N,1-dibenzyl-1H-benzo[d]imidazol-2-amine | 27185-23-5

• 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,1-dibenzyl-1H-benzo[d]imidazol-2-amine
• 英文别名: N,1-dibenzyl-1H-2-aminobenzimidazole；benzyl-(1-benzyl-1H-benzoimidazol-2-yl)-amine；1-Benzyl-2-benzylaminobenzimidazole；N,1-dibenzylbenzimidazol-2-amine
• CAS: 27185-23-5
• 化学式: C₂₁H₁₉N₃
• 分子量: 313.402
• InChiKey: MEIMMRRAQLHVQI-UHFFFAOYSA-N

物化性质

• 沸点：
  528.6±53.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯苯并咪唑 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 13.5h， 生成 N,1-dibenzyl-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903

  摘要：

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.

  DOI：

  10.1016/j.bmcl.2018.12.007

文献信息

• Regioselective N-Alkylation of 2-Aminoimidazoles with Alcohols to 2-(N-Alkylamino)imidazoles Catalyzed by the [Cp*IrCl2]2/K2CO3 System
  作者：Feng Li、Qikai Kang、Haixia Shan、Lin Chen、Jianjiang Xie

  DOI：10.1002/ejoc.201200698

  日期：2012.9

  The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino)imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign.

  在 [Cp*IrCl2]2/K2CO3 系统存在下，使用醇作为烷基化剂，完成 2-氨基咪唑的直接 N-烷基化以得到相应的 2-(N-烷基氨基)咪唑。铱催化的区域选择性反应简单、高效、通用且对环境无害。
• Novel 2-Amino Benzimidazole Derivatives and Their Use As Modulators Of Small-Conductance Calcium-Activated Potassium Channels
  申请人：Sorensen Ulrik Svane

  公开号：US20080200529A1

  公开（公告）日：2008-08-21

  This invention relates to novel 2-amino benzimidazole derivatives useful as modulators of small-conductance calcium-activated potassium channels (SK channels). In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及一种新型2-氨基苯并咪唑衍生物，可用作小通量钙激活钾通道（SK通道）的调节剂。在其他方面，本发明涉及将这些化合物用于治疗方法以及包含本发明化合物的制药组合物。
• NOVEL 2-AMINO BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS MODULATORS OF SMALL-CONDUCTANCE CALCIUM-ACTIVATED POTASSIUM CHANNELS
  申请人：Sørensen Ulrik Svane

  公开号：US20100280087A1

  公开（公告）日：2010-11-04

  This invention relates to novel 2-amino benzimidazole derivatives useful as modulators of small-conductance calcium-activated potassium channels (SK channels). In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及新颖的2-氨基苯并咪唑衍生物，其可用作小电导钙激活钾通道（SK通道）的调节剂。在其他方面，本发明涉及使用这些化合物的方法进行治疗，并且涉及包含本发明化合物的制药组合物。
• Novel 2-amino benzimidazole derivatives and their use as modulators of small-conductance calcium-activated potassium channels.
  申请人：NeuroSearch AS

  公开号：EP2319512A1

  公开（公告）日：2011-05-11

  This invention relates to novel 2-amino benzimidazole derivatives of formula (Ia) and (Ib) useful as modulators of small-conductance calcium-activated potassium channels (SK channels). In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及新型的式(Ia)和(Ib)2-氨基苯并咪唑衍生物，可作为小电导钙激活钾通道（SK 通道）的调节剂。 在其他方面，本发明涉及这些化合物在治疗方法中的用途以及包含本发明化合物的药物组合物。
• Copper-catalyzed synthesis of 2-aminobenzimidazoles from carbonimidoyl dichlorides and amines
  作者：Hui Yu、Qiong Liu、Yuzhe Li、Chongzhi Ni

  DOI：10.1016/j.tetlet.2012.07.072

  日期：2012.9

  A new protocol for the synthesis of a variety of 2-aminobenzimidazole derivatives has been developed. O-haloaryl carbonimidoyl dichloride reacted with anilines to generate an o-haloaryl guanidine intermediate, which underwent copper catalyzed ring closure to afford 2-aminobenzimidazole derivative in moderate yields (c) 2012 Elsevier Ltd. All rights reserved.