Design, synthesis, antiviral and cytotoxic evaluation of novel acyclic phosphonate nucleotide analogues with a 5,6-dihydro-1H-[1,2,3]triazolo[4,5-d]pyridazine-4,7-dione system
Identifieur interne : 000A38 ( Main/Exploration ); précédent : 000A37; suivant : 000A39Design, synthesis, antiviral and cytotoxic evaluation of novel acyclic phosphonate nucleotide analogues with a 5,6-dihydro-1H-[1,2,3]triazolo[4,5-d]pyridazine-4,7-dione system
Auteurs : Emilia Bankowska [Pologne] ; Jan Balzarini [Belgique] ; Iwona E. Głowacka [Pologne] ; Andrzej E. Wr Blewski [Pologne]Source :
- Monatshefte Fur Chemie [ 0026-9247 ] ; 2014.
Abstract
A series of diethyl 2-(4,5-dimethoxycarbonyl-1
The online version of this article (doi:10.1007/s00706-013-1137-x) contains supplementary material, which is available to authorized users.
Url:
DOI: 10.1007/s00706-013-1137-x
PubMed: 26166892
PubMed Central: 4494773
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Design, synthesis, antiviral and cytotoxic evaluation of novel acyclic phosphonate nucleotide analogues with a 5,6-dihydro-1<italic>H</italic>-[1,2,3]triazolo[4,5-<italic>d</italic>]pyridazine-4,7-dione system</title><author><name sortKey="Bankowska, Emilia" sort="Bankowska, Emilia" uniqKey="Bankowska E" first="Emilia" last="Bankowska">Emilia Bankowska</name><affiliation wicri:level="1"><nlm:aff id="Aff1">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="3"><nlm:aff id="Aff2">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author><author><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name><affiliation wicri:level="1"><nlm:aff id="Aff1">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author><author><name sortKey="Wr Blewski, Andrzej E" sort="Wr Blewski, Andrzej E" uniqKey="Wr Blewski A" first="Andrzej E." last="Wr Blewski">Andrzej E. Wr Blewski</name><affiliation wicri:level="1"><nlm:aff id="Aff1">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">26166892</idno><idno type="pmc">4494773</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4494773</idno><idno type="RBID">PMC:4494773</idno><idno type="doi">10.1007/s00706-013-1137-x</idno><date when="2014">2014</date><idno type="wicri:Area/Pmc/Corpus">000147</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000147</idno><idno type="wicri:Area/Pmc/Curation">000147</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000147</idno><idno type="wicri:Area/Pmc/Checkpoint">000416</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000416</idno><idno type="wicri:Area/Ncbi/Merge">000473</idno><idno type="wicri:Area/Ncbi/Curation">000473</idno><idno type="wicri:Area/Ncbi/Checkpoint">000473</idno><idno type="wicri:doubleKey">0026-9247:2014:Bankowska E:design:synthesis:antiviral</idno><idno type="wicri:Area/Main/Merge">000A40</idno><idno type="wicri:Area/Main/Curation">000A38</idno><idno type="wicri:Area/Main/Exploration">000A38</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Design, synthesis, antiviral and cytotoxic evaluation of novel acyclic phosphonate nucleotide analogues with a 5,6-dihydro-1<italic>H</italic>-[1,2,3]triazolo[4,5-<italic>d</italic>]pyridazine-4,7-dione system</title><author><name sortKey="Bankowska, Emilia" sort="Bankowska, Emilia" uniqKey="Bankowska E" first="Emilia" last="Bankowska">Emilia Bankowska</name><affiliation wicri:level="1"><nlm:aff id="Aff1">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="3"><nlm:aff id="Aff2">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author><author><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name><affiliation wicri:level="1"><nlm:aff id="Aff1">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author><author><name sortKey="Wr Blewski, Andrzej E" sort="Wr Blewski, Andrzej E" uniqKey="Wr Blewski A" first="Andrzej E." last="Wr Blewski">Andrzej E. Wr Blewski</name><affiliation wicri:level="1"><nlm:aff id="Aff1">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author></analytic><series><title level="j">Monatshefte Fur Chemie</title><idno type="ISSN">0026-9247</idno><idno type="eISSN">1434-4475</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><sec><title>Abstract</title><p>A series of diethyl 2-(4,5-dimethoxycarbonyl-1<italic>H</italic>-1,2,3-triazol-1-yl)alkylphosphonates was synthesised from <italic>ω</italic>-azidoalkylphosphonates and dimethyl acetylenedicarboxylate and was further transformed into the respective diamides, dihydrazides, and 5,6-dihydro-1<italic>H</italic>-[1,2,3]triazolo[4,5-<italic>d</italic>]pyridazine-4,7-diones as phosphonate analogues of acyclic nucleosides having nucleobases replaced with substituted 1,2,3-triazoles. All compounds containing P–C–C–triazole or P–C–C–CH<sub>2</sub>–triazole moieties exist in single conformations in which the diethoxyphosphoryl and substituted 1,2,3-triazolyl or substituted (1,2,3-triazolyl)methyl groups are oriented <italic>anti</italic>. All phosphonates were evaluated in vitro for activity against a variety of DNA and RNA viruses. None of the compounds were endowed with antiviral activity. They were not cytostatic at 100 μM.</p></sec><sec><title>Graphical abstract</title><p><graphic position="anchor" xlink:href="706_2013_1137_Figa_HTML" id="MO1"></graphic></p></sec><sec><title>Electronic supplementary material</title><p>The online version of this article (doi:10.1007/s00706-013-1137-x) contains supplementary material, which is available to authorized users.</p></sec></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="De Clercq, E" uniqKey="De Clercq E">E De Clercq</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="De Clercq, E" uniqKey="De Clercq E">E De Clercq</name></author><author><name sortKey="Hol, A" uniqKey="Hol A">A Holý</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Naesens, L" uniqKey="Naesens L">L Naesens</name></author><author><name sortKey="Snoeck, R" uniqKey="Snoeck R">R Snoeck</name></author><author><name sortKey="Andrei, G" 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Tronchet</name></author><author><name sortKey="Charollais, Ej" uniqKey="Charollais E">EJ Charollais</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Adiwidjaja, G" uniqKey="Adiwidjaja G">G Adiwidjaja</name></author><author><name sortKey="Meyer, B" uniqKey="Meyer B">B Meyer</name></author><author><name sortKey="Thiem, J" uniqKey="Thiem J">J Thiem</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Buchanan, Gw" uniqKey="Buchanan G">GW Buchanan</name></author><author><name sortKey="Bourque, K" uniqKey="Bourque K">K Bourque</name></author><author><name sortKey="Seeley, A" uniqKey="Seeley A">A Seeley</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Belgique</li><li>Pologne</li></country><region><li>Province du Brabant flamand</li></region><settlement><li>Louvain</li></settlement></list><tree><country name="Pologne"><noRegion><name sortKey="Bankowska, Emilia" sort="Bankowska, Emilia" uniqKey="Bankowska E" first="Emilia" last="Bankowska">Emilia Bankowska</name></noRegion><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name><name sortKey="Wr Blewski, Andrzej E" sort="Wr Blewski, Andrzej E" uniqKey="Wr Blewski A" first="Andrzej E." last="Wr Blewski">Andrzej E. Wr Blewski</name></country><country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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