(2-((2-fluoro-4-nitrophenyl)oxy)ethyl)dimethylamine | 221198-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-((2-fluoro-4-nitrophenyl)oxy)ethyl)dimethylamine
• 英文别名: {2-[(2-Fluoro-4-nitrophenyl)oxy]ethyl}dimethylamine；2-(2-fluoro-4-nitrophenoxy)-N,N-dimethylethanamine
• CAS: 221198-44-3
• 化学式: C₁₀H₁₃FN₂O₃
• 分子量: 228.223
• InChiKey: XOIAHLHBOUVRFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-((2-fluoro-4-nitrophenyl)oxy)ethyl)dimethylamine 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 4-[2-(Dimethylamino)ethoxy]-3-fluoroaniline
  参考文献：
  名称：

  Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies

  摘要：

  VEGFR-2 plays an essential role in angiogenesis and is a central target for anticancer drug discovery. In order to develop novel VEGFR-2 inhibitors, we designed and synthesized 33 biphenyl amides based on our previously reported lead compound. The biological results indicated that four compounds (18b, 20e, 20h and 20j) are potent VEGFR-2 inhibitors which are comparable to positive control. Compound 18b displayed the most potent VEGFR-2 inhibition with IC50 value of 2.02 nM. Moreover, it exhibited promising antiproliferative activity against MCF-7 and SMMC-7721 cells with IC50 values of 1.47 mu M and 5.98 mu M, respectively. Molecular docking and 3D-QSAR studies were also carried out. The results indicated that these biphenyl amides could serve as promising leads for further optimization as novel VEGFR-2 inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.006
• 作为产物：
  描述：

  N,N-二甲基乙醇胺 、 3,4-二氟硝基苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以71%的产率得到(2-((2-fluoro-4-nitrophenyl)oxy)ethyl)dimethylamine
  参考文献：
  名称：

  [EN] THIAZOLE AND OXAZOLE KINASE INHIBITORS
  [FR] INHIBITEURS DE KINASE À BASE DE THIAZOLE ET D'OXAZOLE

  摘要：

  本发明提供了噻唑和恶唑化合物、含有该化合物的组合物，以及它们的制备方法和作为药物的应用方法。

  公开号：

  WO2009076140A1

文献信息

• Thiazole And Oxazole Kinase Inhibitors
  申请人：Adjabeng George

  公开号：US20110098296A1

  公开（公告）日：2011-04-28

  The present invention provides thiazole and oxazole compounds, compositions containing the same, as well as processes for the preparation and methods for their use as pharmaceutical agents.

  本发明提供了噻唑和异噁唑化合物，包含它们的组合物，以及制备它们的方法和用作药物的方法。
• THIAZOLE AND OXAZOLE KINASE INHIBITORS
  申请人：GlaxoSmithKline LLC

  公开号：EP2231625A1

  公开（公告）日：2010-09-29
• [EN] THIAZOLE AND OXAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE À BASE DE THIAZOLE ET D'OXAZOLE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009076140A1

  公开（公告）日：2009-06-18

  The present invention provides thiazole and oxazole compounds, compositions containing the same, as well as processes for the preparation and methods for their use as pharmaceutical agents.

  本发明提供了噻唑和恶唑化合物、含有该化合物的组合物，以及它们的制备方法和作为药物的应用方法。
• Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies
  作者：Wen Lu、Pengfei Li、Yuanyuan Shan、Ping Su、Jinfeng Wang、Yaling Shi、Jie Zhang

  DOI：10.1016/j.bmc.2015.01.006

  日期：2015.3

  VEGFR-2 plays an essential role in angiogenesis and is a central target for anticancer drug discovery. In order to develop novel VEGFR-2 inhibitors, we designed and synthesized 33 biphenyl amides based on our previously reported lead compound. The biological results indicated that four compounds (18b, 20e, 20h and 20j) are potent VEGFR-2 inhibitors which are comparable to positive control. Compound 18b displayed the most potent VEGFR-2 inhibition with IC50 value of 2.02 nM. Moreover, it exhibited promising antiproliferative activity against MCF-7 and SMMC-7721 cells with IC50 values of 1.47 mu M and 5.98 mu M, respectively. Molecular docking and 3D-QSAR studies were also carried out. The results indicated that these biphenyl amides could serve as promising leads for further optimization as novel VEGFR-2 inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.