1‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides
Identifieur interne : 000281 ( Istex/Corpus ); précédent : 000280; suivant : 0002821‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides
Auteurs : Iwona E. Głowacka ; Jan Balzarini ; Dorota G. PiotrowskaSource :
- Archiv der Pharmazie [ 0365-6233 ] ; 2014-07.
Abstract
A new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates (R)‐ and (S)‐16 were obtained from enantiomerically pure (R)‐ and (S)‐1‐tert‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and N‐propargylated nucleobases in good yields. All 1,2,3‐triazolylphosphonates (R)‐ and (S)‐16 were evaluated for their activities against a broad range of DNA and RNA viruses. Compound (R)‐16g (B = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC50 = 45 µM). In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC50 = 2.9, 45, 72, and 96 µM, respectively). Compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.
Among a new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (R)‐16g (B = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.
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DOI: 10.1002/ardp.201300471
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Głowacka, Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90‐151 Łódź, Poland. +48 42 6788398</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: iwona.glowacka@umed.lodz.pl</mods:affiliation></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation><mods:affiliation>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</mods:affiliation></affiliation></author><author><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. 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Piotrowska</name><affiliation><mods:affiliation>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź, Poland</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Archiv der Pharmazie</title><title level="j" type="alt">ARCHIV DER PHARMAZIE</title><idno type="ISSN">0365-6233</idno><idno type="eISSN">1521-4184</idno><imprint><biblScope unit="vol">347</biblScope><biblScope unit="issue">7</biblScope><biblScope unit="page" from="496">496</biblScope><biblScope unit="page" to="505">505</biblScope><biblScope unit="page-count">10</biblScope><date type="published" when="2014-07">2014-07</date></imprint><idno type="ISSN">0365-6233</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0365-6233</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">A new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates (R)‐ and (S)‐16 were obtained from enantiomerically pure (R)‐ and (S)‐1‐tert‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and N‐propargylated nucleobases in good yields. All 1,2,3‐triazolylphosphonates (R)‐ and (S)‐16 were evaluated for their activities against a broad range of DNA and RNA viruses. Compound (R)‐16g (B = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC50 = 45 µM). In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC50 = 2.9, 45, 72, and 96 µM, respectively). Compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.</div><div type="abstract">Among a new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (R)‐16g (B = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Iwona E. Głowacka</name><affiliations><json:string>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź, Poland</json:string><json:string>Dr. Iwona E. 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<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract style="main"><p>A new series of 1‐amino‐3‐(1<hi rend="italic">H</hi>‐1,2,3‐triazol‐1‐yl)propylphosphonates (<hi rend="italic">R</hi>)‐ and (<hi rend="italic">S</hi>)‐<hi rend="bold">16</hi> were obtained from enantiomerically pure (<hi rend="italic">R</hi>)‐ and (<hi rend="italic">S</hi>)‐1‐<hi rend="italic">tert</hi>‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and <hi rend="italic">N</hi>‐propargylated nucleobases in good yields. All 1,2,3‐triazolylphosphonates (<hi rend="italic">R</hi>)‐ and (<hi rend="italic">S</hi>)‐<hi rend="bold">16</hi> were evaluated for their activities against a broad range of DNA and RNA viruses. Compound (<hi rend="italic">R</hi>)‐<hi rend="bold">16g</hi> (<hi rend="bold">B</hi> = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC<hi rend="subscript">50</hi> = 45 µM). In addition, (<hi rend="italic">S</hi>)‐<hi