1-hexadecyl-2,3-dimethylimidazolium ampicillin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-hexadecyl-2,3-dimethylimidazolium ampicillin
• 英文别名: (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;1-hexadecyl-2,3-dimethylimidazol-3-ium
• 化学式: C₁₆H₁₈N₃O₄S*C₂₁H₄₁N₂
• 分子量: 669.973
• InChiKey: XZLNLAAODRNKPA-GSUNRZRUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-dimethyl-3-hexadecylimidazolium bromide 、 ampicillin sodium salt 以 氯仿 、 水 为溶剂， 反应 48.0h， 以94%的产率得到1-hexadecyl-2,3-dimethylimidazolium ampicillin
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of β-Lactam Antibiotic-Based Imidazolium- and Pyridinium-Type Ionic Liquids

  摘要：

  We herein report the preparation and investigation of antibacterial activity of biocidal ionic liquids (ILs) consisting of cationic imidazolium or pyridinium and an anionic β‐lactam antibiotic. The antibacterial properties were quantified by measuring the minimum inhibitory concentration and minimum bactericidal concentration againstEscherichia coli O157:H7,Klebsiella pneumoniae,Staphylococcus aureus, andEnterococcus faecium. In general, the ILs had improved antibacterial activity than their parent materials, whether individually or in combination. In 83% of the experiments, the ampicillin ILs (Amp‐ILs) had better antibacterial activities than their quaternary halide parent materials, whereas in 92% of the experiments, Amp‐ILs outperformed the commercially available sodium ampicillin salt. Amp‐ILs had up to 43 times improved antibacterial activity than sodium ampicillin. Overall, when normalized for ampicillin content, ILs had greater antimicrobial activity againstE. coli O157:H7,K. pneumoniae,S. aureus, andE. faeciumthan sodium ampicillin alone.

  DOI：

  10.1111/j.1747-0285.2011.01114.x

文献信息

• Design, Synthesis, and Biological Evaluation of β-Lactam Antibiotic-Based Imidazolium- and Pyridinium-Type Ionic Liquids
  作者：Marsha R. Cole、Min Li、Bilal El-Zahab、Marlene E. Janes、Daniel Hayes、Isiah M. Warner

  DOI：10.1111/j.1747-0285.2011.01114.x

  日期：2011.7

  We herein report the preparation and investigation of antibacterial activity of biocidal ionic liquids (ILs) consisting of cationic imidazolium or pyridinium and an anionic β‐lactam antibiotic. The antibacterial properties were quantified by measuring the minimum inhibitory concentration and minimum bactericidal concentration againstEscherichia coli O157:H7,Klebsiella pneumoniae,Staphylococcus aureus, andEnterococcus faecium. In general, the ILs had improved antibacterial activity than their parent materials, whether individually or in combination. In 83% of the experiments, the ampicillin ILs (Amp‐ILs) had better antibacterial activities than their quaternary halide parent materials, whereas in 92% of the experiments, Amp‐ILs outperformed the commercially available sodium ampicillin salt. Amp‐ILs had up to 43 times improved antibacterial activity than sodium ampicillin. Overall, when normalized for ampicillin content, ILs had greater antimicrobial activity againstE. coli O157:H7,K. pneumoniae,S. aureus, andE. faeciumthan sodium ampicillin alone.