5-(4-chlorophenyl)-4-phenyl-1H-imidazol-2-amine | 1187925-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-4-phenyl-1H-imidazol-2-amine
• CAS: 1187925-52-5
• 化学式: C₁₅H₁₂ClN₃
• 分子量: 269.733
• InChiKey: WOMKWWQGBONVHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-1-(4-氯苯基)-2-苯基乙基-1-酮 在 肼 作用下， 以 乙腈 为溶剂， 反应 0.42h， 生成 5-(4-chlorophenyl)-4-phenyl-1H-imidazol-2-amine
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148

文献信息

• Antibacterial compounds
  申请人：DISCUVA LTD.

  公开号：US11345694B2

  公开（公告）日：2022-05-31

  The present invention relates to compounds of general formula (II), to compositions comprising these compounds and to methods of treating Enterobacteriaceae bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Enterobacteriaceae.

  本发明涉及通式（II）化合物、包含这些化合物的组合物以及使用这些化合物治疗肠杆菌科细菌疾病和感染的方法。这些化合物可用于治疗由肠杆菌科细菌引起的感染和疾病。
• Microwave-assisted synthesis of substituted 2-amino-1H-imidazoles from imidazo[1,2-a]pyrimidines
  作者：D.S. Ermolat’ev、E.P. Svidritsky、E.V. Babaev、E. Van der Eycken

  DOI：10.1016/j.tetlet.2009.06.128

  日期：2009.9

  An efficient method for the synthesis of mono- and disubstituted 2-amino-1H-imidazoles via microwave-assisted hydrazinolysis of substituted imidazo[1,2-a]pyrimidines is reported. This protocol avoids strong acidic conditions and is superior to the classical cyclocondensation of alpha-haloketones with N-acetylguanidine. (C) 2009 Elsevier Ltd. All rights reserved.
• ANTIBACTERIAL COMPOUNDS
  申请人：DISCUVA LTD.

  公开号：US20210163460A1

  公开（公告）日：2021-06-03

  The present invention relates to compounds of general formula (II), to compositions comprising these compounds and to methods of treating Enterobacteriaceae bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Enterobacteriaceae.