N-(4-(4-(2-(2-Fluoroethoxy)phenyl)piperazin-1-yl)butyl)pyrazolo[1,5-a]pyridine-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-(4-(4-(2-(2-Fluoroethoxy)phenyl)piperazin-1-yl)butyl)pyrazolo[1,5-a]pyridine-2-carboxamide
• 英文别名: N-[4-[4-[2-(2-fluoroethoxy)phenyl]piperazin-1-yl]butyl]pyrazolo[1,5-a]pyridine-2-carboxamide
• 化学式: C₂₄H₃₀FN₅O₂
• 分子量: 439.533
• InChiKey: ASYRWYXXPRLTPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-羟基苯基)哌嗪 在 lithium aluminium tetrahydride 、 potassium carbonate 、 caesium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 51.0h， 生成 N-(4-(4-(2-(2-Fluoroethoxy)phenyl)piperazin-1-yl)butyl)pyrazolo[1,5-a]pyridine-2-carboxamide
  参考文献：
  名称：

  Development of molecular tools based on the dopamine D3 receptor ligand FAUC 329 showing inhibiting effects on drug and food maintained behavior

  摘要：

  Dopamine D-3 receptor-mediated networks have been associated with a wide range of neuropsychiatric diseases, drug addiction and food maintained behavior, which makes D-3 a highly promising biological target. The previously described dopamine D-3 receptor ligand FAUC 329 (1) showed protective effects against dopamine depletion in a MPTP mouse model of Parkinson's disease. We used the radioligand [F-18]2, a [(18)]fluoroethoxy substituted analog of the lead compound 1 as a molecular tool for visualization of D-3-rich brain regions including the islands of Calleja. Furthermore, structural modifications are reported leading to the pyrimidylpiperazine derivatives 3 and 9 displaying superior subtype selectivity and preference over serotonergic receptors. Evaluation of the lead compound 1 on cocaine-seeking behavior in non-human primates showed a substantial reduction in cocaine self-administration behavior and food intake. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.04.036