Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides
Identifieur interne : 000856 ( Istex/Corpus ); précédent : 000855; suivant : 000857Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides
Auteurs : Magdalena Łysakowska ; Jan Balzarini ; Dorota G. PiotrowskaSource :
- Archiv der Pharmazie [ 0365-6233 ] ; 2014-05.
Abstract
Moderate diastereoselectivities (d.e. 2–62%) of isoxazolidine homonucleotides were observed for cycloadditions between N‐methyl‐C‐(diethoxyphosphoryl)nitrone and N‐allyl nucleobases, with trans‐isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil‐containing cycloadducts. The cis‐ and trans‐isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33–100 µM.
Cycloadditions between N‐methyl‐C‐(diethoxyphosphoryl)nitrone and N‐allyl nucleobases led to isoxazolidine homonucleotides, with trans‐isoxazolidines predominating. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but compounds cis‐11 and trans‐11 (B = 5,6‐dimethylbenzo[d]imidazole, 3‐acetylindole, N3‐benzoylbenzuracil) were found to inhibit the proliferation of L1210 cells (IC50 = 33–100 µM).
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DOI: 10.1002/ardp.201300382
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Piotrowska, Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, 90‐151 Łódź, Muszyńskiego 1, Poland. +48 42 678 83 98</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: dorota.piotrowska@umed.lodz.pl</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">5</biblScope><biblScope unit="page" from="341">341</biblScope><biblScope unit="page" to="353">353</biblScope><biblScope unit="page-count">13</biblScope><date type="published" when="2014-05">2014-05</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">Moderate diastereoselectivities (d.e. 2–62%) of isoxazolidine homonucleotides were observed for cycloadditions between N‐methyl‐C‐(diethoxyphosphoryl)nitrone and N‐allyl nucleobases, with trans‐isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil‐containing cycloadducts. The cis‐ and trans‐isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33–100 µM.</div><div type="abstract">Cycloadditions between N‐methyl‐C‐(diethoxyphosphoryl)nitrone and N‐allyl nucleobases led to isoxazolidine homonucleotides, with trans‐isoxazolidines predominating. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but compounds cis‐11 and trans‐11 (B = 5,6‐dimethylbenzo[d]imidazole, 3‐acetylindole, N3‐benzoylbenzuracil) were found to inhibit the proliferation of L1210 cells (IC50 = 33–100 µM).</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Magdalena Łysakowska</name><affiliations><json:string>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland</json:string></affiliations></json:item><json:item><name>Jan Balzarini</name><affiliations><json:string>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</json:string></affiliations></json:item><json:item><name>Dorota G. Piotrowska</name><affiliations><json:string>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland</json:string><json:string>Dr. Dorota G. 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The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil‐containing cycloadducts. The cis‐ and trans‐isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. 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<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract style="main"><p>Moderate diastereoselectivities (d.e. 2–62%) of isoxazolidine homonucleotides were observed for cycloadditions between <hi rend="italic">N</hi>‐methyl‐<hi rend="italic">C</hi>‐(diethoxyphosphoryl)nitrone and <hi rend="italic">N</hi>‐allyl nucleobases, with <hi rend="italic">trans</hi>‐isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil‐containing cycloadducts. The <hi rend="italic">cis</hi>‐ and <hi rend="italic">trans</hi>‐isoxazolidine phosphonates obtained herein were evaluated <hi rend="italic">in vitro</hi> for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC<hi rend="subscript">50</hi> values in the range of 33–100 µM.</p></abstract><abstract style="graphical"><p>Cycloadditions between <hi rend="italic">N</hi>‐methyl‐<hi rend="italic">C</hi>‐(diethoxyphosphoryl)nitrone and <hi rend="italic">N</hi>‐allyl nucleobases led to isoxazolidine homonucleotides, with <hi rend="italic">trans</hi>‐isoxazolidines predominating. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but compounds <hi rend="italic">cis</hi>‐<hi rend="bold">11</hi> and <hi rend="italic">trans</hi>‐<hi rend="bold">11</hi> (<hi rend="bold">B</hi> = 5,6‐dimethylbenzo[<hi rend="italic">d</hi>]imidazole, 3‐acetylindole, <hi rend="italic">N</hi><hi rend="superscript">3</hi>‐benzoylbenzuracil) were found to inhibit the proliferation of L1210 cells (IC<hi rend="subscript">50</hi> = 33–100 µM).
