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 : 000C64 ( Main/Exploration ); précédent : 000C63; suivant : 000C65Benzylidene-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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Le document en format XML
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H/<sup>13</sup>
C-NMR Conformational and X-ray Crystal Structure Studies and <italic>In Vitro</italic>
Antiviral Activity Evaluations</title>
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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>
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<author><name sortKey="Muratovi, Samija" sort="Muratovi, Samija" uniqKey="Muratovi S" first="Samija" last="Muratovi">Samija Muratovi</name>
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<author><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name>
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<author><name sortKey="Cetina, Mario" sort="Cetina, Mario" uniqKey="Cetina M" first="Mario" last="Cetina">Mario Cetina</name>
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</affiliation>
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<author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
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<placeName><settlement type="city">Louvain</settlement>
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<region type="district" nuts="2">Province du Brabant flamand</region>
</placeName>
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<author><name sortKey="Mintas, Mladen" sort="Mintas, Mladen" uniqKey="Mintas M" first="Mladen" last="Mintas">Mladen Mintas</name>
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<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>
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<series><title level="j">Molecules</title>
<idno type="eISSN">1420-3049</idno>
<imprint><date when="2011">2011</date>
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<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>
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<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>
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<name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name>
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<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>
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