4,5-dihydro-4-oxo-1,2,4-triazolo<1,5-a>quinoxaline-2-carboxylic acid | 150454-82-3

• 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: 4,5-dihydro-4-oxo-1,2,4-triazolo<1,5-a>quinoxaline-2-carboxylic acid
• 英文别名: [1,2,4]Triazolo[1,5-a]quinoxaline-2-carboxylic acid, 4,5-dihydro-4-oxo-；4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylic acid
• CAS: 150454-82-3
• 化学式: C₁₀H₆N₄O₃
• 分子量: 230.183
• InChiKey: LVSGNONSJATCHN-UHFFFAOYSA-N

物化性质

• 熔点：
  294-296 °C(Solv: acetone (67-64-1))
• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-4-oxo-1,2,4-triazolo<1,5-a>quinoxaline-2-carboxylic acid 在 palladium on activated charcoal copper(I) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 、 二乙二醇 为溶剂， 反应 14.25h， 生成 1,2,4-triazolo<1,5-a>quinoxaline
  参考文献：
  名称：

  Catarzi, Daniela; Cecchi, Lucia; Colotta, Vittoria, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1161 - 1163

  摘要：

  DOI：
• 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 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到4,5-dihydro-4-oxo-1,2,4-triazolo<1,5-a>quinoxaline-2-carboxylic acid
  参考文献：
  名称：

  Catarzi, Daniela; Cecchi, Lucia; Colotta, Vittoria, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1161 - 1163

  摘要：

  DOI：

文献信息

• 1,2,4-Triazolo[1,5-<i>a</i>]quinoxaline as a Versatile Tool for the Design of Selective Human A₃ Adenosine Receptor Antagonists:  Synthesis, Biological Evaluation, and Molecular Modeling Studies of 2-(Hetero)aryl- and 2-Carboxy-Substitued Derivatives
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Ombretta Lenzi、Guido Filacchioni、Letizia Trincavelli、Claudia Martini、Christian Montopoli、Stefano Moro

  DOI：10.1021/jm0504149

  日期：2005.12.1

  A number of 4-oxo-substituted 1,2,4-triazolo[1,5-alquinoxaline derivatives bearing at position-2 the claimed (hetero)aryl moiety (compounds 1-15) but also a carboxylate group (16-28, 3236) or a hydrogen atom (29-31) were designed as human A(3) (hA(3)) adenosine receptor (AR) antagonists. This study produced some interesting compounds and among them the 2-(4methoxyphenyl)-1,2,4-triazolo[1,5-alquinoxalin-4-one (8), which can be considered one of the most potent and selective hA(3) adenosine receptor antagonists reported till now. Moreover, as a new finding, replacement of the classical 2-(hetero)aryl moiety with a 2-carboxylate function (compounds 16-28 and 32-36) maintained good hA(3) AR binding activity but, most importantly and interestingly, produced a large increase in bA(3) versus hA(1) selectivity. A receptor-based SAR analysis provided new interesting insights about the steric and electrostatic requirements that are important for the anchoring of these derivatives at the hA(3) receptor recognition site, thus highlighting the versatility of the triazoloquinoxaline scaffold for obtaining potent and selective hA(3) AR antagonists.
• 4,5-Dihydro-1,2,4-triazolo[1,5-<i>a</i>]quinoxalin-4-ones:  Excitatory Amino Acid Antagonists with Combined Glycine/NMDA and AMPA Receptor Affinity
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Lucia Cecchi、Guido Filacchioni、Alessandro Galli、Chiara Costagli

  DOI：10.1021/jm981102r

  日期：1999.7.1

  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.
• Catarzi, Daniela; Cecchi, Lucia; Colotta, Vittoria, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1161 - 1163
  作者：Catarzi, Daniela、Cecchi, Lucia、Colotta, Vittoria、Filacchioni, Guido、Melani, Fabrizio

  DOI：——

  日期：——