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- Title
The Novel Chiral 2(5 H)-Furanone Sulfones Possessing Terpene Moiety: Synthesis and Biological Activity.
- Authors
Khabibrakhmanova, Alsu M.; Faizova, Roza G.; Lodochnikova, Olga A.; Zamalieva, Regina R.; Latypova, Liliya Z.; Trizna, Elena Y.; Porfiryev, Andrey G.; Tanaka, Katsunori; Sachenkov, Oskar A.; Kayumov, Airat R.; Kurbangalieva, Almira R.
- Abstract
Over the past decades, 2(5H)-furanone derivatives have been extensively studied because of their promising ability to prevent the biofilm formation by various pathogenic bacteria. Here, we report the synthesis of a series of optically active sulfur-containing 2(5H)-furanone derivatives and characterize their biological activity. Novel thioethers were obtained by an interaction of stereochemically pure 5-(l)-menthyloxy- or 5-(l)-bornyloxy-2(5H)-furanones with aromatic thiols under basic conditions. Subsequent thioethers oxidation by an excess of hydrogen peroxide in acetic acid resulted in the formation of the corresponding chiral 2(5H)-furanone sulfones. The structure of synthesized compounds was confirmed by IR and NMR spectroscopy, HRMS, and single crystal X-ray diffraction. The leading compound, 26, possessing the sulfonyl group and l-borneol moiety, exhibited the prominent activity against Staphylococcus aureus and Bacillus subtilis with MICs of 8 μg/mL. Furthermore, at concentrations of 0.4–0.5 μg/mL, the sulfone 26 increased two-fold the efficacy of aminoglycosides gentamicin and amikacin against S. aureus. The treatment of the model-infected skin wound in the rat with a combination of gentamicin and sulfone 26 speeded up the bacterial decontamination and improved the healing of the wound. The presented results provide valuable new insights into the chemistry of 2(5H)-furanone derivatives and associated biological activities.
- Subjects
BIOSYNTHESIS; MOIETIES (Chemistry); AMIKACIN; TERPENES; SULFONYL group; CHEMICAL synthesis; SULFONES
- Publication
Molecules, 2023, Vol 28, Issue 6, p2543
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28062543