Isoxazolidine Conjugates of N3-Substituted 6-Bromoquinazolinones—Synthesis, Anti-Varizella-Zoster Virus, and Anti-Cytomegalovirus Activity
Identifieur interne : 000711 ( Main/Exploration ); précédent : 000710; suivant : 000712Isoxazolidine Conjugates of N3-Substituted 6-Bromoquinazolinones—Synthesis, Anti-Varizella-Zoster Virus, and Anti-Cytomegalovirus Activity
Auteurs : Magdalena Grabkowska-Dru Yc ; Graciela Andrei ; Dominique Schols ; Robert Snoeck ; Dorota G. PiotrowskaSource :
- Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry [ 1420-3049 ] ; 2018.
Abstract
1,3-Dipolar cycloaddition of
Url:
DOI: 10.3390/molecules23081889
PubMed: 30060562
PubMed Central: 6222691
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Isoxazolidine Conjugates of N3-Substituted 6-Bromoquinazolinones—Synthesis, Anti-Varizella-Zoster Virus, and Anti-Cytomegalovirus Activity</title><author><name sortKey="Grabkowska Dru Yc, Magdalena" sort="Grabkowska Dru Yc, Magdalena" uniqKey="Grabkowska Dru Yc M" first="Magdalena" last="Grabkowska-Dru Yc">Magdalena Grabkowska-Dru Yc</name><affiliation><nlm:aff id="af1-molecules-23-01889">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>magdalena.grabkowska-druzyc@umed.lodz.pl</email></nlm:aff></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation><nlm:aff id="af2-molecules-23-01889">Rega Institute for Medical Research, KU Leuven, Herestraat 49, B-3000 Leuven, Belgium;<email>Graciela.Andrei@rega.kleuven.be</email> (G.A.);<email>Dominique.Schols@rega.kleuven.be</email> (D.S.);<email>Robert.Snoeck@rega.kleuven.be</email> (R.S.)</nlm:aff></affiliation></author><author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><affiliation><nlm:aff id="af2-molecules-23-01889">Rega Institute for Medical Research, KU Leuven, Herestraat 49, B-3000 Leuven, Belgium;<email>Graciela.Andrei@rega.kleuven.be</email> (G.A.);<email>Dominique.Schols@rega.kleuven.be</email> (D.S.);<email>Robert.Snoeck@rega.kleuven.be</email> (R.S.)</nlm:aff></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation><nlm:aff id="af2-molecules-23-01889">Rega Institute for Medical Research, KU Leuven, Herestraat 49, B-3000 Leuven, Belgium;<email>Graciela.Andrei@rega.kleuven.be</email> (G.A.);<email>Dominique.Schols@rega.kleuven.be</email> (D.S.);<email>Robert.Snoeck@rega.kleuven.be</email> (R.S.)</nlm:aff></affiliation></author><author><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name><affiliation><nlm:aff id="af1-molecules-23-01889">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>magdalena.grabkowska-druzyc@umed.lodz.pl</email></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">30060562</idno><idno type="pmc">6222691</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222691</idno><idno type="RBID">PMC:6222691</idno><idno type="doi">10.3390/molecules23081889</idno><date when="2018">2018</date><idno type="wicri:Area/Pmc/Corpus">000648</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000648</idno><idno type="wicri:Area/Pmc/Curation">000648</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000648</idno><idno type="wicri:Area/Pmc/Checkpoint">000130</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000130</idno><idno type="wicri:Area/Ncbi/Merge">000718</idno><idno type="wicri:Area/Ncbi/Curation">000718</idno><idno type="wicri:Area/Ncbi/Checkpoint">000718</idno><idno type="wicri:Area/Main/Merge">000713</idno><idno type="wicri:Area/Main/Curation">000711</idno><idno type="wicri:Area/Main/Exploration">000711</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Isoxazolidine Conjugates of N3-Substituted 6-Bromoquinazolinones—Synthesis, Anti-Varizella-Zoster Virus, and Anti-Cytomegalovirus Activity</title><author><name sortKey="Grabkowska Dru Yc, Magdalena" sort="Grabkowska Dru Yc, Magdalena" uniqKey="Grabkowska Dru Yc M" first="Magdalena" last="Grabkowska-Dru Yc">Magdalena Grabkowska-Dru Yc</name><affiliation><nlm:aff id="af1-molecules-23-01889">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>magdalena.grabkowska-druzyc@umed.lodz.pl</email></nlm:aff></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation><nlm:aff id="af2-molecules-23-01889">Rega Institute for Medical Research, KU Leuven, Herestraat 49, B-3000 Leuven, Belgium;<email>Graciela.Andrei@rega.kleuven.be</email> (G.A.);<email>Dominique.Schols@rega.kleuven.be</email> (D.S.);<email>Robert.Snoeck@rega.kleuven.be</email> (R.S.)