Synthesis and antiproliferative activity of (Z)-1-glycosyl-3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones and (Z)-3-(2-glycosylsulfanyl-4-oxo-4,5-dihydro-thiazol-5-ylidene)indolin-2-ones

Abstract

The reaction of N-glycosylated isatines with imidazolones and thiazolones afforded N-glycosylated (Z)-1-glycosyl-3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones. The reaction of S-glycosylated thiazolones with isatines gave S-glycosylated (Z)-3-(2-glycosylsulfanyl-4-oxo-4,5-dihydro-thiazol-5-ylidene)indolin-2-ones. These molecules represent hybrids of pharmacologically important moieties, including carbohydrates, isatines, 2-thiohydantoin, pseudo-thiohydantoin and rhodanine. The products show a good and selective activity against lung carcinoma cell lines H157. The best activity was obtained for 3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones containing a glucose moiety.