Synthesis, Antiviral and Cytostatic Evaluation of Unsaturated Exomethylene and Keto D-Lyxopyranonucleoside Analogues
dc.creator | Tzioumaki, N. | en |
dc.creator | Tsoukala, E. | en |
dc.creator | Manta, S. | en |
dc.creator | Agelis, G. | en |
dc.creator | Balzarini, J. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:52:44Z | |
dc.date.available | 2015-11-23T10:52:44Z | |
dc.date.issued | 2009 | |
dc.identifier | 10.1002/ardp.200900004 | |
dc.identifier.issn | 0365-6233 | |
dc.identifier.uri | http://hdl.handle.net/11615/34126 | |
dc.description.abstract | This report describes the synthesis of unsaturated exomethylene lyxopyranonucleoside analogues as potential biologically active agents. Commercially available 1,2,3,4-tetra-O-acetyl-alpha-D-lyxopyranose 1 was condensed with silylated thymine and uracil, respectively, deacetylated and acetalated to afford 1-(2,3-O-isopropylidene-alpha-D-lyxopyranosyl)thymine 4a and 1-(2,3-O-isopropylidene-alpha-D-lyxopyranosyl)uracil 4b. The new derivatives 1-(2,3,4-trideoxy-4-methylene-alpha-pent-2-enopyranosyl)thymine 8a. and 1-(2,3,4-trideoxy-4-methylene-alpha-pent-2-enopyranosyl)uracil 8b were prepared via two different key intermediates, 7a, b and 13a, b in order to elucidate the influence of 2',3'-unsaturation and to clarify the difference between the keto and exomethylene group on the biological activity of the target molecules. Compounds 7a, b, 8a, b, and 13a, b were evaluated for their antiviral and cytostatic activity using several virus strains and cell lines. Whereas no marked antiviral activity was noticed, 13a and 13b showed a cytostatic activity that ranged between 7 and 23 mu M for 13a and 26 and 38 mu M for 13b against murine leukemia L1210, human lymphocyte Molt4/C8 and CEM cells, and human breast carcinoma MCF7 cells. | en |
dc.source.uri | <Go to ISI>://WOS:000267480500005 | |
dc.subject | Cytotoxicity | en |
dc.subject | Exomethylene nucleosides | en |
dc.subject | Ketonucleosides | en |
dc.subject | Unsaturated | en |
dc.subject | nucleosides | en |
dc.subject | FLUORO-KETOPYRANOSYL NUCLEOSIDES | en |
dc.subject | ANTI-HIV AGENTS | en |
dc.subject | BIOLOGICAL | en |
dc.subject | EVALUATION | en |
dc.subject | N-4-BENZOYL CYTOSINE | en |
dc.subject | EXOCYCLIC METHYLENE | en |
dc.subject | VICINAL DIOLS | en |
dc.subject | 1,5-ANHYDROHEXITOL NUCLEOTIDES | en |
dc.subject | CONFORMATIONAL-ANALYSIS | en |
dc.subject | N-6-BENZOYL | en |
dc.subject | ADENINE | en |
dc.subject | OLEFINS | en |
dc.subject | Chemistry, Medicinal | en |
dc.subject | Chemistry, Multidisciplinary | en |
dc.subject | Pharmacology & | en |
dc.subject | Pharmacy | en |
dc.title | Synthesis, Antiviral and Cytostatic Evaluation of Unsaturated Exomethylene and Keto D-Lyxopyranonucleoside Analogues | en |
dc.type | journalArticle | en |
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