rend="bold">16c</hi> (<hi rend="bold">B</hi> = adenine), (<hi rend="italic">R</hi>)‐<hi rend="bold">16f</hi> (<hi rend="bold">B</hi> = <hi rend="italic">N</hi><hi rend="superscript">3</hi>‐Bz‐benzuracil), (<hi rend="italic">R</hi>)‐<hi rend="bold">16g</hi> (<hi rend="bold">B</hi> = 3‐acetylindole), and (<hi rend="italic">R</hi>)‐<hi rend="bold">16h</hi> (<hi rend="bold">B</hi> = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC<hi rend="subscript">50</hi> = 2.9, 45, 72, and 96 µM, respectively). Compounds (<hi rend="italic">R</hi>)‐<hi rend="bold">16g</hi>, (<hi rend="italic">S</hi>)‐<hi rend="bold">16g</hi>, and (<hi rend="italic">S</hi>)‐<hi rend="bold">16h</hi> were slightly cytostatic to different tumor cell lines.</p></abstract><abstract style="graphical"><p>Among a new series of 1‐amino‐3‐(1<hi rend="italic">H</hi>‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (<hi rend="italic">R</hi>)‐<hi rend="bold">16g</hi> (<hi rend="bold">B</hi> = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (<hi rend="italic">S</hi>)‐<hi rend="bold">16c</hi> (<hi rend="bold">B</hi> = adenine), (<hi rend="italic">R</hi>)‐<hi rend="bold">16f</hi> (<hi rend="bold">B</hi> = <hi rend="italic">N</hi><hi rend="superscript">3</hi>‐Bz‐benzuracil), (<hi rend="italic">R</hi>)‐<hi rend="bold">16g</hi> (<hi rend="bold">B</hi> = 3‐acetylindole), and (<hi rend="italic">R</hi>)‐<hi rend="bold">16h</hi> (<hi rend="bold">B</hi> = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (<hi rend="italic">R</hi>)‐<hi rend="bold">16g</hi>, (<hi rend="italic">S</hi>)‐<hi rend="bold">16g</hi>, and (<hi rend="italic">S</hi>)‐<hi rend="bold">16h</hi> were slightly cytostatic to different tumor cell lines.
<figure type="box"><media mimeType="image" url="urn:x-wiley:03656233:media:ardp201300471:ardp201300471-content"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="ardp201300471-kwd-0001">Antiproliferative agents</term><term xml:id="ardp201300471-kwd-0002">Antiviral activity</term><term xml:id="ardp201300471-kwd-0003">Cycloaddition</term><term xml:id="ardp201300471-kwd-0004">Cytotoxic activity</term><term xml:id="ardp201300471-kwd-0005">Triazoles</term></keywords><keywords rend="articleCategory"><term>Full Paper</term></keywords><keywords rend="tocHeading1"><term>Full Papers</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc><revisionDesc><change when="2019-12-20" who="#istex" xml:id="pub2tei">formatting</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-42RDGSZV-8/fulltext.txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" xml:lang="en" type="serialArticle" xml:id="ardp201300471"><header><publicationMeta level="product"><doi origin="wiley" registered="yes">10.1002/(ISSN)1521-4184</doi><issn type="print">0365-6233</issn><issn type="electronic">1521-4184</issn><idGroup><id type="product" value="ARDP"></id></idGroup><titleGroup><title type="main" sort="ARCHIV DER PHARMAZIE">Archiv der Pharmazie</title><title type="short">Arch. Pharm. Chem. Life Sci.</title></titleGroup></publicationMeta><publicationMeta level="part" position="70"><doi registered="yes">10.1002/ardp.v347.7</doi><copyright ownership="publisher">© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><numberingGroup><numbering type="journalVolume" number="347">347</numbering><numbering type="journalIssue">7</numbering></numberingGroup><coverDate startDate="2014-07">July 2014</coverDate></publicationMeta><publicationMeta level="unit" position="80" type="article" status="forIssue"><doi>10.1002/ardp.201300471</doi><idGroup><id type="unit" value="ARDP201300471"></id></idGroup><countGroup><count type="pageTotal" number="10"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title><title type="tocHeading1">Full Papers</title></titleGroup><copyright ownership="publisher">© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2013-12-19"></event><event type="manuscriptRevised" date="2014-02-21"></event><event type="manuscriptAccepted" date="2014-02-21"></event><event type="xmlCreated" agent="Thomson Digital" date="2014-04-02"></event><event type="publishedOnlineEarlyUnpaginated" date="2014-04-06"></event><event type="firstOnline" date="2014-04-06"></event><event type="publishedOnlineFinalForm" date="2014-07-01"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.6.4 mode:FullText" date="2015-10-08"></event></eventGroup><numberingGroup><numbering type="pageFirst">496</numbering><numbering type="pageLast">505</numbering></numberingGroup><correspondenceTo><lineatedText><line><b>Correspondence:</b> Dr. Iwona E. Głowacka, Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90‐151 Łódź, Poland.</line><line><b>E‐mail:</b>
