ArticleChemistry (Weinheim an der Bergstrasse, Germany)2014
Synthesis and antiviral properties of spirocyclic [1,2,3]-triazolooxazine nucleosides.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Synthesis and applications of cyclonucleosides: an update (2010-2023).Molecular diversity · 2024Review
- Recent Progress on Synthesis of Functionalized 1,5-Disubstituted Triazoles.Current organic synthesis · 2024Review
- Glycopyranosylidene-Spiro-Morpholinones: Evaluation of the Synthetic Possibilities Based on Glyculosonamide Derivatives and a New Method for the Construction of the Morpholine Ring.Molecules (Basel, Switzerland) · 2022Article
- Modified Nucleosides, Nucleotides and Nucleic Acids via Click Azide-Alkyne Cycloaddition for Pharmacological Applications.Molecules (Basel, Switzerland) · 2021Review
- Synthesis of Spironucleosides: Past and Future Perspectives.Molecules (Basel, Switzerland) · 2017Review
- Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides.Beilstein journal of organic chemistry · 2015Article
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Authors and funding
8 authors.
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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.
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