Original title: Use of 1,3-dioxolanes in the syntheses of alpha-branched alkyl and aryl N-9-[2-(phosphonomethoxy)ethyl]purines
Authors: Pomeisl, Karel ; Holý, Antonín ; Krečmerová, Marcela
Document type: Papers
Conference/Event: Chemistry of Nucleic Acid Components /15./, Český Krumlov (CZ), 2011-06-05 / 2011-06-10
Year: 2011
Language: eng
Abstract: Syntheses of various alkyl and aryl substituted N-9-[2-(phoshonomethoxy)ethyl]purines from a number of 2-alkyl(aryl)-1,3-dioxolanes were developed in preparative yields. The cleavage of a dioxolane ring with Lewis acids was chosen for preparation of suitable phosphonate building blocks as a key reaction step followed by their Mitsunobu reaction with purine bases. Obtained phosphonate derivatives were tested as potential HG(X)PRTase inhibitors. In contrast to previously published N-9-[2-(phosphonoethoxy)ethyl]purines, no inhibitory activity towards this enzyme was observed.
Keywords: acyclic nucleoside phosphonates; dioxolanes; malaria; Mitsunobu reaction
Project no.: CEZ:AV0Z40550506 (CEP), 1M0508 (CEP)
Funding provider: GA MŠk
Host item entry: Chemistry of Nucleic Acid Components. 15th Symposium, ISBN 978-80-86241-37-1

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0198225

Permalink: http://www.nusl.cz/ntk/nusl-55767


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