<email>iwona.glowacka@umed.lodz.pl</email></line><line><b>Fax:</b> +48 42 6788398</line></lineatedText></correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file://ARDP.ARDP201300471.pdf"></link></linkGroup></publicationMeta><contentMeta><titleGroup><title type="main">1‐Amino‐3‐(1<i>H</i>‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides</title><title type="short">1‐Amino‐3‐(1<i>H</i>‐1,2,3‐triazol‐1‐yl)propylphosphonates</title><title type="shortAuthors">I. E. Głowacka <i>et al.</i></title></titleGroup><creators><creator xml:id="ardp201300471-cr-0001" creatorRole="author" affiliationRef="#ardp201300471-aff-0001" corresponding="yes"><personName><givenNames>Iwona E.</givenNames> <familyName>Głowacka</familyName></personName></creator><creator xml:id="ardp201300471-cr-0002" creatorRole="author" affiliationRef="#ardp201300471-aff-0002"><personName><givenNames>Jan</givenNames> <familyName>Balzarini</familyName></personName></creator><creator xml:id="ardp201300471-cr-0003" creatorRole="author" affiliationRef="#ardp201300471-aff-0001"><personName><givenNames>Dorota G.</givenNames> <familyName>Piotrowska</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="ardp201300471-aff-0001" countryCode="PL"><orgDiv>Bioorganic Chemistry Laboratory</orgDiv><orgDiv>Faculty of Pharmacy</orgDiv><orgName>Medical University of Łódź</orgName><address><city>Łódź</city><country>Poland</country></address></affiliation><affiliation xml:id="ardp201300471-aff-0002" countryCode="BE"><orgName>Rega Institute for Medical Research</orgName><address><countryPart>KU Leuven</countryPart><city>Leuven</city><country>Belgium</country></address></affiliation></affiliationGroup><keywordGroup type="author" xml:lang="en"><keyword xml:id="ardp201300471-kwd-0001">Antiproliferative agents</keyword><keyword xml:id="ardp201300471-kwd-0002">Antiviral activity</keyword><keyword xml:id="ardp201300471-kwd-0003">Cycloaddition</keyword><keyword xml:id="ardp201300471-kwd-0004">Cytotoxic activity</keyword><keyword xml:id="ardp201300471-kwd-0005">Triazoles</keyword></keywordGroup><fundingInfo><fundingAgency>Medical University of Łódź internal funds</fundingAgency><fundingNumber>503‐3014‐01</fundingNumber></fundingInfo><fundingInfo><fundingAgency>KU Leuven</fundingAgency><fundingNumber>10/014</fundingNumber></fundingInfo><abstractGroup><abstract type="main"><section xml:id="ardp201300471-sec-0001"><p>A new series of 1‐amino‐3‐(1<i>H</i>‐1,2,3‐triazol‐1‐yl)propylphosphonates (<i>R</i>)‐ and (<i>S</i>)‐<b>16</b> were obtained from enantiomerically pure (<i>R</i>)‐ and (<i>S</i>)‐1‐<i>tert</i>‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and <i>N</i>‐propargylated nucleobases in good yields. All 1,2,3‐triazolylphosphonates (<i>R</i>)‐ and (<i>S</i>)‐<b>16</b> were evaluated for their activities against a broad range of DNA and RNA viruses. Compound (<i>R</i>)‐<b>16g</b> (<b>B</b> = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC<sub>50</sub> = 45 µM). In addition, (<i>S</i>)‐<b>16c</b> (<b>B</b> = adenine), (<i>R</i>)‐<b>16f</b> (<b>B</b> = <i>N</i><sup>3</sup>‐Bz‐benzuracil), (<i>R</i>)‐<b>16g</b> (<b>B</b> = 3‐acetylindole), and (<i>R</i>)‐<b>16h</b> (<b>B</b> = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC<sub>50</sub> = 2.9, 45, 72, and 96 µM, respectively). Compounds (<i>R</i>)‐<b>16g</b>, (<i>S</i>)‐<b>16g</b>, and (<i>S</i>)‐<b>16h</b> were slightly cytostatic to different tumor cell lines.</p></section></abstract><abstract type="graphical"><p>Among a new series of 1‐amino‐3‐(1<i>H</i>‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (<i>R</i>)‐<b>16g</b> (<b>B</b> = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (<i>S</i>)‐<b>16c</b> (<b>B</b> = adenine), (<i>R</i>)‐<b>16f</b> (<b>B</b> = <i>N</i><sup>3</sup>‐Bz‐benzuracil), (<i>R</i>)‐<b>16g</b> (<b>B</b> = 3‐acetylindole), and (<i>R</i>)‐<b>16h</b> (<b>B</b> = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (<i>R</i>)‐<b>16g</b>, (<i>S</i>)‐<b>16g</b>, and (<i>S</i>)‐<b>16h</b> were slightly cytostatic to different tumor cell lines.
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" copyright="© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim" href="urn:x-wiley:03656233:media:ardp201300471:ardp201300471-content"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>1‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>1‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>1‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides</title></titleInfo><name type="personal"><namePart type="given">Iwona E.</namePart><namePart type="family">Głowacka</namePart><affiliation>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź, Poland</affiliation><affiliation>Dr. Iwona E. Głowacka, Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90‐151 Łódź, Poland. +48 42 6788398</affiliation><affiliation>E-mail: iwona.glowacka@umed.lodz.pl</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jan</namePart><namePart type="family">Balzarini</namePart><affiliation>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Dorota G.</namePart><namePart type="family">Piotrowska</namePart><affiliation>Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>Blackwell Publishing Ltd</publisher><dateIssued encoding="w3cdtf">2014-07</dateIssued><dateCreated encoding="w3cdtf">2014-04-02</dateCreated><dateCaptured encoding="w3cdtf">2013-12-19</dateCaptured><dateValid encoding="w3cdtf">2014-02-21</dateValid><copyrightDate encoding="w3cdtf">2014</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><abstract>A new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates (R)‐ and (S)‐16 were obtained from enantiomerically pure (R)‐ and (S)‐1‐tert‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and N‐propargylated nucleobases in good yields. All 1,2,3‐triazolylphosphonates (R)‐ and (S)‐16 were evaluated for their activities against a broad range of DNA and RNA viruses. Compound (R)‐16g (B = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC50 = 45 µM). In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC50 = 2.9, 45, 72, and 96 µM, respectively). Compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.</abstract><abstract type="graphical">Among a new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (R)‐16g (B = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.</abstract><note type="funding">Medical University of Łódź internal funds - No. 503‐3014‐01; </note><note type="funding">KU Leuven - No. 10/014; </note><subject lang="en"><genre>keywords</genre><topic>Antiproliferative agents</topic><topic>Antiviral activity</topic><topic>Cycloaddition</topic><topic>Cytotoxic activity</topic><topic>Triazoles</topic></subject><relatedItem type="host"><titleInfo><title>Archiv der Pharmazie</title></titleInfo><titleInfo type="abbreviated"><title>Arch. Pharm. Chem. Life Sci.</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Full Paper</topic><topic>Full Papers</topic></subject><identifier type="ISSN">0365-6233</identifier><identifier type="eISSN">1521-4184</identifier><identifier type="DOI">10.1002/(ISSN)1521-4184</identifier><identifier type="PublisherID">ARDP</identifier><part><date>2014</date><detail type="volume"><caption>vol.</caption><number>347</number></detail><detail type="issue"><caption>no.</caption><number>7</number></detail><extent unit="pages"><start>496</start><end>505</end><total>10</total></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0001"><titleInfo><title>P. Herdewijn, Modified Nucleosides in Biochemistry, Biotechnology and Medicine, Wiley‐VCH, Weinheim 2008.</title></titleInfo><note type="citation/reference">P. Herdewijn, Modified Nucleosides in Biochemistry, Biotechnology and Medicine, Wiley‐VCH, Weinheim 2008.</note><name type="personal"><namePart type="given">P.</namePart><namePart type="family">Herdewijn</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>book</genre><originInfo><publisher>Wiley‐VCH</publisher><place><placeTerm type="text">Weinheim</placeTerm></place></originInfo><part><date>2008</date></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0002"><titleInfo><title>C. K. Chu, Antiviral Nucleosides: Chiral Synthesis and Chemotherapy, Elsevier B.V., Amsterdam 2003.</title></titleInfo><note type="citation/reference">C. K. Chu, Antiviral Nucleosides: Chiral Synthesis and Chemotherapy, Elsevier B.V., Amsterdam 2003.</note><name type="personal"><namePart type="given">C. K.</namePart><namePart type="family">Chu</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>book</genre><originInfo><publisher>Elsevier B.V</publisher><place><placeTerm type="text">Amsterdam</placeTerm></place></originInfo><part><date>2003</date></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0003"><titleInfo><title>Mol. Biotechnol.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">S. Freeman, J. M. Gardiner, Mol. Biotechnol. 1996, 5, 125–133.</note><name type="personal"><namePart type="given">S.</namePart><namePart type="family">Freeman</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. M.</namePart><namePart type="family">Gardiner</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1996</date><detail type="volume"><caption>vol.</caption><number>5</number></detail><extent unit="pages"><start>125</start><end>133</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0004"><titleInfo><title>Curr. Pharm. Des.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">A. Holý, Curr. Pharm. Des. 2003, 9, 2529–2567.</note><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Holý</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2003</date><detail type="volume"><caption>vol.