6-[5-phenyl-2-(2-trifluoromethylphenyl)-1H-imidazol-4-yl]-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine | 660433-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-[5-phenyl-2-(2-trifluoromethylphenyl)-1H-imidazol-4-yl]-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine
• 英文别名: 1-isopropylsulfonyl-2-amino-6-(2-(2-trifluoromethylphenyl)-5-(phenyl)-imidazol-4-yl)-benzimidazole；6-[5-phenyl-2-[2-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]-1-propan-2-ylsulfonylbenzimidazol-2-amine
• CAS: 660433-13-6
• 化学式: C₂₆H₂₂F₃N₅O₂S
• 分子量: 525.554
• InChiKey: PZIQORVTXWOXED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-(phenylethynyl)-1-(propane-2-sulfonyl)-1H-benzimidazol-2-ylamine 在 potassium permanganate 、 ammonium acetate 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 水 、 丙酮 、 正丁醇 为溶剂， 反应 26.0h， 生成 6-[5-phenyl-2-(2-trifluoromethylphenyl)-1H-imidazol-4-yl]-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine
  参考文献：
  名称：

  Synthesis of Imidazole Based p38 MAP (Mitogen-Activated Protein) Kinase Inhibitors under Buffered Conditions

  摘要：

  This article describes chemistry that was developed to give access to multigram quantities of imidazole 479754 and several related analogues for Eli Lilly's p38 MAPK program targeting therapies to address inflammation. The molecules of interest have an isopropyl sulfonyl group present on the 2-aminobenzimidazole heterocycyle that was found to be labile when heated in polar solvents and/or exposed to high or low pH. Due to this instability issue, the syntheses of the target molecules required optimizing Sonogashira reaction conditions, employing a buffered oxidative method to produce alpha-diones, developing buffered reaction conditions to generate imidazoles, and developing final recrystallization conditions.

  DOI：

  10.1021/op060042t

文献信息

• [EN] BENZIMIDAZOLES AND BENZOTHIAZOLES AS INHIBITORS OF MAP KINASE<br/>[FR] BENZIMIDAZOLES ET BENZOTHIAZOLES UTILISES COMME INHIBITEURS DE LA MAP KINASE
  申请人：LILLY CO ELI

  公开号：WO2004014900A1

  公开（公告）日：2004-02-19

  The present invention provides kinase inhibitors of Formula I: wherein W represents inter alia imidazol, oxazol, pyrazol, thiazol as triazol, which are substituted by phenyl or thienyl. The disclosed compounds inhibit p-38 kinase and are useful in the treatment of metastasis or rheumatoid arthritis.

  本发明提供了一种化合物I的激酶抑制剂：其中W代表咪唑、噁唑、吡唑、噻唑或三唑等，这些化合物被苯基或噻吩基取代。所公开的化合物抑制p-38激酶，在转移或类风湿性关节炎的治疗中很有用。
• BENZIMIDAZOLES AND BENZOTHIAZOLES AS INHIBITORS OF MAP KINASE
  申请人：ELI LILLY AND COMPANY

  公开号：EP1554272A1

  公开（公告）日：2005-07-20