N-(4-(4-(2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)benzo[b]thiophene-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-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)benzo[b]thiophene-2-carboxamide
• 英文别名: N-[4-[4-[2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl]butyl]-1-benzothiophene-2-carboxamide
• 化学式: C₂₆H₃₂F₃N₅OS
• 分子量: 519.634
• InChiKey: XTFNKHQCBITNPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-(tert-butyl)-6-(piperazin-1-yl)-2-(trifluoromethyl)pyrimidine 在 lithium aluminium tetrahydride 、 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 37.0h， 生成 N-(4-(4-(2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)benzo[b]thiophene-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

文献信息

• USE OF DOPAMINE D3 RECEPTOR LIGANDS FOR THE PRODUCTION OF DRUGS FOR TREATING RENAL FUNCTION DISORDERS
  申请人：Muhlbauer Bernd

  公开号：US20060223793A1

  公开（公告）日：2006-10-05

  The invention relates to the use of dopamine D 3 receptor ligands for the production of drugs for treating renal function disorders.

  本发明涉及使用多巴胺 D 3 受体配体生产治疗肾功能紊乱的药物。
• US7098214B1
  申请人：——

  公开号：US7098214B1

  公开（公告）日：2006-08-29
• US8785447B2
  申请人：——

  公开号：US8785447B2

  公开（公告）日：2014-07-22
• Development of molecular tools based on the dopamine D3 receptor ligand FAUC 329 showing inhibiting effects on drug and food maintained behavior
  作者：Anne Stößel、Regine Brox、Nirupam Purkayastha、Harald Hübner、Carsten Hocke、Olaf Prante、Peter Gmeiner

  DOI：10.1016/j.bmc.2017.04.036

  日期：2017.7

  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.