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STEREOCONTROLLED FACILE SYNTHESIS AND BIOLOGICAL EVALUATION OF (3 ' S) AND (3 ' R)-3 '-AMINO (AND AZIDO)-3 '-DEOXY PYRANONUCLEOSIDES
dc.creator | Manta, S. | en |
dc.creator | Parmenopoulou, V. | en |
dc.creator | Kiritsis, C. | en |
dc.creator | Dimopoulou, A. | en |
dc.creator | Kollatos, N. | en |
dc.creator | Papasotiriou, I. | en |
dc.creator | Balzarini, J. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:38:48Z | |
dc.date.available | 2015-11-23T10:38:48Z | |
dc.date.issued | 2012 | |
dc.identifier | 10.1080/15257770.2012.696759 | |
dc.identifier.issn | 1525-7770 | |
dc.identifier.uri | http://hdl.handle.net/11615/30669 | |
dc.description.abstract | This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl-alpha-D-allofuranose followed by hydrolysis and subsequent acetylation afforded 3-azido-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose, which upon coupling with the proper silylated bases, deacetylation, and catalytic hydrogenation, obtained the target 3'-amino-3'-deoxy-beta-D-glucopyranonucleosides. The desired 1-(3'-amino-3'-deoxy-beta-D-allopyranosyl) 5-fluorouracil was readily prepared from the suitable imidazylate sugar after azidation followed by a protection/deprotection sequence and reduction of the unprotected azido precursor. No antiviral activity was observed for the novel nucleosides. Moderate cytostatic activity was recorded for the 5-fluorouracil derivatives. | en |
dc.source.uri | <Go to ISI>://WOS:000307079400002 | |
dc.subject | Azido pyranonucleosides | en |
dc.subject | amino pyranonucleosides | en |
dc.subject | cytostatic activity | en |
dc.subject | 5-fluorouracil | en |
dc.subject | FLUORO-KETOPYRANOSYL NUCLEOSIDES | en |
dc.subject | N-4-BENZOYL CYTOSINE | en |
dc.subject | 3'-AMINO-3'-DEOXYHEXOPYRANOSYL NUCLEOSIDES | en |
dc.subject | N-6-BENZOYL ADENINE | en |
dc.subject | 1,5-ANHYDROHEXITOL NUCLEOSIDES | en |
dc.subject | EXOMETHYLENE PYRANONUCLEOSIDES | en |
dc.subject | EFFICIENT SYNTHESIS | en |
dc.subject | ANTIVIRAL AGENTS | en |
dc.subject | ANTITUMOR AGENTS | en |
dc.subject | DERIVATIVES | en |
dc.subject | Biochemistry & Molecular Biology | en |
dc.title | STEREOCONTROLLED FACILE SYNTHESIS AND BIOLOGICAL EVALUATION OF (3 ' S) AND (3 ' R)-3 '-AMINO (AND AZIDO)-3 '-DEOXY PYRANONUCLEOSIDES | en |
dc.type | journalArticle | en |
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