(+/-)-N-phenyl-N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-2-fluoropropanamide

• 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-phenyl-N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-2-fluoropropanamide
• 英文别名: 2-Fluoro-N-[4-methoxymethyl-1-(2-thiophen-2-yl-ethyl)-piperidin-4-yl]-N-phenyl-propionamide；2-fluoro-N-[4-(methoxymethyl)-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-N-phenylpropanamide
• 化学式: C₂₂H₂₉FN₂O₂S
• 分子量: 404.549
• InChiKey: JSQPDFXSOMVVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-2-fluoropropionyl chloride 、 舒芬太尼杂质 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (+/-)-N-phenyl-N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-2-fluoropropanamide
  参考文献：
  名称：

  18F-Labeled sufentanil for PET-imaging of μ-opioid receptors

  摘要：

  The synthesis of an F-18-labeled sufentanil analogue with apparent high mu-opioid receptor selectivity is reported. Intravenous injection of N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-N-phenyl-2-(+/-)-[F-18]fluoropropan-amide in mice resulted in high brain uptake and a regional brain activity distribution corresponding to the mu-opioid receptor expression pattern. The developed ligand is a promising tracer for extended protocols in mu-opioid receptor mapping and quantitation with positron emission tomography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.049

文献信息

• 18F-Labeled sufentanil for PET-imaging of μ-opioid receptors
  作者：Gjermund Henriksen、Stefan Platzer、Andrea Hauser、Frode Willoch、Achim Berthele、Markus Schwaiger、Hans-Jürgen Wester

  DOI：10.1016/j.bmcl.2005.02.049

  日期：2005.4

  The synthesis of an F-18-labeled sufentanil analogue with apparent high mu-opioid receptor selectivity is reported. Intravenous injection of N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-N-phenyl-2-(+/-)-[F-18]fluoropropan-amide in mice resulted in high brain uptake and a regional brain activity distribution corresponding to the mu-opioid receptor expression pattern. The developed ligand is a promising tracer for extended protocols in mu-opioid receptor mapping and quantitation with positron emission tomography. (c) 2005 Elsevier Ltd. All rights reserved.
• Syntheses, Biological Evaluation, and Molecular Modeling of ¹⁸F-Labeled 4-Anilidopiperidines as μ-Opioid Receptor Imaging Agents
  作者：Gjermund Henriksen、Stefan Platzer、János Marton、Andrea Hauser、Achim Berthele、Markus Schwaiger、Luciana Marinelli、Antonio Lavecchia、Ettore Novellino、Hans-Jürgen Wester

  DOI：10.1021/jm0507274

  日期：2005.12.1

  The synthesis, evaluation, and molecular modeling of a series of F-18-labeled 4-anilidopiperidines with high affinities for they-opioid receptor (mu-OR) are reported. On the basis of the high brain uptake and selective retention in brain regions that contain a high concentration of they-OR, combined with a good metabolic stability, [F-18]fluoro-pentyl carfentanil ([F-18]4) and 2-(+/-)[F-18]-fluoropropyl-sufentanil ([F-18]6) were selected as the lead compounds for further evaluation. The binding affinity to the human mu-OR was 0.74 and 0.13 nM for [F-18]4 and [F-18]6, respectively. In vitro autoradiography of [F-18]4 and [F-18]6 on rat brain sections produced patterns in accordance with the known distribution of mu-OR expression. Structure-activity relationships of the fluorinated compounds are discussed with respect to the interaction with an activated-state model of the mu-OR. Taken together, the in vivo and in vitro data indicate that [F-18]4 and [F-18]6 hold promise for studying they-opioid receptor in humans by means of positron emission tomography.