4-[3-(二甲氨基)丙氧基]-3-氟苯胺 | 221199-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[3-(二甲氨基)丙氧基]-3-氟苯胺
• 英文名称: [3-(4-amino-2-fluorophenoxy)propyl]dimethylamine
• 英文别名: 4-{[3-(dimethylamino)propyl]oxy}-3-fluoroaniline；N-[3-(4-Amino-2-fluorophenoxy)propyl]-N,N-dimethylamine；4-[3-(dimethylamino)propoxy]-3-fluoroaniline
• CAS: 221199-31-1
• 化学式: C₁₁H₁₇FN₂O
• 分子量: 212.267
• InChiKey: TZMBJCIZFGGBDX-UHFFFAOYSA-N

物化性质

• 沸点：
  332.0±32.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  4-[3-(二甲氨基)丙氧基]-3-氟苯胺 、 3-苄氧基-4-甲氧基苯甲酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.25h， 生成 N-{4-[3-(dimethylamino)propoxy]-3-fluorophenyl}-3-benzyloxy-4-methoxybenzamide
  参考文献：
  名称：

  具有抗肿瘤活性的苯甲酰胺化合物及其制备方 法和应用

  摘要：

  本发明公开了一种具有抗肿瘤活性的苯甲酰胺化合物及其制备方法和应用，该化合物的结构式为其中R1为氢或卤素，R2为末端由叔胺基取代的碳原子数为1～4的烷氧基，通过氧原子连接于苯甲酰胺的对位，R3为羟基或甲氧基中的一种，R4为羟基或甲氧基中的另一种。该化合物体外对肿瘤细胞有很好的抑制活性，可用于抗肿瘤药物的制备，尤其是抗肝癌药物和抗乳腺癌药物。本发明提供的苯甲酰胺化合物的制备方法，具有原料易得，反应条件温和，反应过程操作简单，所用试剂便宜的优点。

  公开号：

  CN103980152B
• 作为产物：
  描述：

  2-氟-4-硝基苯酚 在 palladium on activated charcoal 、 氢气 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 4-[3-(二甲氨基)丙氧基]-3-氟苯胺
  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

文献信息

• 2-Pyrimidinyl Pyrazolopyridine Erbb Kinase Inhibitors
  申请人：Uehling Edward David

  公开号：US20080051395A1

  公开（公告）日：2008-02-28

  The present invention provides 2-pyrimidinyl pyrazolopyridine compounds, compositions containing the same, as well as processes for the preparation and their use as pharmaceutical agents.

  本发明提供了2-嘧啶基吡唑吡啶化合物，含有这些化合物的组合物，以及其制备过程和作为药物剂的用途。
• Synthesis of<i>p</i>-<i>O</i>-Alkyl Salicylanilide Derivatives as Novel EGFR Inhibitors
  作者：Li Zhang、Lin Hou、Wenyan Sun、Zidong Yu、Jibo Wang、Hua Gao、Guiming Yang

  DOI：10.1002/ddr.21290

  日期：2016.2

  Preclinical Research

  临床前研究
• 2-pyrimidinyl pyrazolopyridine ErbB kinase inhibitors
  申请人：GlaxoSmithKline LLC

  公开号：US07812022B2

  公开（公告）日：2010-10-12

  The present invention provides 2-pyrimidinyl pyrazolopyridine compounds, compositions containing the same, as well as processes for the preparation and their use as pharmaceutical agents.

  本发明提供了2-嘧啶基吡唑吡啶化合物，含有它们的组合物，以及制备它们的方法和它们作为药物的用途。
• [EN] SUBSTITUTED FUSED HETEROARYL COMPOUND SERVING AS A KINASE INHIBITOR, AND APPLICATIONS THEREOF<br/>[FR] COMPOSÉ HÉTÉROARYLE FUSIONNÉ SUBSTITUÉ SERVANT COMME INHIBITEUR DE KINASE ET SES APPLICATIONS<br/>[ZH] 取代的稠合杂芳基化合物作为激酶抑制剂及其应用
  申请人：IMPACT THERAPEUTICS INC

  公开号：WO2018127195A1

  公开（公告）日：2018-07-12

  本发明提供取代的稠合杂芳基化合物作为激酶抑制剂及其应用。具体而言，本发明提供下式I的化合物，或其可药用盐或前药，其中A1-A4，B1-B3，D1-D4和R1-R3为本文所定义。式I的化合物是激酶抑制剂。因此，本发明的化合物可用于治疗因为DDR功能缺陷而引起的临床病症，例如癌症。
• Discovery of biphenyl-aryl ureas as novel VEGFR-2 inhibitors. Part 4: Exploration of diverse hinge-binding fragments
  作者：Ping Su、Jinfeng Wang、Yaling Shi、Xiaoyan Pan、Ruili Shao、Jie Zhang

  DOI：10.1016/j.bmc.2015.04.071

  日期：2015.7

  VEGFR-2 plays an essential role in angiogenesis and is an important target for cancer therapy. A series of biphenyl-aryl ureas were synthesized and evaluated as novel VEGFR-2 inhibitors. The pyridine, methylamine carbonyl pyridine and pivaloyl amide pyridine were introduced as novel hinge binding fragment. The majority of title compounds displayed potent VEGFR-2 inhibition. In particular, L1, L9, W14 and W15 exhibited significant enzymatic inhibitory activity with IC50 values of 0.36 nM, 0.22 nM, 0.15 nM and 0.14 nM. Compounds L1, L9 and W15 displayed potent antiproliferative activity against A549 and SMMC-7721 cells. SAR study suggested that incorporation of 3-trifluoromethyl and methylamine carbonyl on terminal pyridine could improve VEGFR-2 inhibitory activity. Molecular docking illustrated that urea moiety formed two critical hydrogen bonds with the DFG residues of VEGFR-2. The results indicated that these biphenyl-aryl ureas could serve as promising lead compounds for further optimization. (C) 2015 Elsevier Ltd. All rights reserved.