Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

Bioorg Med Chem Lett. 2007 Dec 15;17(24):6785-9. doi: 10.1016/j.bmcl.2007.10.038. Epub 2007 Oct 17.

Abstract

A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC(50)=2.1 microM, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT.

MeSH terms

  • Adenine / analogs & derivatives
  • Adenine / pharmacology
  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacokinetics
  • Anti-HIV Agents / pharmacology
  • Combinatorial Chemistry Techniques
  • Drug Design
  • HIV / drug effects*
  • HIV / genetics*
  • Molecular Structure
  • Nucleosides* / chemical synthesis
  • Nucleosides* / chemistry
  • Nucleosides* / pharmacokinetics
  • Nucleosides* / pharmacology
  • Organophosphonates* / chemical synthesis
  • Organophosphonates* / chemistry
  • Organophosphonates* / pharmacokinetics
  • Organophosphonates* / pharmacology
  • Reverse Transcriptase Inhibitors* / chemical synthesis
  • Reverse Transcriptase Inhibitors* / chemistry
  • Reverse Transcriptase Inhibitors* / pharmacokinetics
  • Reverse Transcriptase Inhibitors* / pharmacology
  • Structure-Activity Relationship
  • Tenofovir

Substances

  • (5-(6-amino-purin-9-yl)-2,5-dihydrofuran-2-yloxymethyl)phosphonic acid
  • Anti-HIV Agents
  • Nucleosides
  • Organophosphonates
  • Reverse Transcriptase Inhibitors
  • Tenofovir
  • Adenine