(7-Chloro-4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxalin-2-yl)-acetic acid ethyl ester | 237420-99-4

• 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: (7-Chloro-4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxalin-2-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-(7-chloro-4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxalin-2-yl)acetate
• CAS: 237420-99-4
• 化学式: C₁₃H₁₁ClN₄O₃
• 分子量: 306.708
• InChiKey: CXPGPXOXQYMFSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7-Chloro-4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxalin-2-yl)-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到(7-Chloro-4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxalin-2-yl)-acetic acid
  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：

  2-(bromomethyl)-7-chloro-4,5-dihydro-1,2,4-triazolo<1,5-a>quinoxalin-4-one 在 硫酸 作用下， 以 二甲基亚砜 为溶剂， 反应 98.5h， 生成 (7-Chloro-4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxalin-2-yl)-acetic 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