2-(3-Imidazol-1-ylphenyl)guanidine;hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-Imidazol-1-ylphenyl)guanidine;hydrochloride
• 化学式: C₁₀H₁₁N₅*ClH
• 分子量: 237.692
• InChiKey: AJHRNJBPPWCRJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-(dimethylamino)-1-(pyridin-2-yl)prop-2-en-1-one 、 2-(3-Imidazol-1-ylphenyl)guanidine;hydrochloride 在 potassium carbonate 作用下， 以 乙二醇甲醚 为溶剂， 反应 25.0h， 生成 N-(3-咪唑-1-基苯基)-4-吡啶-2-基嘧啶-2-胺
  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：

  间氟硝基苯 在 platinum(IV) oxide 盐酸 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 25.75h， 生成 2-(3-Imidazol-1-ylphenyl)guanidine;hydrochloride
  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

• Process for the synthesis of
  申请人：American Cyanamid Company

  公开号：US05064963A1

  公开（公告）日：1991-11-12

  The invention provides a novel process for producing N-[3-(1H-imidazol-1-yl)phenyl]-4-(substituted)-2 pyrimidinamine compounds in which the substituent is a 2-pyridinyl, 3-pyrindinyl, 4-pyridinyl, 2-furanyl or 2-thienyl group. The process includes the steps of (1) reacting a 3-(1H-imidazol-1-yl)benzamine with cyanamide and a halogen acid while controlling the pH of the reaction between pH about 2 to abourt 3.5 and recovering a [3-(1H-imidazol-1-yl)phenyl] guanidine dihydrohalide and (2) reacting the [3-(1H-imidazol-1-yl)phenyl] guanidine dihydrohalide so recovered with an appropriately substituted 3-dimethylamino-1-(substituted)-2-propen-1-one and a base at a pH of from about 10.5 to about 11.5 and recovering the N-[3-(1H-imidazol-1-yl)phenyl-4-(substituted)-2-pyrimidamine compound so produced. The novel process provides improved yield and purity by adhering to the stated crucial pH ranges.

  该发明提供了一种新型的生产N-[3-(1H-咪唑-1-基)苯基]-4-(取代基)-2-嘧啶胺化合物的方法，其中取代基是2-吡啶基、3-吡啶基、4-吡啶基、2-呋喃基或2-噻吩基。该方法包括以下步骤：(1)在控制反应的pH在约2到约3.5之间的条件下，将3-(1H-咪唑-1-基)苯胺与氰胺和一种卤酸反应，从中回收[3-(1H-咪唑-1-基)苯基]胍二氢卤化物；(2)将回收的[3-(1H-咪唑-1-基)苯基]胍二氢卤化物与适当取代的3-二甲胺基-1-(取代基)-2-丙烯-1-酮和碱在pH约为10.5到约11.5的条件下反应，从中回收所生产的N-[3-(1H-咪唑-1-基)苯基]-4-(取代基)-2-嘧啶胺化合物。这种新型方法通过遵循所述关键的pH范围提高了产量和纯度。
• 4,5,6-Substituted-2-pyrimidinamines
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0233461A2

  公开（公告）日：1987-08-26

  This disclosure describes novel 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines having anti-asthmatic activity.

  本公开介绍了具有抗哮喘活性的新型 4,5,6-取代-N-（取代苯基）-2-嘧啶胺。
• US4788195A
  申请人：——

  公开号：US4788195A

  公开（公告）日：1988-11-29
• US4876252A
  申请人：——

  公开号：US4876252A

  公开（公告）日：1989-10-24