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Preparation and antiviral properties of new acyclic, achiral nucleoside analogues: 1- or 9-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]nucleobases and 1- or 9-[2,3-dihydroxy-2-(hydroxymethyl)-propyl]nucleobases

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dc.contributor.authorBoesen, Thomasen
dc.contributor.authorMadsen, Christianen
dc.contributor.authorPedersen, Daniel Sejeren
dc.contributor.authorNielsen, Brian M.en
dc.contributor.authorPetersen, Asger B.en
dc.contributor.authorPetersen, Michael A.en
dc.contributor.authorMunck, Michael T.en
dc.contributor.authorHenriksen, Ullaen
dc.contributor.authorNielsen, Clausen
dc.contributor.authorDahl, Ottoen
dc.contributor.schoolSchool of Chemistry and Physics : Chemistryen
dc.date.issued2004en
dc.description.abstractAcyclic, achiral nucleoside derivatives 1b-e of adenine, cytosine, 5-methylcytosine, and guanine, containing a 3-hydroxy-2-(hydroxymethyl)prop-1- enyl group on N-1 or N-9, have been prepared analogously to the previously described thymine derivative 1a. In contrast to the adenine and guanine derivatives, the cytosine derivative 9 was unstable, and was obtained in a low yield due to side reactions. These include cleavage of the propenyl group from the base, and the formation of a bicyclic compound. The thymine derivative, although stable under neutral conditions, likewise underwent a reversible cyclization reaction (Michael addition) in the presence of acids or bases. The 5-methylcytosine derivative was stable under neutral and basic conditions. Four other nucleoside derivatives 26a-d containing a 2,3-dihydroxy-2-(hydroxymethyl) propyl group on N-1 or N-9, three of which are new, have likewise been prepared. All compounds were evaluated as antiviral agents against HIV-1 and HSV-1 but were devoid of antiviral activity.en
dc.description.statementofresponsibilityThomas Boesen, Christian Madsen, Daniel Sejer Pedersen, Brian M. Nielsen, Asger B. Petersen, Michael Å. Petersen, Michael Munck, Ulla Henriksen, Claus Nielsen and Otto Dahlen
dc.identifier.citationOrganic and Biomolecular Chemistry, 2004; 2(8):1245-1254en
dc.identifier.doi10.1039/b316304ken
dc.identifier.issn1477-0520en
dc.identifier.urihttp://hdl.handle.net/2440/47543
dc.publisherRoyal Society of Chemistryen
dc.titlePreparation and antiviral properties of new acyclic, achiral nucleoside analogues: 1- or 9-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]nucleobases and 1- or 9-[2,3-dihydroxy-2-(hydroxymethyl)-propyl]nucleobasesen
dc.typeJournal articleen

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