3-acetyl-4,5-dimethoxy-10-[3-(4-methyl)piperazin-1-ylpropoxy]-1,2,3,12-tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline | 733744-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-acetyl-4,5-dimethoxy-10-[3-(4-methyl)piperazin-1-ylpropoxy]-1,2,3,12-tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline
• 英文别名: 1-[14,15-Dimethoxy-6-[3-(4-methylpiperazin-1-yl)propoxy]-11,17-diazapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4(9),5,7,10,12,14,16(20)-octaen-17-yl]ethanone
• CAS: 733744-63-3
• 化学式: C₃₀H₃₆N₄O₄
• 分子量: 516.64
• InChiKey: YIWQQSQZJSTUCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-acetyl-4,5-dimethoxy-10-[3-(4-methyl)piperazin-1-ylpropoxy]-1,2,3,12-tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline 在 盐酸 作用下， 反应 4.0h， 生成 4,5-dimethoxy-10-[3-(4-methyl)piperazin-1-ylpropoxy]-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 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 123.5h， 生成 3-acetyl-4,5-dimethoxy-10-[3-(4-methyl)piperazin-1-ylpropoxy]-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