Stereoisomeric effect on antimicrobial activity of a series of quaternary ammonium salts.
Two homologous series of diastereoisomeric racemic +/- cis and +/- trans-N,N-dimethyl-N-alkyl-2-benzoyloxycyclohexylmethylammonium bromides with the number of carbon atoms in the alkyl chain from six to twenty (m = 6,8 ... 20) were synthesised. Their structures have been elucidated by IR, UV and in some cases also with 1H and 13C NMR spectrometry. The title compounds were assayed for their antimicrobial activity on microorganisms S. aureus, E. coli and C. albicans. The highest antimicrobial activity was observed against S. aureus (log 1/MIC = 5.5 mol-1 dm3) and the lowest against E. coli (log 1/MIC = 4.5 mol-1 dm3). The +/- cis and +/- trans stereoisomers of all eight couples of diastereoisomeric compounds show differences in their physico-chemical characteristics (including partition coefficient and lipophilicity) which is also reflected in the different antimicrobial activity of these diastereoisomers.
Gregán
F
F
Faculty of Pharmacy, Comenius University, Bratislava, Slovakia.
Oremusová
J
J
Remko
M
M
Gregán
J
J
Mlynarcík
D
D
D000890:Anti-Infective Agents / Q000494:pharmacology*; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology*; D012995:Solubility; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D000644:Quaternary Ammonium Compounds