Synthesis of (±)-1,2,3-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides via ‘click’ cycloaddition |
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Authors: | Julie Broggi Nicolas Joubert Sabine Berteina-Raboin Steven P. Nolan |
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Affiliation: | a Institut de Chimie Organique et Analytique (ICOA), UMR 6005, Université d'Orléans, 45067 Orléans, France b Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain c Forschungzentrum Karlsruhe GmbH, Inst. Techn. Chemie, Bereich Chemisch-Physikalische Verfahren, D-7601 Karlsruhe, Germany |
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Abstract: | The synthesis of 1,2,3-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides with different reaction conditions and diverse modulations on the heterocycle residues was developed. Heterocycle moieties were efficiently introduced on the pseudo-sugar either via nucleophilic substitution or via 1,3-dipolar Huisgen cycloaddition. With this latter approach, 1,4-disubstituted and 1,4,5-trisubstituted-(±)-[1,2,3]-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides were prepared from the corresponding azido-carbocycle and various terminal or internal alkynes. Antiviral activities and cellular toxicities of the final compounds were evaluated as smallpox inhibitors. Unfortunately, at concentrations up to 100 mM, none of them inhibited production of vaccinia virus (Lister strain) or cowpox virus (Brighton strain) in vero cells. |
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