Original title: Hetaryl derivatives of 7-deazapurine ribonucleosides: potent cytostatic agents
Authors: Perlíková, Pavla ; Nauš, Petr ; Bourderioux, Aurelie ; Hocek, Michal
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: A series of novel 7-deazapurine ribonucleosides substituted with aryl and hetaryl groups has been prepared. Suzuki or Stille cross-coupling reactions with 6-chloro-7-deazapurine ribonucleosides substituted with H, F of Cl atom in position 7 were used in the key step of the synthesis. Either cross-coupling of protected ribonucleoside with appropriate (het)arylboronic acid or stannane followed by deprotection, or single-step aqueous-phase Suzuki cross-coupling reaction of unprotected 7-deazapurine ribonucleoside with boronic acid provided target (het)aryl-7-deazapurine ribonucleosides. 6-Furyl- and 6-thienyl-7-deazapurine ribonucleosides showed cytostatic effect in multiple cancer cell lines in nanomolar range. Application of cyclosaligenyl and alanyl-ester phosphoramidate prodrugs did not improved cytostatic activity of parent nucleosides.
Keywords: 7-deazapurines; cytostatic; nucleosides
Project no.: CEZ:AV0Z40550506 (CEP), 1M0508 (CEP), 1QS400550501 (CEP), GAP207/11/0344 (CEP)
Funding provider: GA MŠk, GA AV ČR, GA ČR
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/11104/0198822

Permalink: http://www.nusl.cz/ntk/nusl-55826


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Research > Institutes ASCR > Institute of Organic Chemistry and Biochemistry
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