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Synthesis of Uridine with Methylene-2-thiohydantoin as 5-Substituent

✍ Scribed by El-Barbary, Ahmed A. ;Khodair, Ahmed I. ;Pedersen, Erik B. ;Nielsen, Claus

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
241 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

5‐Formyl‐1‐(2,3,5‐tri‐O‐acetyl‐β‐D‐ribofuranosyl)uracil (4) was synthesized from 5‐formyluracil (2) and 1,2,3,5‐tetra‐O‐acetyl‐β‐D‐ribofuranose (3) and condensed with 2‐thiohydantoin derivatives 5 by using piperidine 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 obtained 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. magnified image

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