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

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 a...

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Bibliographic Details
Published in:MolBank 2023-03, Vol.2023 (1), p.M1592
Main Authors: Gilfanov, Ilmir R., Pavelyev, Roman S., Nikitina, Liliya E., Frolova, Larisa L., Popov, Alexey V., Rakhmatullin, Ilfat Z., Klochkov, Vladimir V., Lisovskaya, Svetlana A., Trizna, Elena Yu, Grishaev, Denis Yu, Kayumov, Airat R.
Format: Article
Language:English
Subjects:
Antiinfectives and antibacterials
Antimicrobial agents
Chloride
cis-myrtanic and myrtenic acids
E coli
Editing
Fungi
Fungicides
Mass spectrometry
myrtenol
NMR
Nuclear magnetic resonance
Visualization
Writing
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Summary: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.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1592