diethyl 1-(2-nitrophenyl)-1,2,4-triazole-3,5-dicarboxylate | 150454-80-1

• 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-(2-nitrophenyl)-1,2,4-triazole-3,5-dicarboxylate
• 英文别名: diethyl 1-(2-nitrophenyl)-1,2,4-triazolo-3,5-dicarboxylate
• CAS: 150454-80-1
• 化学式: C₁₄H₁₄N₄O₆
• 分子量: 334.288
• InChiKey: KJYQHURROYKBJS-UHFFFAOYSA-N

物化性质

• 沸点：
  519.4±52.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 1-(2-nitrophenyl)-1,2,4-triazole-3,5-dicarboxylate 在 铁粉 、 溶剂黄146 作用下， 生成 [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
  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：

  2-氯-2-[2-(2-硝基苯基)亚肼基]乙酸乙酯 在 氨 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 生成 diethyl 1-(2-nitrophenyl)-1,2,4-triazole-3,5-dicarboxylate
  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

文献信息

• The chemoselective reduction of nitro compounds: scope of the electrochemical method
  作者：JM Chapuzet、R Labrecque、M Lavoie、E Martel、J Lessard

  DOI：10.1051/jcp/1996930601

  日期：——

  The selective electrohydrogenation of nitro aliphatic and nitro aromatic functional groups in molecules containing other groups that are easy to hydrogenate (activated double bond, carbon-iodine bond, nitrile,) has been sucessfully carried out in slightly acidic (pH = 3) or neutral (pH = 5-6) methanol-water solutions at Devarda copper and Raney cobalt electrodes. The electrochemical synthesis of a quinolone 15 and a quinoxaline 18 is also reported. Preliminary results on the preparative electroreduction of 5-nitroindole 21 on Hg in aqueous methanol with HBr as supporting electrolyte are presented and dicussed for the first time.

  在含有其他易氢化基团（活化双键、碳-碘键、氰基）的分子中，对硝基脂肪族和硝基芳香族官能团的选择性电氢化已在微酸性（pH = 3）或中性（pH = 5-6）的甲醇-水溶液中，在德尔瓦铜和拉尼钴电极上成功进行。本文还报道了喹诺酮15和喹喉18的电化学合成。首次介绍了在含氢溴酸的甲醇水溶液中，在汞上进行5-硝基吲哚21的制备电还原的初步结果，并进行了讨论。
• 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：——
• 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.