SYNTHESIS OF URIDINE WITH METHYLENE-2-THIOHYDANTOIN AS 5-SUBSTITUENT

-l-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)uracil (4) was synthesized from 5-formyluracil (2) and 1,2,3,5-tetra-0-acetyl-beta-D-ribofuranos e (3) and condensed with 2-thiohydantoin derivatives 5 by using piperi dine as the catalyst to give 5-(uridin-5-ylmethylene)-2-thiohydantoin (8a) and 3-phenyl-5-(uridin-5-ylmethylene)-2-thiohydantoin (8b) after deprotection with sodium methoxide in methanol. Compound 8a was also o btained in an inversed reaction sequence from 5-formyluracil starting with condensation with 2-thiohydantoin and then with 3. The compounds 8a and 8b did not show any activity against HSV-1 or HIV-1.