</caption><number>9</number></detail><extent unit="pages"><start>2529</start><end>2567</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0005"><titleInfo><title>Nat. Rev. Drug Discov.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">E. De Clercq, A. Holý, Nat. Rev. Drug Discov. 2005, 4, 928–940.</note><name type="personal"><namePart type="given">E.</namePart><namePart type="family">De Clercq</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Holý</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2005</date><detail type="volume"><caption>vol.</caption><number>4</number></detail><extent unit="pages"><start>928</start><end>940</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0006"><titleInfo><title>Biochem. Pharmacol.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">E. De Clercq, Biochem. Pharmacol. 2007, 73, 911–922.</note><name type="personal"><namePart type="given">E.</namePart><namePart type="family">De Clercq</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2007</date><detail type="volume"><caption>vol.</caption><number>73</number></detail><extent unit="pages"><start>911</start><end>922</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0007"><titleInfo><title>J. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">E. De Clercq, J. Med. Chem. 2010, 53, 1438–1450.</note><name type="personal"><namePart type="given">E.</namePart><namePart type="family">De Clercq</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2010</date><detail type="volume"><caption>vol.</caption><number>53</number></detail><extent unit="pages"><start>1438</start><end>1450</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0008"><titleInfo><title>Med. Res. Rev.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">E. De Clercq, Med. Res. Rev. 2013, 33, 1278–1303.</note><name type="personal"><namePart type="given">E.</namePart><namePart type="family">De Clercq</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2013</date><detail type="volume"><caption>vol.</caption><number>33</number></detail><extent unit="pages"><start>1278</start><end>1303</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0009"><titleInfo><title>Lancet Oncol.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">C. M. Galmarini, J. R. Mackey, C. Dumontet, Lancet Oncol. 2002, 3, 415–424.</note><name type="personal"><namePart type="given">C. M.</namePart><namePart type="family">Galmarini</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. R.</namePart><namePart type="family">Mackey</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">C.</namePart><namePart type="family">Dumontet</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2002</date><detail type="volume"><caption>vol.</caption><number>3</number></detail><extent unit="pages"><start>415</start><end>424</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0010"><titleInfo><title>J. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">T. S. Lin, M. C. Liu, J. Med. Chem. 1985, 28, 971–973.</note><name type="personal"><namePart type="given">T. S.</namePart><namePart type="family">Lin</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M. C.</namePart><namePart type="family">Liu</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1985</date><detail type="volume"><caption>vol.</caption><number>28</number></detail><extent unit="pages"><start>971</start><end>973</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0011"><titleInfo><title>PCT Int. Appl</title></titleInfo><name type="personal"><namePart type="given">I.</namePart><namePart type="family">Gilbert</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">C.</namePart><namePart type="family">Nguyen</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">G. F.</namePart><namePart type="family">Ruda</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Schhipani</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">G.</namePart><namePart type="family">Kasinathan</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">N.‐G.</namePart><namePart type="family">Johansson</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. G.</namePart><namePart type="family">Pacanowska</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>other</genre><part><date>2005</date></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0012"><titleInfo><title>Can. J. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">K. K. Ogilvie, N. Nguyen‐Ba, M. F. Gillen, B. K. Radatus, U. O. Cheriyan, H. R. Hanna, K. O. Smith, K. S. Galloway, Can. J. Chem. 1984, 62, 241–252.</note><name type="personal"><namePart type="given">K. K.</namePart><namePart type="family">Ogilvie</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">N.</namePart><namePart type="family">Nguyen‐Ba</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M. F.</namePart><namePart type="family">Gillen</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">B. K.</namePart><namePart type="family">Radatus</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">U. O.</namePart><namePart type="family">Cheriyan</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">H. R.</namePart><namePart type="family">Hanna</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">K. O.</namePart><namePart type="family">Smith</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">K. S.</namePart><namePart type="family">Galloway</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1984</date><detail type="volume"><caption>vol.</caption><number>62</number></detail><extent unit="pages"><start>241</start><end>252</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0013"><titleInfo><title>J. