4-(3,4-diaminobenzoyl)amino-2,2,6,6-tetramethylpiperidin-1-oxyl | 1365543-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3,4-diaminobenzoyl)amino-2,2,6,6-tetramethylpiperidin-1-oxyl
• CAS: 1365543-44-7
• 化学式: C₁₆H₂₅N₄O₂
• 分子量: 305.4
• InChiKey: ZPPOBRPVCCVSMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  104.28
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(3,4-diaminobenzoyl)amino-2,2,6,6-tetramethylpiperidin-1-oxyl 、 4-[{4-(5-formylbenzimidazol-2-yl)benzoyl}amino]-2,2,6,6-tetramethylpiperidin-1-oxyl 以 乙醇 为溶剂， 反应 6.5h， 以48%的产率得到4-[(4-{5-[5-({[(2,2,6,6-tetramethylpiperidin-1-oxyl)-4-yl]amino}carbonyl)benzimidazol-2-yl]benzimidazol-2-yl}benzoyl)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：

  3,4-二硝基苯甲酰氯 在 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 4-(3,4-diaminobenzoyl)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