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Title
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Synthesis and biological evaluation of some acyclic pyridine C-nucleosides : part 1
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Author
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Abstract
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| 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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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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10.1080/15257779408013225
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Volume/pages
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13
:10
(1994)
, p. 2345-2366
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ISI
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A1994PY42900021
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Full text (Publisher's DOI)
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