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">J. C. Martin, D. P. C. McGee, G. A. Jeffrey, D. W. Hobbs, D. F. Smee, T. R. Matthews, J. P. H. Verheyden, J. Med. Chem. 1986, 29, 1384–1389.</note><name type="personal"><namePart type="given">J. C.</namePart><namePart type="family">Martin</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. P. C.</namePart><namePart type="family">McGee</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">G. A.</namePart><namePart type="family">Jeffrey</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. W.</namePart><namePart type="family">Hobbs</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. F.</namePart><namePart type="family">Smee</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T. R.</namePart><namePart type="family">Matthews</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. P. H.</namePart><namePart type="family">Verheyden</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1986</date><detail type="volume"><caption>vol.</caption><number>29</number></detail><extent unit="pages"><start>1384</start><end>1389</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0014"><titleInfo><title>J. Chem. Soc. Perkin Trans. 1</title></titleInfo><genre>journal-article</genre><note type="citation/reference">M. R. Harnden, R. L. Jarvest, J. Chem. Soc. Perkin Trans. 1 1988, 2777–2784.</note><name type="personal"><namePart type="given">M. R.</namePart><namePart type="family">Harnden</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">R. L.</namePart><namePart type="family">Jarvest</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1988</date><extent unit="pages"><start>2777</start><end>2784</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0015"><titleInfo><title>Nucleosides Nucleotides Nucleic Acids</title></titleInfo><genre>journal-article</genre><note type="citation/reference">D. Zhou, I. M. Lagoja, A. Van Aerschot, Nucleosides Nucleotides Nucleic Acids 2007, 26, 563–566.</note><name type="personal"><namePart type="given">D.</namePart><namePart type="family">Zhou</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">I. M.</namePart><namePart type="family">Lagoja</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Van Aerschot</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2007</date><detail type="volume"><caption>vol.</caption><number>26</number></detail><extent unit="pages"><start>563</start><end>566</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0016"><titleInfo><title>Bioorg. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">K. Clinch, D. R. Crump, G. B. Evans, K. Z. Hazleton, J. M. Mason, V. L. Schramm, P. C. Tyler, Bioorg. Med. Chem. 2013, 21, 5629–5646.</note><name type="personal"><namePart type="given">K.</namePart><namePart type="family">Clinch</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. R.</namePart><namePart type="family">Crump</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">G. B.</namePart><namePart type="family">Evans</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">K. Z.</namePart><namePart type="family">Hazleton</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. M.</namePart><namePart type="family">Mason</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">V. L.</namePart><namePart type="family">Schramm</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">P. C.</namePart><namePart type="family">Tyler</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2013</date><detail type="volume"><caption>vol.</caption><number>21</number></detail><extent unit="pages"><start>5629</start><end>5646</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0017"><titleInfo><title>J. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">D. Hocková, D. T. Keough, Z. Janeba, T.‐H. Wang, J. de Jersey, L. W. Guddat, J. Med. Chem. 2012, 55, 6209–6223.</note><name type="personal"><namePart type="given">D.</namePart><namePart type="family">Hocková</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. T.</namePart><namePart type="family">Keough</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Z.</namePart><namePart type="family">Janeba</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T.‐H.</namePart><namePart type="family">Wang</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J.</namePart><namePart type="family">de Jersey</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">L. W.</namePart><namePart type="family">Guddat</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2012</date><detail type="volume"><caption>vol.</caption><number>55</number></detail><extent unit="pages"><start>6209</start><end>6223</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0018"><titleInfo><title>Bioorg. Med. Chem. Lett.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">Y.‐S. Lee, B. H. Kim, Bioorg. Med. Chem. Lett. 2002, 12, 1395–1397.</note><name type="personal"><namePart type="given">Y.‐S.</namePart><namePart type="family">Lee</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">B. H.</namePart><namePart type="family">Kim</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2002</date><detail type="volume"><caption>vol.</caption><number>12</number></detail><extent unit="pages"><start>1395</start><end>1397</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0019"><titleInfo><title>Eur. J. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">I. E. Głowacka, J. Balzarini, A. E. Wróblewski, Eur. J. Med. Chem. 2013, 70, 706–722.</note><name type="personal"><namePart type="given">I. E.