tert-butyl 4-(4-(2-fluoroethoxy)phenyl)piperazine-1-carboxylate | 913734-71-1

• 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-(4-(2-fluoroethoxy)phenyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[4-(2-fluoroethoxy)phenyl]piperazine-1-carboxylate
• CAS: 913734-71-1
• 化学式: C₁₇H₂₅FN₂O₃
• 分子量: 324.396
• InChiKey: WYGWIBJIVGZYMO-UHFFFAOYSA-N

物化性质

• 沸点：
  448.4±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-(2-fluoroethoxy)phenyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(4-(2-氟乙氧基)苯基)哌嗪
  参考文献：
  名称：

  Novel indole-based sigma-2 receptor ligands: synthesis, structure–affinity relationship and antiproliferative activity

  摘要：

  小说sigma-2 配体1b在DU145细胞中诱导G1期细胞周期停滞并显示抗增殖活性。

  DOI：

  10.1039/c5md00079c
• 作为产物：
  描述：

  1-溴-2-氟乙烷 、 1-Boc-4-(4-羟基苯基)-哌嗪 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以67%的产率得到tert-butyl 4-(4-(2-fluoroethoxy)phenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of novel WAY 100635 derivatives containing a norbornene group and radiofluorination of [¹⁸F]AH1.MZ as a serotonin 5-HT_1Areceptor antagonist for molecular imaging

  摘要：

  5-HT1A受体参与多种精神疾病，活体分子影像学中5-HT1A状态的检测是分析和治疗这些疾病的重要方法。本文报道了三种新的含氟乙基的5-HT1A配体（AH1.MZ、AH2.MZ和AH3.MZ）的合成，它们是含有降冰片烯基团的苯基哌嗪衍生物。AH1.MZ（Ki=4.2nM）和AH2.MZ（Ki=30nM）对5-HT1A受体表现出合理的体外亲和力，而AH3.MZ似乎对5-HT1A受体没有亲和力。AH1.MZ和AH2.MZ的受体特征显示在5-HT系统内的选择性。通过[18F]FETos对[18F]AH1.MZ进行18F标记的放射化学产率>70%。注射液的最终配方包括[18F]FETos前体合成、放射合成和半制备高效液相色谱（HPLC）分离，整个过程不超过130分钟，并通过分析HPLC分析表明[18F]AH1.MZ的纯度>98%。版权所有 © 2009 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1589

文献信息

• Synthesis of novel WAY 100635 derivatives containing a norbornene group and radiofluorination of [¹⁸F]AH1.MZ as a serotonin 5-HT_1Areceptor antagonist for molecular imaging
  作者：Matthias M. Herth、Vasko Kramer、Frank Rösch

  DOI：10.1002/jlcr.1589

  日期：2009.5.30

  5-HT1A receptors are involved in a variety of psychiatric disorders and in vivo molecular imaging of the 5-HT1A status represents an important approach to analyze and treat these disorders. We report herein the synthesis of three new fluoroethylated 5-HT1A ligands (AH1.MZ, AH2.MZ and AH3.MZ) as arylpiperazine derivatives containing a norbornene group. AH1.MZ (Ki= 4.2 nM) and AH2.MZ (Ki=30 nM) showed reasonable in vitro affinities to the 5-HT1A receptor, whereas AH3.MZ appeared to be non-affine toward the 5-HT1A receptor. The receptor profile of AH1.MZ and AH2.MZ showed selectivity within the 5-HT system. 18F-labelling via [18F]FETos to [18F]AH1.MZ was carried out in radiochemical yields of >70%. The final formulation of injectable solutions including [18F]FETos synthon synthesis, radiosynthesis and semi-preparative high-performance liquid chromatography (HPLC) separation took no longer than 130 min and provided [18F]AH1.MZ with a purity of  >98% as indicated by analytical HPLC analyses. Copyright © 2009 John Wiley & Sons, Ltd.

