3-fluoro-4-{[2-(1-piperidinyl)ethyl]oxy}aniline | 851597-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-fluoro-4-{[2-(1-piperidinyl)ethyl]oxy}aniline
• 英文别名: 3-Fluoro-4-[2-(1-piperidinyl)ethoxy]phenylamine；3-fluoro-4-(2-piperidin-1-ylethoxy)aniline
• CAS: 851597-46-1
• 化学式: C₁₃H₁₉FN₂O
• mdl: MFCD08687920
• 分子量: 238.305
• InChiKey: GXKQERCLTFQFAM-UHFFFAOYSA-N

物化性质

• 沸点：
  385.7±32.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 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

反应信息

• 作为反应物：
  描述：

  3-fluoro-4-{[2-(1-piperidinyl)ethyl]oxy}aniline 在 正丁基锂 、 sodium azide 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.0h， 生成 (R)-5-Azidomethyl-3-[3-fluoro-4-(2-piperidin-1-yl-ethoxy)-phenyl]-oxazolidin-2-one
  参考文献：
  名称：

  乙烯-氧间隔基团对利奈唑胺活性的影响：具有硫羰基的强效抗菌剂的合成。

  摘要：

  报道了乙烯-氧间隔基元素在利奈唑胺的杂环和芳环之间的影响。这种间隔基的引入产生了具有较差的抗菌活性的化合物。然而，存在于利奈唑胺类似物中的乙酰胺基团向硫代氨基甲酸酯或硫代乙酰胺官能团的转化恢复了活性。介绍了具有乙烯-氧间隔基团的利奈唑胺类似物的合成以及具有不同杂环的SAR研究以及一些具有强抗菌特性的硫代羰基化合物的制备。

  DOI：

  10.1016/j.bmcl.2003.08.068
• 作为产物：
  描述：

  3,4-二氟硝基苯 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 3-fluoro-4-{[2-(1-piperidinyl)ethyl]oxy}aniline
  参考文献：
  名称：

  乙烯-氧间隔基团对利奈唑胺活性的影响：具有硫羰基的强效抗菌剂的合成。

  摘要：

  报道了乙烯-氧间隔基元素在利奈唑胺的杂环和芳环之间的影响。这种间隔基的引入产生了具有较差的抗菌活性的化合物。然而，存在于利奈唑胺类似物中的乙酰胺基团向硫代氨基甲酸酯或硫代乙酰胺官能团的转化恢复了活性。介绍了具有乙烯-氧间隔基团的利奈唑胺类似物的合成以及具有不同杂环的SAR研究以及一些具有强抗菌特性的硫代羰基化合物的制备。

  DOI：

  10.1016/j.bmcl.2003.08.068

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。
• 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。
• 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.
• 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.
• 2-PYRIMIDINYL PYRAZOLOPYRIDINE ERBB KINASE INHIBITORS
  申请人：SmithKline Beecham Corporation

  公开号：EP1828185B1

  公开（公告）日：2009-05-06