Synthesis and biological properties of new alpha-methylene-gamma-butyrolactones and alpha,beta-unsaturated delta-lactones.
The synthesis of a series of alpha-methylene-gamma-butyrolactones (compounds 4a, 4b, 6-12, 16, 17) and alpha,beta-unsaturated-delta-lactones (compounds 19-23, 25, 26) starting from 4,4-dimethyldihydrofuran-2,3-dione (1) has been described. Their chemical structures were assigned by spectroscopic evidence. These new compounds exhibited significantly different antiproliferative properties against cultured human tumor cell lines with their IC(50) values ranging from 0.88 to>20.00 microM.
Cateni
Francesca
F
Department of Pharmaceutical Sciences, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy.
Zilic
Jelena
J
Zacchigna
Marina
M
Bonivento
Paolo
P
Frausin
Fabiana
F
Scarcia
Vito
V
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007783:Lactones; C014096:alpha-methylene gamma-butyrolactone; D015107:4-Butyrolactone