4-[[4-(4-Methylphenyl)piperazin-1-yl]methyl]benzonitrile | 1012884-83-1

• 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: 4-[[4-(4-Methylphenyl)piperazin-1-yl]methyl]benzonitrile
• CAS: 1012884-83-1
• 化学式: C₁₉H₂₁N₃
• 分子量: 291.396
• InChiKey: TVDCXHFTHLOKKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-甲基苯基)哌嗪 、 对氰基溴化苄 在 triazolylmethyl acrylate resin 、 N-甲基吡咯烷酮 、 TEA 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 4-[[4-(4-Methylphenyl)piperazin-1-yl]methyl]benzonitrile
  参考文献：
  名称：

  Discovery of a dopamine D4 selective PET ligand candidate taking advantage of a click chemistry based REM linker

  摘要：

  Employing D4 selective azaindoles as lead compounds, a focused library of the carbocyclic arene bioisosteres 1 was synthesized when we took advantage of the click chemistry derived triazolylmethyl acrylate resin 2. Ligand binding assays on monoaminergic GPCRs led to SARs that indicated further lead structure optimizations when the attachment of alkoxy substituents provided both an improvement of the biological properties and the opportunity to introduce F-18 as a radioisotope. Finally, radiosynthesis resulted in formation of the radioligand [F-18]7h that showed optimal logD(7.4) of 2.8 and was determined to be highly stable in human serum. Thus, [F-18]7h represents a promising dopamine D4 selective radioligand for positron emission tomography (PET). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.026

文献信息

• Discovery of a dopamine D4 selective PET ligand candidate taking advantage of a click chemistry based REM linker
  作者：Rainer Tietze、Stefan Löber、Harald Hübner、Peter Gmeiner、Torsten Kuwert、Olaf Prante

  DOI：10.1016/j.bmcl.2007.12.026

  日期：2008.2

  Employing D4 selective azaindoles as lead compounds, a focused library of the carbocyclic arene bioisosteres 1 was synthesized when we took advantage of the click chemistry derived triazolylmethyl acrylate resin 2. Ligand binding assays on monoaminergic GPCRs led to SARs that indicated further lead structure optimizations when the attachment of alkoxy substituents provided both an improvement of the biological properties and the opportunity to introduce F-18 as a radioisotope. Finally, radiosynthesis resulted in formation of the radioligand [F-18]7h that showed optimal logD(7.4) of 2.8 and was determined to be highly stable in human serum. Thus, [F-18]7h represents a promising dopamine D4 selective radioligand for positron emission tomography (PET). (C) 2007 Elsevier Ltd. All rights reserved.