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Title
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Synthesis and biological evaluation of some D-Arabino- and D-Lyxofuranosyl-Pyridine C-Nucleosides
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Author
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Abstract
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| 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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Language
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English
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Source (journal)
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Nucleosides and nucleotides. - New York, N.Y.
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Publication
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New York, N.Y.
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1994
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ISSN
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0732-8311
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DOI
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10.1080/15257779408013259
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Volume/pages
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13
:1-3
(1994)
, p. 511-525
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ISI
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A1994NG42900034
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Full text (Publisher's DOI)
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