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Synthesis 2009(5): 841-847
DOI: 10.1055/s-0028-1083369
DOI: 10.1055/s-0028-1083369
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of New Cyclic and Acyclic 5-Halouridine Derivatives as Potential Antiviral Agents
Further Information
Publication History
Received
4 September 2008
Publication Date:
11 February 2009 (online)


Abstract
The synthesis of new cyclic and acyclic nucleoside analogues was achieved by alkylation of 5-halogenated 6-(2,4-dichlorophenoxymethyl)pyrimidine-2,4-dione following the Vorbrüggen coupling procedure. Nucleoside analogues of the 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)-type were obtained as well as analogues of ganciclovir, acyclovir, and ribonucleosides. All compounds were tested against a variety of viruses. Three of the new compounds were potent and selective anti-HIV-1 inhibitors.
Key words
bioorganic chemistry - drugs - antiviral agents - nucleosides - glycosylation