1-(4-Ethoxyphenyl)-2-(trichloromethyl)benzimidazol-5-amine | 1421589-66-3

• 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: 1-(4-Ethoxyphenyl)-2-(trichloromethyl)benzimidazol-5-amine
• 英文别名: 1-(4-ethoxyphenyl)-2-(trichloromethyl)benzimidazol-5-amine
• CAS: 1421589-66-3
• 化学式: C₁₆H₁₄Cl₃N₃O
• 分子量: 370.666
• InChiKey: OGWCCHJEZBBEBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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-(4-Ethoxyphenyl)-2-(trichloromethyl)benzimidazol-5-amine 在 ammonium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-(4-Ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile
  参考文献：
  名称：

  Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles

  摘要：

  A series of potent arenavirus inhibitors sharing a benzimidazole core were previously reported by our group. SAR studies were expanded beyond the previous analysis, which involved the attached phenyl rings and methylamino linker portion, to include modifications focused on the benzimidazole core. These changes included the introduction of various substituents to the bicyclic benzimidazole ring system along with alternate core heterocycles. Many of the analogs containing alternate nitrogen-based bicyclic ring systems were found to retain antiviral potency compared to the benzimidazole series from which we derived our lead compound, ST-193. In fact, 21h, built on an imidazopyridine core, possessed a near tenfold increase in potency against Lassa virus pseudotypes compared to ST-193. As found with the benzimidazole series, broad-spectrum arenavirus activity was also observed for a number of the analogs discovered during this study. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.093
• 作为产物：
  描述：

  1-N-(4-ethoxyphenyl)benzene-1,2,4-triamine 、 2,2,2-三氯乙酰亚胺酸甲酯 在 溶剂黄146 作用下， 反应 4.0h， 以40%的产率得到1-(4-Ethoxyphenyl)-2-(trichloromethyl)benzimidazol-5-amine
  参考文献：
  名称：

  Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles

  摘要：

  A series of potent arenavirus inhibitors sharing a benzimidazole core were previously reported by our group. SAR studies were expanded beyond the previous analysis, which involved the attached phenyl rings and methylamino linker portion, to include modifications focused on the benzimidazole core. These changes included the introduction of various substituents to the bicyclic benzimidazole ring system along with alternate core heterocycles. Many of the analogs containing alternate nitrogen-based bicyclic ring systems were found to retain antiviral potency compared to the benzimidazole series from which we derived our lead compound, ST-193. In fact, 21h, built on an imidazopyridine core, possessed a near tenfold increase in potency against Lassa virus pseudotypes compared to ST-193. As found with the benzimidazole series, broad-spectrum arenavirus activity was also observed for a number of the analogs discovered during this study. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.093