5,6-dihydro-5,11-dioxo-6-(2-pyridylmethyl)-11H-indeno[1,2-c]isoquinoline

• 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: 5,6-dihydro-5,11-dioxo-6-(2-pyridylmethyl)-11H-indeno[1,2-c]isoquinoline
• 英文别名: 6-(pyridin-2-ylmethyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione；6-(pyridin-2-ylmethyl)indeno[1,2-c]isoquinoline-5,11-dione
• 化学式: C₂₂H₁₄N₂O₂
• 分子量: 338.365
• InChiKey: RYCSNCAJGGSBLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-Carboxyphenyl)-1,3-indandion 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 30.0h， 生成 5,6-dihydro-5,11-dioxo-6-(2-pyridylmethyl)-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of novel indenoisoquinoline-propan-2-ol hybrids

  摘要：

  The synthesis of N-substituted indenoisoquinolines was performed by applying a two-step condensation between 2-carboxybenzaldehyde and phthalide, followed by treatment with various primary amines. N-allylindenoisoquinoline was subsequently selected as a substrate for hydroxybromination, providing 6-(3-bromo-2-hydroxy)indenoisoquinoline as a key intermediate for derivatization in the lactam side chain. In this way, a series of 6-(2-hydroxypropyl)indenoisoquinolines bearing various functional groups at the 3'-position were prepared, which can be considered as novel indenoisoquinoline-propan-2-ol hybrid molecules. Subsequent cytotoxic evaluation of 28 indenoisoquinolines against two human cancer cell lines (Hep-G2 and KB) demonstrated a moderate to high antiproliferative activity displayed by 11 indenoisoquinolines thus synthesized. In particular, the introduction of the 2-hydroxypropyl side chain was shown to be beneficial for the overall cytotoxic activity, pointing to the potential relevance of these novel indenoisoquinoline-propan-2-ol hybrids. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.045

文献信息

• 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。
• WO2007/59008
  申请人：——

  公开号：——

  公开（公告）日：——