Sulfides, sulfones, and sulfoxides of the furan-2(5H)-one series. synthesis and structure

Antimicrobial Effects of Sulfonyl Derivative of 2(5H)-Furanone against Planktonic and Biofilm Associated Methicillin-Resistant and -Susceptible Staphylococcus aureus

“…Alternatively, 1× MBC of F105 led to the reduction in the number of viable cells by three orders of magnitude within 12 h. The dose-response curves ( Figure 2B ) confirm the concentration-dependence of F105 effect on cells viability explicitly suggesting that F105 exhibits biocidal activity. Interestingly, our earlier results indicate that the analogs of F105 lacking either sulfonyl group (compound 3 on the Figure 1 ) or l -menthol moiety ( F70 , 3-chloro-5-hydroxy-4-[(4-methylphenylsulfonyl)]-2(5 H )-furanone) exhibited no activity against S. aureus ( Latypova et al, 2014 ; Kayumov et al, 2015a ) (data not shown) suggesting the requirement of both functional groups for bactericidal activity, while in other works the presence of either sulfonyl group or l -menthol moiety increased antibacterial effects ( Meadows and Gervay-Hague, 2006 ; Kudryavtsev et al, 2009 ; Rogers et al, 2010 ; Low et al, 2011 ).…”

“…Next a thiolation reaction of the isolated stereoisomer 2a under basic catalysis was carried out. It is well-known that in the presence of triethylamine reactions of 5-alkoxy-2(5 H )-furanones with thiols proceed with the regioselective substitution of the chlorine atom in the fourth position of the lactone ring ( Kurbangalieva et al, 2007 ; Latypova et al, 2014 ). The reaction was performed in diethyl ether at room temperature with the equimolar ratio of furanone 2a , p -thiocresol and triethylamine resulting in the novel optically pure thioether 3 with 85% yield.…”

“…The reaction was performed in diethyl ether at room temperature with the equimolar ratio of furanone 2a , p -thiocresol and triethylamine resulting in the novel optically pure thioether 3 with 85% yield. Thioether 3 was further subjected to oxidation to the corresponding sulfone 4 using a recently developed selective method ( Latypova et al, 2014 ). The compound 3 was treated with 10-fold excess of 33% hydrogen peroxide in acetic acid at room temperature and the novel optically pure sulfonyl derivative of 2(5 H )-furanone 4 (studied compound F105 , Figure 1 ) was isolated in the form of colorless crystals in 70% yield.…”

“…Several researchers reported that sulfonyl-containing compounds effectively repressed the growth of Staphylococci ( Meadows and Gervay-Hague, 2006 ; Kudryavtsev et al, 2009 ; Low et al, 2011 ) suggesting antibacterial activity of the sulfonyl moiety ( Mohan et al, 2014 ; Thirukovela et al, 2017 ). In contrast, the analogs of F105 lacking either sulfonyl group (compound 3 on the Figure 1 ) or l -menthol moiety (3-chloro-5-hydroxy-4-[(4-methylphenylsulfonyl)]-2(5 H )-furanone) exhibited no activity against S. aureus ( Latypova et al, 2014 ; Kayumov et al, 2015a ) suggesting the requirement of both functional groups for bactericidal activity of F105 .…”

Thio Derivatives of 2(5H)-Furanone As Inhibitors against Bacillus subtilis Biofilms

“…Fig. 1 depicts the structures of the studied compounds: F12 – 5-hydroxy-4-[(4-methylphenyl)sulfonyl]- 3-chloro-2( 5H )-furanone [ 7 ], F15 – 4-benzyl-sulfonyl- 5-hydroxy-3-chloro-2( 5H )-furanone [ 8 ], and F94 – 1,3- bis [3-chloro-5-(1,3-dichloropropane-2-yloxy)- 2( 5H )-furanone-4-ylsulfonyl] propane [ 9 ]; the compounds were synthesized according to the known techniques.…”