5-(Dimethylamino)-N-{4-[2-{4-[4-(1-naphthyl)piperazin-1-yl]butyl}-1,3-dioxotetrahydro-1H-pyrrolo[1,2-c]imidazol-7a(5H)-yl]butyl}naphthalene-1-sulfonamide | 1229035-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(Dimethylamino)-N-{4-[2-{4-[4-(1-naphthyl)piperazin-1-yl]butyl}-1,3-dioxotetrahydro-1H-pyrrolo[1,2-c]imidazol-7a(5H)-yl]butyl}naphthalene-1-sulfonamide
• 英文别名: 5-(dimethylamino)-N-[4-[2-[4-(4-naphthalen-1-ylpiperazin-1-yl)butyl]-1,3-dioxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7a-yl]butyl]naphthalene-1-sulfonamide
• CAS: 1229035-78-2
• 化学式: C₄₀H₅₀N₆O₄S
• 分子量: 710.941
• InChiKey: HNDPSBWXLXUVKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7a-(4-aminobutyl)-2-{4-[4-(1-naphthyl)piperazin-1-yl]butyl}tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 5-(Dimethylamino)-N-{4-[2-{4-[4-(1-naphthyl)piperazin-1-yl]butyl}-1,3-dioxotetrahydro-1H-pyrrolo[1,2-c]imidazol-7a(5H)-yl]butyl}naphthalene-1-sulfonamide
  参考文献：
  名称：

  Development of Fluorescent Ligands for the Human 5-HT_1A Receptor

  摘要：

  In this work, we report the design and synthesis of a set of fluorescent probes targeting the human 5-HT1A receptor (h5-HT1AR). Among the synthesized compounds, derivative 4 deserves special attention as being a high-affinity ligand (K-i = 2 nM) with good fluorescent properties (I-em > 1000 au and a fluorescence quantum yield, Phi(f), of 0.26), which enables direct observation of the h5-HT1AR in cells. Thus, it represents the first efficacious fluorescent probe for the specific labeling of h5-HT1AR in cells. Our results provide the basis for the introduction of a variety of tags in scaffolds of G protein-coupled receptor(GPCR) ligands that enable visualization, covalent binding, or affinity pull-down of receptors. These strategies should contribute to the optimization of the therapeutic exploitation of known or new members of the GPCR superfamily by providing valuable information about their location or level of expression.

  DOI：

  10.1021/ml100053y