N-cyclopentyl-1-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amine | 113181-12-7

• 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: N-cyclopentyl-1-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amine
• 英文别名: N-cyclopentyl-1-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-amine
• CAS: 113181-12-7
• 化学式: C₁₅H₁₇N₅
• 分子量: 267.333
• InChiKey: CFMVTSSGFWTRML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-3-肼基喹噁啉 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 N-cyclopentyl-1-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4-amine
  参考文献：
  名称：

  [1,2,4]Triazolo[4,3-a]quinoxalin-4-amines: a new class of A1 receptor selective adenosine antagonists

  摘要：

  Several [1,2,4]triazolo[4,3-a]quinoxalines that were reported as antidepressants in the patent literature were found to possess moderate affinity for the adenosine A1 and A2 receptors. On the basis of structural parallels with adenine and adenosine, the N-cyclopentyl derivative was synthesized and found to have improved affinity and selectivity for the A1 receptor. In the N-cyclopentyl series, affinity was optimal with trifluoromethyl substitution at the 1-position, resulting in a compound (9) with 7.3 nM A1 affinity and 138-fold selectivity for the A1 receptor.

  DOI：

  10.1021/jm00400a021

文献信息

• (1,2,4)triazolo(4,3-a)quinoxaline-4-amines
  申请人：Warner-Lambert Company

  公开号：US04780464A1

  公开（公告）日：1988-10-25

  A unique series of [1,2,4]triazolo[4,3-a] quinoxaline-4-amine derivatives which show excellent binding affinity at both the A.sub.1 and A.sub.2 adenosine receptor sites. The compounds are useful in treating depression, fatigue, and heart failure. Also disclosed are methods for preparing the compounds, compositions containing the compounds and methods for using them.

  一系列独特的[1,2,4]三唑并[4,3-a]喹喔啉-4-胺衍生物，显示出在A.sub.1和A.sub.2腺苷受体位点上出色的结合亲和力。这些化合物可用于治疗抑郁症、疲劳和心力衰竭。还公开了制备这些化合物的方法、含有这些化合物的组合物以及使用它们的方法。
• US4780464A
  申请人：——

  公开号：US4780464A

  公开（公告）日：1988-10-25
• [1,2,4]Triazolo[4,3-a]quinoxalin-4-amines: a new class of A1 receptor selective adenosine antagonists
  作者：Bharat K. Trivedi、Robert F. Bruns

  DOI：10.1021/jm00400a021

  日期：1988.5

  Several [1,2,4]triazolo[4,3-a]quinoxalines that were reported as antidepressants in the patent literature were found to possess moderate affinity for the adenosine A1 and A2 receptors. On the basis of structural parallels with adenine and adenosine, the N-cyclopentyl derivative was synthesized and found to have improved affinity and selectivity for the A1 receptor. In the N-cyclopentyl series, affinity was optimal with trifluoromethyl substitution at the 1-position, resulting in a compound (9) with 7.3 nM A1 affinity and 138-fold selectivity for the A1 receptor.