Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides

• Published in: European journal of pharmaceutical sciences 2014-12, Vol.65, p.29-37
• Main Authors: Mikláš, R., Miklášová, N., Bukovský, M., Horváth, B., Kubincová, J., Devínsky, F.
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Antimicrobial activity; Bromides - chemical synthesis; Bromides - pharmacology; Camphor - chemical synthesis; Camphor - pharmacology; Critical micelle concentration; Homochiral camphorsulfonamides; Hydrophobic and Hydrophilic Interactions; Micelles; Quaternary Ammonium Compounds - chemical synthesis; Quaternary Ammonium Compounds - pharmacology; Quaternary ammonium salts; Structure-Activity Relationship; Sulfonamides - chemical synthesis; Sulfonamides - pharmacology; Surface Properties; Surface Tension
• ISSN: 0928-0987; 1879-0720
• DOI: 10.1016/j.ejps.2014.08.013

[Display omitted] A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated.