Isoxazolidine Conjugates of N3-Substituted 6-Bromoquinazolinones—Synthesis, Anti-Varizella-Zoster Virus, and Anti-Cytomegalovirus Activity
Identifieur interne : 000E13 ( Main/Merge ); précédent : 000E12; suivant : 000E14Isoxazolidine 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
Links toward previous steps (curation, corpus...)
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PMC:6222691Le document en format XML
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<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>
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<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>
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<author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name>
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<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>
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<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>
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<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>
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<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>
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