Synthesis and Antiviral Activity of Some 5′-<i>N</i>-Phthaloyl-3′-Azido-2′,3′-Dideoxythymidine Analogues

Jan Balzarini; De Clercq Erik; Beata Kamińska; Andrzej Orzeszko

doi:10.1177/095632020301400303

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Synthesis and Antiviral Activity of Some 5′-<i>N</i>-Phthaloyl-3′-Azido-2′,3′-Dideoxythymidine Analogues

Article 2003 en

Authors

JB
Jan Balzarini
De Clercq Erik
KU Leuven
BK
Beata Kamińska

Abstract

1 min read

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.

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Synthesis and Antiviral Activity of Some 5′-<i>N</i>-Phthaloyl-3′-Azido-2′,3′-Dideoxythymidine Analogues

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