N-[6'-(2-diphenylphosphanylbenzoyl)oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl]benzenecarboximidic acid | 1448991-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[6'-(2-diphenylphosphanylbenzoyl)oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl]benzenecarboximidic acid
• CAS: 1448991-80-7
• 化学式: C₄₆H₃₀NO₆P
• 分子量: 723.721
• InChiKey: IJCWXERNPFSBBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  94.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[6'-(2-diphenylphosphanylbenzoyl)oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl]benzenecarboximidic acid 在 双氧水 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 0.25h， 以59%的产率得到3'-benzamido-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl 2-(diphenylphosphoryl)benzoate
  参考文献：
  名称：

  A Reductant-Resistant and Metal-Free Fluorescent Probe for Nitroxyl Applicable to Living Cells

  摘要：

  Nitroxyl (HNO) is a one-electron reduced and protonated derivative of nitric oxide (NO) and has characteristic biological and pharmacological effects distinct from those of NO. However, studies of its biosynthesis and activities are restricted by the lack of versatile FIN detection methods applicable to living cells. Here, we report the first metal-free and reductant-resistant HNO imaging probe available for use in living cells, P-Rhod. It consists of a rhodol derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent rhodol derivative. P-Rhod showed high selectivity for HNO in the presence of various biologically relevant reductants, such as glutathione and ascorbate, in comparison with previous HNO probes. We show that P-Rhod can detect not only HNO enzymatically generated in the horseradish peroxidase-hydroxylamine system in vitro but also intracellular HNO release from Angeli's salt in living cells. These results suggest that P-Rhod is suitable for detection of HNO in living cells.

  DOI：

  10.1021/ja404757s
• 作为产物：
  描述：

  N-(3'-(methoxymethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl)benzamide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[6'-(2-diphenylphosphanylbenzoyl)oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl]benzenecarboximidic acid
  参考文献：
  名称：

  A Reductant-Resistant and Metal-Free Fluorescent Probe for Nitroxyl Applicable to Living Cells

  摘要：

  Nitroxyl (HNO) is a one-electron reduced and protonated derivative of nitric oxide (NO) and has characteristic biological and pharmacological effects distinct from those of NO. However, studies of its biosynthesis and activities are restricted by the lack of versatile FIN detection methods applicable to living cells. Here, we report the first metal-free and reductant-resistant HNO imaging probe available for use in living cells, P-Rhod. It consists of a rhodol derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent rhodol derivative. P-Rhod showed high selectivity for HNO in the presence of various biologically relevant reductants, such as glutathione and ascorbate, in comparison with previous HNO probes. We show that P-Rhod can detect not only HNO enzymatically generated in the horseradish peroxidase-hydroxylamine system in vitro but also intracellular HNO release from Angeli's salt in living cells. These results suggest that P-Rhod is suitable for detection of HNO in living cells.

  DOI：

  10.1021/ja404757s