Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates
Identifieur interne : 000824 ( Main/Exploration ); précédent : 000823; suivant : 000825Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates
Auteurs : Iwona E. Głowacka ; Rafał Gulej ; Piotr Grzonkowski ; Graciela Andrei ; Dominique Schols ; Robert Snoeck ; Dorota G. PiotrowskaSource :
- Molecules [ 1420-3049 ] ; 2016.
Abstract
A novel series of diethyl {4-[(5-substituted-1,3-dioxo-1
Url:
DOI: 10.3390/molecules21111420
PubMed: 27792200
PubMed Central: 6273621
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates</title><author><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name><affiliation><nlm:aff id="af1-molecules-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</nlm:aff></affiliation></author><author><name sortKey="Gulej, Rafal" sort="Gulej, Rafal" uniqKey="Gulej R" first="Rafał" last="Gulej">Rafał Gulej</name><affiliation><nlm:aff id="af1-molecules-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</nlm:aff></affiliation></author><author><name sortKey="Grzonkowski, Piotr" sort="Grzonkowski, Piotr" uniqKey="Grzonkowski P" first="Piotr" last="Grzonkowski">Piotr Grzonkowski</name><affiliation><nlm:aff id="af1-molecules-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</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-21-01420">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-21-01420">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-21-01420">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="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-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">27792200</idno><idno type="pmc">6273621</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273621</idno><idno type="RBID">PMC:6273621</idno><idno type="doi">10.3390/molecules21111420</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000653</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000653</idno><idno type="wicri:Area/Pmc/Curation">000653</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000653</idno><idno type="wicri:Area/Pmc/Checkpoint">000237</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000237</idno><idno type="wicri:Area/Ncbi/Merge">000583</idno><idno type="wicri:Area/Ncbi/Curation">000583</idno><idno type="wicri:Area/Ncbi/Checkpoint">000583</idno><idno type="wicri:Area/Main/Merge">000826</idno><idno type="wicri:Area/Main/Curation">000824</idno><idno type="wicri:Area/Main/Exploration">000824</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates</title><author><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name><affiliation><nlm:aff id="af1-molecules-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</nlm:aff></affiliation></author><author><name sortKey="Gulej, Rafal" sort="Gulej, Rafal" uniqKey="Gulej R" first="Rafał" last="Gulej">Rafał Gulej</name><affiliation><nlm:aff id="af1-molecules-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</nlm:aff></affiliation></author><author><name sortKey="Grzonkowski, Piotr" sort="Grzonkowski, Piotr" uniqKey="Grzonkowski P" first="Piotr" last="Grzonkowski">Piotr Grzonkowski</name><affiliation><nlm:aff id="af1-molecules-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</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-21-01420">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-21-01420">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-21-01420">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="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-21-01420">Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>rafal.gulej@stud.umed.lodz.pl</email> (R.G.);<email>grzonkowskipiotr4@gmail.com</email> (P.G.);<email>dorota.piotrowska@umed.lodz.pl</email> (D.G.P.)</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 diethyl {4-[(5-substituted-1,3-dioxo-1<italic>H</italic>-benzo[<italic>de</italic>]isoquinolin-2(3<italic>H</italic>)-yl)-methyl]-1<italic>H</italic>-1,2,3-triazol-1-yl}alkylphosphonates designed as analogues of amonafide was synthesized. All phosphonates were assessed for antiviral activity against a broad range of DNA and RNA viruses and several of them showed potency against varicella-zoster virus (VZV) [EC<sub>50</sub> (50% effective concentration) = 27.6–91.5 μM]. Compound <bold>16b</bold> exhibited the highest activity against a thymidine kinase-deficient (TK<sup>−</sup>) VZV strain (EC<sub>50</sub> = 27.59 μM), while <bold>16d</bold> was the most potent towards TK<sup>+</sup> VZV (EC<sub>50</sub> = 29.91 μM). Cytostatic properties of the compounds <bold>14a</bold>–<bold>i</bold>–<bold>17a</bold>–<bold>i</bold> were studied on L1210, CEM, HeLa and HMEC-1 cell lines and most of them were slightly cytostatic for HeLa [IC<sub>50</sub> (50% inhibitory concentration) = 29–130 µM] and L1210 cells [IC<sub>50</sub> (50% inhibitory concentration) = 14–142 µM].</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Nagarajan, S" uniqKey="Nagarajan S">S. 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Głowacka</name><name sortKey="Grzonkowski, Piotr" sort="Grzonkowski, Piotr" uniqKey="Grzonkowski P" first="Piotr" last="Grzonkowski">Piotr Grzonkowski</name><name sortKey="Gulej, Rafal" sort="Gulej, Rafal" uniqKey="Gulej R" first="Rafał" last="Gulej">Rafał Gulej</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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