N-(3'-(methoxymethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl)benzamide | 1207538-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(3'-(methoxymethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl)benzamide
• CAS: 1207538-43-9
• 化学式: C₂₉H₂₁NO₆
• 分子量: 479.489
• InChiKey: JBUYBEHYHHEREU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(3'-(methoxymethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl)benzamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-(3-Benzamido-6-oxoxanthen-9-yl)benzoic acid
  参考文献：
  名称：

  研发新型荧光探针的Rhodol荧光团库的构建

  摘要：

  以钯催化的胺化反应为关键步骤，开发了一种高效，简洁的合成铑荧光团的合成方案。该新的合成途径用于构建可用于设计新型荧光探针的rhodol文库。

  DOI：

  10.1021/ol902706b
• 作为产物：
  描述：

  3'-hydroxy-6'-(methoxymethoxy)-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one 在 吡啶 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 N-(3'-(methoxymethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl)benzamide
  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