7-bromo-8-methoxy-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine | 136247-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-bromo-8-methoxy-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
• 英文别名: 8-Methoxy-7-bromo-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine；4-(8-Bromo-7-methoxy-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-5-yl)aniline
• CAS: 136247-22-8
• 化学式: C₁₈H₂₁BrN₂O
• 分子量: 361.282
• InChiKey: WPIFRULRSUCIFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-bromo-8-methoxy-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以62%的产率得到7-bromo-8-hydroxy-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  Fluorescent probes for dopamine receptors: synthesis and characterization of fluorescein and 7-nitrobenz-2-oxa-1,3-diazol-4-yl conjugates of D-1 and D-2 receptor ligands

  摘要：

  Fluorescent probes have been designed and developed for dopamine D-1 and D-2 receptors. Fluorescein and/or NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl) derivatives of PPHT (D-2 agonist), spiperone (D-2 antagonist), SKF 38393 (D-1 agonist), and SKF 83566 (D-1 antagonist) were synthesized via their amino-functionalized analogues and all ligands were pharmacologically evaluated by measuring their ability to displace [H-3]SCH 23390 and [H-3]spiperone from D-1 and D-2 receptor sites in caudate putamen of monkeys (Macaca fascicularis). The fluorescein derivatives of PPHT and SKF 83566 and the NBD derivatives of spiperone and SKF 83566 retained the high affinity and selectivity of the parent ligands. The NBD derivatives of PPHT showed higher D-2 receptor affinity and selectivity than their parent ligands. The enantiomers of the fluorescent derivatives of PPHT were also synthesized and were found to exhibit stereoselectivity in binding to the D-2 receptor, with the S enantiomers having a considerably higher affinity than their R analogues. In contrast to these results, the fluorescein derivative of SKF 38393 showed only a low affinity for the D-1 receptor. These fluorescein- and NBD-coupled D-1 and D-2 receptor ligands have considerable significance as potential probes in the study of distribution of the receptors at the cellular/subcellular level and of their mobility in membranes in normal/diseased states by use of fluorescence microscopic and fluorescence photobleaching recovery techniques, respectively. The development of these novel fluorescent probes should also provide new leads for the design and synthesis of additional fluorescent ligands with better fluorescent properties and/or higher affinity/selectivity for the DA receptors.

  DOI：

  10.1021/jm00115a012
• 作为产物：
  描述：

  8-methoxy-3-methyl-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 在 溴 、 镍 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 7-bromo-8-methoxy-3-methyl-1-(4'-aminophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  Fluorescent probes for dopamine receptors: synthesis and characterization of fluorescein and 7-nitrobenz-2-oxa-1,3-diazol-4-yl conjugates of D-1 and D-2 receptor ligands

  摘要：

  Fluorescent probes have been designed and developed for dopamine D-1 and D-2 receptors. Fluorescein and/or NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl) derivatives of PPHT (D-2 agonist), spiperone (D-2 antagonist), SKF 38393 (D-1 agonist), and SKF 83566 (D-1 antagonist) were synthesized via their amino-functionalized analogues and all ligands were pharmacologically evaluated by measuring their ability to displace [H-3]SCH 23390 and [H-3]spiperone from D-1 and D-2 receptor sites in caudate putamen of monkeys (Macaca fascicularis). The fluorescein derivatives of PPHT and SKF 83566 and the NBD derivatives of spiperone and SKF 83566 retained the high affinity and selectivity of the parent ligands. The NBD derivatives of PPHT showed higher D-2 receptor affinity and selectivity than their parent ligands. The enantiomers of the fluorescent derivatives of PPHT were also synthesized and were found to exhibit stereoselectivity in binding to the D-2 receptor, with the S enantiomers having a considerably higher affinity than their R analogues. In contrast to these results, the fluorescein derivative of SKF 38393 showed only a low affinity for the D-1 receptor. These fluorescein- and NBD-coupled D-1 and D-2 receptor ligands have considerable significance as potential probes in the study of distribution of the receptors at the cellular/subcellular level and of their mobility in membranes in normal/diseased states by use of fluorescence microscopic and fluorescence photobleaching recovery techniques, respectively. The development of these novel fluorescent probes should also provide new leads for the design and synthesis of additional fluorescent ligands with better fluorescent properties and/or higher affinity/selectivity for the DA receptors.

  DOI：

  10.1021/jm00115a012

文献信息

• Method for Generating a Recombinant Clonal Cell Line and Novel Reagents for Use in the Method
  申请人：Hill Stephen John

  公开号：US20110300116A1

  公开（公告）日：2011-12-08

  A method for generating a recombinant clonal cell line expressing a target cell surface receptor at a specific level of expression from a cell population comprising cells transfected with a plasmid encoding the cDNA sequence of the target receptor and expressing the target cell surface receptor, the method comprising (c) incubating the cell population with a receptor specific fluorescent ligand (d) selecting single cells from step (c) expressing the target cell surface receptor by monitoring the specific binding of the fluorescent ligand using flow cytometry; and novel fluorescent ligands.

  一种用于从包含转染携带目标受体cDNA序列的质粒并表达目标细胞表面受体的细胞群体中生成表达特定水平目标细胞表面受体的重组克隆细胞系的方法，该方法包括：(c)将细胞群体与受体特异性荧光配体孵育；(d)通过使用流式细胞仪监测荧光配体的特异结合来选择步骤(c)中表达目标细胞表面受体的单个细胞；以及新型荧光配体。
• A METHOD FOR GENERATING A RECOMBINANT CLONAL CELL LINE AND NOVEL REAGENTS FOR USE IN THE METHOD
  申请人：Cellaura Technologies LTD

  公开号：EP2238248A2

  公开（公告）日：2010-10-13
• [EN] A METHOD FOR GENERATING A RECOMBINANT CLONAL CELL LINE AND NOVEL REAGENTS FOR USE IN THE METHOD<br/>[FR] MÉTHODE D'OBTENTION D'UNE LIGNÉE DE CELLULES CLONALES DE RECOMBINAISON ET NOUVEAUX RÉACTIFS UTILISÉS PAR LA MÉTHODE
  申请人：CELLAURA TECHNOLOGIES LTD

  公开号：WO2009040555A2

  公开（公告）日：2009-04-02

  A method for generating a recombinant clonal cell line expressing a target cell surface receptor at a specific level of expression from a cell population comprising cells transfected with a plasmid encoding the cDNA sequence of the target receptor and expressing the target cell surface receptor, the method comprising (c) incubating the cell population with a receptor specific fluorescent ligand (d) selecting single cells from step (c) expressing the target cell surface receptor by monitoring the specific binding of the fluorescent ligand using flow cytometry; and novel fluorescent ligands.