3-(1-(3-(3-aminopropoxy)-4-(4-methoxy thiazol-2-yl) phenyl)-1H-imidazol-2-yl) propanoic acid | 1421328-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1-(3-(3-aminopropoxy)-4-(4-methoxy thiazol-2-yl) phenyl)-1H-imidazol-2-yl) propanoic acid
• 英文别名: 3-[1-[3-(3-Aminopropoxy)-4-(4-methoxy-1,3-thiazol-2-yl)phenyl]imidazol-2-yl]propanoic acid；3-[1-[3-(3-aminopropoxy)-4-(4-methoxy-1,3-thiazol-2-yl)phenyl]imidazol-2-yl]propanoic acid
• CAS: 1421328-77-9
• 化学式: C₁₉H₂₂N₄O₄S
• 分子量: 402.474
• InChiKey: RMSUCILVQMUEKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-(1H-咪唑-2-基)-丙酸 在 copper(l) iodide 、 氯化亚砜 、 ammonium sulfide 、 potassium carbonate 、 L-脯氨酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 89.0h， 生成 3-(1-(3-(3-aminopropoxy)-4-(4-methoxy thiazol-2-yl) phenyl)-1H-imidazol-2-yl) propanoic acid
  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

文献信息

• Expedient route to functionalized and water soluble 5-6-5 imidazole-phenyl-thiazole based α-helix mimetics
  作者：Christopher G. Cummings、Andrew D. Hamilton

  DOI：10.1016/j.tet.2012.11.070

  日期：2013.2

  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.