Synthesis of (+/-)-1,2,3-triazolo-3 `-deoxy-4 `-hydroxymethyl carbanucleosides via `click' cycloaddition

Julie Broggi, Nicolas Joubert, Silvia Diez-Gonzalez, Sabine Berteina-Raboin, Thomas Zevaco, Steven Patrick Nolan, Luigi A. Agrofoglio

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

The synthesis of 1,2,3-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides with different reaction conditions and diverse modulations on the heterocycle residues was developed. Heterocycle moieties were efficiently introduced on the pseudo-sugar either via nucleophilic substitution or via 1,3-dipolar Huisgen cycloaddition. With this latter approach, 1,4-disubstituted and 1,4,5-trisubstituted-(+/-)-[1,2,3]-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides were prepared from the corresponding azido-carbocycle and various terminal or internal alkynes. Antiviral activities and cellular toxicities of the final compounds were evaluated as smallpox inhibitors. Unfortunately, at concentrations tip to 100 mM, none of them inhibited production of vaccinia virus (Lister strain) or cowpox Virus (Brighton strain) in vero cells. (C) 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1162-1170
Number of pages9
JournalTetrahedron
Volume65
Issue number6
DOIs
Publication statusPublished - 7 Feb 2009

Keywords

  • CARBOCYCLIC NUCLEOSIDES
  • POXVIRUS INFECTIONS
  • ANTIVIRAL ACTIVITY
  • TERMINAL ALKYNES
  • 1,3-DIPOLAR CYCLOADDITION
  • ANTIBACTERIAL ACTIVITY
  • ANTI-HIV-1 ACTIVITY
  • CARBONYL-COMPOUNDS
  • ORTHOPOX VIRUSES
  • GLYCOSYL AZIDES

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