title: Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure.
abstract: The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium-catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro.
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warszawa, Poland.
authors.forename: Rafał
authors.initials: R
authors.lastname: Gawin
authors.forename: Erik
authors.initials: E
authors.lastname: De Clercq
authors.forename: Lieve
authors.initials: L
authors.lastname: Naesens
authors.forename: Mariola
authors.initials: M
authors.lastname: Koszytkowska-Stawińska
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001372:Aza Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D002384:Catalysis; D002460:Cell Line; D004267:DNA Viruses / Q000187:drug effects*; D024882:Drug Resistance, Viral; D006801:Humans; D006865:Hydrogenation; D009705:Nucleosides / Q000138:chemical synthesis / Q000494:pharmacology*; D010165:Palladium / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D012328:RNA Viruses / Q000187:drug effects*; D013329:Structure-Activity Relationship; D000077145:Sulfanilamide; D013424:Sulfanilamides / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D001372:Aza Compounds; D009705:Nucleosides; D011741:Pyrimidine Nucleosides; D013424:Sulfanilamides; D000077145:Sulfanilamide; D010165:Palladium
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