| Synthesis and Biological Evaluation of 3΄-C-Ethynyl and 3΄-C-(1,4-disubstituted-1,2,3-triazolo) Double-Headed Pyranonucleosides. | |
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MedLine Citation:
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PMID: 22530902 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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 N6-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 analogs 8a-h. 3΄-C-Ethynyl pyranonucleosides and the new double-headed 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. |
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Authors:
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Christos Kiritsis; Stella Manta; Ioannis Papasotiriou; Evdoxia Coutouli-Argyropoulou; Sakellarios Trakossas; Jan Balzarini; Dimitri Komiotis |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-4-24 |
Journal Detail:
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Title: Medicinal chemistry (Shariqah (United Arab Emirates)) Volume: - ISSN: 1875-6638 ISO Abbreviation: - Publication Date: 2012 Apr |
Date Detail:
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Created Date: 2012-4-25 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101240303 Medline TA: Med Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Biochemistry and Biotechnology, Laboratory of Bio-organic Chemistry, University of Thessaly, 41221 Larissa, Greece. dkom@bio.uth.gr. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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