3-((5-bromo-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol | 1229037-63-1

• 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: 3-((5-bromo-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol
• 英文别名: 3-[(6-bromo-1H-benzimidazol-2-yl)amino]propan-1-ol
• CAS: 1229037-63-1
• 化学式: C₁₀H₁₂BrN₃O
• 分子量: 270.129
• InChiKey: OYZFCLHACXFALQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-3’,5’-二-叔丁-4’-羟基苯乙酮 、 3-((5-bromo-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以18%的产率得到2-(5-bromo-2-(3-hydroxypropylamino)-1H-benzo[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone
  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
• 作为产物：
  描述：

  2,5-dibromo-1H-benzimidazole 、 3-氨基-1-丙醇 反应 0.5h， 以47%的产率得到3-((5-bromo-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol
  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

文献信息

• Inhibition of Protein Kinase C-Driven Nuclear Factor-κB Activation: Synthesis, Structure−Activity Relationship, and Pharmacological Profiling of Pathway Specific Benzimidazole Probe Molecules
  作者：Satyamaheshwar Peddibhotla、Ranxin Shi、Pasha Khan、Layton H. Smith、Arianna Mangravita-Novo、Michael Vicchiarelli、Ying Su、Karl J. Okolotowicz、John R. Cashman、John C. Reed、Gregory P. Roth

  DOI：10.1021/jm1000248

  日期：2010.6.24

  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.