tert-butyl 4-[2-(4-methoxyphenyl)phenyl]piperazine-1-carboxylate | 1450591-87-3

• 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: tert-butyl 4-[2-(4-methoxyphenyl)phenyl]piperazine-1-carboxylate
• CAS: 1450591-87-3
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: QUUYBIRVRUHLIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  42.01
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[2-(4-methoxyphenyl)phenyl]piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到1-[2-(4-methoxyphenyl)phenyl]piperazine
  参考文献：
  名称：

  Synthesis and evaluation of 1-[2-(4-[11C]methoxyphenyl)phenyl]piperazine for imaging of the serotonin 5-HT7 receptor in the rat brain

  摘要：

  1-[2-(4-Methoxyphenyl)phenyllpiperazine (4) is a potent serotonin 5-HT7 receptor antagonist (K-i; = 2.6 nM) with a low binding affinity for the 5-HT1A receptor (Ki = 476 nM). As a potential positron emission tomography (PET) radiotracer for the 5-HT7 receptor, [C-11](4) was synthesized at high radiochemical yield and specific activity, by O-[C-11]methylation of 2'-(piperazin-1-yl)[1,1'-biphenyl]-4-ol (6) with [C-11]methyl iodide. Autoradiography revealed that [C-11](4) showed in vitro specific binding with 5-HT7 in the rat brain regions, such as the thalamus which is a region with high 5-HT7 expression. Metabolite analysis indicated that intact [C-11](4) in the brain exceeded 90% of the radioactive components at 15 min after the radiotracer injection, although two radiolabeled metabolites were found in the rat plasma. The PET study of rats showed moderated uptake of [C-11](4) in the brain (1.2 SUV), but no significant regional difference in radioactivity in the brain. Pretreatment with 5-HT7-selective antagonist SB269970 (3) did not decrease the uptake of [C-11](4) in the rat brain. Further studies are warranted that focus on the development of PET ligand candidates with higher binding affinity for 5-HT7 and higher in vivo stability in brain than 4. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.020
• 作为产物：
  描述：

  邻碘溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 乙二醇二甲醚 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 tert-butyl 4-[2-(4-methoxyphenyl)phenyl]piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of 1-[2-(4-[11C]methoxyphenyl)phenyl]piperazine for imaging of the serotonin 5-HT7 receptor in the rat brain

  摘要：

  1-[2-(4-Methoxyphenyl)phenyllpiperazine (4) is a potent serotonin 5-HT7 receptor antagonist (K-i; = 2.6 nM) with a low binding affinity for the 5-HT1A receptor (Ki = 476 nM). As a potential positron emission tomography (PET) radiotracer for the 5-HT7 receptor, [C-11](4) was synthesized at high radiochemical yield and specific activity, by O-[C-11]methylation of 2'-(piperazin-1-yl)[1,1'-biphenyl]-4-ol (6) with [C-11]methyl iodide. Autoradiography revealed that [C-11](4) showed in vitro specific binding with 5-HT7 in the rat brain regions, such as the thalamus which is a region with high 5-HT7 expression. Metabolite analysis indicated that intact [C-11](4) in the brain exceeded 90% of the radioactive components at 15 min after the radiotracer injection, although two radiolabeled metabolites were found in the rat plasma. The PET study of rats showed moderated uptake of [C-11](4) in the brain (1.2 SUV), but no significant regional difference in radioactivity in the brain. Pretreatment with 5-HT7-selective antagonist SB269970 (3) did not decrease the uptake of [C-11](4) in the rat brain. Further studies are warranted that focus on the development of PET ligand candidates with higher binding affinity for 5-HT7 and higher in vivo stability in brain than 4. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.020