5-chloro-N2-[4-(4-methylpiperazin-1-yl)phenyl]-N4-phenylpyrimidine-2,4-diamine trifluoroacetate (1:1) | 1352244-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-chloro-N2-[4-(4-methylpiperazin-1-yl)phenyl]-N4-phenylpyrimidine-2,4-diamine trifluoroacetate (1:1)
• 英文别名: 5-chloro-2-N-[4-(4-methylpiperazin-1-yl)phenyl]-4-N-phenylpyrimidine-2,4-diamine;2,2,2-trifluoroacetic acid
• CAS: 1352244-87-1
• 化学式: C₂HF₃O₂*C₂₁H₂₃ClN₆
• 分子量: 508.931
• InChiKey: FOXZSCXRIILUID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  93.6
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-(4-甲基哌嗪)苯胺 、 三氟乙酸 、 2,5-dichloro-N-phenylpyrimidin-4-amine 在 盐酸 作用下， 以 1,4-二氧六环 、 甲乙醚 、 水 、 乙腈 为溶剂， 反应 48.0h， 以71%的产率得到5-chloro-N2-[4-(4-methylpiperazin-1-yl)phenyl]-N4-phenylpyrimidine-2,4-diamine trifluoroacetate (1:1)
  参考文献：
  名称：

  Design, Synthesis, and Anaplastic Lymphoma Kinase (ALK) Inhibitory Activity for a Novel Series of 2,4,8,22-Tetraazatetracyclo[14.3.1.1^3,7.1^9,13]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene Macrocycles

  摘要：

  A novel set of 2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene macrocycles were prepared as potential anaplastic lymphoma kinase (ALK) inhibitors, designed to rigidly lock an energy-minimized bioactive conformation of the diaminopyrimidine (DAP) scaffold, a well-documented kinase platform. From 13 analogues prepared, macrocycle 2m showed the most promising in vitro ALK enzymatic (IC50 = 0.5 nM) and cellular (IC50 = 10 nM) activities. In addition, macrocycle 2m exhibited a favorable kinase selectivity preference for inhibition of ALK relative to the highly homologous insulin receptor (IR) kinase (IR/ALK ratio of 173). The inclusive in vitro biological results for this set of macrocycles validate this scaffold as a viable kinase template and further corroborate recent DAP/ALK solid state studies indicating that the inverted "U" shaped conformation of the acyclic DAPs is a preferred bioactive conformation.

  DOI：

  10.1021/jm201333e