Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations
Identifieur interne : 001411 ( Main/Exploration ); précédent : 001410; suivant : 001412Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations
Auteurs : Davorka Završnik ; Samija Muratovi ; Damjan Makuc [Slovénie] ; Janez Plavec [Slovénie] ; Mario Cetina [Croatie] ; Ante Nagl [Croatie] ; Erik De Clercq [Belgique] ; Jan Balzarini [Belgique] ; Mladen Mintas [Croatie]Source :
- Molecules [ 1420-3049 ] ; 2011.
Abstract
We report on the synthesis of 4-hydroxycoumarin dimers
Url:
DOI: 10.3390/molecules16076023
PubMed: 21772234
PubMed Central: 6264767
Affiliations:
- Belgique, Croatie, Slovénie
- Province du Brabant flamand, Région flamande
- Louvain
- Katholieke Universiteit Leuven
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, <sup>1</sup>H/<sup>13</sup>C-NMR Conformational and X-ray Crystal Structure Studies and <italic>In Vitro</italic> Antiviral Activity Evaluations</title><author><name sortKey="Zavrsnik, Davorka" sort="Zavrsnik, Davorka" uniqKey="Zavrsnik D" first="Davorka" last="Završnik">Davorka Završnik</name><affiliation><nlm:aff id="af1-molecules-16-06023">Faculty of Pharmacy, University of Sarajevo, Čekaluša 90, Sarajevo BA-71000, Bosnia and Hercegovina</nlm:aff><wicri:noCountry code="subfield">Bosnia and Hercegovina</wicri:noCountry></affiliation></author><author><name sortKey="Muratovi, Samija" sort="Muratovi, Samija" uniqKey="Muratovi S" first="Samija" last="Muratovi">Samija Muratovi</name><affiliation><nlm:aff id="af1-molecules-16-06023">Faculty of Pharmacy, University of Sarajevo, Čekaluša 90, Sarajevo BA-71000, Bosnia and Hercegovina</nlm:aff><wicri:noCountry code="subfield">Bosnia and Hercegovina</wicri:noCountry></affiliation></author><author><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name><affiliation wicri:level="1"><nlm:aff id="af2-molecules-16-06023">Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-molecules-16-06023">EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation></author><author><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name><affiliation wicri:level="1"><nlm:aff id="af2-molecules-16-06023">Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-molecules-16-06023">EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af4-molecules-16-06023">Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva cesta 5, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva cesta 5, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation></author><author><name sortKey="Cetina, Mario" sort="Cetina, Mario" uniqKey="Cetina M" first="Mario" last="Cetina">Mario Cetina</name><affiliation wicri:level="1"><nlm:aff id="af5-molecules-16-06023">Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000, Croatia</nlm:aff><country xml:lang="fr">Croatie</country><wicri:regionArea>Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000</wicri:regionArea><wicri:noRegion>Zagreb HR-10000</wicri:noRegion></affiliation></author><author><name sortKey="Nagl, Ante" sort="Nagl, Ante" uniqKey="Nagl A" first="Ante" last="Nagl">Ante Nagl</name><affiliation wicri:level="1"><nlm:aff id="af5-molecules-16-06023">Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000, Croatia</nlm:aff><country xml:lang="fr">Croatie</country><wicri:regionArea>Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000</wicri:regionArea><wicri:noRegion>Zagreb HR-10000</wicri:noRegion></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="4"><nlm:aff id="af6-molecules-16-06023">Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="4"><nlm:aff id="af6-molecules-16-06023">Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author><author><name sortKey="Mintas, Mladen" sort="Mintas, Mladen" uniqKey="Mintas M" first="Mladen" last="Mintas">Mladen Mintas</name><affiliation wicri:level="1"><nlm:aff id="af7-molecules-16-06023">Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, Zagreb HR-10000, Croatia</nlm:aff><country xml:lang="fr">Croatie</country><wicri:regionArea>Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, Zagreb HR-10000</wicri:regionArea><wicri:noRegion>Zagreb HR-10000</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21772234</idno><idno type="pmc">6264767</idno><idno 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type="main">Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, <sup>1</sup>H/<sup>13</sup>C-NMR Conformational and X-ray Crystal Structure Studies and <italic>In Vitro</italic> Antiviral Activity Evaluations</title><author><name sortKey="Zavrsnik, Davorka" sort="Zavrsnik, Davorka" uniqKey="Zavrsnik D" first="Davorka" last="Završnik">Davorka Završnik</name><affiliation><nlm:aff id="af1-molecules-16-06023">Faculty of Pharmacy, University