diethyl 1-[4-chloro-5-(imidazol-1-yl)-2-nitrophenyl]-1,2,4-triazole-3,5-dicarboxylate | 308137-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl 1-[4-chloro-5-(imidazol-1-yl)-2-nitrophenyl]-1,2,4-triazole-3,5-dicarboxylate
• 英文别名: diethyl 1-[4-chloro-5-(imidazol-1-yl)-2-nitrophenyl]-1,2,4-triazolo-3,5-dicarboxylate；Diethyl 1-(4-chloro-5-imidazol-1-yl-2-nitrophenyl)-1,2,4-triazole-3,5-dicarboxylate
• CAS: 308137-62-4
• 化学式: C₁₇H₁₅ClN₆O₆
• 分子量: 434.796
• InChiKey: ABWUDLWKDDRBTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 1-[4-chloro-5-(imidazol-1-yl)-2-nitrophenyl]-1,2,4-triazole-3,5-dicarboxylate 在 sodium hydroxide 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 7-Chloro-8-imidazol-1-yl-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：

  4,5-二氯-2-硝基苯胺 在 氢氧化钾 、 氟硼酸钠 、 硫酸 、 氨 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 10.5h， 生成 diethyl 1-[4-chloro-5-(imidazol-1-yl)-2-nitrophenyl]-1,2,4-triazole-3,5-dicarboxylate
  参考文献：
  名称：

  7-Chloro-4,5-dihydro-8-(1,2,4-triazol-4-yl)- 4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2- carboxylates as Novel Highly Selective AMPA Receptor Antagonists

  摘要：

  DOI：

  10.1021/jm0009686