3-iodo-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide | 688033-18-3

• 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: 3-iodo-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide
• 英文别名: 3-iodo-N-[2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl]benzamide；3-iodo-N-[2-piperidin-1-yl-5-(trifluoromethyl)phenyl]benzamide
• CAS: 688033-18-3
• 化学式: C₁₉H₁₈F₃IN₂O
• 分子量: 474.264
• InChiKey: JBXDMIATNUQYJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  447.5±45.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-乙炔嘧啶-2-胺 、 3-iodo-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 以 乙腈 为溶剂， 以100%的产率得到3-(2-(2-aminopyrimidin-5-yl)ethynyl)-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  Alkynylpyrimidine Amide Derivatives as Potent, Selective, and Orally Active Inhibitors of Tie-2 Kinase

  摘要：

  The recognition that aberrant angiogenesis contributes to the pathology of inflammatory diseases, cancer, and myocardial ischemia has generated considerable interest in the molecular mechanisms that regulate blood vessel growth. The receptor tyrosine kinase Tie-2 is expressed primarily by vascular endothelial cells and is critical for embryonic vasculogenesis. Interference with the Tie-2 pathway by diverse blocking agents such as soluble Tie-2 receptors, anti-Tie-2 intrabodies, anti-Ang-2 antibodies, and peptide-F-c conjugates has been shown to suppress tumor growth in xenograft studies. An alternative strategy for interfering with the Tie-2 signaling pathway involves direct inhibition of the kinase functions of the Tie-2 receptor. Herein we describe the development of alkynylpyrimidine amide derivatives as potent, selective, and orally available ATP-competitive inhibitors of Tie-2 autophosphorylation.

  DOI：

  10.1021/jm061112p
• 作为产物：
  描述：

  3-碘苯甲酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-iodo-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  Alkynylpyrimidine Amide Derivatives as Potent, Selective, and Orally Active Inhibitors of Tie-2 Kinase

  摘要：

  The recognition that aberrant angiogenesis contributes to the pathology of inflammatory diseases, cancer, and myocardial ischemia has generated considerable interest in the molecular mechanisms that regulate blood vessel growth. The receptor tyrosine kinase Tie-2 is expressed primarily by vascular endothelial cells and is critical for embryonic vasculogenesis. Interference with the Tie-2 pathway by diverse blocking agents such as soluble Tie-2 receptors, anti-Tie-2 intrabodies, anti-Ang-2 antibodies, and peptide-F-c conjugates has been shown to suppress tumor growth in xenograft studies. An alternative strategy for interfering with the Tie-2 signaling pathway involves direct inhibition of the kinase functions of the Tie-2 receptor. Herein we describe the development of alkynylpyrimidine amide derivatives as potent, selective, and orally available ATP-competitive inhibitors of Tie-2 autophosphorylation.

  DOI：

  10.1021/jm061112p

文献信息

• Alkynylpyrimidine Amide Derivatives as Potent, Selective, and Orally Active Inhibitors of Tie-2 Kinase
  作者：Victor J. Cee、Brian K. Albrecht、Stephanie Geuns-Meyer、Paul Hughes、Steve Bellon、James Bready、Sean Caenepeel、Stuart C. Chaffee、Angela Coxon、Maurice Emery、Jenne Fretland、Paul Gallant、Yan Gu、Brian L. Hodous、Doug Hoffman、Rebecca E. Johnson、Richard Kendall、Joseph L. Kim、Alexander M. Long、David McGowan、Michael Morrison、Philip R. Olivieri、Vinod F. Patel、Anthony Polverino、David Powers、Paul Rose、Ling Wang、Huilin Zhao

  DOI：10.1021/jm061112p

  日期：2007.2.1

  The recognition that aberrant angiogenesis contributes to the pathology of inflammatory diseases, cancer, and myocardial ischemia has generated considerable interest in the molecular mechanisms that regulate blood vessel growth. The receptor tyrosine kinase Tie-2 is expressed primarily by vascular endothelial cells and is critical for embryonic vasculogenesis. Interference with the Tie-2 pathway by diverse blocking agents such as soluble Tie-2 receptors, anti-Tie-2 intrabodies, anti-Ang-2 antibodies, and peptide-F-c conjugates has been shown to suppress tumor growth in xenograft studies. An alternative strategy for interfering with the Tie-2 signaling pathway involves direct inhibition of the kinase functions of the Tie-2 receptor. Herein we describe the development of alkynylpyrimidine amide derivatives as potent, selective, and orally available ATP-competitive inhibitors of Tie-2 autophosphorylation.