dc.creator | Kiritsis, C. | en |
dc.creator | Manta, S. | en |
dc.creator | Papasotiriou, I. | en |
dc.creator | Coutouli-Argyropoulou, E. | en |
dc.creator | Trakossas, S. | en |
dc.creator | Balzarini, J. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:34:53Z | |
dc.date.available | 2015-11-23T10:34:53Z | |
dc.date.issued | 2012 | |
dc.identifier | 10.2174/157340612800786624 | |
dc.identifier.issn | 15734064 | |
dc.identifier.uri | http://hdl.handle.net/11615/29429 | |
dc.description.abstract | A novel series of 3′-C-ethynyl and 3′-C-(1,4-disubstituted-1,2, 3-triazolo) double-headed pyranonucleosides has been designed and synthesized. Reaction of 3-keto glucoside 1 with ethynyl magnesium bromide gave the desired precursor 3-C-ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (2). Hydrolysis followed by acetylation led to the 1,2,4,6-tetra-O-acetyl-3-C- ethynyl-β-D-allopyranose (3). Compound 3 was condensed with silylated 5-fluorouracil, uracil, thymine, N4-benzoylcytosine and N 6-benzoyladenine, respectively and deacetylated to afford the target 1-(3′-C-ethynyl-β-D-allopyranosyl)nucleosides 5a-c,f,g. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) reaction was utilized to couple the 3′-C-ethynyl pyranonucleoside derivatives with azidoethyl adenine, 5-fluorouracil and thymine, respectively to afford novel triazole double-headed nucleoside analogues 8a-h. 3′-C-Ethynyl pyranonucleosides and the new doubleheaded analogues were evaluated for their antiviral and cytostatic activities. Although none of the compounds showed pronounced cytostatic activity and were devoid of a significant antiviral potential, the double-headed nucleoside derivatives 8a, 8c and 8e showed a moderate cytostatic activity against human cervix carcinoma HeLa cells which may be the basis for the synthesis of analogous derivatives with improved cytostatic potential. © 2012 Bentham Science Publishers. | en |
dc.source.uri | http://www.scopus.com/inward/record.url?eid=2-s2.0-84863669044&partnerID=40&md5=d879ecac00cfbdc630b735f261d51664 | |
dc.subject | Branched-chain nucleosides | en |
dc.subject | C-ethynyl pyranonucleosides | en |
dc.subject | Click chemistry | en |
dc.subject | Double-headed nucleosides | en |
dc.subject | 3' c ethynyl | en |
dc.subject | 3' c(1,4 disubstituted 1,2,3 triazolo) | en |
dc.subject | fluorouracil | en |
dc.subject | nucleoside derivative | en |
dc.subject | thymine | en |
dc.subject | unclassified drug | en |
dc.subject | uracil | en |
dc.subject | acetylation | en |
dc.subject | antiviral activity | en |
dc.subject | article | en |
dc.subject | chemical reaction | en |
dc.subject | controlled study | en |
dc.subject | cycloaddition | en |
dc.subject | cytostasis | en |
dc.subject | drug activity | en |
dc.subject | drug design | en |
dc.subject | drug synthesis | en |
dc.subject | HeLa cell | en |
dc.subject | human | en |
dc.subject | human cell | en |
dc.subject | hydrolysis | en |
dc.subject | polymerization | en |
dc.subject | priority journal | en |
dc.subject | silylation | en |
dc.subject | uterine cervix carcinoma | en |
dc.subject | Animals | en |
dc.subject | Antiviral Agents | en |
dc.subject | Cells, Cultured | en |
dc.subject | Dose-Response Relationship, Drug | en |
dc.subject | HeLa Cells | en |
dc.subject | Humans | en |
dc.subject | Mice | en |
dc.subject | Microbial Sensitivity Tests | en |
dc.subject | Molecular Structure | en |
dc.subject | Nucleosides | en |
dc.subject | Pyrans | en |
dc.subject | Structure-Activity Relationship | en |
dc.subject | Triazoles | en |
dc.subject | Viruses | en |
dc.title | Synthesis and biological evaluation of 3′-c-ethynyl and 3′-c-(1,4-disubstituted-1,2,3-triazolo) double-headed pyranonucleosides | en |
dc.type | journalArticle | en |