of Sarajevo, Čekaluša 90, Sarajevo BA-71000, Bosnia and Hercegovina</nlm:aff><wicri:noCountry code="subfield">Bosnia and Hercegovina</wicri:noCountry></affiliation></author><author><name sortKey="Muratovi, Samija" sort="Muratovi, Samija" uniqKey="Muratovi S" first="Samija" last="Muratovi">Samija Muratovi</name><affiliation><nlm:aff id="af1-molecules-16-06023">Faculty of Pharmacy, University of Sarajevo, Čekaluša 90, Sarajevo BA-71000, Bosnia and Hercegovina</nlm:aff><wicri:noCountry code="subfield">Bosnia and Hercegovina</wicri:noCountry></affiliation></author><author><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name><affiliation wicri:level="1"><nlm:aff id="af2-molecules-16-06023">Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-molecules-16-06023">EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation></author><author><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name><affiliation wicri:level="1"><nlm:aff id="af2-molecules-16-06023">Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-molecules-16-06023">EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af4-molecules-16-06023">Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva cesta 5, Ljubljana SI-1000, Slovenia</nlm:aff><country xml:lang="fr">Slovénie</country><wicri:regionArea>Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva cesta 5, Ljubljana SI-1000</wicri:regionArea><wicri:noRegion>Ljubljana SI-1000</wicri:noRegion></affiliation></author><author><name sortKey="Cetina, Mario" sort="Cetina, Mario" uniqKey="Cetina M" first="Mario" last="Cetina">Mario Cetina</name><affiliation wicri:level="1"><nlm:aff id="af5-molecules-16-06023">Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000, Croatia</nlm:aff><country xml:lang="fr">Croatie</country><wicri:regionArea>Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000</wicri:regionArea><wicri:noRegion>Zagreb HR-10000</wicri:noRegion></affiliation></author><author><name sortKey="Nagl, Ante" sort="Nagl, Ante" uniqKey="Nagl A" first="Ante" last="Nagl">Ante Nagl</name><affiliation wicri:level="1"><nlm:aff id="af5-molecules-16-06023">Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000, Croatia</nlm:aff><country xml:lang="fr">Croatie</country><wicri:regionArea>Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000</wicri:regionArea><wicri:noRegion>Zagreb HR-10000</wicri:noRegion></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="4"><nlm:aff id="af6-molecules-16-06023">Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="4"><nlm:aff id="af6-molecules-16-06023">Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author><author><name sortKey="Mintas, Mladen" sort="Mintas, Mladen" uniqKey="Mintas M" first="Mladen" last="Mintas">Mladen Mintas</name><affiliation wicri:level="1"><nlm:aff id="af7-molecules-16-06023">Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, Zagreb HR-10000, Croatia</nlm:aff><country xml:lang="fr">Croatie</country><wicri:regionArea>Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, Zagreb HR-10000</wicri:regionArea><wicri:noRegion>Zagreb HR-10000</wicri:noRegion></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2011">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>We report on the synthesis of 4-hydroxycoumarin dimers <bold>1</bold>–<bold>15</bold> bearing an aryl substituent on the central linker and fused benzopyranocoumarin derivatives <bold>16</bold>–<bold>20</bold> and on their <italic>in vitro</italic> broad anti-DNA and RNA virus activity evaluations. The chemical identities and structure of compounds <bold>1</bold>–<bold>20</bold> were deduced from their homo- and heteronuclear NMR measurements whereas the conformational properties of <bold>5</bold>, <bold>14</bold> and <bold>20</bold> were assessed by the use of 1D difference NOE enhancements. Unequivocal proof of the stereostructure of compounds <bold>7</bold>, <bold>9</bold>, <bold>16</bold> and <bold>18</bold> was obtained by single crystal X-ray diffraction method. The X-ray crystal structure analysis revealed that two 4-hydroxycoumarin moieties in the 4-trifluoromethylphenyl- and 2-nitrophenyl derivatives (compounds <bold>7</bold> and <bold>9</bold>, respectively) are intramolecularly hydrogen-bonded between hydroxyl and carbonyl oxygen atoms. Consequently, the compounds <bold>7</bold> and <bold>9</bold> adopt conformations in which two 4-hydroxy-coumarin moieties are <italic>anti</italic>-disposed. Antiviral activity evaluation results indicated that the 4-bromobenzylidene derivative of bis-(4-hydroxycoumarin) (compound <bold>3</bold>) possesses inhibitory activity against HSV-1 (KOS), HSV-2 (G), vaccinia virus and HSV-1 TK<sup>-</sup> KOS (ACV<sup>r</sup>) at a concentration of 9–12 μM and at a minimum cytotoxic concentration (MCC) greater than 20 μM. Compounds <bold>4</bold>–<bold>6</bold>, <bold>8</bold>, and <bold>20</bold> were active against feline herpes virus (50% effective concentration, EC<sub>50</sub> = 5–8.1 μM), that is at a 4-7-fold lower concentration than the MCC.