Synthesis, antiviral, cytotoxic and cytostatic evaluation of N1-(phosphonoalkyl)uracil derivatives
Identifieur interne : 000F41 ( Main/Exploration ); précédent : 000F40; suivant : 000F42Synthesis, antiviral, cytotoxic and cytostatic evaluation of N1-(phosphonoalkyl)uracil derivatives
Auteurs : Dorota Rygielska-Tokarska [Pologne] ; Graciela Andrei [Belgique] ; Dominique Schols [Belgique] ; Robert Snoeck [Belgique] ; Iwona E. Głowacka [Pologne]Source :
- Monatshefte Fur Chemie [ 0026-9247 ] ; 2016.
Abstract
A series of
Url:
DOI: 10.1007/s00706-016-1701-2
PubMed: NONE
PubMed Central: 7087680
Affiliations:
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uniqKey="Rygielska Tokarska D" first="Dorota" last="Rygielska-Tokarska">Dorota Rygielska-Tokarska</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.8267.b</institution-id><institution>Bioorganic Chemistry Laboratory, Faculty of Pharmacy,</institution><institution>Medical University of Lodz,</institution></institution-wrap>Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>Muszyńskiego 1, 90-151 Lodz</wicri:regionArea><wicri:noRegion>90-151 Lodz</wicri:noRegion></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation wicri:level="3"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id><institution-id institution-id-type="ISNI">0000000106687884</institution-id><institution>Rega Institute for Medical Research,</institution><institution>KU Leuven,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Louvain, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Minderbroedersstraat 10, 3000 Louvain</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author><author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><affiliation wicri:level="3"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id><institution-id institution-id-type="ISNI">0000000106687884</institution-id><institution>Rega Institute for Medical Research,</institution><institution>KU Leuven,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Louvain, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Minderbroedersstraat 10, 3000 Louvain</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation wicri:level="3"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id><institution-id institution-id-type="ISNI">0000000106687884</institution-id><institution>Rega Institute for Medical Research,</institution><institution>KU Leuven,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Louvain, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Minderbroedersstraat 10, 3000 Louvain</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"><institution-wrap><institution-id institution-id-type="GRID">grid.8267.b</institution-id><institution>Bioorganic Chemistry Laboratory, Faculty of Pharmacy,</institution><institution>Medical University of Lodz,</institution></institution-wrap>Muszyńskiego 1, 90-151 Lodz, Poland</nlm:aff><country xml:lang="fr">Pologne</country><wicri:regionArea>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="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><sec><title>Abstract</title><p id="Par1">A series of <italic>N</italic><sup>1</sup>-(phosphonoalkyl)uracils was prepared in a two-step reaction sequence from <italic>ω</italic>-aminoalkylphosphonates and (<italic>E</italic>)-3-ethoxyacryloyl isocyanate followed by the uracil ring closure. Under standard conditions (NCS; NBS; I<sub>2</sub>/CAN) all <italic>N</italic><sup>1</sup>-(phosphonoalkyl)uracils were transformed into the respective 5-halogeno derivatives to be later benzoylated at N3. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses. One compound was slightly active against human cytomegalovirus in HEL cell cultures (EC<sub>50</sub> = 45 μM) while another showed weak activity against varicella-zoster virus (TK<sup>+</sup> VZV strain OKA and TK<sup>−</sup> VZV strain 07-1) with EC<sub>50</sub> = 43 and 53 µM, respectively. In addition, several compounds exhibited noticeable inhibitory effects on the proliferation of human cervical carcinoma cells (HeLa) at a concentration lower than 200 μM.</p></sec><sec><title>Graphical abstract</title><p id="Par2"><graphic position="anchor" xlink:href="706_2016_1701_Figa_HTML" id="MO1"></graphic></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></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="Freeman, S" uniqKey="Freeman S">S Freeman</name></author><author><name sortKey="Gardiner, Jm" 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B">BH Kim</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Glowacka, Ie" uniqKey="Glowacka I">IE Głowacka</name></author><author><name sortKey="Balzarini, J" uniqKey="Balzarini J">J Balzarini</name></author><author><name sortKey="Schols, D" uniqKey="Schols D">D Schols</name></author><author><name sortKey="Piotrowska, Dg" uniqKey="Piotrowska D">DG Piotrowska</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Song, X P" uniqKey="Song X">X-P Song</name></author><author><name sortKey="Bouillon, C" uniqKey="Bouillon C">C Bouillon</name></author><author><name sortKey="Lescrinier, E" uniqKey="Lescrinier E">E Lescrinier</name></author><author><name sortKey="Herdewijn" uniqKey="Herdewijn">Herdewijn</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Sauer, R" uniqKey="Sauer R">R Sauer</name></author><author><name sortKey="El Tayeb, A" uniqKey="El Tayeb A">A El-Tayeb</name></author><author><name sortKey="Kaulich, M" uniqKey="Kaulich M">M Kaulich</name></author><author><name sortKey="Muller, Ce" uniqKey="Muller C">CE Müller</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Brel, Vk" uniqKey="Brel V">VK Brel</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="Rygielska Tokarska, Dorota" sort="Rygielska Tokarska, Dorota" uniqKey="Rygielska Tokarska D" first="Dorota" last="Rygielska-Tokarska">Dorota Rygielska-Tokarska</name></noRegion><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name></country><country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name></region><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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