1-(2-Nitro-4-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-dicarboxylic acid diethyl ester | 237421-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-Nitro-4-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 1-[2-nitro-4-(trifluoromethyl)phenyl]-1,2,4-triazole-3,5-dicarboxylate
• CAS: 237421-29-3
• 化学式: C₁₅H₁₃F₃N₄O₆
• 分子量: 402.287
• InChiKey: KGBIAQVQGZYNOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2-Nitro-4-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-dicarboxylic acid diethyl ester 在 铁粉 、 溶剂黄146 作用下， 以86%的产率得到4-Oxo-7-trifluoromethyl-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  4,5-Dihydro-1,2,4-triazolo[1,5-a]quinoxalin-4-ones:  Excitatory Amino Acid Antagonists with Combined Glycine/NMDA and AMPA Receptor Affinity

  摘要：

  A series of 4,5-dihydro-1,2,4-triazolo[1,5-alpha]quinoxalin-4-ones bearing different substituents on the benzo-fused ring and at position 2 were synthesized and biologically evaluated for their binding at glycine/NMDA and AMPA receptors. Most of the reported compounds show combined glycine/NMDA and AMPA receptor binding activity providing further evidences of the structural similarities of the binding pockets of both receptor recognition sites. Moreover, this study has pointed out some differences for the binding at each receptor type. In particular, for the glycine/NMDA receptor-ligand interaction, the presence of a free acidic function at position 2 and an electron-withdrawing substituent(s) nonbulkier than chlorine atom(s) on the benzo-fused moiety is required. Functional antagonism at the NMDA receptor-ion channel complex was also performed on some selected compounds.

  DOI：

  10.1021/jm981102r
• 作为产物：
  描述：

  (Ethoxyoxalyl-amino)-[(2-nitro-4-trifluoromethyl-phenyl)-hydrazono]-acetic acid ethyl ester 在 硫酸 作用下， 反应 1.0h， 以41%的产率得到1-(2-Nitro-4-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  4,5-Dihydro-1,2,4-triazolo[1,5-a]quinoxalin-4-ones:  Excitatory Amino Acid Antagonists with Combined Glycine/NMDA and AMPA Receptor Affinity

  摘要：

  A series of 4,5-dihydro-1,2,4-triazolo[1,5-alpha]quinoxalin-4-ones bearing different substituents on the benzo-fused ring and at position 2 were synthesized and biologically evaluated for their binding at glycine/NMDA and AMPA receptors. Most of the reported compounds show combined glycine/NMDA and AMPA receptor binding activity providing further evidences of the structural similarities of the binding pockets of both receptor recognition sites. Moreover, this study has pointed out some differences for the binding at each receptor type. In particular, for the glycine/NMDA receptor-ligand interaction, the presence of a free acidic function at position 2 and an electron-withdrawing substituent(s) nonbulkier than chlorine atom(s) on the benzo-fused moiety is required. Functional antagonism at the NMDA receptor-ion channel complex was also performed on some selected compounds.

  DOI：

  10.1021/jm981102r