1-[2-(dimethylamino)ethyl]-4-hydroxy-4-(piperidin-4-yl)-1H-pyrrolo[3,2-g]isoquinolin-9(4H)-one | 1182125-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[2-(dimethylamino)ethyl]-4-hydroxy-4-(piperidin-4-yl)-1H-pyrrolo[3,2-g]isoquinolin-9(4H)-one
• 英文别名: 1-[2-(dimethylamino)ethyl]-4-hydroxy-4-piperidin-4-ylpyrrolo[3,2-g]isoquinolin-9-one
• CAS: 1182125-66-1
• 化学式: C₂₀H₂₆N₄O₂
• 分子量: 354.452
• InChiKey: DVLVRFYHICOAAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2-(dimethylamino)ethyl]-4-hydroxy-4-(piperidin-4-yl)-1H-pyrrolo[3,2-g]isoquinolin-9(4H)-one 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以24%的产率得到4-[2-(dimethylamino)ethoxy]-1-[2-(dimethylamino)ethyl]-4-(piperidin-4-yl)-1H-pyrrolo[3,2-g]isoquinolin-9(4H)-one
  参考文献：
  名称：

  Synthesis of anticancer compounds, III (Bioorg Med Chem Lett 17, 6091, 2007), carbinol derivatives of azanaphthoquinone annelated pyrroles

  摘要：

  A series of carbinols has been synthesized by attachment of different piperidinyl side chains to the quinone structure of azanaphthoquinone annelated pyrroles. The synthesized compounds were screened for their cytotoxic activities. Compared to previously published results, they exhibited only moderate activities, thus showing that the existence of the quinone moiety seems to be essential for anticancer activities of this group.

  DOI：

  10.1007/s00706-008-0024-3
• 作为产物：
  描述：

  4-(1-benzylpiperidin-4-yl)-1-[2-(dimethylamino)ethyl]-4-hydroxy-1H-pyrrolo[3,2-g]isoquinolin-9(4H)-one 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以66%的产率得到1-[2-(dimethylamino)ethyl]-4-hydroxy-4-(piperidin-4-yl)-1H-pyrrolo[3,2-g]isoquinolin-9(4H)-one
  参考文献：
  名称：

  Synthesis of anticancer compounds, III (Bioorg Med Chem Lett 17, 6091, 2007), carbinol derivatives of azanaphthoquinone annelated pyrroles

  摘要：

  A series of carbinols has been synthesized by attachment of different piperidinyl side chains to the quinone structure of azanaphthoquinone annelated pyrroles. The synthesized compounds were screened for their cytotoxic activities. Compared to previously published results, they exhibited only moderate activities, thus showing that the existence of the quinone moiety seems to be essential for anticancer activities of this group.

  DOI：

  10.1007/s00706-008-0024-3

文献信息

• Synthesis of anticancer compounds, III (Bioorg Med Chem Lett 17, 6091, 2007), carbinol derivatives of azanaphthoquinone annelated pyrroles
  作者：Nipawan Pongprom、Gerhard Müller、Peter Schmidt、Wolfgang Holzer、Helmut Spreitzer

  DOI：10.1007/s00706-008-0024-3

  日期：2009.3

  A series of carbinols has been synthesized by attachment of different piperidinyl side chains to the quinone structure of azanaphthoquinone annelated pyrroles. The synthesized compounds were screened for their cytotoxic activities. Compared to previously published results, they exhibited only moderate activities, thus showing that the existence of the quinone moiety seems to be essential for anticancer activities of this group.