Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides

0361463 - ÚOCHB 2012 RIV CZ eng J - Journal Article
Nauš, Petr - Perlíková, Pavla - Pohl, Radek - Hocek, Michal
Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides.
Collection of Czechoslovak Chemical Communications. Roč. 76, č. 8 (2011), s. 957-988. ISSN 0010-0765
Institutional research plan: CEZ:AV0Z40550506
Keywords : nucleosides * cross-coupling * antitumor agents * purines * 7-deazapurines * 7H-Pyrrolo[2,3d]pyrimidine * cytostatic agents
Subject RIV: CC - Organic Chemistry
Impact factor: 1.283, year: 2011

A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium. Key intermediate 6-chloro-7-deazapurine 2'-C-methyl-beta-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl protected 1,2-anhydro-2-C-methylribofuranose. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3',5'-protected 6-chloro-7-deazapurine ribofuranoside via 2‘-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.
Permanent Link: http://hdl.handle.net/11104/0198771