6-(3-Chloropropyl)-5,3-dimethyoxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline | 951406-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(3-Chloropropyl)-5,3-dimethyoxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
• 英文别名: 6-(3-chloropropyl)-2,3-dimethoxyindeno[1,2-c]isoquinoline-5,11-dione
• CAS: 951406-05-6
• 化学式: C₂₁H₁₈ClNO₄
• 分子量: 383.831
• InChiKey: RBNJUOSLYWNDIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3-Chloropropyl)-5,3-dimethyoxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以98%的产率得到6-(3-Azidopropyl)-5,3-dimethoxy-5,11-dioxo-11H-i ndeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors

  摘要：

  Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.

  DOI：

  10.1021/jm070307+
• 作为产物：
  描述：

  cis-4-carboxy-N-(3-chloropropyl)-3,4-dihydro-6,7-dimethoxy-3-phenyl-1(2H)isoquinolone 在 三氯化铝 、 氯化亚砜 作用下， 以 硝基苯 、 苯 为溶剂， 反应 1.5h， 生成 6-(3-Chloropropyl)-5,3-dimethyoxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors

  摘要：

  Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.

  DOI：

  10.1021/jm070307+

文献信息

• Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors
  作者：Andrew Morrell、Michael Placzek、Seth Parmley、Brian Grella、Smitha Antony、Yves Pommier、Mark Cushman

  DOI：10.1021/jm070307+

  日期：2007.9.1

  Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.