期刊
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY
卷 8, 期 1, 页码 194-201出版社
VERSITA
DOI: 10.2478/s11532-009-0126-8
关键词
Microbicidal activity; Enantiomers; Phenylalanine; Quaternary ammonium compounds; Quantitative structure activity relationships (QSAR)
资金
- [UK/110/2008]
- [VEGA 1/4300/07]
- [VEGA 1/3416/06]
- [VEGA1/4290/07]
- [VEGA 1/0164/08]
We synthesized nine quaternary ammonium compounds (QUATs) starting from phenylalanine, N-alkyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromides, which were prepared as optically pure substances. Five compounds were prepared as S-enantiomers and four compounds as R-enantiomers. These compounds were evaluated by their activities against bacteria and fungi. Three microbial strains were used in the study: the gram-negative bacteria Escherichia coli, the gram-positive bacteria Staphylococcus aureus and the fungi Candida albicans. The activities were expressed as minimum bactericidal or fungicidal concentrations (MBC). The most active compounds were (2S)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide and (2R)-N-tetradecyl-N, N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide, with MBC values exceeding those of commercial benzalkoniumbromide (BAB) used as standard. The relationships between structure and biological activity of the tested QUATs were quantified by the bilinear model (QSAR) and are discussed.
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