Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

Nucleosides Nucleotides Nucleic Acids. 2021;40(1):43-67. doi: 10.1080/15257770.2020.1826516. Epub 2020 Oct 8.

Abstract

An efficient one-pot three-component Kabachnik-Fields reaction of aldehydes (acyclic nucleosides), amines (or amino acid), and triethyl phosphite proceeded for the synthesis of aminophosphonates using natural phosphate coated with iodine (I2@NP) as a catalyst. The novel α-aminophosphonate and phosphonic acid acyclic nucleosides were tested for their anti-HCV and anti-HIV activities. The molecular docking showed that the non-activity of these compounds could be due to the absence of hydrophobic pharmacophores.

Keywords: Acyclic nucleosides; Kabachnik–Fields reaction; catalysis; natural phosphate; α-aminophosphonates.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Chemistry Techniques, Synthetic
  • HIV-1 / drug effects
  • HIV-2 / drug effects
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Nucleosides / pharmacology
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry*
  • Organophosphonates / pharmacology
  • Phosphorous Acids / chemistry*

Substances

  • Antiviral Agents
  • Nucleosides
  • Organophosphonates
  • Phosphorous Acids
  • phosphonic acid