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Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides.

ABSTRACT: An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β-D-psicofuranose to the corresponding azido-derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3-dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.

SUBMITTER: Dell'Isola A

PROVIDER: S-EPMC7162048 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides.

Dell'Isola Antonio A McLachlan Matthew M W MM Neuman Benjamin W BW Al-Mullah Hawaa M N HM Binks Alexander W D AW Elvidge Warren W Shankland Kenneth K Cobb Alexander J A AJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20140731 37

An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β-D-psicofuranose to the corresponding azido-derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3-dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library ...[more]

PMID: 25082061

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