<i>N</i>-(((1<i>S</i>,5<i>R</i>)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-((1<i>R</i>,5<i>S</i>)-6,6-dimethylbicyclo[3.1.1]hept-2-ene/ane-2-carboxamido)-<i>N</i>,<i>N</i>-dimethylpropan-1-aminium Bromide

Abstract

The synthesis of the title compounds was performed from (-)-cis-myrtanic and (-)-myrtenic acids. The compounds obtained were characterized using 1H- and 13C-NMR, IR, and high-resolution mass spectrometry. Despite the presence of quaternary ammonium moiety, both compounds had moderate antimicrobial activity with a MIC of 128 µg/mL on S. aureus and 512 µg/mL on E. coli. The antifungal activity was low on Candida isolates, while also comparable with conventional antimycotic (Fluconazole) on filamentous fungi. These data suggest that two bulky bicyclic terpene fragments apparently both increase lipophilicity and close the quaternary ammonium moiety located in the center of molecules and thus drastically decrease the antimicrobial potential of bipharmacophore.

Keywords

• cis-myrtanic and myrtenic acids
• myrtenol