cyclohexyl-{4-[2-(3,4-dichloro-phenyl)-5-methoxy-benzoimidazol-1-yl]-pyridin-2-yl}-amine | 1428958-79-5

• 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: cyclohexyl-{4-[2-(3,4-dichloro-phenyl)-5-methoxy-benzoimidazol-1-yl]-pyridin-2-yl}-amine
• 英文别名: N-cyclohexyl-4-[2-(3,4-dichlorophenyl)-5-methoxybenzimidazol-1-yl]pyridin-2-amine
• CAS: 1428958-79-5
• 化学式: C₂₅H₂₄Cl₂N₄O
• 分子量: 467.398
• InChiKey: VCPZSBQOFFKKEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclohexyl-{4-[2-(3,4-dichloro-phenyl)-5-methoxy-benzoimidazol-1-yl]-pyridin-2-yl}-amine 在 三溴化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到1-(2-cyclohexylamino-pyridin-4-yl)-2-(3,4-dichloro-phenyl)-1H-benzoimidazol-5-ol
  参考文献：
  名称：

  Syntheses and biological evaluation of 1-heteroaryl-2-aryl-1 H -benzimidazole derivatives as c-Jun N-terminal kinase inhibitors with neuroprotective effects

  摘要：

  1-Heteroaryl-2-aryl-1H-benzimidazole derivatives were synthesized as inhibitors of c-Jun N-terminal kinases, JNK3. Their activities were evaluated through measurement of K-d using SPR, JNK3 kinase assay, and cell-viability of human neuroblastoma cells. Most tested compounds showed high affinity (10 mu M-46 nM) to JNK3. Among them, compound 16f exhibited potent activities (K-d = 46 nM). Especially, 16f was also found to present a potent cell protective effect (IC50 = 1.09 mu M) against toxicity induced by anisomycin, showing a possibility as protective therapeutics in neuronal cell apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.021
• 作为产物：
  描述：

  N-cyclohexyl-1-hydroxy-4-nitropyridin-2-imine 在 potassium phosphate 、 ammonium cerium (IV) nitrate 、 BINAP 、 palladium on activated charcoal 、 氢气 、 双氧水 、 palladium diacetate 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 20.5h， 生成 cyclohexyl-{4-[2-(3,4-dichloro-phenyl)-5-methoxy-benzoimidazol-1-yl]-pyridin-2-yl}-amine
  参考文献：
  名称：

  Syntheses and biological evaluation of 1-heteroaryl-2-aryl-1 H -benzimidazole derivatives as c-Jun N-terminal kinase inhibitors with neuroprotective effects

  摘要：

  1-Heteroaryl-2-aryl-1H-benzimidazole derivatives were synthesized as inhibitors of c-Jun N-terminal kinases, JNK3. Their activities were evaluated through measurement of K-d using SPR, JNK3 kinase assay, and cell-viability of human neuroblastoma cells. Most tested compounds showed high affinity (10 mu M-46 nM) to JNK3. Among them, compound 16f exhibited potent activities (K-d = 46 nM). Especially, 16f was also found to present a potent cell protective effect (IC50 = 1.09 mu M) against toxicity induced by anisomycin, showing a possibility as protective therapeutics in neuronal cell apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.021