6-(5,6-dimethoxy-1H-benzimidazol-2-yl)-N-methylnaphthalen-2-amine | 1489032-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(5,6-dimethoxy-1H-benzimidazol-2-yl)-N-methylnaphthalen-2-amine
• CAS: 1489032-26-9
• 化学式: C₂₀H₁₉N₃O₂
• 分子量: 333.39
• InChiKey: CDBLPOAUZBJXMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.17
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-formyl-N-methyl-2-naphthylamine 、 1,2-二氨基-4,5-二甲氧基苯 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以36%的产率得到6-(5,6-dimethoxy-1H-benzimidazol-2-yl)-N-methylnaphthalen-2-amine
  参考文献：
  名称：

  Benzimidazole-Based Ratiometric Two-Photon Fluorescent Probes for Acidic pH in Live Cells and Tissues

  摘要：

  Many aspects of cell metabolism are controlled by acidic pH. We report a new family of small molecule and ratiometric two photon (TP) probes derived from benzimidazole (BH1-3 and BH1L) for monitoring acidic pH values. These probes are characterized by a strong two-photon excited fluorescence, a marked blue-to-green emission color change in response to pH, pK(a) values ranging from 4.9 to 6.1, a distinctive isoemissive point, negligible cytotoxicity, and high photostability, thereby allowing quantitative analysis of acidic pH. Moreover, we show that BH1L optimized as a lysosomal-targeted probe allows for direct, real-time estimation of the pH values inside lysosomal compartments in live cells as well as in living mouse brain tissues through the use of two-photon microscopy. These findings demonstrate that these probes will find useful applications in biomedical research.

  DOI：

  10.1021/ja409971k