Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs

Nucleosides Nucleotides Nucleic Acids. 2020;39(5):671-687. doi: 10.1080/15257770.2019.1674333. Epub 2019 Oct 7.

Abstract

Novel 7-trifluoromethyl-7-deazapurine ribonucleoside analogs (13a-c) and their Protides (15a-c) were successfully synthesized from ribolactol or 1-α-bromo-ribose derivatives using Silyl-Hilbert-Johnson or nucleobase-anion substitution reactions followed by key aromatic trifluoromethyl substitution. Newly prepared compounds were evaluated against a panel of RNA viruses, including HCV, Ebola or Zika viruses.

Keywords: 7-trifluoromethyl-7-deazapurine ribonucleoside; RNA viruses; Silyl-Hilbert-Johnson; protides.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Ebolavirus / drug effects
  • Hepacivirus / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Prodrugs / chemical synthesis
  • Prodrugs / chemistry
  • Prodrugs / pharmacology*
  • Purines / chemical synthesis
  • Purines / chemistry
  • Purines / pharmacology*
  • Ribonucleosides / chemical synthesis
  • Ribonucleosides / chemistry
  • Ribonucleosides / pharmacology*
  • Zika Virus / drug effects

Substances

  • 7-deazapurine
  • Antiviral Agents
  • Prodrugs
  • Purines
  • Ribonucleosides