76291-91-3Relevant academic research and scientific papers
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 butenolide preparation for straightforward asymmetric syntheses of γ-lactones - Paraconic acids, avenaciolide, and hydroxylated eleutherol
Braukmueller, Stefan,Brueckner, Reinhard
, p. 2110 - 2118 (2007/10/03)
The naturally occurring γ-lactones (+)-methylenolactocin (13) and its enantiomer, (+)-protolichesterinic acid (14) and its enantiomer, (+)-rocellaric acid (15), and the methylene bis(γ-lactone) (-)-avenaciolide (16) were synthesized with 95-98 % ees in very few steps. Enantiocontrol was imposed by the asymmetric dihydroxylation of trans-configured β,γ-unsaturated carboxylic esters (namely compounds 1i, 1j, and 1n) with AD mix-α [for the levorotatory target structures, except for (-)-avenaciolide] or AD mix-β [for the dextrorotatory target structures plus (-)-avenaciolide]. β,γ-Unsaturated carboxylic ester 1e required increased amounts of the oxidant and auxiliary to produce the hydroxy lactone R,R-3e, a precursor of the naphtho-γ-lactone (+)-9-hydroxyeleutherol (12; 96 % ee). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
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%.
Concise syntheses of natural γ-butyrolactones, (+)-trans-whisky lactone, (+)-trans-cognac lactone, (-)-methylenolactocin, (+)-nephrosteranic acid, and (+)-roccellaric acid using novel chiral butenolide synthons
Takahata,Uchida,Momose
, p. 5628 - 5633 (2007/10/03)
cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition - quenching of these butenolides under complete stereocontrol provided several polysubstituted γ-butyrolactones including flavor components [(±)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].
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.
DIANIONS OF N-MONOSUBSTITUTED-3-(PHENYLSULFONYL)PROPANAMIDES. CONVENIENT REAGENTS FOR THE SYNTHESIS OF 5-ALKYL-2(5H)-FURANONES
Tanaka, Kazuhiko,Wakita, Hisanori,Yoda, Hidemi,Kaji, Aritsune
, p. 1359 - 1362 (2007/10/02)
Treatment of N-phenyl-3-(phenylsulfonyl)propanamide with 2 equiv. of butyllithium at -78 deg C afforded the dianion.Aldehydes and ketones upon treatment with the dianion provided stable γ-hydroxy amides, which were converted in good yields to 5-alkyl-2(5H)-furanones.Optically active (R)- and (S)-5-octyl-2(5H)-furanones, and (R)- and (S)-5-tridecyl-2(5H)-furanones were prepared from aldehydes and the dianions, derived from chiral N-monosubstituted-3-(phenylsulfonyl)propanamides.
PREPARATION D'ALKYL-4 γ-LACTONES INSATUREES OPTIQUEMENT PURES. APPLICATION A LA SYNTHESE DE LA (+) TETRAHYDROCERULENINE
Vigneron, J. P.,Blanchard, J. M.
, p. 1739 - 1742 (2007/10/02)
Optically pure enantiomers of unsaturated 4-alkyl γ-lactones are synthesized from optically active propargylic carbinols obtained by asymmetric reduction of α-acetylenic ketones with the complex . (+) Tetrahydrocerulenin is prepared from the butenolide 6 obtained by this way.