  5-HT1A受体参与多种精神疾病，活体分子影像学中5-HT1A状态的检测是分析和治疗这些疾病的重要方法。本文报道了三种新的含氟乙基的5-HT1A配体（AH1.MZ、AH2.MZ和AH3.MZ）的合成，它们是含有降冰片烯基团的苯基哌嗪衍生物。AH1.MZ（Ki=4.2nM）和AH2.MZ（Ki=30nM）对5-HT1A受体表现出合理的体外亲和力，而AH3.MZ似乎对5-HT1A受体没有亲和力。AH1.MZ和AH2.MZ的受体特征显示在5-HT系统内的选择性。通过[18F]FETos对[18F]AH1.MZ进行18F标记的放射化学产率>70%。注射液的最终配方包括[18F]FETos前体合成、放射合成和半制备高效液相色谱（HPLC）分离，整个过程不超过130分钟，并通过分析HPLC分析表明[18F]AH1.MZ的纯度>98%。版权所有 © 2009 John Wiley & Sons, Ltd.
• LIGANDS FOR IMAGING CARDIAC INNERVATION
  申请人：Purohit Ajay

  公开号：US20100221182A1

  公开（公告）日：2010-09-02

  Novel compounds that find use as imaging agents within nuclear medicine applications (PET imaging) for imaging of cardiac innervation are disclosed. These PET based radiotracers may exhibit increased stability, decreased NE release (thereby reducing side effects), improved quantitative data, and/or high affinity for VMAT over prior radiotracers. Methods of using the compounds to image cardiac innervation are also provided. In some instances the compounds are developed by derivatizing certain compounds with 18 F in a variety of positions: aryl, alkyl, a keto, benzylic, beta-alkylethers, gamma-propylalkylethers and beta-proplylalkylethers. Alternatively or additionally, a methyl group a is added to the amine, and/or the catechol functionality is either eliminated or masked as a way of making these compounds more stable.

  本发明揭示了一种新型化合物，可用作核医学应用（PET成像）中的成像剂，用于成像心脏神经。这些基于PET的放射性示踪剂可能表现出增加的稳定性，减少NE释放（从而减少副作用），改善定量数据和/或高亲和力，以VMAT优于先前的放射性示踪剂。还提供了使用这些化合物成像心脏神经的方法。在某些情况下，这些化合物是通过在各种位置上衍生化某些化合物与18F而开发出来的：芳基，烷基，酮，苄基，β-烷基醚，γ-丙基烷基醚和β-丙基烷基醚。或者，还可以添加甲基基团到胺中，和/或消除或掩盖儿茶酚的功能，以使这些化合物更加稳定。
• Ligands for imaging cardiac innervation
  申请人：Purohit Ajay

  公开号：US08491868B2

  公开（公告）日：2013-07-23

  Novel compounds that find use as imaging agents within nuclear medicine applications (PET imaging) for imaging of cardiac innervation are disclosed. These PET based radiotracers may exhibit increased stability, decreased NE release (thereby reducing side effects), improved quantitative data, and/or high affinity for VMAT over prior radiotracers. Methods of using the compounds to image cardiac innervation are also provided. In some instances the compounds are developed by derivatizing certain compounds with 18F in a variety of positions: aryl, alkyl, a keto, benzylic, beta-alkylethers, gamma-propylalkylethers and beta-proplylalkylethers. Alternatively or additionally, a methyl group a is added to the amine, and/or the catechol functionality is either eliminated or masked as a way of making these compounds more stable.

  本发明公开了一种新型化合物，其可用作核医学应用（PET成像）中的成像剂，用于成像心脏神经。这些基于PET的放射性示踪剂可能表现出增加的稳定性、减少NE释放（从而减少副作用）、改善的定量数据和/或高亲和力，以VMAT优于先前的放射性示踪剂。还提供了使用这些化合物成像心脏神经的方法。在某些情况下，这些化合物是通过在各种位置上衍生化某些化合物与18F相结合而开发的：芳基，烷基，酮基，苄基，β-烷基醚，γ-丙基烷基醚和β-丙基烷基醚。或者，还可以在胺基上添加甲基，和/或消除或掩盖儿茶酚的功能，以使这些化合物更加稳定。
• WO2008/83056
  申请人：——

  公开号：——

  公开（公告）日：——
• N-[3-BROMO-4-(3- [18F]FLUOROPROPOXY)-BENZYL]-GUANIDINE FOR IMAGING CARDIAC INNERVATION
  申请人：Lantheus Medical Imaging, Inc.

  公开号：EP2114873B1

  公开（公告）日：2013-02-20