methyl 6-[(2-methylquinolin-6-yl)amino]-6-oxohexanoate | 872537-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 6-[(2-methylquinolin-6-yl)amino]-6-oxohexanoate
• 英文别名: Hexanoic acid, 6-[(2-methyl-6-quinolinyl)amino]-6-oxo-, methyl ester
• CAS: 872537-06-9
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: AKIRPLFYEPZSTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-[(2-methylquinolin-6-yl)amino]-6-oxohexanoate 在 sodium acetate 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 36.5h， 生成 1-ethyl-2-[(1E,3E)-3-(1-ethylquinolin-2(1H)-ylidene)prop-1-enyl]-6-[(6-methoxy-6-oxohexanoyl)amino]quinolinium iodide
  参考文献：
  名称：

  On the Use of Nonfluorescent Dye Labeled Ligands in FRET-Based Receptor Binding Studies

  摘要：

  The efficiency of fluorescence resonance energy transfer (FRET) is dependent upon donor-acceptor proximity and spectral overlap, whether the acceptor partner is fluorescent or not. We report here on the design, synthesis, and characterization of two novel pirenzepine derivatives that were coupled to patent blue VF and pinacyanol dyes. These nonfluorescent compounds, when added to cells stably expressing enhanced green fluorescent protein (EGFP)fused muscarinic M1 receptors, promote EGFP fluorescence extinction in a time-, concentration-, and atropine-dependent manner. They display nanomolar affinity for the muscarinic receptor, determined using either FRET or classical radioligand binding conditions. We provide evidence that these compounds behave as potent acceptors of energy from excited EGFP with quenching efficiencies comparable to those of analogous fluorescent bodipy or rhodamine red pirenzepine derivatives. The advantages they offer over fluorescent ligands are illustrated and discussed in terms of reliability, sensitivity, and wider applicability of FRET-based receptor binding assays.

  DOI：

  10.1021/jm050459+
• 作为产物：
  描述：

  脂肪酸甲酯 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl 6-[(2-methylquinolin-6-yl)amino]-6-oxohexanoate
  参考文献：
  名称：

  On the Use of Nonfluorescent Dye Labeled Ligands in FRET-Based Receptor Binding Studies

  摘要：

  The efficiency of fluorescence resonance energy transfer (FRET) is dependent upon donor-acceptor proximity and spectral overlap, whether the acceptor partner is fluorescent or not. We report here on the design, synthesis, and characterization of two novel pirenzepine derivatives that were coupled to patent blue VF and pinacyanol dyes. These nonfluorescent compounds, when added to cells stably expressing enhanced green fluorescent protein (EGFP)fused muscarinic M1 receptors, promote EGFP fluorescence extinction in a time-, concentration-, and atropine-dependent manner. They display nanomolar affinity for the muscarinic receptor, determined using either FRET or classical radioligand binding conditions. We provide evidence that these compounds behave as potent acceptors of energy from excited EGFP with quenching efficiencies comparable to those of analogous fluorescent bodipy or rhodamine red pirenzepine derivatives. The advantages they offer over fluorescent ligands are illustrated and discussed in terms of reliability, sensitivity, and wider applicability of FRET-based receptor binding assays.

  DOI：

  10.1021/jm050459+

文献信息

• On the Use of Nonfluorescent Dye Labeled Ligands in FRET-Based Receptor Binding Studies
  作者：Chouaib Tahtaoui、Fabrice Guillier、Philippe Klotz、Jean-Luc Galzi、Marcel Hibert、Brigitte Ilien

  DOI：10.1021/jm050459+

  日期：2005.12.1

  The efficiency of fluorescence resonance energy transfer (FRET) is dependent upon donor-acceptor proximity and spectral overlap, whether the acceptor partner is fluorescent or not. We report here on the design, synthesis, and characterization of two novel pirenzepine derivatives that were coupled to patent blue VF and pinacyanol dyes. These nonfluorescent compounds, when added to cells stably expressing enhanced green fluorescent protein (EGFP)fused muscarinic M1 receptors, promote EGFP fluorescence extinction in a time-, concentration-, and atropine-dependent manner. They display nanomolar affinity for the muscarinic receptor, determined using either FRET or classical radioligand binding conditions. We provide evidence that these compounds behave as potent acceptors of energy from excited EGFP with quenching efficiencies comparable to those of analogous fluorescent bodipy or rhodamine red pirenzepine derivatives. The advantages they offer over fluorescent ligands are illustrated and discussed in terms of reliability, sensitivity, and wider applicability of FRET-based receptor binding assays.