2-(4-phenyl-1H-imidazol-1-yl)ethanamine | 838892-89-0

• 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-(4-phenyl-1H-imidazol-1-yl)ethanamine
• 英文别名: 2-(4-phenyl-1H-imidazol-1-yl)ethan-1-amine；2-(4-phenylimidazol-1-yl)ethanamine
• CAS: 838892-89-0
• 化学式: C₁₁H₁₃N₃
• mdl: MFCD09909018
• 分子量: 187.244
• InChiKey: OLOQGQICYXJXOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-(4-phenyl-1H-imidazol-1-yl)ethyl)isoindoline-1,3-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以55%的产率得到2-(4-phenyl-1H-imidazol-1-yl)ethanamine
  参考文献：
  名称：

  [EN] INDANE DERIVATES AS MUSCARINIC RECEPTOR AGONISTS
  [FR] DERIVES D'INDANE UTILISES COMME AGONISTES DU RECEPTEUR MUSCARINIQUE

  摘要：

  这项发明涉及到Formula I的化合物，这些化合物是M-1肌氨酸受体的激动剂。

  公开号：

  WO2005009941A1

文献信息

• Structure Based Development of Phenylimidazole-Derived Inhibitors of Indoleamine 2,3-Dioxygenase
  作者：Sanjeev Kumar、Daniel Jaller、Bhumika Patel、Judith M. LaLonde、James B. DuHadaway、William P. Malachowski、George C. Prendergast、Alexander J. Muller

  DOI：10.1021/jm800512z

  日期：2008.8.1

  Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. With the goal of developing more potent IDO inhibitors, a systematic study of 4-phenylimidazole (4-PI) derivatives was undertaken. Computational docking experiments guided design and synthesis efforts with analogues of 4-PI. In particular, three interactions of 4-PI analogues with IDO were studied: the active site entrance, the interior of the active site, and the heme iron binding. The three most potent inhibitors (1, 17, and 18) appear to exploit interactions with C129 and S167 in the interior of the active site. All three inhibitors are approximately 10-fold more potent than 4-PI. The study represents the first example of enzyme inhibitor development with the recently reported crystal structure of IDO and offers important lessons in the search for more potent inhibitors.