S-glucosylated hydantoins as new antiviral agents.
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-beta-D-glucopyranosyl)-2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl)-2-(2,3,4,6-tetra-O-acety l-beta-D- glucopyranosyl)-2-thiohydantoin.
el-Barbary
A A
AA
Department of Chemistry, Odense University, Denmark.
Khodair
A I
AI
Pedersen
E B
EB
Nielsen
C
C
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D018258:Herpesvirus 2, Human / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010669:Phenylthiohydantoin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014709:Vero Cells
D000998:Antiviral Agents; C085368:3-phenyl-5-(2-thienylmethylene)-2-(2,3,4,6-tetra-O-acetylglucopyranosyl)-2-thiohydantoin; C085369:3-(4-chlorophenyl)-5-(2-thienylmethylene)-2-(2,3,4,6-tetra-O-acetylglucopyranosyl)-2-thiohydantoin; D010669:Phenylthiohydantoin