New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity
Identifieur interne : 000563 ( Ncbi/Merge ); précédent : 000562; suivant : 000564New 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
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<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>
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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-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>
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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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(D.S.);<email>Robert.Snoeck@rega.kleuven.be</email>
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<author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name>
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(G.A.);<email>Dominique.Schols@rega.kleuven.be</email>
(D.S.);<email>Robert.Snoeck@rega.kleuven.be</email>
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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-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>
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<series><title level="j">Molecules</title>
<idno type="eISSN">1420-3049</idno>
<imprint><date when="2016">2016</date>
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<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. Bastlund</name>
</author>
<author><name sortKey="Gramowski Voss, A" uniqKey="Gramowski Voss A">A. Gramowski-Voss</name>
</author>
<author><name sortKey="Jensen, A A" uniqKey="Jensen A">A.A. Jensen</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Tyurenkov, I N" uniqKey="Tyurenkov I">I.N. Tyurenkov</name>
</author>
<author><name sortKey="Ozerov, A A" uniqKey="Ozerov A">A.A. Ozerov</name>
</author>
<author><name sortKey="Solodunova, E A" uniqKey="Solodunova E">E.A. Solodunova</name>
</author>
<author><name sortKey="Archakova, Y V" uniqKey="Archakova Y">Y.V. Archakova</name>
</author>
<author><name sortKey="Shmatova, E N" uniqKey="Shmatova E">E.N. Shmatova</name>
</author>
<author><name sortKey="Sampieva, K T" uniqKey="Sampieva K">K.T. Sampieva</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Kashaw, S K" uniqKey="Kashaw S">S.K. Kashaw</name>
</author>
<author><name sortKey="Gupta, V" uniqKey="Gupta V">V. Gupta</name>
</author>
<author><name sortKey="Kashaw, V" uniqKey="Kashaw V">V. Kashaw</name>
</author>
<author><name sortKey="Mishra, P" uniqKey="Mishra P">P. Mishra</name>
</author>
<author><name sortKey="Stables, J P" uniqKey="Stables J">J.P. Stables</name>
</author>
<author><name sortKey="Jain, N K" uniqKey="Jain N">N.K. Jain</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Chandregowda, V" uniqKey="Chandregowda V">V. Chandregowda</name>
</author>
<author><name sortKey="Kus, A K" uniqKey="Kus A">A.K. Kus</name>
</author>
<author><name sortKey="Chandrasekara Reddy, G" uniqKey="Chandrasekara Reddy G">G. Chandrasekara Reddy</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Abbas, S E" uniqKey="Abbas S">S.E. Abbas</name>
</author>
<author><name sortKey="Abdel Gawad, N M" uniqKey="Abdel Gawad N">N.M. Abdel Gawad</name>
</author>
<author><name sortKey="Georgey, H H" uniqKey="Georgey H">H.H. Georgey</name>
</author>
<author><name sortKey="Abdullah, J H" uniqKey="Abdullah J">J.H. Abdullah</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Noolvi, M N" uniqKey="Noolvi M">M.N. Noolvi</name>
</author>
<author><name sortKey="Patel, H M" uniqKey="Patel H">H.M. Patel</name>
</author>
<author><name sortKey="Bhardwaj, V" uniqKey="Bhardwaj V">V. Bhardwaj</name>
</author>
<author><name sortKey="Chauhan, A" uniqKey="Chauhan A">A. Chauhan</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Ahmed, M F" uniqKey="Ahmed M">M.F. Ahmed</name>
</author>
<author><name sortKey="Youns, M" uniqKey="Youns M">M. Youns</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Gupta, V D" uniqKey="Gupta V">V.D. Gupta</name>
</author>
