N-[4-(4-aminophenyl)butyl]-3α-[bis(4'-fluorophenyl)methoxy]tropane | 203048-97-9

• 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: N-[4-(4-aminophenyl)butyl]-3α-[bis(4'-fluorophenyl)methoxy]tropane
• CAS: 203048-97-9
• 化学式: C₃₀H₃₄F₂N₂O
• 分子量: 476.61
• InChiKey: SHGBXYCHZGQKIJ-WLNZHLEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[4-(4-aminophenyl)butyl]-3α-[bis(4'-fluorophenyl)methoxy]tropane 在 一氯化碘 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以57%的产率得到
  参考文献：
  名称：

  A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane

  摘要：

  A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3 alpha-[bis(4'-fluorophenyl)methoxy]tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the I-125 analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10139-1
• 作为产物：
  描述：

  nor-3α-[bis(4'-fluorophenyl)methoxy]tropane 在 palladium on activated charcoal aluminium hydride 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 N-[4-(4-aminophenyl)butyl]-3α-[bis(4'-fluorophenyl)methoxy]tropane
  参考文献：
  名称：

  A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane

  摘要：

  A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3 alpha-[bis(4'-fluorophenyl)methoxy]tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the I-125 analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10139-1

文献信息

• Novel Tropane-Based Irreversible Ligands for the Dopamine Transporter
  作者：Mu-Fa Zou、Theresa Kopajtic、Jonathan L. Katz、Sara Wirtz、Joseph B. Justice,、Amy Hauck Newman

  DOI：10.1021/jm0101904

  日期：2001.12.1

  3alpha-(diphenylmethoxy)tropane (benztropine) and its analogues are tropane ring-containing dopamine uptake inhibitors that display binding and behavioral profiles that are distinct from cocaine. We previously prepared a benztropine-based photoaffinity label [125I]-(N-[4-(4'-azido-3'-iodophenyl)butyl]-3alpha-[bis(4'-fluorophenyl)methoxy]tropane, [125I]1, that covalently attached to the 1-2 transmembrane

  3alpha-（二苯基甲氧基）托烷（苯并tro庚因）及其类似物是含托烷环的多巴胺摄取抑制剂，其表现出与可卡因不同的结合和行为特征。我们先前曾制备过基于苯氧平的光亲和标记[125I]-（N- [4-（4'-叠氮基3'-碘苯基）丁基] -3alpha- [双（4'-氟苯基）甲氧基]托烷，[125I] 1，与多巴胺转运蛋白（DAT）的1-2跨膜跨区共价连接，这与可卡因基光亲和标记[125I] 2（RTI 82）标记的4-7跨膜跨区相反。为了进一步表征这些不同的结合结构域，具有从托烷环的相同位置延伸的4'-叠氮基-3'-碘苯基取代基的光亲和配体是理想的。为了确定最终的相同的N-取代的2的类似物，研究了鉴定该取代基与苯并氮平系列中的烷烃氮之间的最佳烷基接头的方法。为此，N- [4-（4'-azido-3'-合成了3α-[双（4'-氟苯基）甲氧基]托烷的碘代苯基）丙基]类似物（9a），以及不需要不可逆
• A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane
  作者：Gregory E. Agoston、Roxanne Vaughan、John R. Lever、Sari Izenwasser、Phyllis D. Terry、Amy Hauck Newman

  DOI：10.1016/s0960-894x(97)10139-1

  日期：1997.12

  A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3 alpha-[bis(4'-fluorophenyl)methoxy]tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the I-125 analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT. Published by Elsevier Science Ltd.