76291-91-3Relevant articles and documents
Design, synthesis and biological evaluation of potential antibacterial butyrolactones
Sweidan, Alaa,Chollet-Krugler, Marylene,van de Weghe, Pierre,Chokr, Ali,Tomasi, Sophie,Bonnaure-Mallet, Martine,Bousarghin, Latifa
, p. 5823 - 5833 (2016/10/30)
Novel butyrolactone analogues were designed and synthesized based on the known lichen antibacterial compounds, lichesterinic acids (B-10 and B-11), by substituting different functional groups on the butyrolactone ring trying to enhance its activity. All synthesized butyrolactone analogues were evaluated for their in vitro antibacterial activity against Streptococcus gordonii. Among the derivatives, B-12 and B-13 had the lowest MIC of 9.38 μg/mL where they have shown to be stronger bactericidals, by 2–3 times, than the reference antibiotic, doxycycline. These two compounds were then checked for their cytotoxicity against human gingival epithelial cell lines, Ca9–22, and macrophages, THP-1, by MTT and LDH assays which confirmed their safety against the tested cell lines. A preliminary study of the structure–activity relationships unveiled that the functional groups at the C4position had an important influence on the antibacterial activity. An optimum length of the alkyl chain at the C5position registered the best antibacterial inhibitory activity however as its length increased the bactericidal effect increased as well. This efficiency was attained by a carboxyl group substitution at the C4position indicating the important dual role contributed by these two substituents which might be involved in their mechanism of action.
Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)- catalysts: Synthesis of enantiomerically pure butenolides and γ- butyrolactones
Bertus,Phansavath,Ratovelomanana-Vidal,Genet,Touati,Homri,Hassine, B. Ben
, p. 1369 - 1380 (2007/10/03)
A series of β-hydroxy sulfones were synthesized with high enantioselectivities via a new enantioselective ruthenium-catalyzed hydrogenation using MeO-BIPHEP as a ligand. Some β-hydroxy sulfones were used in the synthesis of optically active butenolides and γ-butyrolactones with high yields and enantioselectivities over 95%.
Novel Asymetric Synthesis of γ-Alkylated Lactones via Successive Alkylation and Reduction of Chiral Cyclic Imides with C2-Symmetry
Yoda, Hidemi,Shirakawa, Koji,Takabe, Kunihiko
, p. 489 - 490 (2007/10/02)
Consecutive treatment of chiral cyclic imides containing a C2-axis of symmetry with Grignard reagents and sodium borohydride followed by cyclization furnished γ-alkylated lactones with high diastereoselectivity.Products were converted to synthetically useful R-butenolides after removal of the chirality inducing groups.
