SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME ACYCLIC PYRIDINE C-NUCLEOSIDES .1.

The reaction between 3-bromo-5-chloromethylpyridine hydrochloride (($) under bar 4) with the mono sodium salt of ethylene glycol was investi gated. 3-Bromo-5-(2-hydroxyethoxymethyl) pyridine (($) under bar 5) wa s synthesized and converted to the 3-carboxy analogue using butyllithi um and CO,. Subsequent treatment with diazomethane and ammonolysis gav e the corresponding acyclic nicotinamide C-nucleosides. The latter com pounds were converted into the thioamide analogues by reaction with La wesson's reagent. The pyridine N-oxide derivatives were obtained by tr eatment with peracetic acid or hydrogen peroxide. Ah compounds were id entified with the aid of H-1- and C-13-NMR and mass spectrometry. The acyclic pyridine C-nucleosides were evaluated against a number of vira l strains and cancer cell lines but no significant biological activity was found.