</namePart><namePart type="family">Głowacka</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J.</namePart><namePart type="family">Balzarini</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A. E.</namePart><namePart type="family">Wróblewski</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2013</date><detail type="volume"><caption>vol.</caption><number>70</number></detail><extent unit="pages"><start>706</start><end>722</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0020"><titleInfo><title>Arch. Pharm. Chem. Life Sci.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">I. E. Głowacka, J. Balzarini, A. E. Wróblewski, Arch. Pharm. Chem. Life Sci. 2013, 346, 278–291.</note><name type="personal"><namePart type="given">I. E.</namePart><namePart type="family">Głowacka</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J.</namePart><namePart type="family">Balzarini</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A. E.</namePart><namePart type="family">Wróblewski</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2013</date><detail type="volume"><caption>vol.</caption><number>346</number></detail><extent unit="pages"><start>278</start><end>291</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0021"><titleInfo><title>Bioorg. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">C. Schultz, Bioorg. Med. Chem. 2003, 11, 885–898.</note><name type="personal"><namePart type="given">C.</namePart><namePart type="family">Schultz</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2003</date><detail type="volume"><caption>vol.</caption><number>11</number></detail><extent unit="pages"><start>885</start><end>898</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0022"><titleInfo><title>J. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">S. J. Hecker, M. D. Erion, J. Med. Chem. 2008, 51, 2328–2345.</note><name type="personal"><namePart type="given">S. J.</namePart><namePart type="family">Hecker</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M. D.</namePart><namePart type="family">Erion</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2008</date><detail type="volume"><caption>vol.</caption><number>51</number></detail><extent unit="pages"><start>2328</start><end>2345</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0023"><titleInfo><title>Bioorg. Med. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">I. E. Głowacka, J. Balzarini, D. G. Piotrowska, Bioorg. Med. Chem., under review.</note><name type="personal"><namePart type="given">I. E.</namePart><namePart type="family">Głowacka</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J.</namePart><namePart type="family">Balzarini</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. G.</namePart><namePart type="family">Piotrowska</namePart><role><roleTerm type="text">author</roleTerm></role></name></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0024"><titleInfo><title>J. Org. Chem.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">A. Piperno, S. V. Giofrè, D. Iannazzo, R. Romeo, G. Romeo, U. Chiacchio, A. Rescifina, D. G. Piotrowska, J. Org. Chem. 2010, 75, 2798–2805.</note><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Piperno</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">S. V.</namePart><namePart type="family">Giofrè</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D.</namePart><namePart type="family">Iannazzo</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">R.</namePart><namePart type="family">Romeo</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">G.</namePart><namePart type="family">Romeo</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">U.</namePart><namePart type="family">Chiacchio</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Rescifina</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">D. G.</namePart><namePart type="family">Piotrowska</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2010</date><detail type="volume"><caption>vol.</caption><number>75</number></detail><extent unit="pages"><start>2798</start><end>2805</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0025"><titleInfo><title>Tetrahedron: Asymmetry</title></titleInfo><genre>journal-article</genre><note type="citation/reference">D. G. Piotrowska, I. E. Głowacka, Tetrahedron: Asymmetry 2007, 18, 2787–2790.</note><name type="personal"><namePart type="given">D. G.</namePart><namePart type="family">Piotrowska</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">I. E.</namePart><namePart type="family">Głowacka</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2007</date><detail type="volume"><caption>vol.</caption><number>18</number></detail><extent unit="pages"><start>2787</start><end>2790</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0026"><titleInfo><title>Synth. Commun.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">A. Ryglowski, R. Lazaro, M. L. Roumestant, Ph. Viallefont, Synth. Commun. 1996, 26, 1739–1746.</note><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Ryglowski</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">R.</namePart><namePart type="family">Lazaro</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M. L.</namePart><namePart type="family">Roumestant</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Ph.</namePart><namePart type="family">Viallefont</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1996</date><detail type="volume"><caption>vol.