N-<4-butyl>-2-anthraquinonecarboxamide | 158331-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-<4-butyl>-2-anthraquinonecarboxamide
• CAS: 158331-40-9
• 化学式: C₂₄H₂₆N₂O₅
• 分子量: 422.481
• InChiKey: SQVPAGSSFYDRIB-UHFFFAOYSA-N

物化性质

• 沸点：
  636.4±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-<4-butyl>-2-anthraquinonecarboxamide 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 以71%的产率得到N-(4-aminobutyl)-2-anthraquinonecarboxamide hydrochloride
  参考文献：
  名称：

  Photo-oxidation of duplex DNA with the stable trioxatriangulenium ion

  摘要：

  We show that 5'-Gs in 5'-GG-3' duplex DNA dinucleotide steps are preferentially oxidized by the trioxatriangulenium ion (TOTA(circle plus)) upon photo-activation, an oxidation pattern characteristic of guanine radical cation formation. Some photo-oxidation of the 3'G in 5'GG3' steps and of isolated guanines is also observed but reactions carried out in D2O reveal only a minor increase in oxidation damage at these sites, indicating that electron transfer is the primary mechanism of guanine oxidation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00121-5
• 作为产物：
  描述：

  蒽醌-2-羧酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-<4-butyl>-2-anthraquinonecarboxamide
  参考文献：
  名称：

  Cationic Anthraquinone Derivatives as Catalytic DNA Photonucleases: Mechanisms for DNA Damage and Quinone Recycling

  摘要：

  Ammonium-substituted anthraquinone derivatives have been found to catalyze DNA cleavage upon irradiation with 350 nm light. Picosecond laser spectroscopy demonstrates that the excited quinones react with DNA by two separate oxidative pathways: electron transfer from a nearby base and hydrogen atom abstraction from the deoxyribose component of the nucleic acid backbone. Photo-oxidation of DNA by either pathway yields the one-electron-reduced form of the quinone as a byproduct. Back electron transfer from the reduced quinone to the oxidized base is the predominant decay path for the reduced quinone formed by the electron transfer pathway while that formed by hydrogen atom abstraction is converted back to the ground-state, fully oxidized form by reduction of molecular oxygen. The resulting superoxide anion is detected by its reduction of cytochrome c. Comparison of the spectroscopic data for two quinones with significantly different cleavage efficiencies suggests that DNA cleavage by these quinone reagents results from the hydrogen-abstraction chemistry. The laser experiments further indicate that the quinone completes one cycle of excitation, oxidation of DNA, and reduction of oxygen within 10 mu s, illustrating the potential utility of these agents for double-stranded cleavage of DNA.

  DOI：

  10.1021/ja00101a005