(R/S)-1-<3-(5-hydroxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl>-4-phenylpiperazine | 214957-39-8

• 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: (R/S)-1-<3-(5-hydroxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl>-4-phenylpiperazine
• CAS: 214957-39-8
• 化学式: C₂₃H₃₀N₂O
• 分子量: 350.504
• InChiKey: PTUGBNSJPFUESG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.71
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [11C]methyl iodide 、 (R/S)-1-<3-(5-hydroxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl>-4-phenylpiperazine 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R/S)--1-<3-(5-methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl>-4-phenylpiperazine
  参考文献：
  名称：

  Synthesis and Biodistribution of (R,S)-[O-Methyl-11C]-1-[3-(5-Methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl]-4-Phenylpiperazine (PNU-157760), A Putative Radioligand for 5-HT1AReceptors

  摘要：

  Racemic 1-[3-(5-methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl]-4-phenylpiperazine (PNU-157760) was labeled with carbon-11 (t(1/2) = 20.4 min) as a putative radioligand for the noninvasive assessment of 5-HT1A receptors in vivo with positron emission tomography (PET). The radiochemical synthesis consisted of O-methylation of desmethyl precursor with [C-11]methyl iodide in the presence of potassium tert-butoxide in DMF. The desmethyl precursor for the radiosynthesis of [C-11]PNU-157760, was prepared by a convenient one-step demethylation of PNU-157760 with boron tribromide. (R,S)-[O-Methyl-C-11]-1-[3-(5-methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl] with >99% radiochemical purity was obtained in 30 min with a radiochemical yield of 10 +/- 5% (EOS, nondecay corrected) and a specific radioactivity of 2.5 +/- 1 Ci/mu mol. Biodistribution studies in rats showed that [C-11]PNU-157760 readily crosses the blood-brain barrier with a maximum of brain uptake at 30 min after injection; however, the low specific-to-nonspecific binding ratio in vivo as evidenced by the low hippocampus/cerebellum uptake ratio (1.17 at 60 min postinjection) does not make [C-11]PNU-157760 a promising radioligand for serotonin 5-HT1A receptors. (C) 1998 Academic Press

  DOI：

  10.1006/bioo.1998.1089
• 作为产物：
  描述：

  1-phenyl-4-[3-(1,2,3,4-tetrahydro-5-methoxy-1-naphthalenyl)propyl]piperazine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到(R/S)-1-<3-(5-hydroxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl>-4-phenylpiperazine
  参考文献：
  名称：

  Synthesis and Biodistribution of (R,S)-[O-Methyl-11C]-1-[3-(5-Methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl]-4-Phenylpiperazine (PNU-157760), A Putative Radioligand for 5-HT1AReceptors

  摘要：

  Racemic 1-[3-(5-methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl]-4-phenylpiperazine (PNU-157760) was labeled with carbon-11 (t(1/2) = 20.4 min) as a putative radioligand for the noninvasive assessment of 5-HT1A receptors in vivo with positron emission tomography (PET). The radiochemical synthesis consisted of O-methylation of desmethyl precursor with [C-11]methyl iodide in the presence of potassium tert-butoxide in DMF. The desmethyl precursor for the radiosynthesis of [C-11]PNU-157760, was prepared by a convenient one-step demethylation of PNU-157760 with boron tribromide. (R,S)-[O-Methyl-C-11]-1-[3-(5-methoxy-1,2,3,4-tetrahydro-1-naphtalenyl)propyl] with >99% radiochemical purity was obtained in 30 min with a radiochemical yield of 10 +/- 5% (EOS, nondecay corrected) and a specific radioactivity of 2.5 +/- 1 Ci/mu mol. Biodistribution studies in rats showed that [C-11]PNU-157760 readily crosses the blood-brain barrier with a maximum of brain uptake at 30 min after injection; however, the low specific-to-nonspecific binding ratio in vivo as evidenced by the low hippocampus/cerebellum uptake ratio (1.17 at 60 min postinjection) does not make [C-11]PNU-157760 a promising radioligand for serotonin 5-HT1A receptors. (C) 1998 Academic Press

  DOI：

  10.1006/bioo.1998.1089