6-(3-chloropropyl)-9-fluoro-5,6-dihydro-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline | 1196110-29-8

• 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)-9-fluoro-5,6-dihydro-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
• CAS: 1196110-29-8
• 化学式: C₁₉H₁₂ClFN₂O₄
• 分子量: 386.767
• InChiKey: ZICORAMTYXFNID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  82.21
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-(3-chloropropyl)-9-fluoro-5,6-dihydro-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline 在 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 6-(3-[(1-methylpiperazinyl)-1-propyl])-9-fluoro-3-amin-o-5,6-dihydro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Synthesis and biological evaluations of novel indenoisoquinolines as topoisomerase I inhibitors

  摘要：

  A series of novel indenoisoquinoline derivatives were synthesized. The anticancer activities of these molecules were tested in human cancer cell lines A549, HepG2, and HCT-116. These compounds were also tested for their activity of topoisomerase I (top1) inhibition. Among them, compound 25 was found to be 10-times more potent in cell-killing activity for both cell lines HepG2 and HCT-116 than reported compound 11, with IC50 of 0.019 and 0.093 mu M, respectively. Compound 25 was also found to have stronger top1 inhibition activity than 11 in our inhibition assay. Further in vivo evaluations of compound 25 are in progress and will be reported in due course. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.019
• 作为产物：
  描述：

  4-硝基邻苯二价酸酐 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 氯仿 、 硝基苯 、 甲苯 为溶剂， 反应 1.5h， 生成 6-(3-chloropropyl)-9-fluoro-5,6-dihydro-3-nitro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Synthesis and biological evaluations of novel indenoisoquinolines as topoisomerase I inhibitors

  摘要：

  A series of novel indenoisoquinoline derivatives were synthesized. The anticancer activities of these molecules were tested in human cancer cell lines A549, HepG2, and HCT-116. These compounds were also tested for their activity of topoisomerase I (top1) inhibition. Among them, compound 25 was found to be 10-times more potent in cell-killing activity for both cell lines HepG2 and HCT-116 than reported compound 11, with IC50 of 0.019 and 0.093 mu M, respectively. Compound 25 was also found to have stronger top1 inhibition activity than 11 in our inhibition assay. Further in vivo evaluations of compound 25 are in progress and will be reported in due course. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.019