8-methoxy-3-methyl-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine | 116234-47-0

• 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: 8-methoxy-3-methyl-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
• 英文别名: 7-methoxy-3-methyl-5-(4-nitrophenyl)-1,2,4,5-tetrahydro-3-benzazepine
• CAS: 116234-47-0
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: MORFJJINRZSEGO-UHFFFAOYSA-N

物化性质

• 沸点：
  457.0±45.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methoxy-3-methyl-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 在 溴 、 三溴化硼 、 镍 、 一水合肼 、 溶剂黄146 、 potassium iodide 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 正丁醇 为溶剂， 反应 10.0h， 生成 7-bromo-8-hydroxy-3-methyl-1-<4'-<(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino>phenyl>-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：

  (P-硝基苯基)环氧乙烷 在 甲酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 50.0h， 生成 8-methoxy-3-methyl-1-(4'-nitrophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  D-1多巴胺受体的高亲和力和立体选择性光亲和标记的发展：7- [125I] iodo-8-hydroxy-3-methyl-1-（4'-azidophenyl）-2,3,4的合成和拆分，5-四氢-1H-3-苯并ze庚因。

  摘要：

  在较早的论文中，我们报道了（+-）-7-iodo-8-hydroxy-3-methyl-1-（4'-azidophenyl）-2,3,4,5-tetrahydro-1H-3-的开发苯并ze庚因（I-MAB）及其125I类似物（[125I] I-MAB）作为D-1多巴胺受体的选择性，高亲和力光亲和标记。在这份报告中，我们现在描述犬纹状体膜中I-MAB的完整合成和拆分以及立体异构体的药理特性。R-（+）-I-MAB显示出高度特异性的多巴胺D-1受体结合（KD = 0.28 nM），并选择性和立体选择性地与D-1受体结合。这些结果进一步证实了先前的建议，即在苯并ze庚因系列的DA激动剂和拮抗剂中，活性主要存在于R-（+）对映异构体中，S-（-）对映异构体的效力或活性大大降低。此外，R-（+）-[125I] I-MAB 经光解后，鉴定神经元D-1受体的配体结合亚基，十二烷基硫酸钠-聚丙烯酰胺凝胶电

  DOI：

  10.1021/jm00164a009

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 photoaffinity label for the D-1 dopamine receptor, (RS)-7-[125I]iodo-8-hydroxy-3-methyl-1-(4'-azidophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine, selectively identifies the ligand binding subunits of the receptor
  作者：Nandkishore Baindur、John L. Neumeyer、Hyman B. Niznik、Natalie H. Bzowej、Kieth R. Jarvie、Phillip Seeman、Russell K. Garlick、Joseph J. Miller

  DOI：10.1021/jm00119a003

  日期：1988.11
• 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.
• [EN] COMPOSITIONS AND METHODS FOR MODULATING DOPAMINE RECEPTOR ACTIVITY<br/>[FR] COMPOSITIONS ET MÉTHODES PERMETTANT DE MODULER L'ACTIVITÉ DU RÉCEPTEUR DE LA DOPAMINE
  申请人：[en]THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：WO2023220526A1

  公开（公告）日：2023-11-16

  The present disclosure provides conjugates and systems for modulating the activity of a ligand-binding polypeptide such as a D2 dopamine receptor. Such conjugates comprising an affinity agent, a linker; a photoisomerizable group and a ligand that binds to a target ligand-binding polypeptide. The present disclosure provides methods of modulating the activity of a D2 dopamine receptor. The present disclosure provides methods of treating Parkinson's disease in an individual.