N-[(4-tert-butylphenyl)methyl]-1-(4-methoxyphenyl)benzimidazol-5-amine | 1366232-47-4

• 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: N-[(4-tert-butylphenyl)methyl]-1-(4-methoxyphenyl)benzimidazol-5-amine
• CAS: 1366232-47-4
• 化学式: C₂₅H₂₇N₃O
• 分子量: 385.509
• InChiKey: JQEILBLBISTELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N1-(4-methoxyphenyl)benzene-1,2,4-triamine 在 盐酸 、 三乙酰氧基硼氢化钠 作用下， 以 水 为溶剂， 反应 6.0h， 生成 N-[(4-tert-butylphenyl)methyl]-1-(4-methoxyphenyl)benzimidazol-5-amine
  参考文献：
  名称：

  苯并咪唑衍生物作为潜在拉沙病毒抑制剂的设计、合成和生物学评价。

  摘要：

  拉沙病毒 (LASV) 引起拉沙热，这是一种高度传染性和致命性的急性病毒性出血热病原体。目前，仍然没有有效的治疗方法，迫切需要开发新的治疗方法。一些靶向沙粒病毒包膜糖蛋白复合物 (GPC) 的苯并咪唑化合物是有前途的 LASV 抑制剂。在这项研究中，我们基于苯并咪唑结构合成了两个系列的 LASV 抑制剂。建立了带有 LASV GPC 的慢病毒假型以鉴定病毒进入抑制剂。表面等离子体共振 (SPR) 进一步用于验证潜在化合物的结合活性。化合物7d-Z、7h-Z、13c、13d和13f表现出相对优异的抗病毒活性，IC50值范围为7.58至15.46 nM，SI值在1251以上。这五种代表性化合物在 SPR 研究中表现出更强的结合亲和力和较低的平衡解离常数 (KD < 8.25 × 10-7 M)。化合物 7h-Z 显示出最强的抗病毒活性 (IC50 = 7.58 nM) 和相对较高的 SI 值

  DOI：

  10.3390/molecules28041579

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.
• 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