6-(3-bromopropyl)-3-nitro-5H-indeno[1,2-c]isoquinoline-5,11-(6H)-dione | 744229-14-9

• 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-bromopropyl)-3-nitro-5H-indeno[1,2-c]isoquinoline-5,11-(6H)-dione
• 英文别名: 6-(3-bromopropyl)-5,6-dihydro-5,11-dioxo-3-nitro-11H-indeno[1,2-c]isoquinoline；6-(3-bromopropyl)-3-nitroindeno[1,2-c]isoquinoline-5,11-dione
• CAS: 744229-14-9
• 化学式: C₁₉H₁₃BrN₂O₄
• 分子量: 413.227
• InChiKey: FITHFPHFIGGTGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 6-(3-bromopropyl)-3-nitro-5H-indeno[1,2-c]isoquinoline-5,11-(6H)-dione 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 AM-10–63
  参考文献：
  名称：

  Nitrated Indenoisoquinolines as Topoisomerase I Inhibitors:  A Systematic Study and Optimization

  摘要：

  The biological activity of indenoisoquinoline topoisomerase I (Topl) inhibitors can be greatly enhanced depending on the choice of substituents on the aromatic rings and lactam side chain. Previously, it was discovered that a 3-nitro group and a 9-methoxy group afforded enhanced biological activity. In the present investigation, indenoisoquinoline analogues were systematically prepared using combinations of nitro groups, methoxy groups, and hydrogen atoms in an effort to understand the contribution of each group toward cytotoxicity and Top I inhibition. Analysis of the biological results suggests that the nitro group is important for Top I inhibition and the methoxy group improves cytotoxicity. In addition, previously identified structure-activity relationships were utilized to select favorable lactam side chain functionalities for incorporation on the aromatic skeleton of analogues in this study. As a result, this investigation has provided optimal Topl inhibitors equipotent to camptothecin that demonstrate low nanomolar cytotoxicities toward cancer cells.

  DOI：

  10.1021/jm070361q
• 作为产物：
  描述：

  6-(3-bromo-1-propyl)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline 生成 6-(3-bromopropyl)-3-nitro-5H-indeno[1,2-c]isoquinoline-5,11-(6H)-dione
  参考文献：
  名称：

  Synthesis of indenoisoquinolines

  摘要：

  描述了Indenoisoquinolines和dihydroindenoisoquinolines。特别是，描述了具有一个或多个电子提取取代基的这类化合物。描述了这些分子在国家癌症研究所对55种细胞系进行的体外抗癌活性测试。描述了对这些化合物进行的拓扑异构酶I（top1）抑制测试。

  公开号：

  US20060025595A1

文献信息

• Synthesis of indenoisoquinolines
  申请人：Cushman S. Mark

  公开号：US20060025595A1

  公开（公告）日：2006-02-02

  Indenoisoquinolines and dihydroindenoisoquinolines are described. In particular, such compounds possessing one or more electron withdrawing substituents are described. The in vitro anticancer activities of these molecules tested in the National Cancer Institute's screen of 55 cell lines is described. The compounds tested for topoisomerase I (top1) inhibition is described.

  描述了Indenoisoquinolines和dihydroindenoisoquinolines。特别是，描述了具有一个或多个电子提取取代基的这类化合物。描述了这些分子在国家癌症研究所对55种细胞系进行的体外抗癌活性测试。描述了对这些化合物进行的拓扑异构酶I（top1）抑制测试。
• N-Substituted Indenoisoquinolines and Syntheses Thereof
  申请人：Cushman Mark S.

  公开号：US20080318995A1

  公开（公告）日：2008-12-25

  N-Substituted indenoisoquinoline compounds, and pharmaceutical formulations of N-substituted indenoisoquinoline compounds are described. Also described are processes for preparing N-substituted indenoisoquinoline compounds. Also described are methods for treating cancer in mammals using the described N-substituted indenoisoquinoline compounds or pharmaceutical formulations thereof.

  本发明涉及N-取代的茚并异喹啉化合物及其制备方法，以及N-取代的茚并异喹啉化合物的药物制剂。同时，还描述了制备N-取代的茚并异喹啉化合物的方法。本发明还涉及使用所述的N-取代的茚并异喹啉化合物或其药物制剂治疗哺乳动物癌症的方法。
• N-substituted indenoisoquinolines and syntheses thereof
  申请人：Cushman Mark S.

  公开号：US20120101119A1

  公开（公告）日：2012-04-26

  N-Substituted indenoisoquinoline compounds, and pharmaceutical formulations of N-substituted indenoisoquinoline compounds are described. Also described are processes for preparing N-substituted indenoisoquinoline compounds. Also described are methods for treating cancer in mammals using the described N-substituted indenoisoquinoline compounds or pharmaceutical formulations thereof.

  本发明涉及N-取代吲哚异喹啉化合物及其药物制剂。还描述了制备N-取代吲哚异喹啉化合物的过程。还描述了使用所述N-取代吲哚异喹啉化合物或其药物制剂治疗哺乳动物癌症的方法。
• N-SUBSTITUTED INDENOISOQUINOLINES AND SYNTHESES THEREOF
  申请人：CUSHMAN Mark S.

  公开号：US20140336188A1

  公开（公告）日：2014-11-13

  N-Substituted indenoisoquinoline compounds, and pharmaceutical formulations of N-substituted indenoisoquinoline compounds are described. Also described are processes for preparing N-substituted indenoisoquinoline compounds. Also described are methods for treating cancer in mammals using the described N-substituted indenoisoquinoline compounds or pharmaceutical formulations thereof.

  本文描述了N-取代吲哚异喹啉化合物及其药物配方，并描述了制备N-取代吲哚异喹啉化合物的过程。同时，本文还描述了使用所述N-取代吲哚异喹啉化合物或其药物配方治疗哺乳动物癌症的方法。
• A PROCESS FOR PREPARING N-SUBSTITUTED INDENOISOQUINOLINES
  申请人：Purdue Research Foundation

  公开号：EP3112349A2

  公开（公告）日：2017-01-04

  A process for preparing a compound of the formula without isolating an intermediate product, the process comprising: reacting a compound of the formula with a compound of the formula and cyclizing the intermediate product.

  一种制备式化合物的工艺 不分离中间产物的制备方法，该方法包括 与一种式化合物反应 和 环化中间产物。