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Weinmann, I" uniqKey="Weinmann I">I. Weinmann</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Marcu, M G" uniqKey="Marcu M">M.G. Marcu</name></author><author><name sortKey="Schulte, W T" uniqKey="Schulte W">W.T. Schulte</name></author><author><name sortKey="Neckers, L" uniqKey="Neckers L">L. Neckers</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Borges, F" uniqKey="Borges F">F. Borges</name></author><author><name sortKey="Roleira, F" uniqKey="Roleira F">F. Roleira</name></author><author><name sortKey="Milhazes, N" uniqKey="Milhazes N">N. Milhazes</name></author><author><name sortKey="Santana, L" uniqKey="Santana L">L. Santana</name></author><author><name sortKey="Uriarte, E" uniqKey="Uriarte E">E. Uriarte</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chiang, C C" uniqKey="Chiang C">C.C. Chiang</name></author><author><name sortKey="Hsu, L Y" uniqKey="Hsu L">L.Y. Hsu</name></author><author><name sortKey="Tsai, H J" uniqKey="Tsai H">H.J. Tsai</name></author><author><name sortKey="Yao, C W" uniqKey="Yao C">C.W. Yao</name></author><author><name sortKey="Chang, T C" uniqKey="Chang T">T.C. Chang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey=" Avar, S" uniqKey=" Avar S">S. Ćavar</name></author><author><name sortKey="Kova, F" uniqKey="Kova F">F. Kovač</name></author><author><name sortKey="Maksimovi, M" uniqKey="Maksimovi M">M. Maksimović</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Jung, J C" uniqKey="Jung J">J.C. Jung</name></author><author><name sortKey="Park, O S" uniqKey="Park O">O.S. Park</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Symeonidis, T" uniqKey="Symeonidis T">T. Symeonidis</name></author><author><name sortKey="Chamilos, M" uniqKey="Chamilos M">M. Chamilos</name></author><author><name sortKey="Hadjipavlou Litina, D J" uniqKey="Hadjipavlou Litina D">D.J. Hadjipavlou-Litina</name></author><author><name sortKey="Kallitsakis, M" uniqKey="Kallitsakis M">M. Kallitsakis</name></author><author><name sortKey="Litinas, K E" uniqKey="Litinas K">K.E. Litinas</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kostova, I" uniqKey="Kostova I">I. Kostova</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Nolan, A K" uniqKey="Nolan A">A.K. Nolan</name></author><author><name sortKey="Doncaster, R J" uniqKey="Doncaster R">R.J. Doncaster</name></author><author><name sortKey="Dunstan, S M" uniqKey="Dunstan S">S.M. Dunstan</name></author><author><name sortKey="Scot, A K" uniqKey="Scot A">A.K. Scot</name></author><author><name sortKey="Frenkel, D" uniqKey="Frenkel D">D. Frenkel</name></author><author><name sortKey="Siegel, D" uniqKey="Siegel D">D. Siegel</name></author><author><name sortKey="Ross, D" uniqKey="Ross D">D. Ross</name></author><author><name sortKey="Barnes, J" uniqKey="Barnes J">J. Barnes</name></author><author><name sortKey="Levy, C" uniqKey="Levy C">C. Levy</name></author><author><name sortKey="Leys, D" uniqKey="Leys D">D. Leys</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Mahajan, D H" uniqKey="Mahajan D">D.H. Mahajan</name></author><author><name sortKey="Pannecouque, C" uniqKey="Pannecouque C">C. Pannecouque</name></author><author><name sortKey="De Clercq, E" uniqKey="De Clercq E">E. De Clercq</name></author><author><name sortKey="Chikhalia, K H" uniqKey="Chikhalia K">K.H. Chikhalia</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Zhao, H" uniqKey="Zhao H">H. Zhao</name></author><author><name sortKey="Neamati, N" uniqKey="Neamati N">N. Neamati</name></author><author><name sortKey="Hong, H" uniqKey="Hong H">H. Hong</name></author><author><name sortKey="Mazumder, A" uniqKey="Mazumder A">A. Mazumder</name></author><author><name sortKey="Wang, S" uniqKey="Wang S">S. Wang</name></author><author><name sortKey="Sunder, S" uniqKey="Sunder S">S. Sunder</name></author><author><name sortKey="Milne George, W A" uniqKey="Milne George W">W.A. Milne George</name></author><author><name sortKey="Pommier, Y" uniqKey="Pommier Y">Y. Pommier</name></author><author><name sortKey="Burke, T R" uniqKey="Burke T">T.R. Burke</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Francois, K O" uniqKey="Francois K">K.O. François</name></author><author><name sortKey="Auwerx, J" uniqKey="Auwerx J">J. Auwerx</name></author><author><name sortKey="Schols, D" uniqKey="Schols D">D. Schols</name></author><author><name sortKey="Balzarini, J" uniqKey="Balzarini