8-AZA ANALOGS OF DEAZA PURINE NUCLEOSIDES - SYNTHESIS AND BIOLOGICAL EVALUATION OF 8-AZA-1-DEAZAADENOSINE AND 2'-DEOXY-8-AZA-1-DEAZAADENOSINE

The syntheses of 7-amino-3-(beta-D-ribofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (8-aza-1-deazaadenosine) (2) and 7-amino-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (2'-deoxy-8-aza-1-deazaadenosine) (3) by glycosylation of the anion of 7-chloro-3H-1,2,3-triazolo[4,5-b]pyridine are described. The anomeric configuration as well as the position of glycosylation were determined by H-1, C-13 NMR, UV and N.O.E. difference spectroscopy. The cytotoxicity of these nucleosides against several murine and human tumor cell lines is discussed. Compounds 2 and 3 proved to be good inhibitors of adenosine deaminase.