5-[18F]fluoropentyl bromide | 872043-56-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 5-[18F]fluoropentyl bromide
• CAS: 872043-56-6
• 化学式: C₅H₁₀BrF
• 分子量: 168.038
• InChiKey: GMYIZICPHREVDH-JZRMKITLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  7.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  5-[18F]fluoropentyl bromide 、 4-(苯基丙酰氨基)哌啶-4-羧酸甲酯 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以57%的产率得到methyl 1-(5-(18F)fluoranylpentyl)-4-(N-propanoylanilino)piperidine-4-carboxylate
  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：

  1,5-二溴戊烷 在 [K/K₂₂₂]⁺(18F)^- 作用下， 以 乙腈 为溶剂， 反应 0.13h， 生成 5-[18F]fluoropentyl bromide
  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