2-(5-amino-2-(3-hydroxypropylamino)-1H-benzo[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone | 1135306-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-amino-2-(3-hydroxypropylamino)-1H-benzo[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone
• 英文别名: 2-[5-Amino-2-(3-hydroxypropylamino)benzimidazol-1-yl]-1-(3,5-ditert-butyl-4-hydroxyphenyl)ethanone
• CAS: 1135306-20-5
• 化学式: C₂₆H₃₆N₄O₃
• 分子量: 452.597
• InChiKey: ZJMAIGXEAQQGDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-hydroxypropylamino)-5-nitro-1H-benzo[d]imidazol-1-yl)ethanone 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以28%的产率得到2-(5-amino-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

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.