{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:39:57Z","timestamp":1785890397500,"version":"3.56.0"},"reference-count":92,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2023,3,10]],"date-time":"2023-03-10T00:00:00Z","timestamp":1678406400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Kazan Federal University","award":["FZSM-2023-0018"],"award-info":[{"award-number":["FZSM-2023-0018"]}]},{"name":"Kazan Federal University","award":["20-04-00247"],"award-info":[{"award-number":["20-04-00247"]}]},{"name":"RFBR","award":["FZSM-2023-0018"],"award-info":[{"award-number":["FZSM-2023-0018"]}]},{"name":"RFBR","award":["20-04-00247"],"award-info":[{"award-number":["20-04-00247"]}]},{"name":"State Assignment of the Federal Research Center \u201cKazan Scientific Center\u201d, Russian Academy of Sciences","award":["FZSM-2023-0018"],"award-info":[{"award-number":["FZSM-2023-0018"]}]},{"name":"State Assignment of the Federal Research Center \u201cKazan Scientific Center\u201d, Russian Academy of Sciences","award":["20-04-00247"],"award-info":[{"award-number":["20-04-00247"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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 \u03bcg\/mL. Furthermore, at concentrations of 0.4\u20130.5 \u03bcg\/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.<\/jats:p>","DOI":"10.3390\/molecules28062543","type":"journal-article","created":{"date-parts":[[2023,3,13]],"date-time":"2023-03-13T03:28:33Z","timestamp":1678678113000},"page":"2543","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["The Novel Chiral 2(5H)-Furanone Sulfones Possessing Terpene Moiety: Synthesis and Biological Activity"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7525-0133","authenticated-orcid":false,"given":"Alsu M.","family":"Khabibrakhmanova","sequence":"first","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roza G.","family":"Faizova","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9614-5092","authenticated-orcid":false,"given":"Olga A.","family":"Lodochnikova","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"},{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov Street, 420088 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5102-1907","authenticated-orcid":false,"given":"Regina R.","family":"Zamalieva","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liliya Z.","family":"Latypova","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9881-0559","authenticated-orcid":false,"given":"Elena Y.","family":"Trizna","sequence":"additional","affiliation":[{"name":"Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrey G.","family":"Porfiryev","sequence":"additional","affiliation":[{"name":"Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katsunori","family":"Tanaka","sequence":"additional","affiliation":[{"name":"Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako-shi 351-0198, Japan"},{"name":"Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8554-2938","authenticated-orcid":false,"given":"Oskar A.","family":"Sachenkov","sequence":"additional","affiliation":[{"name":"N.I. Lobachevsky Institute of Mathematics and Mechanics, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7195-1557","authenticated-orcid":false,"given":"Airat R.","family":"Kayumov","sequence":"additional","affiliation":[{"name":"Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2436-7427","authenticated-orcid":false,"given":"Almira R.","family":"Kurbangalieva","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1200","DOI":"10.2174\/1568026615666150915111741","article-title":"Sulfur containing scaffolds in drugs: Synthesis and application in medicinal chemistry","volume":"16","author":"Feng","year":"2016","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1007\/s41061-017-0169-9","article-title":"Sulfur-containing agrochemicals","volume":"375","author":"Devendar","year":"2017","journal-title":"Top. Curr. 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