,乙基酯 在 90percent aq. HNO₃ 作用下， 以70%的产率得到ethyl 8-nitro-4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate
  参考文献：
  名称：

  Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173

  摘要：

  A seires of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure-activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N-3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 muM AMPA or NMDA in mouse cortical wedge preparations.

  DOI：

  10.1021/jm010862q

文献信息

• Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-<i>a</i>]quinoxaline-2-carboxylates Analogues of TQX-173
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Guido Filacchioni、Alessandro Galli、Chiara Costagli、Vincenzo Carlà

  DOI：10.1021/jm010862q

  日期：2001.9.1

  A seires of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure-activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N-3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 muM AMPA or NMDA in mouse cortical wedge preparations.