1-[2-(4-hydroxyphenyl)phenyl]piperazine | 1450591-86-2

• 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: 1-[2-(4-hydroxyphenyl)phenyl]piperazine
• 英文别名: 1-[(4-hydroxyphenyl)phenyl]piperazine
• CAS: 1450591-86-2
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: YQJGHNXALFYTHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [11C]methyl iodide 、 1-[2-(4-hydroxyphenyl)phenyl]piperazine 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.05h， 生成 1-[2-(4-[11C]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：

  tert-butyl 4-[2-(4-acetoxyphenyl)phenyl]piperazine-1-carboxylate 在 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 1-[2-(4-hydroxyphenyl)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

文献信息

• Synthesis, radiolabeling and in vivo evaluation of [11C](R)-1-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol, a potential PET radioligand for the 5-HT7 receptor
  作者：Hanne D. Hansen、Enza Lacivita、Pantaleo Di Pilato、Matthias M. Herth、Szabolcs Lehel、Anders Ettrup、Valdemar L. Andersen、Agnete Dyssegaard、Paola De Giorgio、Roberto Perrone、Francesco Berardi、Nicola Antonio Colabufo、Mauro Niso、Gitte M. Knudsen、Marcello Leopoldo

  DOI：10.1016/j.ejmech.2014.03.066

  日期：2014.5

  novel serotonin 7 (5-HT7) receptor PET radioligand we synthesized and evaluated a new series of biphenylpiperazine derivatives in vitro. Among the studied compounds, (R)-1-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]-3-(2-pyrazinyloxy)-2-propanol ((R)-16), showed the best combination of affinity, selectivity, and lipophilicity, and was thus chosen for carbon-11 labelling and evaluation in pigs. After

  在寻找新型的5-羟色胺7（5-HT 7）受体PET放射性配体中，我们合成和评价了一系列的联苯哌嗪衍生物的体外新系列。在研究的化合物中，（R）-1- [4- [2-（4-甲氧基苯基）苯基]哌嗪-1-基] -3-（2-吡嗪基氧基）-2-丙醇（（R）-16），显示出亲和力，选择性和亲脂性的最佳组合，因此被选择用于猪的碳11标记和评估。静脉注射后，[ 11 C]（R）-16进入猪脑并显示出可逆的示踪动力学。用5-HT 7受体选择性拮抗剂SB-269970进行预处理（1）导致[ 11 C]（R）-16结合的有限减少，这表明该放射性配体不是在体内对大脑5-HT 7受体成像的最佳选择，但它可以作为新型化合物的先导化合物5-HT 7受体PET放射性配体。