Anti-HIV Derivatives of 1-(2,3-Dideoxy-3-N-hydroxyamino-β-D-threo-pentofuranosyl)thymine
- 1 September 1994
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 13 (9) , 1871-1889
- https://doi.org/10.1080/15257779408010670
Abstract
Representative examples of the title compounds including bicyclic analogs (7–9) in which a perhydro-1,3-oxazine is ortho-fused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HIV-1 and HIV-2 replication in CEM cells (50% inhibitory concentration: 0.80–4.3μg/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these β-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HIV active nucleosides bearing this configuration.Keywords
This publication has 13 references indexed in Scilit:
- Molecular mechanical parameters (MM2 force field) for the N(sp3)-O(sp3) bondInternational Journal of Biological Macromolecules, 1993
- Synthesis and anti-HIV activity of 3′-deoxy-3′-(N-hydroxyamino) analogues of nucleosidesBioorganic & Medicinal Chemistry Letters, 1992
- Semianalytical treatment of solvation for molecular mechanics and dynamicsJournal of the American Chemical Society, 1990
- Macromodel—an integrated software system for modeling organic and bioorganic molecules using molecular mechanicsJournal of Computational Chemistry, 1990
- 3′-Deoxy-3′-Hydroxyamino-β-D-Xylofuranosyluracil and Derivatives ThereofNucleosides, Nucleotides and Nucleic Acids, 1988
- Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2',3'-dideoxynucleosides.Proceedings of the National Academy of Sciences, 1986
- 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro.Proceedings of the National Academy of Sciences, 1985
- The tert-Butyldimethylsilyl Group as a Protecting Group in DeoxynucleosidesCanadian Journal of Chemistry, 1973
- Équilibres conformationnels de glucides au niveau de liaisons σ SP2-SP3Carbohydrate Research, 1973
- Nuclear Spin Coupling Between Geminal Hydrogen AtomsThe Journal of Chemical Physics, 1965