2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazole-5-carbaldehyde | 1365543-37-8

• 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-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazole-5-carbaldehyde
• CAS: 1365543-37-8
• 化学式: C₂₁H₂₃N₃O₄
• 分子量: 381.431
• InChiKey: TXJDLDZABSSFNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.31
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazole-5-carbaldehyde 、 3,4-二氨基苯甲酸 在 sodium metabisulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以6.34 g的产率得到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
• 作为产物：
  描述：

  N-(叔丁氧羰基)乙醇胺 在 sodium metabisulfite 、 二异丁基氢化铝 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 17.0h， 生成 2-{4-[2-(1,1-dimethylethoxycarbonylamino)ethoxy]phenyl}benzimidazole-5-carbaldehyde
  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