Title
Synthesis and biological evaluation of some acyclic pyridine C-nucleosides : part 1 Synthesis and biological evaluation of some acyclic pyridine C-nucleosides : part 1
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
New York, N.Y. ,
Subject
Chemistry
Biology
Source (journal)
Nucleosides and nucleotides. - New York, N.Y.
Volume/pages
13(1994) :10 , p. 2345-2366
ISSN
0732-8311
ISI
A1994PY42900021
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The reaction between 3-bromo-5-chloromethylpyridine hydrochloride (($) under bar 4) with the mono sodium salt of ethylene glycol was investigated. 3-Bromo-5-(2-hydroxyethoxymethyl) pyridine (($) under bar 5) was synthesized and converted to the 3-carboxy analogue using butyllithium and CO,. Subsequent treatment with diazomethane and ammonolysis gave the corresponding acyclic nicotinamide C-nucleosides. The latter compounds were converted into the thioamide analogues by reaction with Lawesson's reagent. The pyridine N-oxide derivatives were obtained by treatment with peracetic acid or hydrogen peroxide. Ah compounds were identified with the aid of H-1- and C-13-NMR and mass spectrometry. The acyclic pyridine C-nucleosides were evaluated against a number of viral strains and cancer cell lines but no significant biological activity was found.
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