N-(3-methoxypropyl)-5,6-dimethyl-1H-benzo[d]imidazol-2-amine | 1229037-66-4

• 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: N-(3-methoxypropyl)-5,6-dimethyl-1H-benzo[d]imidazol-2-amine
• CAS: 1229037-66-4
• 化学式: C₁₃H₁₉N₃O
• 分子量: 233.313
• InChiKey: SLKQBHDNJNYHOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.94
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-溴-3’,5’-二-叔丁-4’-羟基苯乙酮 、 N-(3-methoxypropyl)-5,6-dimethyl-1H-benzo[d]imidazol-2-amine 以 正丁醇 为溶剂， 生成 2-(2-(3-methoxypropylamino)-5,6-dimethyl-1H-benzo-[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone
  参考文献：
  名称：

  Selective benzimidazole inhibitors of the antigen receptor-mediated NF-κB activation pathway

  摘要：

  Dysregulated antigen receptor-mediated NF-kappa B activation can contribute to development of autoimmunity, chronic inflammation, and malignancy. A chemical biology screening strategy has identified a substituted benzimidazole that selectively inhibits antigen receptor-mediated NF-kappa B activation without blocking other NF-kappa B activation pathways. A library of analogs was synthesized and the structure-activity relationship and metabolic stability for the series is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.039
• 作为产物：
  描述：

  2-bromo-5,6-dimethyl-1H-benzo[d]imidazole 、 3-甲氧基丙胺 反应 0.5h， 以93%的产率得到N-(3-methoxypropyl)-5,6-dimethyl-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Inhibition of Protein Kinase C-Driven Nuclear Factor-κB Activation: Synthesis, Structure−Activity Relationship, and Pharmacological Profiling of Pathway Specific Benzimidazole Probe Molecules

  摘要：

  A unique series of biologically active chemical probes that selectively inhibit NF-kappa B activation induced by protein kinase C (PKC) pathway activators have been identified through a cell-based phenotypic reporter gene assay. These 2-aminobenzimidazoles represent initial chemical tools to be used in gaining further understanding on the cellular mechanisms driven by B and T cell antigen receptors. Starting from the founding member of this chemical series 1a (notated in PubChem as CID-2858522), we report the chemical synthesis, SAR studies, and pharmacological profiling of this pathway-selective inhibitor of NF-kappa B activation.

  DOI：

  10.1021/jm1000248