Premium
Synthesis and Antiviral Properties of Spirocyclic [1,2,3]‐Triazolooxazine Nucleosides
Author(s) -
Dell'Isola Antonio,
McLachlan Matthew M. W.,
Neuman Benjamin W.,
AlMullah Hawaa M. N.,
Binks Alexander W. D.,
Elvidge Warren,
Shankland Kenneth,
Cobb Alexander J. A.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403560
Subject(s) - chemistry , sonogashira coupling , propargyl alcohol , adduct , combinatorial chemistry , alcohol , derivative (finance) , alkylation , propargyl , hydroamination , stereochemistry , organic chemistry , catalysis , palladium , intramolecular force , financial economics , economics
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.