Original title: Nucleosides and nucleotides containing 8-aza-7,9-dideazaxanthine
Translated title: Nukleosidy a nukleotidy obsahující 8-aza-7,9-dideazaxanthin
Authors: Mařák, David ; Otmar, Miroslav ; Dračínský, Martin ; Votruba, Ivan ; Holý, Antonín
Document type: Papers
Conference/Event: Symposium on Chemistry of Nucleic Acid Components /14./, Český Krumlov (CZ), 2008-06-08 / 2008-06-13
Year: 2008
Language: eng
Abstract: [eng] [cze]
The described preparation of 8-aza-7,9-dideazaxanthine from 1,3-dibenzyluracil and TosMIC was improved by using AlCl3 for final debenzylation. Treatment of 6-dibromomethyl- 5-formyluracil with benzyl-, 4-methoxybenzyl-, and 1-adamantylamine gave the corresponding 8-alkyl-8-aza-7,9-dideazaxanthines. N1- and N8-(8-phosphonooctyl)-8-aza-7,9-dideazaxanthines were prepared and found as inhibitors of thymidine phosphorylase (V79 cells, human placenta, Escherichia coli). IC50 values ranged at 3–27 .mu.M. 8-Aza-7,9-dideazaxanthin byl připraven pomocí TosMIC a 1,3-dibenzyluracilu. Postup byl vylepšen užitím AlCl3 pro finální debenzylaci. 8-Alkyl-8-aza-7,9-dideazaxanthiny byly připraveny reakcí 6-dibromomethyl-5-formyluracilu s benzyl-, 4 methoxybenzyl-, a 1 adamantylaminem. Bylo zjištěno že N1- a N8-(8-fosfonooktyl)-8-aza-7,9-dideazaxanthin jsou učinnými inhibitory thymidin fosforylasy (V79 buňky, lidská placenta, Escherichia coli). Hodnoty IC50 3–27 .mu.M.
Keywords: 8-Aza-7,9-dideaza; debenzylation; thymidine phosporylase; xanthine
Project no.: CEZ:AV0Z40550506 (CEP), 1M0508 (CEP), 1QS400550501 (CEP), 1UC1A1062540-01
Funding provider: GA MŠk, GA AV ČR, NIH
Host item entry: Chemistry of Nucleic Acid Components, ISBN 978-80-86241-29-6

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/11104/0162022

Permalink: http://www.nusl.cz/ntk/nusl-38985


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Research > Institutes ASCR > Institute of Organic Chemistry and Biochemistry
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