2-amino-4-(3-(5-nitro-1H-indole-2-carboxamido)phenyl)-1H-imidazol-3-ium chloride | 1609461-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(3-(5-nitro-1H-indole-2-carboxamido)phenyl)-1H-imidazol-3-ium chloride
• 英文别名: N-[3-(2-amino-1H-imidazol-3-ium-5-yl)phenyl]-5-nitro-1H-indole-2-carboxamide;chloride
• CAS: 1609461-65-5
• 化学式: C₁₈H₁₄N₆O₃*ClH
• 分子量: 398.808
• InChiKey: SQEHZPVUQHJQIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-硝基吲哚-2-甲酸 在 N-甲基吗啉 、 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 2-amino-4-(3-(5-nitro-1H-indole-2-carboxamido)phenyl)-1H-imidazol-3-ium chloride
  参考文献：
  名称：

  Inhibition of biofilm formation by conformationally constrained indole-based analogues of the marine alkaloid oroidin

  摘要：

  Herein, we describe indole-based analogues of oroidin as a novel class of 2-aminoimidazole-based inhibitors of methicillin-resistant Staphylococcus aureus biofilm formation and, to the best of our knowledge, the first reported 2-aminoimidazole-based inhibitors of Streptococcus mutans biofilm formation. This study highlighted the indole moiety as a dibromopyrrole mimetic for obtaining inhibitors of S. aureus and S. mutans biofilm formation. The most potent compound in the series, 5-(trifluoromethoxy) indole-based analogue 4b (MBIC50 = 20 mu M), emerged as a promising hit for further optimisation of novel inhibitors of S. aureus and S. mutans biofilms. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.094

文献信息

• Inhibition of biofilm formation by conformationally constrained indole-based analogues of the marine alkaloid oroidin
  作者：Žiga Hodnik、Joanna M. Łoś、Aleš Žula、Nace Zidar、Žiga Jakopin、Marcin Łoś、Marija Sollner Dolenc、Janez Ilaš、Grzegorz Węgrzyn、Lucija Peterlin Mašič、Danijel Kikelj

  DOI：10.1016/j.bmcl.2014.03.094

  日期：2014.6

  Herein, we describe indole-based analogues of oroidin as a novel class of 2-aminoimidazole-based inhibitors of methicillin-resistant Staphylococcus aureus biofilm formation and, to the best of our knowledge, the first reported 2-aminoimidazole-based inhibitors of Streptococcus mutans biofilm formation. This study highlighted the indole moiety as a dibromopyrrole mimetic for obtaining inhibitors of S. aureus and S. mutans biofilm formation. The most potent compound in the series, 5-(trifluoromethoxy) indole-based analogue 4b (MBIC50 = 20 mu M), emerged as a promising hit for further optimisation of novel inhibitors of S. aureus and S. mutans biofilms. (C) 2014 Elsevier Ltd. All rights reserved.