1-(2-(4-chlorophenoxy)ethyl)-1H-benzo[d]imidazol-2-amine | 364617-45-8

• 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: 1-(2-(4-chlorophenoxy)ethyl)-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-[2-(4-Chloro-phenoxy)-ethyl]-1H-benzoimidazol-2-ylamine；1-[2-(4-chlorophenoxy)ethyl]benzimidazol-2-amine
• CAS: 364617-45-8
• 化学式: C₁₅H₁₄ClN₃O
• 分子量: 287.749
• InChiKey: RHYRBJPJWNQOPR-UHFFFAOYSA-N

物化性质

• 溶解度：
  25.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-(4-chlorophenoxy)ethyl)-1H-benzo[d]imidazol-2-amine 在 C.I.酸性橙108 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 9-(2-(4-chlorophenoxy)ethyl)-2-ethyl-9H-benzo[d]imidazo[1,2-a]imidazole
  参考文献：
  名称：

  Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

  摘要：

  In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.030
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 1-(2-溴乙氧基)-4-氯苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以48%的产率得到1-(2-(4-chlorophenoxy)ethyl)-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

  摘要：

  In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.030

文献信息

• Synthesis of 9-Substituted Imidazo[1,2-a]benzimidazoles Containing a 5-Nitrofuran-2-yl Fragment
  作者：T. A. Kuzmenko、L. N. Divaeva、Yu. A. Sayapin、A. S. Morkovnik、G. S. Borodkin

  DOI：10.1134/s1070428019100130

  日期：2019.10

  9-Substituted 2-(5-nitrofuran-2-yl)-9H-imidazo[1,2-a]benzimidazoles were synthesized for the first time by cyclization of quaternary salts obtained from 1-substituted benzimidazol-2-amines and 2-bromo-1-(5-nitrofuran-2-yl)ethan-1-one. 9-R-2-Methyl(aryl)-9H-imidazo[1,2-a]benzimidazoles reacted with 5-nitrofuran2-carbaldehyde and 4-nitrobenzaldehyde to give the corresponding secondary alcohols as a result of aldehyde addition to the 3-position of the tricyclic system. The Witting olefination of ethyl 2-(bromomethyl)-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate afforded 2-ethenylimidazo[1,2-a]benzimidazoles.