Methyl 6-(3-azidopropyl)-3-nitro-5,11-dioxoindeno[1,2-c]isoquinoline-9-carboxylate | 951405-80-4

• 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: Methyl 6-(3-azidopropyl)-3-nitro-5,11-dioxoindeno[1,2-c]isoquinoline-9-carboxylate
• CAS: 951405-80-4
• 化学式: C₂₁H₁₅N₅O₆
• 分子量: 433.38
• InChiKey: KSOXIPMQOVYYLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 6-(3-azidopropyl)-3-nitro-5,11-dioxoindeno[1,2-c]isoquinoline-9-carboxylate 在 亚磷酸三乙酯 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 6-(3-aminopropyl)-5,6-dihydro-9-methoxycarbonyl-3-nitro-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+
• 作为产物：
  描述：

  Methyl 6-(3-chloropropyl)-3-nitro-5,11-dioxoindeno[1,2-c]isoquinoline-9-carboxylate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以73%的产率得到Methyl 6-(3-azidopropyl)-3-nitro-5,11-dioxoindeno[1,2-c]isoquinoline-9-carboxylate
  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+