Syntheses, Activites Biologiques et Etude Conformationnelle D'Alcynyl-5 Desoxy-2′ Uridines

Abstract 5-Alkynyl 2′-deoxyuridines were prepared in low to modest yields by the palladium and nickel-catalyzed reaction of alkynylzinc reagents with 0–3′, 5′-bis (trimethylsilyl) deoxyuridine in THF. 1H-NMR and 13C-NMR studies showed that, in DMSO-d6, these synthesized nucleosides have the anti conformation as for the glycosidic bond and that the S conformation of the 2-deoxyribose ring is preponderant. 5-(5-Chloro-1-pentynyl) dUrd (6c) exhibited a potent antiviral activity, reminiscent of that reported before for 5-ethynyl-dUrd and 5-propynyl-dUrd. However, none of these 5-ethynyl-dUrd analogues proved selective in its antiviral action.