4,8-dichloro-2-phenyl-1,2,4-triazolo[1,5-a]quinoxalin-4-amine | 168210-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,8-dichloro-2-phenyl-1,2,4-triazolo[1,5-a]quinoxalin-4-amine
• 英文别名: 4,8-Dichloro-2-phenyl-[1,2,4]triazolo[1,5-a]quinoxaline；4,8-dichloro-2-phenyl-[1,2,4]triazolo[1,5-a]quinoxaline
• CAS: 168210-17-1
• 化学式: C₁₅H₈Cl₂N₄
• 分子量: 315.161
• InChiKey: DQMVYGPEBCYSOQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,8-dichloro-2-phenyl-1,2,4-triazolo[1,5-a]quinoxalin-4-amine 在 氨 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以47%的产率得到8-Chloro-2-phenyl-[1,2,4]triazolo[1,5-a]quinoxalin-4-amine
  参考文献：
  名称：

  Synthesis of some tricyclic heteroaromatic systems and their A1 and A2a adenosine binding activity

  摘要：

  The syntheses, A(1) and A(2a) adenosine receptor affinities and structure-activity relationships of some 2-aryl-1,2,4-triazolo[1,5-a]quinoxalines, 2-arylimidazo[1,2-a]quinoxalines, 1-arylimidazo[1,5-a]quinoxalines are reported and compared with that of a previously reported 2-phenylpyrazolo[1,5-a]quinoxaline. The results show that some triazoloquinoxalines are potent and specific A(1) adenosine receptor ligands and that the replacement of either nitrogen at position 1 or 3 of the triazoloquinoxaline moiety with a CH brought about a decrease in affinity at both adenosine receptors.

  DOI：

  10.1016/0223-5234(96)88218-3
• 作为产物：
  描述：

  8-chloro-2-phenyl-[1,2,4]triazolo[1,5-a]quinoxalin-4(5H)-one 在 吡啶 、 五氯化磷 、 三氯氧磷 作用下， 反应 3.0h， 以30%的产率得到4,8-dichloro-2-phenyl-1,2,4-triazolo[1,5-a]quinoxalin-4-amine
  参考文献：
  名称：

  Synthesis of some tricyclic heteroaromatic systems and their A1 and A2a adenosine binding activity

  摘要：

  The syntheses, A(1) and A(2a) adenosine receptor affinities and structure-activity relationships of some 2-aryl-1,2,4-triazolo[1,5-a]quinoxalines, 2-arylimidazo[1,2-a]quinoxalines, 1-arylimidazo[1,5-a]quinoxalines are reported and compared with that of a previously reported 2-phenylpyrazolo[1,5-a]quinoxaline. The results show that some triazoloquinoxalines are potent and specific A(1) adenosine receptor ligands and that the replacement of either nitrogen at position 1 or 3 of the triazoloquinoxaline moiety with a CH brought about a decrease in affinity at both adenosine receptors.

  DOI：

  10.1016/0223-5234(96)88218-3

文献信息

• 2-Aryl-8-chloro-1,2,4-triazolo[1,5-a]quinoxalin-4-amines as highly potent A1 and A3 adenosine receptor antagonists
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Francesca Romana Calabri、Ombretta Lenzi、Guido Filacchioni、Letizia Trincavelli、Claudia Martini、Andrea Tralli、Christian Montopoli、Stefano Moro

  DOI：10.1016/j.bmc.2004.10.050

  日期：2005.2

  hydrogen-bonding interactions with specific sites on the A3 AR, has been confirmed. Using our recently published hA3 receptor model, to better elucidate our experimental results, we decided to theoretically depict the putative TM binding motif of the herein reported 1,2,4-triazolo[1,5-a]quinoxaline derivatives on human A3 receptor. Structure-activity relationships have been explained analyzing the three-dimensional

  一些2-芳基-8-氯-1,2,4-三唑并[1,5-a]喹喔啉衍生物2-18，是通过在4-氨基部分（酰基或氨基甲酰基）或2-氨基上引入不同的取代基而获得的先前报道的8-氯-2-苯基-1,2,4-三唑[1,5-a]喹喔啉-4-胺（1）的-苯环（4-OCH3）已被合成并在放射性配体结合中进行了测试牛A1和A（2A）以及克隆的人A1和A3腺苷受体的RNA检测。合理设计的8-氯-2-（4-甲氧基-苯基）-1,2,4-三唑并[1,5-a]喹喔啉-4-乙酰基胺（14）被认为是最有效的药物之一，而hA3与迄今为止，已有hA1选择性AR拮抗剂报道。化合物2-18的结构活性关系与先前报道的2-芳基-1,2,4-三唑并[4,3-a]喹喔啉（A系列）和2-芳基吡唑并[3,4- c]喹啉（系列B），因此暗示了类似的AR绑定模式。实际上，已经确认了强酸性NH质子供体和位置4处的C = O质子受体对A3受体-配体相互作用的重要性，能够与A3
• Synthesis of some tricyclic heteroaromatic systems and their A1 and A2a adenosine binding activity
  作者：V Colotta、L Cecchi、D Catarzi、G Filacchioni、C Martini、P Tacchi、A Lucacchini

  DOI：10.1016/0223-5234(96)88218-3

  日期：1995.1

  The syntheses, A(1) and A(2a) adenosine receptor affinities and structure-activity relationships of some 2-aryl-1,2,4-triazolo[1,5-a]quinoxalines, 2-arylimidazo[1,2-a]quinoxalines, 1-arylimidazo[1,5-a]quinoxalines are reported and compared with that of a previously reported 2-phenylpyrazolo[1,5-a]quinoxaline. The results show that some triazoloquinoxalines are potent and specific A(1) adenosine receptor ligands and that the replacement of either nitrogen at position 1 or 3 of the triazoloquinoxaline moiety with a CH brought about a decrease in affinity at both adenosine receptors.