3-amino-4-ethoxy-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzamide | 1436405-90-1

• 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: 3-amino-4-ethoxy-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzamide
• CAS: 1436405-90-1
• 化学式: C₁₈H₁₇N₅O₂
• 分子量: 335.365
• InChiKey: VLNZQJHGNQUWMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  103.02
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)but-2-enoic acid hydrobromide 、 3-amino-4-ethoxy-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzamide 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 4.5h， 以22%的产率得到3-(4-(dimethylamino)but-2-enamido)-4-ethoxy-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

  摘要：

  36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values <1 mu M for EGFR and <5 mu M for A-549 and HL60 cells growth inhibition. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.053
• 作为产物：
  描述：

  4-ethoxy-3-nitro-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzamide 在 盐酸 、 铁粉 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 5.0h， 以84%的产率得到3-amino-4-ethoxy-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

  摘要：

  36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values <1 mu M for EGFR and <5 mu M for A-549 and HL60 cells growth inhibition. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.053