</nlm:aff></affiliation></author><author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><affiliation><nlm:aff id="af2-molecules-23-01889">Rega Institute for Medical Research, KU Leuven, Herestraat 49, B-3000 Leuven, Belgium;<email>Graciela.Andrei@rega.kleuven.be</email> (G.A.);<email>Dominique.Schols@rega.kleuven.be</email> (D.S.);<email>Robert.Snoeck@rega.kleuven.be</email> (R.S.)</nlm:aff></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation><nlm:aff id="af2-molecules-23-01889">Rega Institute for Medical Research, KU Leuven, Herestraat 49, B-3000 Leuven, Belgium;<email>Graciela.Andrei@rega.kleuven.be</email> (G.A.);<email>Dominique.Schols@rega.kleuven.be</email> (D.S.);<email>Robert.Snoeck@rega.kleuven.be</email> (R.S.)</nlm:aff></affiliation></author><author><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name><affiliation><nlm:aff id="af1-molecules-23-01889">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>magdalena.grabkowska-druzyc@umed.lodz.pl</email></nlm:aff></affiliation></author></analytic><series><title level="j">Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry</title><idno type="eISSN">1420-3049</idno><imprint><date when="2018">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>1,3-Dipolar cycloaddition of <italic>N</italic>-methyl <italic>C</italic>-(diethoxyphosphoryl) nitrone to N3-substituted 6-bromo-2-vinyl-3<italic>H</italic>-quinazolin-4-ones gave (3-diethoxyphosphoryl) isoxazolidines substituted at C5 with quinazolinones modified at N3. All isoxazolidine cycloadducts were screened for antiviral activity against a broad spectrum of DNA and RNA viruses. Several isoxazolidines inhibited the replication of both thymidine kinase wild-type and deficient (TK<sup>+</sup> and TK<sup>−</sup>) varicella-zoster virus strains at EC<sub>50</sub> in the 5.4–13.6 μΜ range, as well as human cytomegalovirus (EC<sub>50</sub> = 8.9–12.5 μΜ). Isoxazolidines <italic>trans</italic>-<bold>11b</bold>, <italic>trans</italic>-<bold>11c</bold>, <italic>trans</italic>-<bold>11e</bold>, <italic>trans</italic>-<bold>11f</bold>/<italic>cis</italic>-<bold>11f</bold>, <italic>trans</italic>-<bold>11g</bold>, <italic>trans</italic>-<bold>11h</bold>, and <italic>trans</italic>-<bold>11i</bold>/<italic>cis</italic>-<bold>11i</bold> exhibited moderate cytostatic activity towards the human lymphocyte cell line CEM (IC<sub>50</sub> = 9.6–17 μM).</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Konig, B" uniqKey="Konig B">B. König</name></author><author><name sortKey="Gr Tzei, M A" uniqKey="Gr Tzei M">M.A. Grätzei</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hollier, L M" uniqKey="Hollier L">L.M. Hollier</name></author><author><name sortKey="Grissom, H" uniqKey="Grissom H">H. 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Bergman</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list></list><tree><noCountry><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><name sortKey="Grabkowska Dru Yc, Magdalena" sort="Grabkowska Dru Yc, Magdalena" uniqKey="Grabkowska Dru Yc M" first="Magdalena" last="Grabkowska-Dru Yc">Magdalena Grabkowska-Dru Yc</name><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name><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></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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