S-Glucosylated Hydantoins as New Antiviral Agents

Abstract

S-Glycosylation took place on reaction of 5-alkylidene- and 5-arylidene-3-aryl-2-thiohydantoins with glycosyl halides under alkaline conditions. Bisglucosylation also took place when N-3 unsubstituted hydantoins were reacted. The bisglucosylated hydantoins produced N-3 glucosylated hydantoins on treatment with ammonia in methanol. In antiviral studies the most active compounds against both HSV-1 and HSV-2 were 5-(2-thienylmethylene)-3-phenyl-2-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl)-2-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-2-thiohydantoin. © 1994, American Chemical Society. All rights reserved.