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Synthesis and anti-HIV activity of 5-alkoxymethyl-3'-azido-2',3- dideoxyuridines. 1993

A E Abdel-Megied, and P Hansen, and E B Pedersen, and C Nielsen, and C M Nielsen
Department of Chemistry, Odense University, Denmark.

Methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-furanosi de (3) was coupled with silylated 5-hydroxymethyluracil (1a) and its C1-C6 alkyl ethers 1b-g to give the corresponding protected nucleosides 4a-g which were deprotected with Bu4NF to afford 3-azido nucleosides 5a-g and 6a-g. The alpha-anomers 6f,g show moderate activity against HIV. No significant activity against HSV-1 was found for the compounds 5 and 6.

UI MeSH Term Description Entries
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D015215 Zidovudine A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. AZT (Antiviral),Azidothymidine,3'-Azido-2',3'-Dideoxythymidine,3'-Azido-3'-deoxythymidine,AZT Antiviral,AZT, Antiviral,BW A509U,BWA-509U,Retrovir,3' Azido 2',3' Dideoxythymidine,3' Azido 3' deoxythymidine,Antiviral AZT,BWA 509U,BWA509U
D015497 HIV-1 The type species of LENTIVIRUS and the etiologic agent of AIDS. It is characterized by its cytopathic effect and affinity for the T4-lymphocyte. Human immunodeficiency virus 1,HIV-I,Human Immunodeficiency Virus Type 1,Immunodeficiency Virus Type 1, Human
D018139 Simplexvirus A genus of the family HERPESVIRIDAE, subfamily ALPHAHERPESVIRINAE, consisting of herpes simplex-like viruses. The type species is HERPESVIRUS 1, HUMAN. Herpes Simplex Virus,Herpesvirus 1, Saimiriine,Herpesvirus 1, Saimirine,Herpesvirus 16, Cercopithecine,Marmoset Virus,Cercopithecine Herpesvirus 16,Herpes Labialis Virus,Herpes-T Virus,Herpesvirus 1 (alpha), Saimirine,Herpesvirus Hominis,Herpesvirus Papio 2,Herpesvirus Platyrhinae,Marmoset Herpesvirus,Saimiriine Herpesvirus 1,Herpes Labialis Viruses,Herpes Simplex Viruses,Herpes T Virus,Herpes-T Viruses,Herpesvirus Homini,Herpesvirus, Marmoset,Herpesviruses, Marmoset,Homini, Herpesvirus,Hominis, Herpesvirus,Labialis Virus, Herpes,Labialis Viruses, Herpes,Marmoset Herpesviruses,Marmoset Viruses,Platyrhinae, Herpesvirus,Saimirine Herpesvirus 1,Simplexviruses,Virus, Herpes Labialis,Viruses, Herpes Labialis

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