N1,N1-dimethyl-N4-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N1,N1-dimethyl-N4-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine
• 英文别名: 4-N,4-N-dimethyl-1-N-(4-pyridin-3-ylpyrimidin-2-yl)benzene-1,4-diamine
• 化学式: C₁₇H₁₇N₅
• 分子量: 291.355
• InChiKey: IVUTXEBXRBVZBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N1,N1-dimethyl-N4-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine 生成 4-N,4-N-dimethyl-1-N-(4-pyridin-3-ylpyrimidin-2-yl)benzene-1,4-diamine;trihydrochloride
  参考文献：
  名称：

  TORLEY, LAWRENCE W.;JOHNSON, BERNARD D.;DUSZA, JOHN P.

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基-对苯二胺 在 盐酸 、 potassium carbonate 作用下， 以 乙二醇甲醚 为溶剂， 反应 25.25h， 生成 N1,N1-dimethyl-N4-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,4-diamine
  参考文献：
  名称：

  Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors

  摘要：

  The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2-pyrimidinamine (1-27) was chosen for toxicological evaluation.

  DOI：

  10.1021/jm00071a002

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.
• 4,5,6-Substituted-2-pyrimidinamines
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0233461B1

  公开（公告）日：1996-03-20
• US4788195A
  申请人：——

  公开号：US4788195A

  公开（公告）日：1988-11-29