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†
Friedrich Erben,Holger Feist,Dennis Kleeblatt,Martin Hein,Abdul Matin,Jamshed Iqbal
RSC Advances Pub Date : 01/28/2014 00:00:00 , DOI:10.1039/C3RA44362K
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.

Graphical abstract: 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