N-(5-羟基-1H-苯并[d]咪唑-2-基)-乙酰胺 | 30502-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: N-(5-羟基-1H-苯并[d]咪唑-2-基)-乙酰胺
• 英文名称: 2-Acetamido-5(6)-hydroxybenzimidazol
• 英文别名: N-(5-hydroxy-1(3)H-benzoimidazol-2-yl)-acetamide；5-hydroxy-2-acetylaminobenzimidazole；N-(6-hydroxy-1H-benzimidazol-2-yl)acetamide
• CAS: 30502-59-1
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: IZLMKPTXRGBSTQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-羟基-1H-苯并[d]咪唑-2-基)-乙酰胺 在 palladium on activated charcoal 氢气 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(5-(2-amino-5-pyridyloxy)-1H-benzimidazol-2-yl)acetamide
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051

文献信息

• Chemical compounds
  申请人：——

  公开号：US20040082583A1

  公开（公告）日：2004-04-29

  Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR2抑制剂有用的苯并咪唑衍生物。所述发明还包括制备这种苯并咪唑衍生物的方法，以及在治疗过度增殖性疾病中使用它们的方法。
• Novel Benzimidazole and Benzothiazole Derivatives, Method for Preparing Same, Use Thereof as Drugs, Pharmaceutical Compositions and Novel Use Especially as c-MET Inhibitors
  申请人：NEMECEK Conception

  公开号：US20080194555A1

  公开（公告）日：2008-08-14

  This invention relates to benzimidazole and benzothiazole compounds of formula (I) to methods of preparing such compounds, pharmaceutical compositions comprising such compounds, and to methods of treatment comprising administering of such compounds.

  本发明涉及公式（I）的苯并咪唑和苯并噻唑化合物的制备方法，包括这些化合物的制药组合物，以及包括这些化合物的治疗方法的管理方法。
• CHEMICAL COMPOUNDS
  申请人：Cheung Mui

  公开号：US20070249600A1

  公开（公告）日：2007-10-25

  Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR2抑制剂有用的苯并咪唑衍生物。所述发明还包括制备这种苯并咪唑衍生物的方法，以及在治疗过度增生性疾病中使用它们的方法。
• BENZIMIDAZOLE DERIVATIVES USEFUL AS TIE-2 AND/OR VEGFR-2 INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1341771A2

  公开（公告）日：2003-09-10
• US7238813B2
  申请人：——

  公开号：US7238813B2

  公开（公告）日：2007-07-03