3-(dimethylamino)-1-(4-pyridinyl)-2-buten-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(dimethylamino)-1-(4-pyridinyl)-2-buten-1-one
• 英文别名: (Z)-3-(dimethylamino)-1-pyridin-4-ylbut-2-en-1-one
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: QERHIRHODWYXGV-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenylguanidine hydrochloride 、 3-(dimethylamino)-1-(4-pyridinyl)-2-buten-1-one 在 potassium carbonate 作用下， 以 乙二醇甲醚 为溶剂， 反应 25.0h， 以35%的产率得到(4-Methyl-6-pyridin-4-yl-pyrimidin-2-yl)-phenyl-amine
  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

• US4551530A
  申请人：——

  公开号：US4551530A

  公开（公告）日：1985-11-05
• Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors
  作者：Rolf Paul、William A. Hallett、John W. Hanifin、Marvin F. Reich、Bernard D. Johnson、Robert H. Lenhard、John P. Dusza、Suresh S. Kerwar、Yang I Lin

  DOI：10.1021/jm00071a002

  日期：1993.9

  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.