Publication Type |
Journal Article |
Title |
Synthesis of Purine Nucleosides from D- Glucuronic Acid Derivatives and Evaluation of Their Cholinesterase- Inhibitory Activities |
Authors |
Nuno Manuel Xavier Stefan Schwarz P. D. Vaz Rene Csuk Amélia P. Rauter |
Groups |
HC |
Journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
Year |
2014 |
Month |
May |
Volume |
2014 |
Number |
13 |
Pages |
2770-2779 |
Abstract |
Glucuronolactones were used as precursors for N-9 and N-7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N-9,N-7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to -configured N-9- and N-7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (K-i = 14.78-50.53 M). The best inhibition was shown by the furanosyl N-9-linked uronamide-based purine nucleoside. |
DOI |
http://dx.doi.org/10.1002/ejoc.201301913 |
ISBN |
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Publisher |
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Book Title |
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ISSN |
1434-193X |
EISSN |
1099-0690 |
Conference Name |
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Bibtex ID |
ISI:000334783300017 |
Observations |
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