New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity
Identifieur interne : 000841 ( Main/Exploration ); précédent : 000840; suivant : 000842New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity
Auteurs : Dorota G. Piotrowska ; Graciela Andrei ; Dominique Schols ; Robert Snoeck ; Magdalena Grabkowska-Dru YcSource :
- Molecules [ 1420-3049 ] ; 2016.
Abstract
A novel series of (3-diethoxyphosphoryl)isoxazolidines substituted at C5 with various quinazolinones have been synthesized by the 1,3-dipolar cycloaddition of
Url:
DOI: 10.3390/molecules21070959
PubMed: 27455228
PubMed Central: 6273226
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity</title><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-21-00959">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-21-00959">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 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-21-00959">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 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-21-00959">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 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="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-21-00959">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">27455228</idno><idno type="pmc">6273226</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273226</idno><idno type="RBID">PMC:6273226</idno><idno type="doi">10.3390/molecules21070959</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000652</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000652</idno><idno type="wicri:Area/Pmc/Curation">000652</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000652</idno><idno type="wicri:Area/Pmc/Checkpoint">000251</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000251</idno><idno type="wicri:Area/Ncbi/Merge">000563</idno><idno type="wicri:Area/Ncbi/Curation">000563</idno><idno type="wicri:Area/Ncbi/Checkpoint">000563</idno><idno type="wicri:Area/Main/Merge">000843</idno><idno type="wicri:Area/Main/Curation">000841</idno><idno type="wicri:Area/Main/Exploration">000841</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity</title><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-21-00959">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-21-00959">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 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-21-00959">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 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-21-00959">Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 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="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-21-00959">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</title><idno type="eISSN">1420-3049</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>A novel series of (3-diethoxyphosphoryl)isoxazolidines substituted at C5 with various quinazolinones have been synthesized by the 1,3-dipolar cycloaddition of <italic>N</italic>-methyl-C-(diethoxyphosphoryl)nitrone with <italic>N</italic>3-substitued 2-vinyl-3<italic>H</italic>-quinazolin-4-ones. All isoxazolidines were assessed for antiviral activity against a broad range of DNA and RNA viruses. Isoxazolidines <italic>trans</italic>-<bold>11f</bold>/<italic>cis</italic>-<bold>11f</bold> (90:10), <italic>trans</italic>-<bold>11h</bold> and <italic>trans</italic>-<bold>11i</bold>/<italic>cis</italic>-<bold>11i</bold> (97:3) showed weak activity (EC<sub>50</sub> = 6.84, 15.29 and 9.44 μM) toward VZV (TK<sup>+</sup> strain) which was only one order of magnitude lower than that of acyclovir used as a reference drug. Phosphonates <italic>trans</italic>-<bold>11b</bold>/<italic>cis</italic>-<bold>11b</bold> (90:10), <italic>trans</italic>-<bold>11c</bold>, <italic>trans</italic>-<bold>11e</bold>/<italic>cis</italic>-<bold>11e</bold> (90:10) and <italic>trans</italic>-<bold>11g</bold> appeared slightly active toward cytomegalovirus (EC<sub>50</sub> = 27–45 μM). Compounds containing benzyl substituents at N3 in the quinazolinone skeleton exhibited slight antiproliferative activity towards the tested immortalized cells with IC<sub>50</sub> in the 21–102 μM range.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Hammer, H" uniqKey="Hammer H">H. Hammer</name></author><author><name sortKey="Bader, B M" uniqKey="Bader B">B.M. Bader</name></author><author><name sortKey="Ehnert, C" uniqKey="Ehnert C">C. Ehnert</name></author><author><name sortKey="Bundgaard, C" uniqKey="Bundgaard C">C. Bundgaard</name></author><author><name sortKey="Bunch, L" uniqKey="Bunch L">L. Bunch</name></author><author><name sortKey="Hoestgaard Jensen, K" uniqKey="Hoestgaard Jensen K">K. Hoestgaard-Jensen</name></author><author><name sortKey="Schroeder, O H U" uniqKey="Schroeder O">O.H.-U. Schroeder</name></author><author><name sortKey="Bastlund, J F" uniqKey="Bastlund J">J.F. 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Takao</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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