Publication Type Journal Article
Title Synthesis of Triazole-Containing Furanosyl Nucleoside Analogues and Their Phosphate, Phosphoramidate or Phoshonate Derivatives as Potential Sugar Diphosphate or Nucleotide Mimetics
Authors Andreia Fortuna Paulo J. Costa M.Fatima M.Piedade M. Conceição Oliveira Nuno Manuel Xavier
Groups BioMol HC
Journal CHEMPLUSCHEM
Year 2020
Month August
Volume 85
Number 8
Pages 1676-1691
Abstract The synthesis of stable and potentially bioactive xylofuranosyl nucleoside analogues and potential sugar diphosphate or nucleotide mimetics comprising a 1,2,3-triazole moiety is reported. 3 -O-Methyl-branchedN-benzyltriazole isonucleosides were accessed in 5-7 steps and 42-54 \% overall yields using a Cu(I)-catalyzed cycloaddition of 3-O-propargyl-1,2-O-isopropylidene-alpha-D-xylofuranose with benzyl azide as key step. Related isonucleotides were obtained by 5-O-phosphorylation of acetonide-protected 3-O-propargyl xylofuranose and further click cycloaddition or by Staudinger-phosphite reaction of a 5-azidoN-benzyltriazole isonucleoside. Hydroxy-, amino- or bromomethyl triazole 5 -isonucleosides were synthesized by thermal cycloaddition of 5-azido 3-O-benzyl/dodecyl xylofuranoses with propargyl alcohol, propargylamine or propargyl bromide. Better yields (82-85 \%) were obtained when using propargyl alcohol and a high 1,4-regioselectivity was attained with propargyl bromide. FurtherO/N-phosphorylation or Arbuzov reaction led to (triazolyl)methyl phosphates, phosphoramidates or phosphonates. The latter were converted into uracil nucleoside 5 -(triazolyl)methyl phosphonates as prospective nucleoside diphosphate mimetics.
DOI http://dx.doi.org/10.1002/cplu.202000424
ISBN
Publisher WILEY-V C H VERLAG GMBH
Book Title
ISSN 2192-6506
EISSN
Conference Name
Bibtex ID ISI:000563997000009
Observations
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