Title
Synthesis and biological evaluation of some D-Arabino- and D-Lyxofuranosyl-Pyridine C-Nucleosides
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) :1-3 , p. 511-525
ISSN
0732-8311
ISI
A1994NG42900034
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The addition reaction of either 3-bromo-5-lithiopyridine (2a) or 3-cyano-5-lithiopyridine (2b) to 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (1) or 2,4:3,5-di-O-benzylidene-aldehydo-D-lyxose (8) gave respectively a D-gluco/D-manno mixture of 3-bromo- and 3-cyano-5-(2,3:4,5-di-O-isopropylidene-pentitol-1-yl)pyridine (3a,b) or a D-galacto/D-talo mixture of respectively 3-bromo- and 3-cyano-5-(2,4:3,5-di-O-benzylidene-pentitol-1-yl)pyridine (9a,b). Mesylation of C-1' followed by reaction with CF3COOH/H2O resulted in the formation of the corresponding D-arabino- or D-lyxofuranosyl pyridine C-nucleosides. The cyano group of (5b) and (11b) was converted into a carbamoyl group using Amberlite IRA 400 (OH-). 3-Cyano-5-D-arabinofuranosylpyridine (5b) was converted into 3-thiocarbamoyl-5-D-arabinofuranosylpyridine (7) using H2S and triethylamine. None of the test compounds showed a marked cytostatic or antiviral activity in vitro.
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