2-(2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazol-5-yl)benzimidazole-5-carboxylic acid | 1365543-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazol-5-yl)benzimidazole-5-carboxylic acid
• CAS: 1365543-39-0
• 化学式: C₂₈H₂₇N₅O₅
• 分子量: 513.553
• InChiKey: NFVXWIDQFRPSLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  142.22
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazol-5-yl)benzimidazole-5-carboxylic acid 、 4-氨基-TEMPO 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以64%的产率得到4-{[2-(2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazol-5-yl)benzimidazole-5-carbonyl]amino}-2,2,6,6-tetramethylpiperidin-1-oxyl
  参考文献：
  名称：

  Novel bisbenzimide-nitroxides for nuclear redox imaging in living cells

  摘要：

  Nuclear oxidative stress damages genomic DNA and may lead to cell death, leading to aging and aging-related disorders. Though it is important to measure the nuclear oxidative stress separately, there are still little examples that applicable to living cells. We have designed and synthesized three bisbenzimide-nitroxides as probes to selectively visualize nuclear redox changes in terms of fluorescence. Compound 3, containing two radical moieties, showed the largest reduction-induced fluorescence change, with good localization in nuclei. RAW264.7 murine macrophage cells were loaded with compound 3 and then treated with 100 mu M hydrogen peroxide for 5 min to show the fluorescence increase. This fluorescence increase was inhibited by pretreatment of 1 mM ascorbic acid. These results show that compound 3 was suitable for nuclear-specific redox imaging in murine macrophages. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.042
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲酸 在 sodium metabisulfite 、 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 2-(2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazol-5-yl)benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  Novel bisbenzimide-nitroxides for nuclear redox imaging in living cells

  摘要：

  Nuclear oxidative stress damages genomic DNA and may lead to cell death, leading to aging and aging-related disorders. Though it is important to measure the nuclear oxidative stress separately, there are still little examples that applicable to living cells. We have designed and synthesized three bisbenzimide-nitroxides as probes to selectively visualize nuclear redox changes in terms of fluorescence. Compound 3, containing two radical moieties, showed the largest reduction-induced fluorescence change, with good localization in nuclei. RAW264.7 murine macrophage cells were loaded with compound 3 and then treated with 100 mu M hydrogen peroxide for 5 min to show the fluorescence increase. This fluorescence increase was inhibited by pretreatment of 1 mM ascorbic acid. These results show that compound 3 was suitable for nuclear-specific redox imaging in murine macrophages. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.042