452296-51-4Relevant articles and documents
Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives
?enel, Petr,Tichotová, Lucie,Votruba, Ivan,Buchta, Vladimír,?pulák, Marcel,Kune?, Ji?í,Nobilis, Milan,Krenk, Ond?ej,Pour, Milan
supporting information; experimental part, p. 1988 - 2000 (2010/05/18)
5-Acetoxymethyl-3-(4-bromophenyl)-2,5-dihydrofuran-2-one previously described as highly antifungally active was found to provide the corresponding 5-methylene derivative via an unusual DMSO-promoted elimination of the ester group at C5 under antifungal assay conditions. Since the latter possessed nearly the same antifungal effect as that originally reported for the former, the 5-acetoxymethyl furanone just served as a precursor of the actual antifungally active species. A few series of compounds with alkyloxy, aryloxy and alkylidene substituents at C5 of the parent furanone structure were therefore prepared and evaluated. In line with the ease of elimination of the substituent from C5, low activities of the 5-alkoxy compounds were observed. On the other hand, their 5-aryloxymethyl congeners were found to be capable of liberating the antifungally active 5-methylene furanone into the testing medium. The antifungal effect of the 5-alkylidene derivatives was highly sensitive to substitution of the alkylidene moiety; a substituent in the allylic position was necessary for a compound to retain high activity. Parallel evaluation of cytostatic activity showed moderate activities of the antifungally active derivatives against HeLa S3 and CCRF-CEM lines. Cell cycle analysis of CCRF-CEM cells following the treatment with 5-methylene-3-(4-bromophenyl)-2,5-dihydrofuran-2-one revealed that this compound is a necrotic agent.
E/Z Isomerization of 3,3-disubstituted allylic thioethers
Havranek, Miroslav,Sauerberg, Per,Kratina, Pavel,Pihera, Pavel
, p. 6970 - 6973 (2008/02/13)
Allylic thioethers of the general structure 1 underwent E/Z isomerization during both basic and acidic hydrolysis of the ester moiety at the remote end of the molecule. The isomerization was dependent on the substitution of the allylic moiety. The presenc
NOVEL COMPOUNDS, THEIR PREPARATION AND USE
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, (2010/02/14)
Novel compounds of the general formula (I), in which the variables are as defined in claim 1, the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compound