Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity
Identifieur interne : 000316 ( Istex/Corpus ); précédent : 000315; suivant : 000317Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity
Auteurs : Iwona E. Głowacka ; Jan Balzarini ; Andrzej E. Wr BlewskiSource :
- Archiv der Pharmazie [ 0365-6233 ] ; 2014-07.
Abstract
A new series of 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates as acyclic nucleotide analogs were synthesized from diethyl (2‐chloroacetamido)methylphosphonate via azidation followed by 1,3‐dipolar cycloaddition with selected alkynes derived from natural nucleobases or their mimetics. All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonate 6e substituted with the N3‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.
New 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates were synthesized as acyclic nucleotide analogs and tested for their antiviral activities against DNA and RNA viruses. [(1,2,3‐Triazol‐1‐yl)‐acetamido]methylphosphonate 6e (n = 1; R = N3‐Bz‐benzuracil) was found to be active against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cells.
Url:
DOI: 10.1002/ardp.201300468
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All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonate 6e substituted with the N3‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.</div><div type="abstract">New 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates were synthesized as acyclic nucleotide analogs and tested for their antiviral activities against DNA and RNA viruses. [(1,2,3‐Triazol‐1‐yl)‐acetamido]methylphosphonate 6e (n = 1; R = N3‐Bz‐benzuracil) was found to be active against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cells.</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Iwona E. 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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2013-12-17"></event><event type="manuscriptRevised" date="2014-01-28"></event><event type="manuscriptAccepted" date="2014-01-31"></event><event type="xmlCreated" agent="Thomson Digital" date="2014-03-19"></event><event type="publishedOnlineEarlyUnpaginated" date="2014-03-25"></event><event type="firstOnline" date="2014-03-25"></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">506</numbering><numbering type="pageLast">514</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 42 678 83 98</line></lineatedText></correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file://ARDP.ARDP201300468.pdf"></link></linkGroup></publicationMeta><contentMeta><titleGroup><title type="main">Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity</title><title type="short">[(1,2,3‐Triazol‐1‐yl)acetamido]methylphosphonates</title><title type="shortAuthors">I. E. Głowacka <i>et al.</i></title></titleGroup><creators><creator xml:id="ardp201300468-cr-0001" creatorRole="author" affiliationRef="#ardp201300468-aff-0001" corresponding="yes"><personName><givenNames>Iwona E.</givenNames> <familyName>Głowacka</familyName></personName></creator><creator xml:id="ardp201300468-cr-0002" creatorRole="author" affiliationRef="#ardp201300468-aff-0002"><personName><givenNames>Jan</givenNames> <familyName>Balzarini</familyName></personName></creator><creator xml:id="ardp201300468-cr-0003" creatorRole="author" affiliationRef="#ardp201300468-aff-0001"><personName><givenNames>Andrzej E.</givenNames> <familyName>Wróblewski</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="ardp201300468-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="ardp201300468-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="ardp201300468-kwd-0001">Antiviral</keyword><keyword xml:id="ardp201300468-kwd-0002">Cycloaddition</keyword><keyword xml:id="ardp201300468-kwd-0003">Synthesis</keyword><keyword xml:id="ardp201300468-kwd-0004">Triazoles</keyword></keywordGroup><fundingInfo><fundingAgency>Medical University of Łódź internal funds</fundingAgency><fundingNumber>503‐3014‐01</fundingNumber></fundingInfo><fundingInfo><fundingAgency>KU Leuven (GOA no. 10/014)</fundingAgency></fundingInfo><abstractGroup><abstract type="main"><section xml:id="ardp201300468-sec-0001"><p>A new series of 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates as acyclic nucleotide analogs were synthesized from diethyl (2‐chloroacetamido)methylphosphonate via azidation followed by 1,3‐dipolar cycloaddition with selected alkynes derived from natural nucleobases or their mimetics. All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonate <b>6e</b> substituted with the <i>N</i><sup>3</sup>‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC<sub>50</sub> = 45 µM) in HeLa cell cultures.</p></section></abstract><abstract type="graphical"><p>New 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates were synthesized as acyclic nucleotide analogs and tested for their antiviral activities against DNA and RNA viruses. [(1,2,3‐Triazol‐1‐yl)‐acetamido]methylphosphonate <b>6e</b> (<i>n</i> = 1; R = <i>N</i><sup>3</sup>‐Bz‐benzuracil) was found to be active against the vesicular stomatitis virus (EC<sub>50</sub> = 45 µM) in HeLa cells.
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" copyright="© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim" href="urn:x-wiley:03656233:media:ardp201300468:ardp201300468-content"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>[(1,2,3‐Triazol‐1‐yl)acetamido]methylphosphonates</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Novel Acyclic Phosphonylated 1,2,3‐Triazolonucleosides with an Acetamidomethyl Linker: Synthesis and Biological Activity</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 42 678 83 98</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">Andrzej E.</namePart><namePart type="family">Wróblewski</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">2014-03-19</dateCreated><dateCaptured encoding="w3cdtf">2013-12-17</dateCaptured><dateValid encoding="w3cdtf">2014-01-31</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 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates as acyclic nucleotide analogs were synthesized from diethyl (2‐chloroacetamido)methylphosphonate via azidation followed by 1,3‐dipolar cycloaddition with selected alkynes derived from natural nucleobases or their mimetics. All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonate 6e substituted with the N3‐Bz‐benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.</abstract><abstract type="graphical">New 4‐substituted [(1,2,3‐triazol‐1‐yl)acetamido]methylphosphonates were synthesized as acyclic nucleotide analogs and tested for their antiviral activities against DNA and RNA viruses. [(1,2,3‐Triazol‐1‐yl)‐acetamido]methylphosphonate 6e (n = 1; R = N3‐Bz‐benzuracil) was found to be active against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cells.</abstract><note type="funding">Medical University of Łódź internal funds - No. 503‐3014‐01; </note><note type="funding">KU Leuven (GOA no. 10/014)</note><subject lang="en"><genre>keywords</genre><topic>Antiviral</topic><topic>Cycloaddition</topic><topic>Synthesis</topic><topic>Triazoles</topic></subject><relatedItem type="host"><titleInfo><title>Archiv der Pharmazie</title></titleInfo><titleInfo type="abbreviated"><title>Arch. Pharm. Chem. 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