<18F>-1-methyl-4-(2-fluorophenyl)-1,2,3,6-tetrahydropyridine

• 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: <18F>-1-methyl-4-(2-fluorophenyl)-1,2,3,6-tetrahydropyridine
• 英文别名: 4-(2-(18F)fluoranylphenyl)-1-methyl-3,6-dihydro-2H-pyridine
• 化学式: C₁₂H₁₄FN
• 分子量: 190.25
• InChiKey: OZOBAIOGYAVMGE-HSGWXFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-methyl-4-<2-(1-piperidinylazo)phenyl>-1,2,3,6-tetrahydropyridine 在 fluorine-18 、 甲烷磺酸 作用下， 反应 0.5h， 以4%的产率得到<18F>-1-methyl-4-(2-fluorophenyl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Design and synthesis of 18F-labeled neurotoxic analogs of MPTP

  摘要：

  We report on the synthesis of two fluorine-18 labeled analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). A piperidyl triazene was fluorinated to produce [F-18]-1-methyl-4-(2-fluorophenyl)-1,2,3,6-tetrahydropyridine (2'-F-MPTP, 12) in very low yield, and 1-methyl-4-[2-(fluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine (2'-FCH2-MPTP, 11) was labeled with F-18 by nucleophilic displacement of the corresponding chloride in 60% yield. The biodistribution in mice of the latter radiotracer and its oxidation to 1-methyl-4-[2-(fluoromethyl)phenyl]pyridinium (2'-FCH2-MPP+, 6) is also reported. The kinetics of oxidation of 2'-FCH2-MPTP and its solvolysis products (the corresponding 2'-hydroxymethyl and 2'-chloromethyl analogs) by rat liver monoamine oxidase were investigated. 2'-FCH2-MPTP accumulated to a useful degree in the brain, was oxidized by monoamine oxidase in vitro, was converted to the oxidation product in brain in vivo, and had a neurotoxic potency similar to that of MPTP. We feel it may be useful as an F-18-labeled radiopharmaceutical for positron tomographic studies of the mechanisms of MPTP toxicity.

  DOI：

  10.1021/jm00061a021

文献信息

• Design and synthesis of 18F-labeled neurotoxic analogs of MPTP
  作者：Marc S. Berridge、Lawrence M. Sayre、Pramod K. Arora、Andrew H. Terris、Naji J. Riachi、Sami I. Harik

  DOI：10.1021/jm00061a021

  日期：1993.4

  We report on the synthesis of two fluorine-18 labeled analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). A piperidyl triazene was fluorinated to produce [F-18]-1-methyl-4-(2-fluorophenyl)-1,2,3,6-tetrahydropyridine (2'-F-MPTP, 12) in very low yield, and 1-methyl-4-[2-(fluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine (2'-FCH2-MPTP, 11) was labeled with F-18 by nucleophilic displacement of the corresponding chloride in 60% yield. The biodistribution in mice of the latter radiotracer and its oxidation to 1-methyl-4-[2-(fluoromethyl)phenyl]pyridinium (2'-FCH2-MPP+, 6) is also reported. The kinetics of oxidation of 2'-FCH2-MPTP and its solvolysis products (the corresponding 2'-hydroxymethyl and 2'-chloromethyl analogs) by rat liver monoamine oxidase were investigated. 2'-FCH2-MPTP accumulated to a useful degree in the brain, was oxidized by monoamine oxidase in vitro, was converted to the oxidation product in brain in vivo, and had a neurotoxic potency similar to that of MPTP. We feel it may be useful as an F-18-labeled radiopharmaceutical for positron tomographic studies of the mechanisms of MPTP toxicity.