2-(furan-2-carboxamido)-N-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide | 1446200-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(furan-2-carboxamido)-N-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide
• 英文别名: 2-(furan-2-carbonylamino)-N-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]-1,3-thiazole-4-carboxamide
• CAS: 1446200-54-9
• 化学式: C₁₇H₁₀F₃N₅O₃S
• 分子量: 421.359
• InChiKey: WUTIYWPTAVOYGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-三氟甲基-1H-苯并咪唑-2-胺 、 2-(2-呋喃基氨基)-1,3-噻唑-4-羧酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以35%的产率得到2-(furan-2-carboxamido)-N-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide
  参考文献：
  名称：

  2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε

  摘要：

  In this study we identified two heterocyclic compounds (5 and 6) as potent and specific inhibitors of CK1 delta (IC50 = 0.040 and 0.042 mu M, respectively). Whereas compound 5 exhibited fivefold higher affinity towards CK1 delta than to CK1 epsilon (IC50 CK1 epsilon = 0.199 mu M), compound 6 also inhibited CK1 epsilon (IC50 = 0.0326 mu M) in the same range as CK1 delta. Selected compound 5 was screened over 442 kinases identifying 5 as a highly potent and selective inhibitor of CK1 delta. X-ray analysis of 5 bound to CK1 delta demonstrated its binding mode. In addition, characterization of 5 and 6 in a cell biological approach revealed the ability of both compounds to inhibit proliferation of tumor cell lines in a dose and cell line specific manner. In summary, our optimizations lead to the development of new highly selective CK1 delta and epsilon specific inhibitors with biological activity.

  DOI：

  10.1007/s00726-012-1234-x