1-(4-(5-(2-(3,5-bis(trifluoromethyl)phenylamino)pyrimidin-4-yl)pyridin-2-yl)phenyl)ethanone | 1234327-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(5-(2-(3,5-bis(trifluoromethyl)phenylamino)pyrimidin-4-yl)pyridin-2-yl)phenyl)ethanone
• 英文别名: 1-[4-[5-[2-[3,5-Bis(trifluoromethyl)anilino]pyrimidin-4-yl]pyridin-2-yl]phenyl]ethanone
• CAS: 1234327-29-7
• 化学式: C₂₅H₁₆F₆N₄O
• 分子量: 502.419
• InChiKey: VXRGPDVSDCXFPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-(4-(5-(2-aminopyrimidin-4-yl)pyridin-2-yl)phenyl)ethanone 、 3,5-双三氟甲基溴苯 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 12.0h， 以69%的产率得到1-(4-(5-(2-(3,5-bis(trifluoromethyl)phenylamino)pyrimidin-4-yl)pyridin-2-yl)phenyl)ethanone
  参考文献：
  名称：

  Design and synthesis of new anticancer pyrimidines with multiple-kinase inhibitory effect

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.04.037

文献信息

• 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.