N-[3-(2-Imidazol-1-yl-ethoxy)-phenyl]-guanidine | 742662-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[3-(2-Imidazol-1-yl-ethoxy)-phenyl]-guanidine
• 英文别名: 2-[3-(2-Imidazol-1-ylethoxy)phenyl]guanidine
• CAS: 742662-24-4
• 化学式: C₁₂H₁₅N₅O
• 分子量: 245.284
• InChiKey: OGNLKMYSFKXOFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-1-(2-thienyl)-2-propen-1-one 、 N-[3-(2-Imidazol-1-yl-ethoxy)-phenyl]-guanidine 在 potassium carbonate 作用下， 以 乙二醇甲醚 为溶剂， 反应 25.0h， 生成 N-[3-[2-(1H-imidazol-1-yl)ethoxy]phenyl]-4-(thien-2-yl)-2-pyrimidinamine
  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
• 作为产物：
  描述：

  1-(2-氯乙氧基)-3-硝基苯 在 platinum(IV) oxide 盐酸 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 N-[3-(2-Imidazol-1-yl-ethoxy)-phenyl]-guanidine
  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

• Potent and selective inhibitors of the Abl-kinase: phenylamino-pyrimidine (PAP) derivatives
  作者：Jürg Zimmermann、Elisabeth Buchdunger、Helmut Mett、Thomas Meyer、Nicholas B. Lydon

  DOI：10.1016/s0960-894x(96)00601-4

  日期：1997.1

  Due to its relatively clear etiology, Chronic myelogenous leukemia (CML) represents an ideal disease target for a therapy using a selective inhibitor of the Bcr-Abl tyrosine protein kinase. Extensive optimization of the class of phenylamino-pyrimidines yielded highly potent and selective Bcr-Abl kinase inhibitors. Compound 1 shows high potency (IC50 = 38 nM) and selectivity for the Abl tyrosine protein kinase at the in vitro level. (C) 1997, Elsevier Science Ltd.
• 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.