</caption><number>26</number></detail><extent unit="pages"><start>1739</start><end>1746</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0027"><titleInfo><title>Phosphorus Sulfur Silicon</title></titleInfo><genre>journal-article</genre><note type="citation/reference">S. Hannour, A. Ryglowski, M. L. Roumestant, P. H. Viallefont, J. Martinez, F. Ouazzani, A. El Hallaoui, Phosphorus Sulfur Silicon 1998, 134/135, 419–430.</note><name type="personal"><namePart type="given">S.</namePart><namePart type="family">Hannour</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Ryglowski</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M. L.</namePart><namePart type="family">Roumestant</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">P. H.</namePart><namePart type="family">Viallefont</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J.</namePart><namePart type="family">Martinez</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">F.</namePart><namePart type="family">Ouazzani</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A.</namePart><namePart type="family">El Hallaoui</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1998</date><detail type="volume"><caption>vol.</caption><number>134/135</number></detail><extent unit="pages"><start>419</start><end>430</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0028"><titleInfo><title>Nucleosides Nucleotides Nucleic Acids</title></titleInfo><genre>journal-article</genre><note type="citation/reference">H. B. Lazrek, M. Taourirte, T. Oulih, J. L. Barascut, J. L. Imbach, C. Pannecouque, M. Witvrouw, E. De Clercq, Nucleosides Nucleotides Nucleic Acids 2001, 20, 1949–1960.</note><name type="personal"><namePart type="given">H. B.</namePart><namePart type="family">Lazrek</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.</namePart><namePart type="family">Taourirte</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T.</namePart><namePart type="family">Oulih</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. L.</namePart><namePart type="family">Barascut</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. L.</namePart><namePart type="family">Imbach</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">C.</namePart><namePart type="family">Pannecouque</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.</namePart><namePart type="family">Witvrouw</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">E.</namePart><namePart type="family">De Clercq</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2001</date><detail type="volume"><caption>vol.</caption><number>20</number></detail><extent unit="pages"><start>1949</start><end>1960</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0029"><titleInfo><title>Tetrahedron</title></titleInfo><genre>journal-article</genre><note type="citation/reference">W. E. Lindsell, Ch. Murray, P. N. Preston, T. A. J. Woodman, Tetrahedron 2000, 56, 1233–1245.</note><name type="personal"><namePart type="given">W. E.</namePart><namePart type="family">Lindsell</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Ch.</namePart><namePart type="family">Murray</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">P. N.</namePart><namePart type="family">Preston</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T. A. J.</namePart><namePart type="family">Woodman</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2000</date><detail type="volume"><caption>vol.</caption><number>56</number></detail><extent unit="pages"><start>1233</start><end>1245</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0030"><titleInfo><title>Tetrahedron</title></titleInfo><genre>journal-article</genre><note type="citation/reference">A. Casaschi, R. Grigg, J. M. Sansano, Tetrahedron 2001, 57, 607–615.</note><name type="personal"><namePart type="given">A.</namePart><namePart type="family">Casaschi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">R.</namePart><namePart type="family">Grigg</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J. M.</namePart><namePart type="family">Sansano</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2001</date><detail type="volume"><caption>vol.</caption><number>57</number></detail><extent unit="pages"><start>607</start><end>615</end></extent></part></relatedItem><relatedItem type="references" displayLabel="ardp201300471-cit-0031"><titleInfo><title>Synthesis</title></titleInfo><genre>journal-article</genre><note type="citation/reference">L. Pérez‐Serrano, L. Casarrubios, G. Dominguez, P. González‐Pérez, J. Pérez‐Castells, Synthesis 2002, 13, 1810–1812.</note><name type="personal"><namePart type="given">L.</namePart><namePart type="family">Pérez‐Serrano</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">L.</namePart><namePart type="family">Casarrubios</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">G.</namePart><namePart type="family">Dominguez</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">P.</namePart><namePart type="family">González‐Pérez</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">J.</namePart><namePart type="family">Pérez‐Castells</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>2002</date><detail type="volume"><caption>vol.</caption><number>13</number></detail><extent unit="pages"><start>1810</start><end>1812</end></extent></part></relatedItem><identifier type="istex">210DAF20D408EBD544BC6EC5D27C7ABC0BADBAA7</identifier><identifier type="ark">ark:/67375/WNG-42RDGSZV-8</identifier><identifier type="DOI">10.1002/ardp.201300471</identifier><identifier type="ArticleID">ARDP201300471</identifier><accessCondition type="use and reproduction" contentType="copyright">© 2014 WILEY-VCH Verlag GmbH & Co. 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