<author><name sortKey="Singh, J" uniqKey="Singh J">J. Singh</name>
</author>
<author><name sortKey="Kinger, M" uniqKey="Kinger M">M. Kinger</name>
</author>
<author><name sortKey="Arora, A K" uniqKey="Arora A">A.K. Arora</name>
</author>
<author><name sortKey="Jaswal, V S" uniqKey="Jaswal V">V.S. Jaswal</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Chen, M" uniqKey="Chen M">M. Chen</name>
</author>
<author><name sortKey="Li, P" uniqKey="Li P">P. Li</name>
</author>
<author><name sortKey="Hu, D" uniqKey="Hu D">D. Hu</name>
</author>
<author><name sortKey="Zeng, S" uniqKey="Zeng S">S. Zeng</name>
</author>
<author><name sortKey="Li, T" uniqKey="Li T">T. Li</name>
</author>
<author><name sortKey="Jin, L" uniqKey="Jin L">L. Jin</name>
</author>
<author><name sortKey="Xue, W" uniqKey="Xue W">W. Xue</name>
</author>
<author><name sortKey="Song, B" uniqKey="Song B">B. Song</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Long, C" uniqKey="Long C">C. Long</name>
</author>
<author><name sortKey="Li, P" uniqKey="Li P">P. Li</name>
</author>
<author><name sortKey="Chen, M" uniqKey="Chen M">M. Chen</name>
</author>
<author><name sortKey="Dong, L" uniqKey="Dong L">L. Dong</name>
</author>
<author><name sortKey="Hu, D" uniqKey="Hu D">D. Hu</name>
</author>
<author><name sortKey="Song, B" uniqKey="Song B">B. Song</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Kumar, K S" uniqKey="Kumar K">K.S. Kumar</name>
</author>
<author><name sortKey="Swastika, G" uniqKey="Swastika G">G. Swastika</name>
</author>
<author><name sortKey="Ravichandran, V" uniqKey="Ravichandran V">V. Ravichandran</name>
</author>
<author><name sortKey="Pandy, V" uniqKey="Pandy V">V. Pandy</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Schroeder, C E" uniqKey="Schroeder C">C.E. Schroeder</name>
</author>
<author><name sortKey="Yao, T" uniqKey="Yao T">T. Yao</name>
</author>
<author><name sortKey="Sotsky, J" uniqKey="Sotsky J">J. Sotsky</name>
</author>
<author><name sortKey="Smith, R A" uniqKey="Smith R">R.A. Smith</name>
</author>
<author><name sortKey="Roy, S" uniqKey="Roy S">S. Roy</name>
</author>
<author><name sortKey="Chu, Y K" uniqKey="Chu Y">Y.-K. Chu</name>
</author>
<author><name sortKey="Guo, H" uniqKey="Guo H">H. Guo</name>
</author>
<author><name sortKey="Tower, N A" uniqKey="Tower N">N.A. Tower</name>
</author>
<author><name sortKey="Noah, T J W" uniqKey="Noah T">T.J.W. Noah</name>
</author>
<author><name sortKey="Mckellip, S" uniqKey="Mckellip S">S. McKellip</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Rohini, R" uniqKey="Rohini R">R. Rohini</name>
</author>
<author><name sortKey="Reddy, P M" uniqKey="Reddy P">P.M. Reddy</name>
</author>
<author><name sortKey="Shanker, K" uniqKey="Shanker K">K. Shanker</name>
</author>
<author><name sortKey="Hu, A" uniqKey="Hu A">A. Hu</name>
</author>
<author><name sortKey="Ravinder, V" uniqKey="Ravinder V">V. Ravinder</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Raju, G N" uniqKey="Raju G">G.N. Raju</name>
</author>
<author><name sortKey="Sai, K B" uniqKey="Sai K">K.B. Sai</name>
</author>
<author><name sortKey="Resshma, V" uniqKey="Resshma V">V. Resshma</name>
</author>
<author><name sortKey="Sudarshini, N" uniqKey="Sudarshini N">N. Sudarshini</name>
</author>
<author><name sortKey="Sowmya, P L" uniqKey="Sowmya P">P.L. Sowmya</name>
</author>
<author><name sortKey="Nalini, Y" uniqKey="Nalini Y">Y. Nalini</name>
</author>
<author><name sortKey="Nadendla, R R" uniqKey="Nadendla R">R.R. Nadendla</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Rakesh, K P" uniqKey="Rakesh K">K.P. Rakesh</name>
</author>
<author><name sortKey="Ramesh, S" uniqKey="Ramesh S">S. Ramesh</name>
</author>
<author><name sortKey="Kumar, H M M" uniqKey="Kumar H">H.M.M. Kumar</name>
</author>
<author><name sortKey="Chandan, S" uniqKey="Chandan S">S. Chandan</name>
</author>
<author><name sortKey="Gowda, D C" uniqKey="Gowda D">D.C. Gowda</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Kumar, R" uniqKey="Kumar R">R. Kumar</name>
