methyl 3-(1-(3-bromo-4-carbamothioylphenyl)-1H-imidazol-2-yl)propanoate | 1421329-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(1-(3-bromo-4-carbamothioylphenyl)-1H-imidazol-2-yl)propanoate
• CAS: 1421329-53-4
• 化学式: C₁₄H₁₄BrN₃O₂S
• 分子量: 368.254
• InChiKey: CALIPLZCEIMKMV-UHFFFAOYSA-N

物化性质

• 沸点：
  535.9±60.0 °C(predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  70.14
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(1-(3-bromo-4-carbamothioylphenyl)-1H-imidazol-2-yl)propanoate 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 methyl 3-(1-(4'-amino-6-(4-methoxythiazol-2-yl)biphenyl-3-yl)-1H-imidazol-2-yl)propanoate
  参考文献：
  名称：

  Expedient route to functionalized and water soluble 5-6-5 imidazole-phenyl-thiazole based α-helix mimetics

  摘要：

  A range of small molecule scaffolds have been shown to act as structural and functional mimics of alpha-helices by mimicking the i, i+4, and i+7 positions, often found at the interface of PPIs. These molecules, though potent, possess complicating features-either low water solubility, or maintenance of conformation by hydrogen-bonding networks. We have addressed these limitations by developing a scaffold with increased water solubility. Herein we present a rapid synthetic pathway to a library of 56 compounds based on a 5-6-5 scaffold, containing an imidazole-phenyl-thiazole core; the route is flexible and allows rapid installation of different substituents via high-yielding Ullman and Suzuki couplings and Hantsch thiazole syntheses. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.11.070
• 作为产物：
  描述：

  methyl 3-(1-(3-bromo-4-cyanophenyl)-1H-imidazol-2-yl)propanoate 在 ammonium sulfide 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以86%的产率得到methyl 3-(1-(3-bromo-4-carbamothioylphenyl)-1H-imidazol-2-yl)propanoate
  参考文献：
  名称：

  Expedient route to functionalized and water soluble 5-6-5 imidazole-phenyl-thiazole based α-helix mimetics

  摘要：

  A range of small molecule scaffolds have been shown to act as structural and functional mimics of alpha-helices by mimicking the i, i+4, and i+7 positions, often found at the interface of PPIs. These molecules, though potent, possess complicating features-either low water solubility, or maintenance of conformation by hydrogen-bonding networks. We have addressed these limitations by developing a scaffold with increased water solubility. Herein we present a rapid synthetic pathway to a library of 56 compounds based on a 5-6-5 scaffold, containing an imidazole-phenyl-thiazole core; the route is flexible and allows rapid installation of different substituents via high-yielding Ullman and Suzuki couplings and Hantsch thiazole syntheses. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.11.070