1-(4-Ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile | 1366232-86-1

• 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)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile
• CAS: 1366232-86-1
• 化学式: C₂₅H₂₄N₄O
• 分子量: 396.492
• InChiKey: PKZSQIDDNYZXST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-Ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carbonitrile 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以42%的产率得到1-(4-Ethoxyphenyl)-5-[(4-ethylphenyl)methylamino]benzimidazole-2-carboxamide
  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 在 ammonium hydroxide 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.5h， 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

文献信息

• Antiviral Drugs for Treatment of Arenavirus Infection
  申请人：Dai Dongcheng

  公开号：US20120071447A1

  公开（公告）日：2012-03-22

  Methods, compounds, and pharmaceutical compositions for treating an arenavirus infections are disclosed. Methods for preparing the compounds and pharmaceutical compositions are also disclosed. The novel compounds and compositions are used for treatment of an arenavirus infections, which include but are not limited to the following viruses: Junin, Machupo, Guanarito, Sabia, Lassa, Tacaribe, Pichinde, and LCMV.
• US8871746B2
  申请人：——

  公开号：US8871746B2

  公开（公告）日：2014-10-28