Synthesis and antiviral activity of some 5'-N-phthaloyl-3'-azido-2',3'-dideoxythymidine analogues

Antivir Chem Chemother. 2003 May;14(3):139-44. doi: 10.1177/095632020301400303.

Abstract

A variety of substituted 5'-N-phthaloyl-3'-azido-2',3'-dideoxythymidine derivatives has been evaluated for their activity against HIV-1, HIV-2 and Moloney murine sarcoma virus (MSV) in cell culture. Most of the 3'-azido-2',3'-dideoxythymidine (AZT, zidovudine) derivatives showed antiviral activity in the lower micromolar concentration range and there was a close correlation between their anti-HIV and anti-MSV activity (r = 0.99). The adamantyl phthaloyl derivative was active at submicromolar concentrations. None of the compounds showed marked cytostatic activity. They did not inhibit recombinant HIV-1 reverse transcriptase. All compounds were inactive against HIV in thymidine kinase-deficient cells, pointing to the compounds' requirement to release free AZT to afford antiviral efficacy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / metabolism
  • Anti-HIV Agents / pharmacology
  • Cell Transformation, Viral
  • Cells, Cultured
  • HIV / drug effects
  • Humans
  • Imides / chemistry*
  • Mice
  • Microbial Sensitivity Tests
  • Prodrugs / metabolism
  • Prodrugs / pharmacology
  • Reverse Transcriptase Inhibitors / chemical synthesis
  • Reverse Transcriptase Inhibitors / pharmacology
  • Sarcoma Viruses, Murine / drug effects
  • Virus Replication / drug effects
  • Zidovudine / analogs & derivatives*
  • Zidovudine / metabolism
  • Zidovudine / pharmacology

Substances

  • Anti-HIV Agents
  • Imides
  • Prodrugs
  • Reverse Transcriptase Inhibitors
  • Zidovudine