methyl 4-((4-chloro-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)benzoate | 1432515-97-3

• 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: methyl 4-((4-chloro-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)benzoate
• CAS: 1432515-97-3
• 化学式: C₁₆H₁₅ClN₆O₂
• 分子量: 358.787
• InChiKey: LBIBUZXNCFIPIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 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：
  0.12
• 拓扑面积：
  104.82
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 4-((4-chloro-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)benzoate 在 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.5h， 生成 methyl 4-((4-((5-methyl-1H-pyrazol-3-yl)amino)-6-(4-(methylsulfonyl)piperazin-1-yl)pyrimidin-2-yl)amino)benzoate
  参考文献：
  名称：

  Design, synthesis and bioevaluation of N-trisubstituted pyrimidine derivatives as potent aurora A kinase inhibitors

  摘要：

  The design and synthesis of a new series of N-trisubstituted (at C2, C4 and C6 respectively) pyrimidine derivatives were reported, their in vitro structure-activity relationships vs. aurora A kinase were also discussed. Our results demonstrated that the introduction of characteristic N-substituted side chain at C2 of pyrimidines possessed a potent aurora A inhibitory activity, the position and the nature of the substituents on the phenyl ring of aniline side chain played key roles in cellular kinase inhibitory potency. Most tested compounds exhibited good inhibitory activities against aurora A kinase and various human tumor cell lines. Compounds 7j, 7m-n and 7p showed strong growth-inhibitory activities in the solid CNE-2 tumor cell and selectively blocked cell-cycle progression at the G(2)/M phase. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.027
• 作为产物：
  描述：

  2,6-dichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine 、 4-氨基苯甲酸甲酯 在 对甲苯磺酸 作用下， 以 正丁醇 为溶剂， 反应 12.0h， 以65%的产率得到methyl 4-((4-chloro-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)benzoate
  参考文献：
  名称：

  Design, synthesis and bioevaluation of N-trisubstituted pyrimidine derivatives as potent aurora A kinase inhibitors

  摘要：

  The design and synthesis of a new series of N-trisubstituted (at C2, C4 and C6 respectively) pyrimidine derivatives were reported, their in vitro structure-activity relationships vs. aurora A kinase were also discussed. Our results demonstrated that the introduction of characteristic N-substituted side chain at C2 of pyrimidines possessed a potent aurora A inhibitory activity, the position and the nature of the substituents on the phenyl ring of aniline side chain played key roles in cellular kinase inhibitory potency. Most tested compounds exhibited good inhibitory activities against aurora A kinase and various human tumor cell lines. Compounds 7j, 7m-n and 7p showed strong growth-inhibitory activities in the solid CNE-2 tumor cell and selectively blocked cell-cycle progression at the G(2)/M phase. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.027