N-((benzofuran-2-yl)methyl)-N'-(3'-(3''-fluoropropoxy)benzyl)piperazine | 1239983-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-((benzofuran-2-yl)methyl)-N'-(3'-(3''-fluoropropoxy)benzyl)piperazine
• 英文别名: 1-(1-Benzofuran-2-ylmethyl)-4-[[3-(3-fluoropropoxy)phenyl]methyl]piperazine
• CAS: 1239983-31-3
• 化学式: C₂₃H₂₇FN₂O₂
• 分子量: 382.478
• InChiKey: YVFOUXAUJUJYKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-((benzofuran-2-yl)methyl)-N'-(3'-hydroxybenzyl)piperazine 、 3-氟甲苯磺酸丙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以62%的产率得到N-((benzofuran-2-yl)methyl)-N'-(3'-(3''-fluoropropoxy)benzyl)piperazine
  参考文献：
  名称：

  Design, Synthesis, and Structure−Affinity Relationships of Regioisomeric N-Benzyl Alkyl Ether Piperazine Derivatives as σ-1 Receptor Ligands

  摘要：

  A series of N-(benzofuran-2-ylmethyl)-N'-benzylpiperazines bearing alkyl or fluoroalkyl aryl ethers were synthesized and evaluated at various central nervous system receptors. Examination of in vitro sigma(1) {[H-3](+)-pentazocinel and sigma(2) ([H-3]DTG) receptor binding profiles of piperazines 11-13 and 25-36 revealed several highly potent and sigma(1) selective ligands, notably, N-(benzofuran-2-ylmethyl)-N'-(4'-methoxybenzyl)piperazine (13, K-i = 2.7 nM, sigma(2)/sigma(1) = 38) and N-(benzofuran-2-ylmethyl)-N'-(4'-(2 ''-fluoroethoxy)benzyl)piperazine (30, K-i = 2.6 nM, sigma(2)/sigma(1) = 187). Structural features for optimal sigma(1) receptor affinity and selectivity over the 07 receptor were identified. On the basis of its favorable log D value, 13 was selected as a candidate for the development of a sigma(1) receptor positron emission tomography radiotracer. [C-11]13 showed high uptake in the brain and other a receptor-rich organs of a Papio hamadryas baboon. The in vivo evaluation of [C-11]13 indicates that this radiotracer is a suitable candidate for imaging the sigma(1) receptor in neurodegenerative processes.

  DOI：

  10.1021/jm100639f

文献信息

• Design, Synthesis, and Structure−Affinity Relationships of Regioisomeric <i>N</i>-Benzyl Alkyl Ether Piperazine Derivatives as σ-1 Receptor Ligands
  作者：Iman A. Moussa、Samuel D. Banister、Corinne Beinat、Nicolas Giboureau、Aaron J. Reynolds、Michael Kassiou

  DOI：10.1021/jm100639f

  日期：2010.8.26

  A series of N-(benzofuran-2-ylmethyl)-N'-benzylpiperazines bearing alkyl or fluoroalkyl aryl ethers were synthesized and evaluated at various central nervous system receptors. Examination of in vitro sigma(1) [H-3](+)-pentazocinel and sigma(2) ([H-3]DTG) receptor binding profiles of piperazines 11-13 and 25-36 revealed several highly potent and sigma(1) selective ligands, notably, N-(benzofuran-2-ylmethyl)-N'-(4'-methoxybenzyl)piperazine (13, K-i = 2.7 nM, sigma(2)/sigma(1) = 38) and N-(benzofuran-2-ylmethyl)-N'-(4'-(2 ''-fluoroethoxy)benzyl)piperazine (30, K-i = 2.6 nM, sigma(2)/sigma(1) = 187). Structural features for optimal sigma(1) receptor affinity and selectivity over the 07 receptor were identified. On the basis of its favorable log D value, 13 was selected as a candidate for the development of a sigma(1) receptor positron emission tomography radiotracer. [C-11]13 showed high uptake in the brain and other a receptor-rich organs of a Papio hamadryas baboon. The in vivo evaluation of [C-11]13 indicates that this radiotracer is a suitable candidate for imaging the sigma(1) receptor in neurodegenerative processes.