7-acetamido-4-(2'-nitrophenyl)-5,8-dimethoxyquinoline | 957110-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-acetamido-4-(2'-nitrophenyl)-5,8-dimethoxyquinoline
• 英文别名: N-[5,8-dimethoxy-4-(2-nitrophenyl)quinolin-7-yl]acetamide
• CAS: 957110-16-6
• 化学式: C₁₉H₁₇N₃O₅
• 分子量: 367.361
• InChiKey: WRTPLNWAYPXOAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-acetamido-4-(2'-nitrophenyl)-5,8-dimethoxyquinoline 在 硫酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 7-cyano-5,8-dimethoxy-4-(2-nitrophenyl)quinolinone
  参考文献：
  名称：

  [EN] TOPOISOMERASE INHIBITORS AND METHODS OF MAKING AND USE AS THERAPEUTIC AGENTS
  [FR] INHIBITEURS DE TOPOISOMÉRASE ET MÉTHODES DE FABRICATION ET D'UTILISATION COMME AGENTS THÉRAPEUTIQUES

  摘要：

  该发明提供了通过抑制哺乳动物中的TopoIIa来抑制癌症生长或转移的方法。该发明还提供了TopoIIa的小分子抑制剂，可用于该发明的方法中，以及含有治疗有效化合物的药物组合物和使用它们的方法。

  公开号：

  WO2013071306A1
• 作为产物：
  描述：

  4-甲氧基-2-硝基酚 在 1,1'-双(二苯基膦)二茂铁 、 palladium on activated charcoal 、 palladium diacetate 甲酸 、 PPA 、 硝酸 、 溶剂黄146 、 三乙胺 、 环己烯 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 33.83h， 生成 7-acetamido-4-(2'-nitrophenyl)-5,8-dimethoxyquinoline
  参考文献：
  名称：

  The Total Synthesis of Neoamphimedine

  摘要：

  Neoamphimedine, a pyridoacridine alkaloid from Xestospongia sp., is a potent antitumor agent both in vitro and in vivo. Neoamphimedine can efficiently induce topoisomerase II mediated catenation of plasmid DNA in vitro and is the only member of more than one hundred pyridoacridines thus far to have this mechanism of action. Herein we report the first total synthesis of neoamphimedine.

  DOI：

  10.1021/jo7017813

文献信息

• [EN] TOPOISOMERASE II-alpha INHIBITORS AND METHODS OF TREATING CANCER USING THE SAME<br/>[FR] INHIBITEURS DE LA TOPOISOMÉRASE II-ALPHA ET MÉTHODES DE TRAITEMENT DU CANCER À L'AIDE DE CES INHIBITEURS
  申请人：UNIV COLORADO REGENTS

  公开号：WO2020205991A1

  公开（公告）日：2020-10-08

  A compound, or a pharmaceutically acceptable salt, solvate or prodrug thereof, having the chemical structure of formula I as defined in the text and methods of using these compounds to inhibit topoisomerase IIα and treat or prevent metastasis of cancer in a subject.

  一种具有化学结构为式I所定义的化合物，或其药用可接受的盐、溶剂合物或前药，以及使用这些化合物来抑制拓扑异构酶IIα并治疗或预防受试者的癌症转移的方法。
• [EN] TOPOISOMERASE INHIBITORS AND METHODS OF MAKING AND USE AS THERAPEUTIC AGENTS<br/>[FR] INHIBITEURS DE TOPOISOMÉRASE ET MÉTHODES DE FABRICATION ET D'UTILISATION COMME AGENTS THÉRAPEUTIQUES
  申请人：UNIV COLORADO

  公开号：WO2013071306A1

  公开（公告）日：2013-05-16

  The invention provides methods of inhibiting the growth or metastasis of cancer in a mammal by inhibiting TopoIIa in the mammal. The invention also provides small molecule inhibitors of TopoIIa useful in the methods of the invention and pharmaceutical compositions containing the therapeutically effective compounds and methods of using the same.

  该发明提供了通过抑制哺乳动物中的TopoIIa来抑制癌症生长或转移的方法。该发明还提供了TopoIIa的小分子抑制剂，可用于该发明的方法中，以及含有治疗有效化合物的药物组合物和使用它们的方法。
• Drug Design Targeting T-Cell Factor-Driven Epithelial–Mesenchymal Transition as a Therapeutic Strategy for Colorectal Cancer
  作者：Adedoyin D. Abraham、Hector Esquer、Qiong Zhou、Nicholas Tomlinson、Brayden D. Hamill、Joshua M. Abbott、Linfeng Li、Laura A. Pike、Sébastien Rinaldetti、Dominique A. Ramirez、Paul J. Lunghofer、Jose D. Gomez、Jerome Schaack、Travis Nemkov、Angelo D’Alessandro、Kirk C. Hansen、Daniel L. Gustafson、Wells A. Messersmith、Daniel V. LaBarbera

  DOI：10.1021/acs.jmedchem.9b01065

  日期：2019.11.27

  Metastasis is the cause of 90% of mortality in cancer patients. For metastatic colorectal cancer (mCRC), the standard-of-care drug therapies only palliate the symptoms but are ineffective, evidenced by a low survival rate of similar to 11%. T-cell factor (TCF) transcription is a major driving force in CRC, and we have characterized it to be a master regulator of epithelial-mesenchymal transition (EMT). EMT transforms relatively benign epithelial tumor cells into quasi-mesenchymal or mesenchymal cells that possess cancer stem cell properties, promoting multidrug resistance and metastasis. We have identified topoisomerase II alpha (TOP2A) as a DNA-binding factor required for TCF-transcription. Herein, we describe the design, synthesis, biological evaluation, and in vitro and in vivo pharmacokinetic analysis of TOP2A ATP-competitive inhibitors that prevent TCF-transcription and modulate or reverse EMT in mCRC. Unlike TOP2A poisons, ATP-competitive inhibitors do not damage DNA, potentially limiting adverse effects. This work demonstrates a new therapeutic strategy targeting TOP2A for the treatment of mCRC and potentially other types of cancers.
• TOPOISOMERASE INHIBITORS AND METHODS OF MAKING AND USE AS THERAPEUTIC AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, a body corporate

  公开号：US20140309257A1

  公开（公告）日：2014-10-16

  The invention provides methods of inhibiting the growth or metastasis of cancer in a mammal by inhibiting TopoIIa in the mammal. The invention also provides small molecule inhibitors of TopoIIa useful in the methods of the invention and pharmaceutical compositions containing the therapeutically effective compounds and methods of using the same.
• The Total Synthesis of Neoamphimedine
  作者：Daniel V. LaBarbera、Tim S. Bugni、Chris M. Ireland

  DOI：10.1021/jo7017813

  日期：2007.10.1

  Neoamphimedine, a pyridoacridine alkaloid from Xestospongia sp., is a potent antitumor agent both in vitro and in vivo. Neoamphimedine can efficiently induce topoisomerase II mediated catenation of plasmid DNA in vitro and is the only member of more than one hundred pyridoacridines thus far to have this mechanism of action. Herein we report the first total synthesis of neoamphimedine.