dc.creator | Agelis, G. | en |
dc.creator | Tzioumaki, N. | en |
dc.creator | Boti, T. | en |
dc.creator | Cencic, A. A. | en |
dc.creator | Komiotis, D. | en |
dc.date.accessioned | 2015-11-23T10:21:44Z | |
dc.date.available | 2015-11-23T10:21:44Z | |
dc.date.issued | 2007 | |
dc.identifier | 10.1016/j.bmc.2007.05.055 | |
dc.identifier.issn | 0968-0896 | |
dc.identifier.uri | http://hdl.handle.net/11615/25366 | |
dc.description.abstract | A new series of unsaturated pyranonucleosides with an exocyclic methylene group and thymine as heterocyclic base have been designed and synthesized. D-Galactose (1) was readily transformed in three steps into the corresponding 1-(beta-D-galactopyranosyl)thymine (2). Selective protection of the primary hydroxyl group of 2 with a t-butyldimethylsilyl (TBDMS) group, followed by specific acetalation, and oxidation gave 1-(6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-beta-D-lyxo-hexopyranosyl-2-ulose)thymine (5). Wittig reaction of the ketonucleoside 5, deprotection and tritylation of the 6'-hydroxyl group gave 1-(2-deoxy-2-methylene-6-O-trityl-beta-D-lyxo-hexopyranosyl)thymine (9). Exomethylene pyranonucleoside 9 was converted to the olefinic derivative 10, which after detritylation afforded the title compound 1-(2,3,4-trideoxy-2-methylene-beta-D-glycero-hex-3-enopyranosyl)thymine (11). These novel synthesized compounds were evaluated for antiviral activity against rotaviral infection and cytotoxicity in colon cancer. As compared to AZT, compounds 1-(2-deoxy-2-methylene-beta-D-lyxo-hexopyranosyl)thymine (7) and 1-(beta-D-lyxo-hexopyranosyl-2-ulose)thymine (8) showed to be more efficient, in rotavirus infections and in treatment of colon cancer. (c) 2007 Elsevier Ltd. All rights reserved. | en |
dc.source | Bioorganic & Medicinal Chemistry | en |
dc.source.uri | <Go to ISI>://WOS:000248172700009 | |
dc.subject | exomethylene nucleosides | en |
dc.subject | ketonucleosides | en |
dc.subject | unsaturated nucleosides | en |
dc.subject | olefination | en |
dc.subject | antiviral | en |
dc.subject | anti-tumor activity | en |
dc.subject | POTENTIAL ANTIVIRAL AGENTS | en |
dc.subject | MECHANISM-BASED INHIBITORS | en |
dc.subject | ONE-STEP | en |
dc.subject | CONVERSION | en |
dc.subject | ANTI-TUMOR ACTIVITY | en |
dc.subject | RIBONUCLEOTIDE REDUCTASE | en |
dc.subject | VICINAL | en |
dc.subject | DIOLS | en |
dc.subject | EXOCYCLIC METHYLENE | en |
dc.subject | NUCLEOSIDE ANALOGS | en |
dc.subject | 1,5-ANHYDROHEXITOL | en |
dc.subject | NUCLEOTIDES | en |
dc.subject | UNSATURATED KETONUCLEOSIDES | en |
dc.subject | Biochemistry & Molecular Biology | en |
dc.subject | Chemistry, Medicinal | en |
dc.subject | Chemistry, | en |
dc.subject | Organic | en |
dc.title | Exomethylene pyranonucleosides: Efficient synthesis and biological evaluation of 1-(2,3,4-trideoxy-2-methylene-beta-D-glycero-hex-3-enopyranosyl)thymine | en |
dc.type | journalArticle | en |