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 : 000959 ( Pmc/Curation ); précédent : 000958; suivant : 000960Benzylidene-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
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Davorka Završnik<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>
<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>
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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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" 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>
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<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>
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<author><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name>
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<wicri:regionArea>EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000</wicri:regionArea>
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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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<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>
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<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>
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<wicri:regionArea>Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000</wicri:regionArea>
</affiliation>
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<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>
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<wicri:regionArea>Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000</wicri:regionArea>
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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>
<affiliation wicri:level="1"><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>
</affiliation>
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<author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<affiliation wicri:level="1"><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>
</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>
</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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</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">21772234</article-id>
<article-id pub-id-type="pmc">6264767</article-id>
<article-id pub-id-type="doi">10.3390/molecules16076023</article-id>
<article-id pub-id-type="publisher-id">molecules-16-06023</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
</subj-group>
</article-categories>
<title-group><article-title>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</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Završnik</surname>
<given-names>Davorka</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-16-06023">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Muratović</surname>
<given-names>Samija</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-16-06023">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Makuc</surname>
<given-names>Damjan</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-16-06023">2</xref>
<xref ref-type="aff" rid="af3-molecules-16-06023">3</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Plavec</surname>
<given-names>Janez</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-16-06023">2</xref>
<xref ref-type="aff" rid="af3-molecules-16-06023">3</xref>
<xref ref-type="aff" rid="af4-molecules-16-06023">4</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Cetina</surname>
<given-names>Mario</given-names>
</name>
<xref ref-type="aff" rid="af5-molecules-16-06023">5</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Nagl</surname>
<given-names>Ante</given-names>
</name>
<xref ref-type="aff" rid="af5-molecules-16-06023">5</xref>
</contrib>
<contrib contrib-type="author"><name><surname>De Clercq</surname>
<given-names>Erik</given-names>
</name>
<xref ref-type="aff" rid="af6-molecules-16-06023">6</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Balzarini</surname>
<given-names>Jan</given-names>
</name>
<xref ref-type="aff" rid="af6-molecules-16-06023">6</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Mintas</surname>
<given-names>Mladen</given-names>
</name>
<xref ref-type="aff" rid="af7-molecules-16-06023">7</xref>
<xref rid="c1-molecules-16-06023" ref-type="corresp">*</xref>
</contrib>
</contrib-group>
<aff id="af1-molecules-16-06023"><label>1</label>
Faculty of Pharmacy, University of Sarajevo, Čekaluša 90, Sarajevo BA-71000, Bosnia and Hercegovina</aff>
<aff id="af2-molecules-16-06023"><label>2</label>
Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana SI-1000, Slovenia</aff>
<aff id="af3-molecules-16-06023"><label>3</label>
EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1000, Slovenia</aff>
<aff id="af4-molecules-16-06023"><label>4</label>
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva cesta 5, Ljubljana SI-1000, Slovenia</aff>
<aff id="af5-molecules-16-06023"><label>5</label>
Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, Zagreb HR-10000, Croatia</aff>
<aff id="af6-molecules-16-06023"><label>6</label>
Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium</aff>
<aff id="af7-molecules-16-06023"><label>7</label>
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, Zagreb HR-10000, Croatia</aff>
<author-notes><corresp id="c1-molecules-16-06023"><label>*</label>
Author to whom correspondence should be addressed; E-Mail: <email>mladen.mintas@fkit.hr</email>
; Tel.: +385-1-4597-214; Fax: +385-1-4597-250.</corresp>
</author-notes>
<pub-date pub-type="epub"><day>19</day>
<month>7</month>
<year>2011</year>
</pub-date>
<pub-date pub-type="collection"><month>7</month>
<year>2011</year>
</pub-date>
<volume>16</volume>
<issue>7</issue>
<fpage>6023</fpage>
<lpage>6040</lpage>
<history><date date-type="received"><day>13</day>
<month>6</month>
<year>2011</year>
</date>
<date date-type="rev-recd"><day>06</day>
<month>7</month>
<year>2011</year>
</date>
<date date-type="accepted"><day>12</day>
<month>7</month>
<year>2011</year>
</date>
</history>
<permissions><copyright-statement>© 2011 by the authors;</copyright-statement>
<copyright-year>2011</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 license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/3.0/">http://creativecommons.org/licenses/by/3.0/</ext-link>
).</license-p>
</license>
</permissions>
<abstract><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>
</abstract>
<kwd-group><kwd>4-hydroxycoumarin</kwd>
<kwd>benzopyranocoumarin</kwd>
<kwd>antiviral activity</kwd>
<kwd><sup>1</sup>
H/<sup>13</sup>
C-NMR conformational study</kwd>
<kwd>X-ray diffraction</kwd>
</kwd-group>
</article-meta>
</front>
</pmc>
</record>
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