Synthesis, antiviral, cytotoxic and cytostatic evaluation of N1-(phosphonoalkyl)uracil derivatives
Identifieur interne : 000306 ( Pmc/Curation ); précédent : 000305; suivant : 000307Synthesis, 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
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis, antiviral, cytotoxic and cytostatic evaluation of <italic>N</italic><sup>1</sup>-(phosphonoalkyl)uracil derivatives</title><author><name sortKey="Rygielska Tokarska, Dorota" sort="Rygielska Tokarska, Dorota" 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></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation wicri:level="1"><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></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></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmc">7087680</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7087680</idno><idno type="RBID">PMC:7087680</idno><idno type="doi">10.1007/s00706-016-1701-2</idno><idno type="pmid">NONE</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000306</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000306</idno><idno type="wicri:Area/Pmc/Curation">000306</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000306</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis, antiviral, cytotoxic and cytostatic evaluation of <italic>N</italic><sup>1</sup>-(phosphonoalkyl)uracil derivatives</title><author><name sortKey="Rygielska Tokarska, Dorota" sort="Rygielska Tokarska, Dorota" 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></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation wicri:level="1"><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></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></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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<front><journal-meta><journal-id journal-id-type="nlm-ta">Monatsh Chem</journal-id><journal-id journal-id-type="iso-abbrev">Monatsh. Chem</journal-id><journal-title-group><journal-title>Monatshefte Fur Chemie</journal-title></journal-title-group><issn pub-type="ppub">0026-9247</issn><issn pub-type="epub">1434-4475</issn><publisher><publisher-name>Springer Vienna</publisher-name><publisher-loc>Vienna</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmc">7087680</article-id><article-id pub-id-type="publisher-id">1701</article-id><article-id pub-id-type="doi">10.1007/s00706-016-1701-2</article-id><article-categories><subj-group subj-group-type="heading"><subject>Original Paper</subject></subj-group></article-categories><title-group><article-title>Synthesis, antiviral, cytotoxic and cytostatic evaluation of <italic>N</italic><sup>1</sup>-(phosphonoalkyl)uracil derivatives</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Rygielska-Tokarska</surname><given-names>Dorota</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Andrei</surname><given-names>Graciela</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Schols</surname><given-names>Dominique</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Snoeck</surname><given-names>Robert</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author" corresp="yes"><name><surname>Głowacka</surname><given-names>Iwona E.</given-names></name><address><email>iwona.glowacka@umed.lodz.pl</email></address><xref ref-type="aff" rid="Aff1">1</xref></contrib><aff id="Aff1"><label>1</label><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</aff><aff id="Aff2"><label>2</label><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</aff></contrib-group><pub-date pub-type="epub"><day>1</day><month>3</month><year>2016</year></pub-date><pub-date pub-type="ppub"><year>2016</year></pub-date><volume>147</volume><issue>6</issue><fpage>1081</fpage><lpage>1090</lpage><history><date date-type="received"><day>17</day><month>12</month><year>2015</year></date><date date-type="accepted"><day>9</day><month>2</month><year>2016</year></date></history><permissions><copyright-statement>© Springer-Verlag Wien 2016</copyright-statement><license><license-p>This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.</license-p></license></permissions><abstract id="Abs1"><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></abstract><kwd-group xml:lang="en"><title>Keywords</title><kwd>Nucleotides</kwd><kwd>Halogenation</kwd><kwd>Antiviral activity</kwd><kwd>NMR spectroscopy</kwd><kwd>Cyclizations</kwd></kwd-group><funding-group><award-group><funding-source><institution>Medical University of Lodz</institution></funding-source><award-id>503/3-014-1/503-06-300</award-id><principal-award-recipient><name><surname>Głowacka</surname><given-names>Iwona E.</given-names></name></principal-award-recipient></award-group></funding-group><funding-group><award-group><funding-source><institution-wrap><institution-id institution-id-type="FundRef">http://dx.doi.org/10.13039/501100005888</institution-id><institution>Uniwersytet Medyczny w Lodzi (PL)</institution></institution-wrap></funding-source><award-id>502-03-/3-014-01/502-34-038</award-id><principal-award-recipient><name><surname>Rygielska-Tokarska</surname><given-names>Dorota</given-names></name></principal-award-recipient></award-group></funding-group><funding-group><award-group><funding-source><institution-wrap><institution-id institution-id-type="FundRef">http://dx.doi.org/10.13039/501100004040</institution-id><institution>KU Leuven</institution></institution-wrap></funding-source><award-id>GOA no. 10/014</award-id><principal-award-recipient><name><surname>Schols</surname><given-names>Dominique</given-names></name></principal-award-recipient></award-group></funding-group><custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name><meta-value>© Springer-Verlag Wien 2016</meta-value></custom-meta></custom-meta-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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