| 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 |
|
| Publisher |
|
| Book Title |
|
| ISSN |
1434-193X |
| EISSN |
1099-0690 |
| Conference Name |
|
| Bibtex ID |
ISI:000334783300017 |
| Observations |
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