</author>
<author><name sortKey="Shukla, R K" uniqKey="Shukla R">R.K. Shukla</name>
</author>
<author><name sortKey="Shukla, A" uniqKey="Shukla A">A. Shukla</name>
</author>
<author><name sortKey="Tyagi, N" uniqKey="Tyagi N">N. Tyagi</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Serya, R A T" uniqKey="Serya R">R.A.T. Serya</name>
</author>
<author><name sortKey="Abbas, A H" uniqKey="Abbas A">A.H. Abbas</name>
</author>
<author><name sortKey="Ismail, N S M" uniqKey="Ismail N">N.S.M. Ismail</name>
</author>
<author><name sortKey="Esmat, A" uniqKey="Esmat A">A. Esmat</name>
</author>
<author><name sortKey="Abou El Ella, D A" uniqKey="Abou El Ella D">D.A. Abou El Ella</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Rakesh, K P" uniqKey="Rakesh K">K.P. Rakesh</name>
</author>
<author><name sortKey="Manukumar, H M" uniqKey="Manukumar H">H.M. Manukumar</name>
</author>
<author><name sortKey="Gowda, D C" uniqKey="Gowda D">D.C. Gowda</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Kumar, D" uniqKey="Kumar D">D. Kumar</name>
</author>
<author><name sortKey="Lal, R" uniqKey="Lal R">R. Lal</name>
</author>
<author><name sortKey="Rani, S" uniqKey="Rani S">S. Rani</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Pines, M" uniqKey="Pines M">M. Pines</name>
</author>
<author><name sortKey="Spector, I" uniqKey="Spector I">I. Spector</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Marzaro, G" uniqKey="Marzaro G">G. Marzaro</name>
</author>
<author><name sortKey="Castagliuolo, I" uniqKey="Castagliuolo I">I. Castagliuolo</name>
</author>
<author><name sortKey="Schirato, G" uniqKey="Schirato G">G. Schirato</name>
</author>
<author><name sortKey="Palu, G" uniqKey="Palu G">G. Palu</name>
</author>
<author><name sortKey="Dalla Via, M" uniqKey="Dalla Via M">M. Dalla Via</name>
</author>
<author><name sortKey="Chilin, A" uniqKey="Chilin A">A. Chilin</name>
</author>
<author><name sortKey="Brun, P" uniqKey="Brun P">P. Brun</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Ghosh, S K" uniqKey="Ghosh S">S.K. Ghosh</name>
</author>
<author><name sortKey="Nagarajan, R" uniqKey="Nagarajan R">R. Nagarajan</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Asif, M" uniqKey="Asif M">M. Asif</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Chawla, A" uniqKey="Chawla A">A. Chawla</name>
</author>
<author><name sortKey="Batra, C" uniqKey="Batra C">C. Batra</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Rajput, R" uniqKey="Rajput R">R. Rajput</name>
</author>
<author><name sortKey="Mishra, A P" uniqKey="Mishra A">A.P. Mishra</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Rajput, R" uniqKey="Rajput R">R. Rajput</name>
</author>
<author><name sortKey="Mishra, A P" uniqKey="Mishra A">A.P. Mishra</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Arora, R" uniqKey="Arora R">R. Arora</name>
</author>
<author><name sortKey="Kappor, A" uniqKey="Kappor A">A. Kappor</name>
</author>
<author><name sortKey="Gill, N S" uniqKey="Gill N">N.S. Gill</name>
</author>
<author><name sortKey="Rana, A C" uniqKey="Rana A">A.C. Rana</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Selvam, T" uniqKey="Selvam T">T. Selvam</name>
</author>
<author><name sortKey="Kumar, P V" uniqKey="Kumar P">P.V. Kumar</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Vogtle, M M" uniqKey="Vogtle M">M.M. Vogtle</name>
</author>
<author><name sortKey="Marzinzik, A L" uniqKey="Marzinzik A">A.L. Marzinzik</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Shen, S" uniqKey="Shen S">S. Shen</name>
</author>
<author><name sortKey="Li, W" uniqKey="Li W">W. Li</name>
</author>
<author><name sortKey="Wang, J" uniqKey="Wang J">J. Wang</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="An, C Y" uniqKey="An C">C.-Y. An</name>
</author>
<author><name sortKey="Li, X M" uniqKey="Li X">X.-M. Li</name>
</author>
<author><name sortKey="Li, C S" uniqKey="Li C">C.-S. Li</name>
