N-benzyl-2-hydroxyiminomethyl-3-(p-fluorophenyl)imidazolium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-2-hydroxyiminomethyl-3-(p-fluorophenyl)imidazolium bromide
• 英文别名: (NE)-N-[[1-benzyl-3-(4-fluorophenyl)imidazol-1-ium-2-yl]methylidene]hydroxylamine;bromide
• 化学式: Br*C₁₇H₁₅FN₃O
• 分子量: 376.228
• InChiKey: APCBKTHREUDKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-氟苯基)咪唑 在 正丁基锂 、 盐酸羟胺 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 N-benzyl-2-hydroxyiminomethyl-3-(p-fluorophenyl)imidazolium bromide
  参考文献：
  名称：

  Synthesis and antimicrobial profile of N-substituted imidazolium oximes and their monoquaternary salts against multidrug resistant bacteria

  摘要：

  Two different series of N-substituted imidazolium oximes and their monoquaternary salts were synthesized and biologically tested with respect to their ability to inhibit growth a diverse panel of antibiotic susceptible Gram-positive and antibiotic resistant Gram-negative bacteria as well fungal strains. The newly synthesized compounds were analyzed by spectral studies to confirm their structure. The preliminary results showed that all compounds tested possess promising antimicrobial potential against both susceptible Gram-positive and antibiotic resistant Gram-negative isolates, exhibiting a wide range of MIC values from 0.14 to 100.0 mu g/mL. The structure-activity relationship demonstrates that the p-methylphenyl and p-fluorophenyl groups in monoquaternary salts 6 and 7 attached directly to the imidazolium ring could be essential for observed remarkable inhibitory profiles against clinically important pathogens Pseudomonas aeruginosa (MIC = 0.14 mu g/mL) and Klebsiella pneumoniae (MIC = 1.56 mu g/mL). Furthermore, the broth microdilution assay was then used to investigate the antiresistance efficacy of compound 7 against fourteen extended-spectrum beta-lactamase (ESBL)-producing strains in comparison to eight clinically relevant antibiotics. Compound 7 exhibited a remarkable antiresistance profiles ranging between 0.39 and 12.50 mu g/mL against all of ESBL-producing strains, which leads to the suggestion that may be interesting candidate for development of new antimicrobials to combat multidrug resistant Gram-negative bacteria. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.041