Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents.
A series of 3-alkyl-5-((Z))-arylidene-2-thiohydantoins 4a-1 were synthesized from the direct condensation of the aromatic aldehydes with 3-alkyl-2-thiohydantoins 3a-c, which in turn were prepared from the reaction of glycine (1) and alkyl isothiocyanates 2a-c. The alkylation of 4a-1 with methylthioethyl chloride gave 5-((Z))-arylidene-3-alkyl-S-(2-methylthioethyl)-2-thiohydantoins 5a-e. S-Glucosylation took place on the reaction of 4a-1 with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide under anhydrous alkaline conditions. These structures have been confirmed from a model study of the coupling of 4a with methylthioethyl chloride and alpha-D-glucose pentaacetate, respectively under Lewis acid conditions.
Khodair
A I
AI
Chemistry Department, Faculty of Education, Tanta University Kafr El-Sheikh, Egypt. ahem.khodair@excite.com
D000478:Alkylation; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013867:Thiohydantoins / Q000138:chemical synthesis* / Q000737:chemistry
D016588:Anticarcinogenic Agents; D000998:Antiviral Agents; D013867:Thiohydantoins; D005947:Glucose