3-((5,6-dimethyl-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol | 301163-47-3

• 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-((5,6-dimethyl-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol
• 英文别名: 3-(5,6-Dimethyl-1h-benzo[d]imidazol-2-ylamino)propan-1-ol；3-[(5,6-dimethyl-1H-benzimidazol-2-yl)amino]propan-1-ol
• CAS: 301163-47-3
• 化学式: C₁₂H₁₇N₃O
• 分子量: 219.286
• InChiKey: XIDOTXVRIXICOW-UHFFFAOYSA-N

物化性质

• 沸点：
  447.5±47.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  3-((5,6-dimethyl-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol 在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以65%的产率得到N-(3-azidopropyl)-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
• 作为产物：
  描述：

  1,3-二氢-5,6-二甲基-2H-苯并咪唑-2-硫酮 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 生成 3-((5,6-dimethyl-1H-benzo[d]imidazol-2-yl)amino)propan-1-ol
  参考文献：
  名称：

  Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

  摘要：

  核因子κB（NF-κB）的激活以及相关的上游信号转导途径长期以来与多种炎症性疾病的发病机制有关，并最近被认为与癌症的发病有关。本报告提供了五种与途径相关的小分子化学探针的综合和基于化合物的属性摘要，这些探针是在国家卫生研究院分子图书馆探针中心网络（NIH-MLPCN）倡议下确定和优化的。本文讨论的化学探针代表了NF-κB信号通路的首创性、非激酶基础的调节剂，这些探针是通过细胞表型或特定蛋白靶向的筛选策略确定和优化的。因此，由此产生的新化学探针可能有助于更好地理解这一高度复杂的生化信号网络，并有望推动将来向临床环境中的治疗转化。

  DOI：

  10.3762/bjoc.9.103

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.