2-[2-[5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yloxy]ethoxy]ethanol | 1318249-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-[2-[5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yloxy]ethoxy]ethanol
• 英文别名: 2-[2-[[5-[3-(4-Cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]ethoxy]ethanol
• CAS: 1318249-99-8
• 化学式: C₂₇H₄₄N₂O₃
• 分子量: 444.658
• InChiKey: IJBACKZSXZIUKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-[5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yloxy]ethoxy]ethanol 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 31.0h， 生成 2-[2-[1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy]ethoxy]ethylamine
  参考文献：
  名称：

  Fluorescent Derivatives of σ Receptor Ligand 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) as a Tool for Uptake and Cellular Localization Studies in Pancreatic Tumor Cells

  摘要：

  Fluorescent derivatives of sigma(2) high affinity ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) were synthesized. NBD or dansyl fluorescent tags were connected through a 5- or 6-atom linker in two diverse positions of 1 structure. Good sigma(2) affinities were obtained when the fluorescent tag was linked to 5-methoxytetralin nucleus replacing the methyl function. NBD-bearing compound 16 displayed high sigma(2) affinity (K(i) = 10.8 nM) and a optimal fluorescent properties. Its uptake in pancreatic tumor cells was evaluated by flow cytometry, showing that it partially occurs through endocytosis. In proliferating cells, the uptake was higher supporting that sigma(2) receptors are markers of cell proliferation and that the higher the proliferation is, the stronger the antiproliferative effect of sigma(2) agonists is. Colocalization of 16 with subcellular organelles was studied by confocal microscopy: the greatest was in endoplasmic reticulum and lysosomes. Fluorescent sigma(2) ligands show their potential in clarifying the mechanisms of action of sigma(2) receptors.

  DOI：

  10.1021/jm200591t
• 作为产物：
  描述：

  2-氯乙氧基乙醇 、 5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-ol 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以62%的产率得到2-[2-[5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yloxy]ethoxy]ethanol
  参考文献：
  名称：

  Fluorescent Derivatives of σ Receptor Ligand 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) as a Tool for Uptake and Cellular Localization Studies in Pancreatic Tumor Cells

  摘要：

  Fluorescent derivatives of sigma(2) high affinity ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) were synthesized. NBD or dansyl fluorescent tags were connected through a 5- or 6-atom linker in two diverse positions of 1 structure. Good sigma(2) affinities were obtained when the fluorescent tag was linked to 5-methoxytetralin nucleus replacing the methyl function. NBD-bearing compound 16 displayed high sigma(2) affinity (K(i) = 10.8 nM) and a optimal fluorescent properties. Its uptake in pancreatic tumor cells was evaluated by flow cytometry, showing that it partially occurs through endocytosis. In proliferating cells, the uptake was higher supporting that sigma(2) receptors are markers of cell proliferation and that the higher the proliferation is, the stronger the antiproliferative effect of sigma(2) agonists is. Colocalization of 16 with subcellular organelles was studied by confocal microscopy: the greatest was in endoplasmic reticulum and lysosomes. Fluorescent sigma(2) ligands show their potential in clarifying the mechanisms of action of sigma(2) receptors.

  DOI：

  10.1021/jm200591t

文献信息

• Fluorescent Derivatives of σ Receptor Ligand 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) as a Tool for Uptake and Cellular Localization Studies in Pancreatic Tumor Cells
  作者：Carmen Abate、John R. Hornick、Dirk Spitzer、William G. Hawkins、Mauro Niso、Roberto Perrone、Francesco Berardi

  DOI：10.1021/jm200591t

  日期：2011.8.25

  Fluorescent derivatives of sigma(2) high affinity ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) were synthesized. NBD or dansyl fluorescent tags were connected through a 5- or 6-atom linker in two diverse positions of 1 structure. Good sigma(2) affinities were obtained when the fluorescent tag was linked to 5-methoxytetralin nucleus replacing the methyl function. NBD-bearing compound 16 displayed high sigma(2) affinity (K(i) = 10.8 nM) and a optimal fluorescent properties. Its uptake in pancreatic tumor cells was evaluated by flow cytometry, showing that it partially occurs through endocytosis. In proliferating cells, the uptake was higher supporting that sigma(2) receptors are markers of cell proliferation and that the higher the proliferation is, the stronger the antiproliferative effect of sigma(2) agonists is. Colocalization of 16 with subcellular organelles was studied by confocal microscopy: the greatest was in endoplasmic reticulum and lysosomes. Fluorescent sigma(2) ligands show their potential in clarifying the mechanisms of action of sigma(2) receptors.