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Synthesis of Uridine with Methylene‐2‐thiohydantoin as 5‐Substituent
Author(s) -
ElBarbary Ahmed A.,
Khodair Ahmed I.,
Pedersen Erik B.,
Nielsen Claus
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940613
Subject(s) - chemistry , sodium methoxide , methanol , methylene , uridine , uracil , substituent , isoquinoline , condensation , medicinal chemistry , organic chemistry , rna , dna , biochemistry , physics , gene , thermodynamics
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.