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