Truncated phosphonated C-1'-branched N,O-nucleosides: a new class of antiviral agents

Bioorg Med Chem. 2012 Jun 1;20(11):3652-7. doi: 10.1016/j.bmc.2012.03.047. Epub 2012 Mar 29.

Abstract

Truncated phosphonated C-1'-branched N,O-nucleosides have been synthesized in good yields by 1,3-dipolar cycloaddition methodology, starting from N-methyl-C-(diethoxyphosphoryl)nitrone 7. Preliminary biological assays show that β-anomers are able to inhibit HIV in vitro infection at concentrations in the micromolar range. Higher SI values with respect to AZT indicated that the compounds were endowed with low cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cells, Cultured
  • Drug Evaluation, Preclinical
  • HIV Infections / drug therapy
  • Human T-lymphotropic virus 1 / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Leukocytes, Mononuclear / virology
  • Molecular Structure
  • Nitrogen Oxides / chemistry
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / pharmacology*
  • Organic Chemistry Phenomena
  • Organophosphonates / chemistry
  • Structure-Activity Relationship
  • Zidovudine / pharmacology

Substances

  • Anti-HIV Agents
  • Antiviral Agents
  • Nitrogen Oxides
  • Nucleosides
  • Organophosphonates
  • nitrones
  • Zidovudine