S-Glycosylation took place on reaction of 5-alkylidene- and 5-aryliden
e-3-aryl-2-thiohydantoins with glycosyl halides under alkaline conditi
ons. Bisglucosylation also took place when N-3 unsubstituted hydantoin
s were reacted. The bisglucosylated hydantoins produced N-3 glucosylat
ed hydantoins on treatment with ammonia in methanol. In antiviral stud
ies 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-beta-D-glucopyra
nosyl) -2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl)
-2- (2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin.