Synthesis of Hydantoin Nucleosides with Naphthylmethylene Substituents in the 5-Position

Abstract

(Z)-5-(Naphthylmethylene)-2-thiohydantoin derivatives (3a,b,12a-d) were prepared directly fiom condensations of 2-thiohydantoin derivatives (1,l la,b) with naphthaldehydes. Bisglycosylation took place on reaction of (Z)-5-(naphthylmethylene)- 2-thiohydantoin derivatives (3a,b) with glycosyl halides (4a,b) under alkaline conditions. The bisglycosilated hydantoins produced N₃ glycosylated hydantoins on treatment with ammonia in methanol. (Z)-5-(2-Naphthylmethylene)-2-(benzylidene E-hydrazono)hydantoin (9a) and (Z)-5-(2-naphthylmethylene)-2-(polyhydroxyalkylidene E-hydrazono)hydantoins (9b,c) were prepared fiom the reaction of (Z)-5-(2-naphthyylmethylene)-2- methylmercaptohydantoin (7) with benzylidene E-hydrazone (8a) and monosaccharide E-hydrazones (8b,c). S-Glycosylation also took place when N₃ substituted hydantoins were reacted. The hydantoin nucleosides were tested for their potential activity against HTV and HSV.