1-(4-Butylphenyl)benzimidazol-5-amine | 1406439-21-1

• 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-Butylphenyl)benzimidazol-5-amine
• CAS: 1406439-21-1
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: AFEWOCBVXWNXNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Butylphenyl)benzimidazol-5-amine 、 丙酮 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

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

  摘要：

  A chemically diverse library of about 400,000 small molecules was screened for antiviral activity against lentiviral pseudotypes with the Lassa virus envelope glycoprotein (LASV GP) gene incorporated. High-throughput screening resulted in discovery of a hit compound (ST-37) possessing a benzimidazole core which led to a potent compound series. Herein, we report SAR studies which involved structural modifications to the phenyl rings and methylamino linker portion attached to the benzimidazole core. Many analogs in this study possessed single digit nanomolar potency against LASV pseudotypes. Compounds in this benzimidazole series also exhibited nanomolar antiviral activity against pseudotypes generated from other arenavirus envelopes indicating the potential for development of a broad-spectrum inhibitor. Ultimately, lead compound ST-193 was identified and later found to be efficacious in a lethal LASV guinea pig model showing superior protection compared to ribavirin treatment. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.095
• 作为产物：
  描述：

  4-正丁基苯胺 在 盐酸 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 1-(4-Butylphenyl)benzimidazol-5-amine
  参考文献：
  名称：

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

  摘要：

  A chemically diverse library of about 400,000 small molecules was screened for antiviral activity against lentiviral pseudotypes with the Lassa virus envelope glycoprotein (LASV GP) gene incorporated. High-throughput screening resulted in discovery of a hit compound (ST-37) possessing a benzimidazole core which led to a potent compound series. Herein, we report SAR studies which involved structural modifications to the phenyl rings and methylamino linker portion attached to the benzimidazole core. Many analogs in this study possessed single digit nanomolar potency against LASV pseudotypes. Compounds in this benzimidazole series also exhibited nanomolar antiviral activity against pseudotypes generated from other arenavirus envelopes indicating the potential for development of a broad-spectrum inhibitor. Ultimately, lead compound ST-193 was identified and later found to be efficacious in a lethal LASV guinea pig model showing superior protection compared to ribavirin treatment. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.095

文献信息

• Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole
  作者：Dongcheng Dai、James R. Burgeson、Dima N. Gharaibeh、Amy L. Moore、Ryan A. Larson、Natasha R. Cerruti、Sean M. Amberg、Tove’ C. Bolken、Dennis E. Hruby

  DOI：10.1016/j.bmcl.2012.11.095

  日期：2013.2

  A chemically diverse library of about 400,000 small molecules was screened for antiviral activity against lentiviral pseudotypes with the Lassa virus envelope glycoprotein (LASV GP) gene incorporated. High-throughput screening resulted in discovery of a hit compound (ST-37) possessing a benzimidazole core which led to a potent compound series. Herein, we report SAR studies which involved structural modifications to the phenyl rings and methylamino linker portion attached to the benzimidazole core. Many analogs in this study possessed single digit nanomolar potency against LASV pseudotypes. Compounds in this benzimidazole series also exhibited nanomolar antiviral activity against pseudotypes generated from other arenavirus envelopes indicating the potential for development of a broad-spectrum inhibitor. Ultimately, lead compound ST-193 was identified and later found to be efficacious in a lethal LASV guinea pig model showing superior protection compared to ribavirin treatment. (c) 2012 Elsevier Ltd. All rights reserved.