(3-{4,5-Dimethoxy-3-[2-(4-methyl-piperazin-1-yl)-acetyl]-1,2,3,12-tetrahydro-3,7-diaza-indeno[2,1-a]phenalen-10-yloxy}-propyl)-carbamic acid benzyl ester | 733744-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3-{4,5-Dimethoxy-3-[2-(4-methyl-piperazin-1-yl)-acetyl]-1,2,3,12-tetrahydro-3,7-diaza-indeno[2,1-a]phenalen-10-yloxy}-propyl)-carbamic acid benzyl ester
• CAS: 733744-81-5
• 化学式: C₃₈H₄₃N₅O₆
• 分子量: 665.789
• InChiKey: ODIJVWPPACNBKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  105.7
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3-{4,5-Dimethoxy-3-[2-(4-methyl-piperazin-1-yl)-acetyl]-1,2,3,12-tetrahydro-3,7-diaza-indeno[2,1-a]phenalen-10-yloxy}-propyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以403 mg的产率得到10-(3-aminopropoxy)-4,5-dimethoxy-3-[2-(4-methyl)piperazin-1-yl]-1,2,3,12-tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline
  参考文献：
  名称：

  DNA Binding To Guide the Development of Tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline Derivatives as Cytotoxic Agents

  摘要：

  The tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline chromophore was initially designed as a DNA intercalating unit because of its planar structure. Unexpectedly, one molecule (15d) bearing two N-methylpiperazine chains on both sides of this condensed pentacyclic skeleton fits into the minor groove of DNA and preferentially recognizes AT-rich sequences. The monosubstituted compound 16d was identified as a potent cytotoxic DNA intercalator, whereas the disubstituted analogue 15d represents a new structural motif for the development of DNA sequence-reading small molecules.

  DOI：

  10.1021/jm0400193
• 作为产物：
  描述：

  5-羟基-1-茚酮 在 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 15.5h， 生成 (3-{4,5-Dimethoxy-3-[2-(4-methyl-piperazin-1-yl)-acetyl]-1,2,3,12-tetrahydro-3,7-diaza-indeno[2,1-a]phenalen-10-yloxy}-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  DNA Binding To Guide the Development of Tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline Derivatives as Cytotoxic Agents

  摘要：

  The tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline chromophore was initially designed as a DNA intercalating unit because of its planar structure. Unexpectedly, one molecule (15d) bearing two N-methylpiperazine chains on both sides of this condensed pentacyclic skeleton fits into the minor groove of DNA and preferentially recognizes AT-rich sequences. The monosubstituted compound 16d was identified as a potent cytotoxic DNA intercalator, whereas the disubstituted analogue 15d represents a new structural motif for the development of DNA sequence-reading small molecules.

  DOI：

  10.1021/jm0400193