J">J. Balzarini</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Manolov, I" uniqKey="Manolov I">I. Manolov</name></author><author><name sortKey="Danchev, N D" uniqKey="Danchev N">N.D. Danchev</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Manolov, I" uniqKey="Manolov I">I. Manolov</name></author><author><name sortKey="Danchev, N D" uniqKey="Danchev N">N.D. Danchev</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Mazumder, A" uniqKey="Mazumder A">A. Mazumder</name></author><author><name sortKey="Wang, S" uniqKey="Wang S">S. Wang</name></author><author><name sortKey="Neamati, N" uniqKey="Neamati N">N. Neamati</name></author><author><name sortKey="Niklaus, M" uniqKey="Niklaus M">M. Niklaus</name></author><author><name sortKey="Sunder, S" uniqKey="Sunder S">S. Sunder</name></author><author><name sortKey="Chen, J" uniqKey="Chen J">J. Chen</name></author><author><name sortKey="Milne, G W A" uniqKey="Milne G">G.W.A. Milne</name></author><author><name sortKey="Rice, W G" uniqKey="Rice W">W.G. Rice</name></author><author><name sortKey="Burke, T R" uniqKey="Burke T">T.R. Burke</name></author><author><name sortKey="Pommier, Y" uniqKey="Pommier Y">Y. Pommier</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kostova, I" uniqKey="Kostova I">I. Kostova</name></author><author><name sortKey="Momekov, G" uniqKey="Momekov G">G. Momekov</name></author><author><name sortKey="Tzanova, T" uniqKey="Tzanova T">T. Tzanova</name></author><author><name sortKey="Karaivanova, M" uniqKey="Karaivanova M">M. Karaivanova</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Arora, R B" uniqKey="Arora R">R.B. Arora</name></author><author><name sortKey="Krishnaswamy, N R" uniqKey="Krishnaswamy N">N.R. Krishnaswamy</name></author><author><name sortKey="Seshadri, T R" uniqKey="Seshadri T">T.R. Seshadri</name></author><author><name sortKey="Seth, S D S" uniqKey="Seth S">S.D.S. Seth</name></author><author><name sortKey="Sharma, B R" uniqKey="Sharma B">B.R. Sharma</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Manolov, I" uniqKey="Manolov I">I. Manolov</name></author><author><name sortKey="Maichle Mossmer, C" uniqKey="Maichle Mossmer C">C. Maichle-Mössmer</name></author><author><name sortKey="Nicolova, I" uniqKey="Nicolova I">I. Nicolova</name></author><author><name sortKey="Danchev, N" uniqKey="Danchev N">N. Danchev</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Manolov, I" uniqKey="Manolov I">I. Manolov</name></author><author><name sortKey="Maichle Mossmer, C" uniqKey="Maichle Mossmer C">C. Maichle-Mössmer</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Valente, E J" uniqKey="Valente E">E.J. Valente</name></author><author><name sortKey="Eggleston, D S" uniqKey="Eggleston D">D.S. Eggleston</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Stanchev, S" uniqKey="Stanchev S">S. Stanchev</name></author><author><name sortKey="Maichle Mossmer, C" uniqKey="Maichle Mossmer C">C. Maichle-Mössmer</name></author><author><name sortKey="Manolov, I" uniqKey="Manolov I">I. Manolov</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Sheldrick, G M" uniqKey="Sheldrick G">G.M. Sheldrick</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Farrugia, L J" uniqKey="Farrugia L">L.J. Farrugia</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Spek, A L" uniqKey="Spek A">A.L. Spek</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Belgique</li><li>Croatie</li><li>Slovénie</li></country><region><li>Province du Brabant flamand</li><li>Région flamande</li></region><settlement><li>Louvain</li></settlement><orgName><li>Katholieke Universiteit Leuven</li></orgName></list><tree><noCountry><name sortKey="Muratovi, Samija" sort="Muratovi, Samija" uniqKey="Muratovi S" first="Samija" last="Muratovi">Samija Muratovi</name><name sortKey="Zavrsnik, Davorka" sort="Zavrsnik, Davorka" uniqKey="Zavrsnik D" first="Davorka" last="Završnik">Davorka Završnik</name></noCountry><country name="Slovénie"><noRegion><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name></noRegion><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name></country><country name="Croatie"><noRegion><name sortKey="Cetina, Mario" sort="Cetina, Mario" uniqKey="Cetina M" first="Mario" last="Cetina">Mario Cetina</name></noRegion><name sortKey="Mintas, Mladen" sort="Mintas, Mladen" uniqKey="Mintas M" first="Mladen" last="Mintas">Mladen Mintas</name><name sortKey="Nagl, Ante" sort="Nagl, Ante" uniqKey="Nagl A" first="Ante" last="Nagl">Ante Nagl</name></country><country name="Belgique"><region name="Région flamande"><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></region><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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