</author>
<author><name sortKey="Gao, S S" uniqKey="Gao S">S.-S. Gao</name>
</author>
<author><name sortKey="Shang, Z" uniqKey="Shang Z">Z. Shang</name>
</author>
<author><name sortKey="Wang, B G" uniqKey="Wang B">B.-G. Wang</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Li, C S" uniqKey="Li C">C.-S. Li</name>
</author>
<author><name sortKey="An, C Y" uniqKey="An C">C.-Y. An</name>
</author>
<author><name sortKey="Li, X M" uniqKey="Li X">X.-M. Li</name>
</author>
<author><name sortKey="Gao, S S" uniqKey="Gao S">S.-S. Gao</name>
</author>
<author><name sortKey="Cui, C M" uniqKey="Cui C">C.-M. Cui</name>
</author>
<author><name sortKey="Sun, H F" uniqKey="Sun H">H.-F. Sun</name>
</author>
<author><name sortKey="Wang, B G" uniqKey="Wang B">B.-G. Wang</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Kornsakulkarn, J" uniqKey="Kornsakulkarn J">J. Kornsakulkarn</name>
</author>
<author><name sortKey="Saepua, S" uniqKey="Saepua S">S. Saepua</name>
</author>
<author><name sortKey="Srijomthong, K" uniqKey="Srijomthong K">K. Srijomthong</name>
</author>
<author><name sortKey="Rachtawee, P" uniqKey="Rachtawee P">P. Rachtawee</name>
</author>
<author><name sortKey="Thongpanchang, C" uniqKey="Thongpanchang C">C. Thongpanchang</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Liu, S" uniqKey="Liu S">S. Liu</name>
</author>
<author><name sortKey="Wang, W" uniqKey="Wang W">W. Wang</name>
</author>
<author><name sortKey="Jiang, L" uniqKey="Jiang L">L. Jiang</name>
</author>
<author><name sortKey="Wan, S" uniqKey="Wan S">S. Wan</name>
</author>
<author><name sortKey="Zhang, L" uniqKey="Zhang L">L. Zhang</name>
</author>
<author><name sortKey="Yu, R" uniqKey="Yu R">R. Yu</name>
</author>
<author><name sortKey="Jiang, T" uniqKey="Jiang T">T. Jiang</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Ahmed, M F" uniqKey="Ahmed M">M.F. Ahmed</name>
</author>
<author><name sortKey="Belal, A" uniqKey="Belal A">A. Belal</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Piotrowska, D G" uniqKey="Piotrowska D">D.G. Piotrowska</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Witt, A" uniqKey="Witt A">A. Witt</name>
</author>
<author><name sortKey="Bergman, J" uniqKey="Bergman J">J. Bergman</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Makhloufi, A" uniqKey="Makhloufi A">A. Makhloufi</name>
</author>
<author><name sortKey="Wahl, M" uniqKey="Wahl M">M. Wahl</name>
</author>
<author><name sortKey="Frank, W" uniqKey="Frank W">W. Frank</name>
</author>
<author><name sortKey="Ganter, C" uniqKey="Ganter C">C. Ganter</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Piotrowska, D G" uniqKey="Piotrowska D">D.G. Piotrowska</name>
</author>
<author><name sortKey="Cieslak, M" uniqKey="Cieslak M">M. Cieslak</name>
</author>
<author><name sortKey="Krolewska, K" uniqKey="Krolewska K">K. Krolewska</name>
</author>
<author><name sortKey="Wr Blewski, A E" uniqKey="Wr Blewski A">A.E. Wróblewski</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Grabkowska Dru Yc, M" uniqKey="Grabkowska Dru Yc M">M. Grabkowska-Drużyc</name>
</author>
<author><name sortKey="Balzarini, J" uniqKey="Balzarini J">J. Balzarini</name>
</author>
<author><name sortKey="Piotrowska, D G" uniqKey="Piotrowska D">D.G. Piotrowska</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Karplus, M" uniqKey="Karplus M">M. Karplus</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Benezra, C" uniqKey="Benezra C">C. Benezra</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Neeser, J R" uniqKey="Neeser J">J.-R. Neeser</name>
</author>
<author><name sortKey="Tronchet, J M J" uniqKey="Tronchet J">J.M.J. Tronchet</name>
</author>
<author><name sortKey="Charollais, E J" uniqKey="Charollais E">E.J. Charollais</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Adiwidjaja, G" uniqKey="Adiwidjaja G">G. Adiwidjaja</name>
</author>
<author><name sortKey="Meyer, B" uniqKey="Meyer B">B. Meyer</name>
</author>
