Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  • Herdewijn, Piet
  • Balzarini, Jan
  • Baba, M
  • Pauwels, R
  • Van Aerschot, Arthur
  • Janssen, Gerardus
  • De Clercq, Erik
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Publication date
October 1988
Publisher
American Chemical Society (ACS)
Journal
Journal of Medicinal Chemistry

Abstract

A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3...

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