5-[3-(N-benzyloxycarbonyl)aminopropoxy]indan-1-one | 733744-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-[3-(N-benzyloxycarbonyl)aminopropoxy]indan-1-one
• CAS: 733744-56-4
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: CJKONSOKWSFDRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-[3-(N-benzyloxycarbonyl)aminopropoxy]indan-1-one 在 palladium on activated charcoal 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 14.5h， 生成 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 、 benzyl (3-chloropropyl)carbamate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以66%的产率得到5-[3-(N-benzyloxycarbonyl)aminopropoxy]indan-1-one
  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