Synthesis and biological activity of benzo-fused 7-deazaadenosine analogues. 5- and 6-substituted 4-amino- or 4-alkylpyrimido[4,5-b]indole ribonucleosides

Bioorg Med Chem. 2013 Sep 1;21(17):5362-72. doi: 10.1016/j.bmc.2013.06.011. Epub 2013 Jun 17.

Abstract

Two series of new 4-aminopyrimido[4,5-b]indole ribonucleosides bearing phenyl or hetaryl group at position 5 or 6 have been prepared by Suzuki or Stille cross-coupling reactions employing X-Phos ligand with (het)arylboronic acids or stannanes. A series of 4-substituted nucleosides has been also prepared by Pd-catalyzed cross-couplings or nucleophilic substitution. Some of these compounds displayed moderate antiviral activities against HCV and dengue viruses.

Keywords: Anti-dengue virus activity; Nucleosides; Pyrimido[4,5-b]indoles; Suzuki and Stille cross-coupling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Antiviral Agents / toxicity
  • Catalysis
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dengue Virus / drug effects
  • HL-60 Cells
  • HeLa Cells
  • Hep G2 Cells
  • Hepacivirus / drug effects
  • Humans
  • Indoles / chemistry*
  • Palladium / chemistry
  • Ribonucleosides / chemistry*
  • Ribonucleosides / pharmacology
  • Ribonucleosides / toxicity

Substances

  • Antiviral Agents
  • Indoles
  • Ribonucleosides
  • Palladium
  • indole
  • Adenosine