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Deprecated: Implicit conversion from float 235.6 to int loses precision in C:\Inetpub\vhosts\kidney.de\httpdocs\pget.php on line 534 Chemistry 2014 ; 20 (37): 11685-9 Nephropedia Template TP
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Synthesis and antiviral properties of spirocyclic 1,2,3 -triazolooxazine nucleosides #MMPMID25082061
Chemistry 2014[Sep]; 20 (37): 11685-9 PMID25082061show ga
An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of beta-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.