<author><name sortKey="Thiem, J" uniqKey="Thiem J">J. Thiem</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Buchanan, G W" uniqKey="Buchanan G">G.W. Buchanan</name>
</author>
<author><name sortKey="Bourque, K" uniqKey="Bourque K">K. Bourque</name>
</author>
<author><name sortKey="Seeley, A" uniqKey="Seeley A">A. Seeley</name>
</author>
</analytic>
</biblStruct>
<biblStruct><analytic><author><name sortKey="Hayato, N" uniqKey="Hayato N">N. Hayato</name>
</author>
<author><name sortKey="Noriki, K" uniqKey="Noriki K">K. Noriki</name>
</author>
<author><name sortKey="Takao, S" uniqKey="Takao S">S. Takao</name>
</author>
</analytic>
</biblStruct>
</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Molecules</journal-id>
<journal-id journal-id-type="iso-abbrev">Molecules</journal-id>
<journal-id journal-id-type="publisher-id">molecules</journal-id>
<journal-title-group><journal-title>Molecules</journal-title>
</journal-title-group>
<issn pub-type="epub">1420-3049</issn>
<publisher><publisher-name>MDPI</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">27455228</article-id>
<article-id pub-id-type="pmc">6273226</article-id>
<article-id pub-id-type="doi">10.3390/molecules21070959</article-id>
<article-id pub-id-type="publisher-id">molecules-21-00959</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
</subj-group>
</article-categories>
<title-group><article-title>New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Piotrowska</surname>
<given-names>Dorota G.</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-21-00959">1</xref>
<xref rid="c1-molecules-21-00959" ref-type="corresp">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Andrei</surname>
<given-names>Graciela</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-21-00959">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Schols</surname>
<given-names>Dominique</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-21-00959">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Snoeck</surname>
<given-names>Robert</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-21-00959">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Grabkowska-Drużyc</surname>
<given-names>Magdalena</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-21-00959">1</xref>
</contrib>
</contrib-group>
<contrib-group><contrib contrib-type="editor"><name><surname>McPhee</surname>
<given-names>Derek J.</given-names>
</name>
<role>Academic Editor</role>
</contrib>
</contrib-group>
<aff id="af1-molecules-21-00959"><label>1</label>
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland;<email>magdalena.grabkowska-druzyc@umed.lodz.pl</email>
</aff>
<aff id="af2-molecules-21-00959"><label>2</label>
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.)</aff>
<author-notes><corresp id="c1-molecules-21-00959"><label>*</label>
Correspondence: <email>dorota.piotrowska@umed.lodz.pl</email>
; Tel.: +48-42-677-92-35; Fax: +48-42-678-83-98</corresp>
</author-notes>
<pub-date pub-type="epub"><day>22</day>
<month>7</month>
<year>2016</year>
</pub-date>
<pub-date pub-type="collection"><month>7</month>
<year>2016</year>
</pub-date>
<volume>21</volume>
<issue>7</issue>
<elocation-id>959</elocation-id>
<history><date date-type="received"><day>16</day>
<month>6</month>
<year>2016</year>
</date>
<date date-type="accepted"><day>19</day>
<month>7</month>
<year>2016</year>
</date>
</history>
<permissions><copyright-statement>© 2016 by the authors.</copyright-statement>
<copyright-year>2016</copyright-year>
<license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>
).</license-p>
</license>
</permissions>
<abstract><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>
</abstract>
<kwd-group><kwd>phosphonate</kwd>
<kwd>isoxazolidine</kwd>
<kwd>quinazolinones</kwd>
<kwd>antiviral</kwd>
<kwd>cytostatic</kwd>
</kwd-group>
</article-meta>
</front>
</pmc>
<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>
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