Synthesis and Biological Evaluation of Some D-Arabino- and D-Lyxofuranosyl-Pyridine C-Nucleosides |
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| Authors: | F. Verberckmoes E. L. Esmans J. Balzarini E. De Clercq |
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| Affiliation: | 1. University of Antwerp (RUCA), Department of Chemistry , Groenenborgerlaan 171, B-2020, Antwerp, Belgium;2. University of Leuven, Rega-Institute for Medical Research , Minderbroedersstraat 10, B-3000, Leuven, Belgium |
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| Abstract: | 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-arabinofuianosylpyridine (5b) was converted into 3-thiocarbamoyl-5-D-arabinofuranosyl-pyridine (7) using H2S and triethylamine. None of the test compounds showed a marked cytostatic or antiviral activity in vitro. |
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