ethyl 1-(5-methyl-2-nitrophenyl)-3-(4-methoxyphenyl)-1,2,4-triazolo-5-carboxylate | 872311-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(5-methyl-2-nitrophenyl)-3-(4-methoxyphenyl)-1,2,4-triazolo-5-carboxylate
• 英文别名: Ethyl 5-(4-methoxyphenyl)-2-(5-methyl-2-nitrophenyl)-1,2,4-triazole-3-carboxylate
• CAS: 872311-83-6
• 化学式: C₁₉H₁₈N₄O₅
• 分子量: 382.376
• InChiKey: CCUGPRZDXSDQMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 1-(5-methyl-2-nitrophenyl)-3-(4-methoxyphenyl)-1,2,4-triazolo-5-carboxylate 在 铁粉 、 溶剂黄146 作用下， 反应 0.17h， 以70%的产率得到2-(4-methoxyphenyl)-8-methyl-5H-[1,2,4]triazolo[1,5-a]quinoxalin-4-one
  参考文献：
  名称：

  1,2,4-Triazolo[1,5-a]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

  摘要：

  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.

  DOI：

  10.1021/jm0504149
• 作为产物：
  描述：

  (5-甲基-2-硝基苯基)肼 在 吡啶 、 氨 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 6.0h， 生成 ethyl 1-(5-methyl-2-nitrophenyl)-3-(4-methoxyphenyl)-1,2,4-triazolo-5-carboxylate
  参考文献：
  名称：

  1,2,4-Triazolo[1,5-a]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

  摘要：

  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.

  DOI：

  10.1021/jm0504149