tert-butyl 4-(4-(5-chloro-1H-indole-2-carboxamido)phenyl)-2-amino-1H-imidazole-1-carboxylate | 1609461-70-2

• 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: tert-butyl 4-(4-(5-chloro-1H-indole-2-carboxamido)phenyl)-2-amino-1H-imidazole-1-carboxylate
• CAS: 1609461-70-2
• 化学式: C₂₃H₂₂ClN₅O₃
• 分子量: 451.912
• InChiKey: JCLLMYLIVVYWCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  115.03
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-(5-chloro-1H-indole-2-carboxamido)phenyl)-2-amino-1H-imidazole-1-carboxylate 在 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 以71%的产率得到2-amino-4-(4-(5-chloro-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
• 作为产物：
  描述：

  5-氯吲哚-2-羧酸 、 tert-butyl 2-amino-4-(4-aminophenyl)-1H-imidazole-1-carboxylate 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以55%的产率得到tert-butyl 4-(4-(5-chloro-1H-indole-2-carboxamido)phenyl)-2-amino-1H-imidazole-1-carboxylate
  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