Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents

A series of 3-alkyl-5-((Z))-arylidene-2-thiohydantoins 4a-1 were synthesize d from the direct condensation of the aromatic aldehydes with 3-alkyl-2-thi ohydantoins 3a-c. which in turn were prepared from the reaction of glycine (1) and alkyl isothiocyanates 2a-c. The alkylation of 4a-1 with methylthioe thyl chloride gave 5-((Z)-arylidene-3-alkyl-S-(2-methylthioethyl)-2-thiohyd antoins 5a-e. S-Glucosylation took place on the reaction of 4a-1 with 2,3,4 ,6-tetra-O-acetyl-alpha -D-glucopyranosyl bromide under anhydrous alkaline conditions. These structures have been confirmed from a model study of the coupling of 4a with methylthioethyl chloride and alpha -D-glucose pentaacet ate, respectively under Lewis acid conditions.