(+/-)-2-[18F]fluoropropionic acid chloride | 114435-84-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (+/-)-2-[18F]fluoropropionic acid chloride
• 英文别名: (+/-)-2-(18F)fluoropropionyl chloride
• CAS: 114435-84-6
• 化学式: C₃H₄ClFO
• 分子量: 109.517
• InChiKey: SEZRREGFJFZQQD-SFIIULIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-苯基-1-(2-苯乙基)-4-哌啶胺 、 (+/-)-2-[18F]fluoropropionic acid chloride 以 四氢呋喃 为溶剂， 以36%的产率得到2-(18F)fluoranyl-N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
  参考文献：
  名称：

  Syntheses, Biological Evaluation, and Molecular Modeling of ¹⁸F-Labeled 4-Anilidopiperidines as μ-Opioid Receptor Imaging Agents

  摘要：

  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.

  DOI：

  10.1021/jm0507274
• 作为产物：
  描述：

  2-bromopropionic acid 9'-anthrylmethyl ester 在 [K/K₂₂₂]⁺(18F)^- 、 四甲基氢氧化铵 、 邻苯二甲酰氯 作用下， 以 乙腈 、 四氢呋喃 为溶剂， 生成 (+/-)-2-[18F]fluoropropionic acid chloride
  参考文献：
  名称：

  Syntheses, Biological Evaluation, and Molecular Modeling of ¹⁸F-Labeled 4-Anilidopiperidines as μ-Opioid Receptor Imaging Agents

  摘要：

  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.

  DOI：

  10.1021/jm0507274

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.