0310039 - ÚOCHB 2009 RIV CZ eng C - Conference Paper (international conference)
Mařák, David - Otmar, Miroslav - Dračínský, Martin - Votruba, Ivan - Holý, Antonín
Nucleosides and nucleotides containing 8-aza-7,9-dideazaxanthine.
[Nukleosidy a nukleotidy obsahující 8-aza-7,9-dideazaxanthin.]
Chemistry of Nucleic Acid Components. Praha: Institute of Organic Chemistry and Biochemistry ASCR, 2008 - (Hocek, M.), s. 426-428. Collection Symposium Series, 10. ISBN 978-80-86241-29-6.
[Symposium on Chemistry of Nucleic Acid Components /14./. Český Krumlov (CZ), 08.06.2008-13.06.2008]
R&D Projects: GA MŠMT 1M0508; GA AV ČR 1QS400550501
Grant - others:NIH(US) 1UC1A1062540-01
Institutional research plan: CEZ:AV0Z40550506
Keywords : 8-Aza-7,9-dideaza * xanthine * thymidine phosporylase * debenzylation
Subject RIV: CC - Organic Chemistry

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.
Permanent Link: http://hdl.handle.net/11104/0162022