2-(2-(3-methoxypropylamino)-5,6-dimethyl-1H-benzo-[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone | 1189164-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-(3-methoxypropylamino)-5,6-dimethyl-1H-benzo-[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone
• 英文别名: 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(2-(3-methoxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone；2-(2-(3-methoxypropylamino)-5,6-dimethyl-1H-benzo[d]imidazol-1-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone；1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-[2-(3-methoxypropylamino)-5,6-dimethylbenzimidazol-1-yl]ethanone
• CAS: 1189164-47-3
• 化学式: C₂₉H₄₁N₃O₃
• 分子量: 479.663
• InChiKey: OCJFISAERVJZBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  76.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• INHIBITORS OF ANTIGEN RECEPTOR-INDUCED NF-kappa B ACTIVATION
  申请人：REED John C.

  公开号：US20090247520A1

  公开（公告）日：2009-10-01

  A method to identify selective inhibitors of antigen receptor-mediated NF-κB activation is provided, as well as compositions having one or more of those inhibitors and methods of using those inhibitors.

  提供了一种识别抗原受体介导的NF-κB激活的选择性抑制剂的方法，以及具有一个或多个这些抑制剂的组合物和使用这些抑制剂的方法。
• Selective benzimidazole inhibitors of the antigen receptor-mediated NF-κB activation pathway
  作者：Karl J. Okolotowicz、Ranxin Shi、Xueying Zheng、Mary MacDonald、John C. Reed、John R. Cashman

  DOI：10.1016/j.bmc.2010.01.039

  日期：2010.3

  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.
• INHIBITORS OF ANTIGEN RECEPTOR-INDUCED NF- KAPPA B ACTIVATION
  申请人：Burnham Institute for Medical Research

  公开号：EP2268620A2

  公开（公告）日：2011-01-05
• [EN] INHIBITORS OF ANTIGEN RECEPTOR-INDUCED NF-?B ACTIVATION<br/>[FR] INHIBITEURS DE L'ACTIVATION DE NF-?B INDUITE PAR RÉCEPTEUR D'ANTIGÈNE
  申请人：BURNHAM INST MEDICAL RESEARCH

  公开号：WO2009120874A2

  公开（公告）日：2009-10-01

  A method to identify selective inhibitors of antigen receptor-mediated NF-кB activation is provided, as well as compositions having one or more of those inhibitors and methods of using those inhibitors.
• 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.