4-(2,4-difluorophenyl)pyrimidine-2-carboxamide | 1491142-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(2,4-difluorophenyl)pyrimidine-2-carboxamide
• CAS: 1491142-19-8
• 化学式: C₁₁H₇F₂N₃O
• 分子量: 235.193
• InChiKey: OHFFNMSKKMEKLA-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C
• 沸点：
  425.7±53.0 °C(predicted)
• 密度：
  1.397±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,4-difluorophenyl)pyrimidine-2-carboxamide 在 氯化亚砜 、 硫酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(3-fluoro-4-(6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yloxy)phenyl)-4-(2,4-difluorophenyl)pyrimidine-2-carboxamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of quinoline derivatives bearing the pyridine/pyrimidine scaffold were synthesized, and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against 5 cancer cell lines (HT-29, H460, MKN-45, A549, and U87MG) were evaluated in vitro. Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 18b (c-Met half-maximal inhibitory concentration [IC50] = 1.39 nM) showed a 7.3-fold increase in activity against HT-29 cell line in vitro. Structure activity relationship studies indicated that regulation of the electron density on the pyridine/pyrimidine ring to a proper degree was a key factor in improving the antitumor activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.019
• 作为产物：
  描述：

  (2E)-1-(2,4-difluorophenyl)-3-(dimethylamino)prop-2-en-1-one 在 ferrous(II) sulfate heptahydrate 、 硫酸 、 双氧水 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 4-(2,4-difluorophenyl)pyrimidine-2-carboxamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of quinoline derivatives bearing the pyridine/pyrimidine scaffold were synthesized, and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against 5 cancer cell lines (HT-29, H460, MKN-45, A549, and U87MG) were evaluated in vitro. Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 18b (c-Met half-maximal inhibitory concentration [IC50] = 1.39 nM) showed a 7.3-fold increase in activity against HT-29 cell line in vitro. Structure activity relationship studies indicated that regulation of the electron density on the pyridine/pyrimidine ring to a proper degree was a key factor in improving the antitumor activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.019