8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-one

• 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: 8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-one
• 英文别名: 8,9-Dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one；5-[2-(dimethylamino)ethyl]-8,9-dimethoxyisoquinolino[4,3-c]quinolin-6-one
• 化学式: C₂₂H₂₃N₃O₃
• 分子量: 377.443
• InChiKey: OFULLGQVONRWKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯喹啉 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 silver carbonate 、 苯酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.92h， 生成 8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-one
  参考文献：
  名称：

  Nitro and amino substitution within the A-ring of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: influence on topoisomerase I-targeting activity and cytotoxicity

  摘要：

  Recently, 5H-8 9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h][1,6]naphthyridin-6-one, 1, was identified as a TOP1-targeting agent with pronounced antitumor activity. In the present study, the effect on activity of substituting, a single nitro or amino group in the A-ring in lieu of the methylenedioxy moiety of 1 was evaluated. The presence of either a nitro or amino substituent at the 4-position had a pronounced adverse affect on both TOP1-targeting activity and cytotoxicity. To a lesser extent, derivatives with a nitro or amino substituent at the 1-position were also less active than 1. Replacement of the methylenedioxy moiety of 1 with either a nitro or amino substituent at either the 2- and 3-position did result in analogues with potent TOP1-targeting activity and cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.076

文献信息

• Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds
  申请人：Smaill Jeffrey B.

  公开号：US20100173332A1

  公开（公告）日：2010-07-08

  A method utilising one or more fluorogenic probes, for the detection of nitroreductase activity. The non-fluorescent probes are reduced in the presence of nitroreductase to form fluorescent derivatives that may be detected using fluorescence spectroscopy. In particular, the method may be used to detect and/or identify a plurality of nitroreductase in a single test environment

  一种利用一个或多个荧光探针检测硝基还原酶活性的方法。非荧光探针在硝基还原酶存在下被还原成荧光衍生物，可以使用荧光光谱法检测。特别地，该方法可用于在单个测试环境中检测和/或鉴定多种硝基还原酶。
• Nitro and amino substituted topoisomerase agents
  申请人：——

  公开号：US20040102443A1

  公开（公告）日：2004-05-27

  The invention provides compounds of formula I: 1 wherein R 1 -R 9 , W, and X have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions. comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I, and therapeutic methods for treating cancer and infections using compounds of formula I.

  本发明提供了公式I的化合物：1其中R1-R9、W和X具有规范中定义的任何含义及其药学上可接受的盐。本发明还提供了包括公式I化合物的制药组合物，制备公式I化合物的过程，用于制备公式I化合物的中间体，以及使用公式I化合物治疗癌症和感染的治疗方法。
• [EN] NITRO AND AMINO SUBSTITUTED DIBENZONAPHTHYRIDINES AS TOPOISOMERASE AGENTS<br/>[FR] AGENTS TOPOISOMERASE NITRO ET AMINO SUBSTITUES
  申请人：UNIV RUTGERS

  公开号：WO2004014906A3

  公开（公告）日：2004-04-29
• US6992089B2
  申请人：——

  公开号：US6992089B2

  公开（公告）日：2006-01-31
• Nitro and amino substitution within the A-ring of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: influence on topoisomerase I-targeting activity and cytotoxicity
  作者：Alexander L Ruchelman、John E Kerrigan、Tsai-Kun Li、Nai Zhou、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/j.bmc.2004.03.076

  日期：2004.7

  Recently, 5H-8 9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h][1,6]naphthyridin-6-one, 1, was identified as a TOP1-targeting agent with pronounced antitumor activity. In the present study, the effect on activity of substituting, a single nitro or amino group in the A-ring in lieu of the methylenedioxy moiety of 1 was evaluated. The presence of either a nitro or amino substituent at the 4-position had a pronounced adverse affect on both TOP1-targeting activity and cytotoxicity. To a lesser extent, derivatives with a nitro or amino substituent at the 1-position were also less active than 1. Replacement of the methylenedioxy moiety of 1 with either a nitro or amino substituent at either the 2- and 3-position did result in analogues with potent TOP1-targeting activity and cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.