N-acetoxy-N-acetyl-3-aminobenzanthrone | 206192-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-acetoxy-N-acetyl-3-aminobenzanthrone
• 英文别名: [Acetyl-(7-oxobenzo[a]phenalen-3-yl)amino] acetate
• CAS: 206192-82-7
• 化学式: C₂₁H₁₅NO₄
• 分子量: 345.354
• InChiKey: CCRSIGYHQIENSR-UHFFFAOYSA-N

物化性质

• 沸点：
  546.166±43.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.378±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetoxy-N-acetyl-3-aminobenzanthrone 在 lithium hydroxide 作用下， 以 水 、 乙二醇 、 乙腈 为溶剂， 反应 720.0h， 生成 3-amino-2-(2'-deoxyguanosin-8-yl)benzanthrone
  参考文献：
  名称：

  An Unusual DNA Adduct Derived from the Powerfully Mutagenic Environmental Contaminant 3-Nitrobenzanthrone

  摘要：

  The covalent binding of an N-hydroxy metabolite of the powerfully mutagenic 3-nitrobenzanthrone (NBA) to 2'-deoxyguanosine (dG) and calf thymus DNA has been investigated in vitro. The major adduct obtained from the reaction of the N-acetoxy-N-acetyl derivative (N-Aco-N-Ac-ABA) of 3-aminobenzanthrone (ABA) and dG was identified as N-acetyl-3-amino-2-2'-deoxyguanosin-8-yl) benzanthrone (dG-N-Ac-ABA) by H-1 NMR and mass spectroscopies as well as by the reaction of N-Aco-N-Ac-ABA with the double-stranded calf thymus DNA. The coupling with the dG moiety occurred exclusively at C-2 of benzanthrone (BA), suggesting a significant contribution of a resonance-stabilized arenium ion intermediate derived from BA to the production of this new type of adduct. The preferred conformation of the adduct has been shown to be syn by H-1 and C-13 NMR.

  DOI：

  10.1021/tx980104b
• 作为产物：
  描述：

  苯并蒽酮 在 palladium on activated charcoal 硝酸 、 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-acetoxy-N-acetyl-3-aminobenzanthrone
  参考文献：
  名称：

  An Unusual DNA Adduct Derived from the Powerfully Mutagenic Environmental Contaminant 3-Nitrobenzanthrone

  摘要：

  The covalent binding of an N-hydroxy metabolite of the powerfully mutagenic 3-nitrobenzanthrone (NBA) to 2'-deoxyguanosine (dG) and calf thymus DNA has been investigated in vitro. The major adduct obtained from the reaction of the N-acetoxy-N-acetyl derivative (N-Aco-N-Ac-ABA) of 3-aminobenzanthrone (ABA) and dG was identified as N-acetyl-3-amino-2-2'-deoxyguanosin-8-yl) benzanthrone (dG-N-Ac-ABA) by H-1 NMR and mass spectroscopies as well as by the reaction of N-Aco-N-Ac-ABA with the double-stranded calf thymus DNA. The coupling with the dG moiety occurred exclusively at C-2 of benzanthrone (BA), suggesting a significant contribution of a resonance-stabilized arenium ion intermediate derived from BA to the production of this new type of adduct. The preferred conformation of the adduct has been shown to be syn by H-1 and C-13 NMR.

  DOI：

  10.1021/tx980104b