1-(4-ethylphenyl)-2-(2-imino-3-methyl-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone hydrobromide | 1607834-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-ethylphenyl)-2-(2-imino-3-methyl-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone hydrobromide
• 英文别名: 1-(4-Ethylphenyl)-2-(2-imino-3-methylbenzimidazol-1-yl)ethanone;hydrobromide；1-(4-ethylphenyl)-2-(2-imino-3-methylbenzimidazol-1-yl)ethanone;hydrobromide
• CAS: 1607834-10-5
• 化学式: BrH*C₁₈H₁₉N₃O
• 分子量: 374.28
• InChiKey: KLWUAOMNICGLKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-2-硝基苯胺 在 盐酸 、 氢气 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 20.0~150.0 ℃ 、101.33 kPa 条件下， 反应 31.5h， 生成 1-(4-ethylphenyl)-2-(2-imino-3-methyl-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone hydrobromide
  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

• Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action
  作者：Marc Peter Windisch、Suyeon Jo、Hee-Young Kim、Soo-Hyun Kim、Keumhyun Kim、Sunju Kong、Hyangsuk Jeong、Sujin Ahn、Zaesung No、Jong Yeon Hwang

  DOI：10.1016/j.ejmech.2014.03.030

  日期：2014.5

  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.