Title
Synthesis and biological evaluation of some acyclic pyridine-C-nucleosides : part 2 Synthesis and biological evaluation of some acyclic pyridine-C-nucleosides : part 2
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
15(1996) :6 , p. 1203-1221
ISSN
0732-8311
ISI
A1996UR88700008
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
3-Bromo-5-(2-hydroxyethylthiomethyl)pyridine ((7) under bar) was synthesized by reaction of 3-bromo-5-chloromethylpyridine hydrochloride ((6) under bar) with the mono sodium salt of 2-mercaptoethanol. 3-Bromo-5-hydroxymethylpyridine (<(10)under bar>) was, after protection as a silyl ether, converted to the 3-carboxy analogue using BuLi and CO2. After deprotection with NH4F, the alcohol function was chlorinated using SOCl2. Finally, attachment of the acyclic chain and ammonolysis gave the acyclic nicotinamide nucleosides. Treatment of the latter compounds with Lawesson's reagent gave the thioamide analogues. All compounds were identified by NMR and DCI-MS. The acyclic pyridine C-nucleosides were evaluated against a series of tumor-cell lines and a variety of viruses. No marked biological activity was found.
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