5-fluoro-N2-(4-morpholinophenyl)-N4-propyl-2,4-diaminepyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 5-fluoro-N2-(4-morpholinophenyl)-N4-propyl-2,4-diaminepyrimidine
• 英文别名: 5-fluoro-2-N-(4-morpholin-4-ylphenyl)-4-N-propylpyrimidine-2,4-diamine
• 化学式: C₁₇H₂₂FN₅O
• 分子量: 331.393
• InChiKey: ABVMIFDZAPOLCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(4-硝基苯基)吗啉 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 乙酸乙酯 、 异丙醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 5-fluoro-N2-(4-morpholinophenyl)-N4-propyl-2,4-diaminepyrimidine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,4-diaminopyrimidines as selective Aurora A kinase inhibitors

  摘要：

  The Aurora kinases are a family of serine/threonine kinases that interact with components of the mitotic apparatus and serve as potential therapeutic targets in oncology. Here we synthesized 15 2,4diaminopyrimidines and evaluated their biological activities, including antiproliferation, inhibition against Aurora kinases and cell cycle effects. These compounds generally exhibited more potent cytotoxicity against tumor cell lines compared with the VX-680 control, especially compound 11c, which showed the highest cytotoxicities, with IC50 values of 0.5-4.0 mu M. Compound 11c had more than 35-fold more selectivity for Aurora A over Aurora B, and molecular docking analysis indicated that compound 11c form better interaction with Aurora A both from the perspective of structure and energy. Furthermore, compound 11c induced G2/M cell cycle arrest in HeLa cells. This series of compounds has the potential for further development as selective Aurora A inhibitors for anticancer activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.044