Synthesis of hydantoin nucleosides with naphthylmethylene substituents in the 5-position

(Z)-5-(Naphthylmethylene)-2-thiohydantoin derivatives (3a,b,12a-'d) were prepared directly from condensations of 2-thiohydantoin derivatives (1,11a,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 Ng glycosylated hydantoins on treatment with ammonia in methanol. (Z)5-(2-Naphthylmethylene)-2-(benzylidene E-hydrazono)hydantoin (sa) and (Z)5-(2-naphthylmethylene)-2-(polyhydroxy E-hydrazono)hydantoins (9b,c) were prepared from 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 N-3 substituted hydantoins were reacted. The hydantoin nucleosides were tested for their potential activity against HIV and HSV.