Synthesis and Biological Evaluation of Novel 1,2,3‐Triazolonucleotides
Identifieur interne : 000860 ( Istex/Corpus ); précédent : 000859; suivant : 000861Synthesis and Biological Evaluation of Novel 1,2,3‐Triazolonucleotides
Auteurs : Iwona E. Głowacka ; Jan Balzarini ; Andrzej E. Wr BlewskiSource :
- Archiv der Pharmazie [ 0365-6233 ] ; 2013-04.
English descriptors
- Teeft :
- Alkyne, Anal, Analog, Antiviral, Azide, Biological evaluation, Bioorg, Calcd, Cd3od, Cdcl3, Cell cultures, Chem, Chloroform, Clercq, Cytostatic, Diethyl, General procedure, Gmbh, Haromat, Hela, Kgaa, Lett, Methanol, Mmol, Nmax, Nucleic acids, Nucleobases, Nucleoside, Pch2, Pharm, Phosphonate, Phosphonic, Phosphonic acid, Pocc, Silica, Test compounds, Tetrahedron, Verlag, Verlag gmbh, Weinheim, Weinheim synthesis.
Abstract
A general procedure for the preparation of 1,2,3‐triazole analogs of nucleosides from diethyl 2‐azidoethoxymethyl‐ and 2‐azidoethoxyethylphosphonates was elaborated. The application of microwave irradiation shortened the reaction time to 10 min in comparison to ca. 48 h when 1,3‐dipolar cycloadditions were performed under standard conditions. All compounds were evaluated in vitro for inhibitory activity against a broad variety of DNA and RNA viruses. None of the compounds were antivirally active at subtoxic concentrations. Compound 17k exhibited moderate inhibitory effects on the proliferation of human T‐lymphocyte cells (IC50 = 64 µM for CEM).
The inhibitory activity of cell proliferation for HEL cells as well as L1210, CEM, and HeLa cells of several 1,2,3‐triazole analogs of nucleotides was evaluated. The 1,2,3‐triazole derivatives appeared to be cytostatic (with IC50 values reaching the middle to higher micromolar range: 60–250 µM).
Url:
DOI: 10.1002/ardp.201200421
Links to Exploration step
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Pharm. Pharm. Med. Chem.</title></titleGroup></publicationMeta><publicationMeta level="part" position="40"><doi origin="wiley" registered="yes">10.1002/ardp.v346.4</doi><numberingGroup><numbering type="journalVolume" number="346">346</numbering><numbering type="journalIssue">4</numbering></numberingGroup><coverDate startDate="2013-04">April 2013</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="4" status="forIssue"><doi origin="wiley" registered="yes">10.1002/ardp.201200421</doi><idGroup><id type="unit" value="ARDP201200421"></id></idGroup><countGroup><count type="pageTotal" number="14"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title><title type="tocHeading1">Full Papers</title></titleGroup><copyright ownership="publisher">Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2012-11-05"></event><event type="manuscriptAccepted" date="2012-12-21"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:3.2.0 mode:FullText" date="2013-04-08"></event><event type="publishedOnlineEarlyUnpaginated" date="2013-02-21"></event><event type="firstOnline" date="2013-02-21"></event><event type="publishedOnlineFinalForm" date="2013-04-08"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-05"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.6.4 mode:FullText" date="2015-10-01"></event></eventGroup><numberingGroup><numbering type="pageFirst">278</numbering><numbering type="pageLast">291</numbering></numberingGroup><correspondenceTo>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Muszyńskiego 1, 90‐151 Łódź, Poland. Fax: +48 42 678 83 98</correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ARDP.ARDP201200421.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="7"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="67"></count><count type="wordTotal" number="10415"></count></countGroup><titleGroup><title type="main" xml:lang="en">Synthesis and Biological Evaluation of Novel 1,2,3‐Triazolonucleotides</title><title type="short" xml:lang="en">Synthesis and Biological Evaluation of 1,2,3‐Triazolonucleotides</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1" corresponding="yes"><personName><givenNames>Iwona E.</givenNames><familyName>Głowacka</familyName></personName><contactDetails><email>iwona.glowacka@umed.lodz.pl</email></contactDetails></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Jan</givenNames><familyName>Balzarini</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Andrzej E.