N-(2-benzofuranylmethyl)-N'-[4-(2-tosyloxyethyl)benzyl]piperazine | 1345585-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-benzofuranylmethyl)-N'-[4-(2-tosyloxyethyl)benzyl]piperazine
• CAS: 1345585-71-8
• 化学式: C₂₉H₃₂N₂O₅S
• 分子量: 520.649
• InChiKey: WXHFWTGPFPNODB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(2-benzofuranylmethyl)-N'-[4-(2-tosyloxyethyl)benzyl]piperazine 在 Kryptofix222[18F]钾盐 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 N-(2-benzofuranylmethyl)-N'-[4-(2-fluoroethoxy)benzyl]piperazine
  参考文献：
  名称：

  Synthesis and in vivo evaluation of [18F]N-(2-benzofuranylmethyl)-N′-[4-(2-fluoroethoxy)benzyl]piperazine, a novel σ1 receptor PET imaging agent

  摘要：

  N-(2-Benzofuranylmethyl)-N'-[4-(2-fluoroethoxy)benzyl]piperazine (6, sigma(1) K-i = 2.6 nM) was radiolabeled with fluorine-18 to provide a potential sigma(1) receptor radioligand for use in positron emission tomography (PET). Radiofluorination of the appropriate tosylate precursor furnished [F-18]6 with a specific activity of 45 GBq/mu mol, in an average radiochemical yield of 18% and greater than 98% radiochemical purity. MicroPET imaging in Papio hamadryas baboon brain revealed [F-18]6 uptake consistent with sigma receptor distribution, and specificity for sigma receptors was demonstrated in a haloperidol pre-treated animal. [F-18]6 possesses suitable properties for PET imaging of sigma(1) receptors, and further investigation of this sigma(1) receptor tracer is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.028
• 作为产物：
  描述：

  N-((benzofuran-2-yl)methyl)-N'-(4'-hydroxybenzyl)piperazine 、 1,2-双甲苯氧基乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以61%的产率得到N-(2-benzofuranylmethyl)-N'-[4-(2-tosyloxyethyl)benzyl]piperazine
  参考文献：
  名称：

  Synthesis and in vivo evaluation of [18F]N-(2-benzofuranylmethyl)-N′-[4-(2-fluoroethoxy)benzyl]piperazine, a novel σ1 receptor PET imaging agent

  摘要：

  N-(2-Benzofuranylmethyl)-N'-[4-(2-fluoroethoxy)benzyl]piperazine (6, sigma(1) K-i = 2.6 nM) was radiolabeled with fluorine-18 to provide a potential sigma(1) receptor radioligand for use in positron emission tomography (PET). Radiofluorination of the appropriate tosylate precursor furnished [F-18]6 with a specific activity of 45 GBq/mu mol, in an average radiochemical yield of 18% and greater than 98% radiochemical purity. MicroPET imaging in Papio hamadryas baboon brain revealed [F-18]6 uptake consistent with sigma receptor distribution, and specificity for sigma receptors was demonstrated in a haloperidol pre-treated animal. [F-18]6 possesses suitable properties for PET imaging of sigma(1) receptors, and further investigation of this sigma(1) receptor tracer is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.028