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Synthesis of pyrimidine acyclonucleosides
Author(s) -
Abrams H. M.,
Ho L.,
Chu S. H.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180520
Subject(s) - chemistry , cytidine , pyrimidine , uracil , uridine , nucleoside , thymidine , thymidine phosphorylase , stereochemistry , side chain , protecting group , combinatorial chemistry , organic chemistry , biochemistry , in vitro , dna , rna , enzyme , alkyl , gene , polymer
Nucleoside analogues of uridine, 5‐bromo‐, 5‐iodo‐, and 5‐fluorouridines, thymidine and cytidine were prepared by condensing appropriately substituted 2,4‐dimethoxypyrimidines with an acyclic side chain in the form of a benzoylated halo‐ether, and subsequent removal of the protecting benzoyl group in base. The 2′‐ O ‐ p ‐tosylates of these nucleoside analogues could then be modified to 2′‐halo‐, azido‐, and amino derivatives. Many of these compounds are competitive inhibitors of uridine phosphorylase in vitro , the most active being 5‐methyl‐1‐(2′‐hydroxyethoxymethyl)uracil.