2-(11-formyl-10-hydroxy-8-bromo-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid | 1333432-86-2

• 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: 2-(11-formyl-10-hydroxy-8-bromo-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid
• CAS: 1333432-86-2
• 化学式: C₂₅H₁₃BrO₆
• 分子量: 489.279
• InChiKey: KORXAPGKBNMDQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104.81
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(11-formyl-10-hydroxy-8-bromo-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid 在 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(8-bromo-11-(((6-(2-ethoxy-2-oxoethoxy)-2-methylquinolin-8-yl)amino)methyl)-10-hydroxy-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid
  参考文献：
  名称：

  Seminaphthofluorescein-Based Fluorescent Probes for Imaging Nitric Oxide in Live Cells

  摘要：

  Fluorescent turn-on probes for nitric oxide based on seminaphthofluorescein scaffolds were prepared and spectroscopically characterized. The Cu(II) complexes of these fluorescent probes react with NO under anaerobic conditions to yield a 20-45-fold increase in integrated emission. The seminaphthofluorescein-based probes emit at longer wavelengths than the parent FL1 and FL2 fluorescein-based generations of NO probes, maintaining emission maxima between 550 and 625 nm. The emission profiles depend on the excitation wavelength; maximum fluorescence turn-on is achieved at excitations between 535 and 575 nm. The probes are highly selective for NO over other biologically relevant reactive nitrogen and oxygen species including NO3-, NO2-, HNO, ONOO-, NO2, OCl-, and H2O2. The seminaphthofluorescein-based probes can be used to visualize endogenously produced NO in live cells, as demonstrated using Raw 264.7 macrophages.

  DOI：

  10.1021/ic200986v
• 作为产物：
  描述：

  8-bromo-11-(bromomethyl)-3'-oxo-3 'H-spiro[benzo[c]xanthene-7,1'-isobenzofuran]-3,10-diyl dibenzoate 在 碳酸氢钠 、 二甲基亚砜 、 盐酸 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以5%的产率得到2-(11-formyl-10-hydroxy-8-bromo-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid
  参考文献：
  名称：

  Seminaphthofluorescein-Based Fluorescent Probes for Imaging Nitric Oxide in Live Cells

  摘要：

  Fluorescent turn-on probes for nitric oxide based on seminaphthofluorescein scaffolds were prepared and spectroscopically characterized. The Cu(II) complexes of these fluorescent probes react with NO under anaerobic conditions to yield a 20-45-fold increase in integrated emission. The seminaphthofluorescein-based probes emit at longer wavelengths than the parent FL1 and FL2 fluorescein-based generations of NO probes, maintaining emission maxima between 550 and 625 nm. The emission profiles depend on the excitation wavelength; maximum fluorescence turn-on is achieved at excitations between 535 and 575 nm. The probes are highly selective for NO over other biologically relevant reactive nitrogen and oxygen species including NO3-, NO2-, HNO, ONOO-, NO2, OCl-, and H2O2. The seminaphthofluorescein-based probes can be used to visualize endogenously produced NO in live cells, as demonstrated using Raw 264.7 macrophages.

  DOI：

  10.1021/ic200986v