N1,N1-diphenyl-N4-(4-(6-phenylpyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine | 1048004-11-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N1,N1-diphenyl-N4-(4-(6-phenylpyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine
• 英文别名: 4-N,4-N-diphenyl-1-N-[4-(6-phenylpyridin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine
• CAS: 1048004-11-0
• 化学式: C₃₃H₂₅N₅
• 分子量: 491.595
• InChiKey: IFHDZQYUGWAIDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(6-phenylpyridin-3-yl)pyrimidin-2-amine 、 4-溴三苯胺 在 bis-triphenylphosphine-palladium(II) chloride 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以31%的产率得到N1,N1-diphenyl-N4-(4-(6-phenylpyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine
  参考文献：
  名称：

  Synthesis of New N-Arylpyrimidin-2-amine Derivatives Using a Palladium Catalyst

  摘要：

  通过应用优化的Buchwald-Hartwig氨基化条件，使用二氯双(三苯基膦)钯(II)、xantphos和叔丁醇钠，在氮气氛围下于回流甲苯中，从相应的胺合成了新型N-芳基-4-(吡啶-3-基)嘧啶-2-胺衍生物。所得到的N-芳基衍生物产率从中等到良好，范围在27%至82%之间。描述的程序可广泛用于制备新型杂环化合物。新化合物的结构通过FT-NMR、FT-IR和元素分析得到了确认。

  DOI：

  10.3390/molecules13040818

文献信息

• Synthesis of New N-Arylpyrimidin-2-amine Derivatives Using a Palladium Catalyst
  作者：Ibrahim El-Deeb、Jae Ryu、So Lee

  DOI：10.3390/molecules13040818

  日期：——

  New N-aryl-4-(pyridin-3-yl)pyrimidin-2-amine derivatives were synthesizedfrom the corresponding amines, applying optimized Buchwald-Hartwig aminationconditions using dichlorobis(triphenylphosphine)Pd(II), xantphos and sodium tertbutoxidein refluxing toluene under a nitrogen atmosphere. The target N-aryl derivativeswere obtained in moderate to good yields ranging from 27% to 82%. The proceduredescribed could be widely employed for the preparation of new heterocyclic compounds.The structures of the new compounds were confirmed by FT-NMR, FT-IR and elementalanalysis.

  通过应用优化的Buchwald-Hartwig氨基化条件，使用二氯双(三苯基膦)钯(II)、xantphos和叔丁醇钠，在氮气氛围下于回流甲苯中，从相应的胺合成了新型N-芳基-4-(吡啶-3-基)嘧啶-2-胺衍生物。所得到的N-芳基衍生物产率从中等到良好，范围在27%至82%之间。描述的程序可广泛用于制备新型杂环化合物。新化合物的结构通过FT-NMR、FT-IR和元素分析得到了确认。
• Design and synthesis of new anticancer pyrimidines with multiple-kinase inhibitory effect
  作者：Ibrahim Mustafa El-Deeb、So Ha Lee

  DOI：10.1016/j.bmc.2010.04.037

  日期：2010.6.1

  A new series of N-substituted-2-aminopyrimidines based on the '4-(pyridin-3-yl)pyrimidin-2-amine' scaffold of Imatinib has been designed and synthesized. A selected group from the target compounds was tested over a panel of 60 cancer cell lines at a single dose concentration of 10 mu M, and the two most active compounds, 25b and 30, were further tested in a five-dose testing mode to determine their IC50 values over the 60 cell lines. Compound 30 has showed good potencies and high efficacies, and was accordingly tested at a single dose concentration of 10 mu M over a panel of 54 kinases. At this concentration, the compound has showed multiple inhibitions over a number of oncogenic kinases, including ABL1, AKT1, LCK, C-SRC, PIM1, FLT3, FYN, and KDR. A molecular modeling study was made by docking of the most active compound 30 and its inactive analog 29 into the kinase domain of ABL1 to investigate their possible binding interactions. (C) 2010 Elsevier Ltd. All rights reserved.