</givenNames><familyName>Wróblewski</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="PL" type="organization"><unparsedAffiliation>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland</unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="BE" type="organization"><unparsedAffiliation>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Antiviral</keyword><keyword xml:id="kwd2">Aziodophosphonates</keyword><keyword xml:id="kwd3">Cycloaddition</keyword><keyword xml:id="kwd4">Cytostatic</keyword><keyword xml:id="kwd5">1,2,3‐Triazoles</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>A general procedure for the preparation of 1,2,3‐triazole analogs of nucleosides from diethyl 2‐azidoethoxymethyl‐ and 2‐azidoethoxyethylphosphonates was elaborated. The application of microwave irradiation shortened the reaction time to 10 min in comparison to ca. 48 h when 1,3‐dipolar cycloadditions were performed under standard conditions. All compounds were evaluated <i>in vitro</i> for inhibitory activity against a broad variety of DNA and RNA viruses. None of the compounds were antivirally active at subtoxic concentrations. Compound <b>17k</b> exhibited moderate inhibitory effects on the proliferation of human T‐lymphocyte cells (IC<sub>50</sub> = 64 µM for CEM).</p></abstract><abstract type="graphical" xml:lang="en"><p>The inhibitory activity of cell proliferation for HEL cells as well as L1210, CEM, and HeLa cells of several 1,2,3‐triazole analogs of nucleotides was evaluated. The 1,2,3‐triazole derivatives appeared to be cytostatic (with IC<sub>50</sub> values reaching the middle to higher micromolar range: 60–250 µM). <blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY‐VCH Verlag" href="urn:x-wiley:03656233:media:ARDP201200421:content"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis and Biological Evaluation of Novel 1,2,3‐Triazolonucleotides</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Synthesis and Biological Evaluation of 1,2,3‐Triazolonucleotides</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Synthesis and Biological Evaluation of Novel 1,2,3‐Triazolonucleotides</title></titleInfo><name type="personal"><namePart type="given">Iwona E.</namePart><namePart type="family">Głowacka</namePart><affiliation>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland</affiliation><affiliation>E-mail: iwona.glowacka@umed.lodz.pl</affiliation><affiliation>Correspondence address: Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Muszyńskiego 1, 90‐151 Łódź, Poland. Fax: +48 42 678 83 98</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>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, 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>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2013-04</dateIssued><dateCaptured encoding="w3cdtf">2012-11-05</dateCaptured><dateValid encoding="w3cdtf">2012-12-21</dateValid><copyrightDate encoding="w3cdtf">2013</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">7</extent><extent unit="tables">1</extent><extent unit="references">67</extent><extent unit="words">10415</extent></physicalDescription><abstract lang="en">A general procedure for the preparation of 1,2,3‐triazole analogs of nucleosides from diethyl 2‐azidoethoxymethyl‐ and 2‐azidoethoxyethylphosphonates was elaborated. The application of microwave irradiation shortened the reaction time to 10 min in comparison to ca. 48 h when 1,3‐dipolar cycloadditions were performed under standard conditions. All compounds were evaluated in vitro for inhibitory activity against a broad variety of DNA and RNA viruses. None of the compounds were antivirally active at subtoxic concentrations. Compound 17k exhibited moderate inhibitory effects on the proliferation of human T‐lymphocyte cells (IC50 = 64 µM for CEM).</abstract><abstract type="graphical" lang="en">The inhibitory activity of cell proliferation for HEL cells as well as L1210, CEM, and HeLa cells of several 1,2,3‐triazole analogs of nucleotides was evaluated. The 1,2,3‐triazole derivatives appeared to be cytostatic (with IC50 values reaching the middle to higher micromolar range: 60–250 µM).</abstract><subject lang="en"><genre>keywords</genre><topic>Antiviral</topic><topic>Aziodophosphonates</topic><topic>Cycloaddition</topic><topic>Cytostatic</topic><topic>1,2,3‐Triazoles</topic></subject><relatedItem type="host"><titleInfo><title>Archiv der Pharmazie</title></titleInfo><titleInfo type="abbreviated"><title>Arch. Pharm. Pharm. Med. 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