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<email>dorota.piotrowska@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.ARDP201300382.pdf"></link></linkGroup></publicationMeta><contentMeta><titleGroup><title type="main">Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides</title><title type="short">Isoxazolidine Analogs of Homonucleotides</title><title type="shortAuthors">M. Łysakowska <i>et al.</i></title></titleGroup><creators><creator xml:id="ardp201300382-cr-0001" creatorRole="author" affiliationRef="#ardp201300382-aff-0001"><personName><givenNames>Magdalena</givenNames> <familyName>Łysakowska</familyName></personName></creator><creator xml:id="ardp201300382-cr-0002" creatorRole="author" affiliationRef="#ardp201300382-aff-0002"><personName><givenNames>Jan</givenNames> <familyName>Balzarini</familyName></personName></creator><creator xml:id="ardp201300382-cr-0003" creatorRole="author" affiliationRef="#ardp201300382-aff-0001" corresponding="yes"><personName><givenNames>Dorota G.</givenNames> <familyName>Piotrowska</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="ardp201300382-aff-0001" countryCode="PL"><orgDiv>Faculty of Pharmacy, Bioorganic Chemistry Laboratory</orgDiv><orgName>Medical University of Łódź</orgName><address><city>Łódź</city><country>Poland</country></address></affiliation><affiliation xml:id="ardp201300382-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="ardp201300382-kwd-0001">Antiproliferative agents</keyword><keyword xml:id="ardp201300382-kwd-0002">Cycloaddition</keyword><keyword xml:id="ardp201300382-kwd-0003">Isoxazolidines</keyword></keywordGroup><fundingInfo><fundingAgency>Medical University of Łódź</fundingAgency><fundingNumber>503/3‐014‐1/503‐06‐300</fundingNumber><fundingNumber>502‐03‐/3‐014‐01/502‐34‐030</fundingNumber></fundingInfo><fundingInfo><fundingAgency>KU Leuven</fundingAgency><fundingNumber>GOA 10/014</fundingNumber></fundingInfo><abstractGroup><abstract type="main"><section xml:id="ardp201300382-sec-0001"><p>Moderate diastereoselectivities (d.e. 2–62%) of isoxazolidine homonucleotides were observed for cycloadditions between <i>N</i>‐methyl‐<i>C</i>‐(diethoxyphosphoryl)nitrone and <i>N</i>‐allyl nucleobases, with <i>trans</i>‐isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil‐containing cycloadducts. The <i>cis</i>‐ and <i>trans</i>‐isoxazolidine phosphonates obtained herein were evaluated <i>in vitro</i> for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC<sub>50</sub> values in the range of 33–100 µM.</p></section></abstract><abstract type="graphical"><p>Cycloadditions between <i>N</i>‐methyl‐<i>C</i>‐(diethoxyphosphoryl)nitrone and <i>N</i>‐allyl nucleobases led to isoxazolidine homonucleotides, with <i>trans</i>‐isoxazolidines predominating. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but compounds <i>cis</i>‐<b>11</b> and <i>trans</i>‐<b>11</b> (<b>B</b> = 5,6‐dimethylbenzo[<i>d</i>]imidazole, 3‐acetylindole, <i>N</i><sup>3</sup>‐benzoylbenzuracil) were found to inhibit the proliferation of L1210 cells (IC<sub>50</sub> = 33–100 µM).
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" copyright="© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim" href="urn:x-wiley:03656233:media:ardp201300382:ardp201300382-content"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Isoxazolidine Analogs of Homonucleotides</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides</title></titleInfo><name type="personal"><namePart type="given">Magdalena</namePart><namePart type="family">Łysakowska</namePart><affiliation>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland</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>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź, Poland</affiliation><affiliation>Dr. Dorota G. Piotrowska, Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, 90‐151 Łódź, Muszyńskiego 1, Poland. +48 42 678 83 98</affiliation><affiliation>E-mail: dorota.piotrowska@umed.lodz.pl</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">2014-05</dateIssued><dateCreated encoding="w3cdtf">2014-02-13</dateCreated><dateCaptured encoding="w3cdtf">2013-10-09</dateCaptured><dateValid encoding="w3cdtf">2013-11-22</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>Moderate diastereoselectivities (d.e. 2–62%) of isoxazolidine homonucleotides were observed for cycloadditions between N‐methyl‐C‐(diethoxyphosphoryl)nitrone and N‐allyl nucleobases, with trans‐isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil‐containing cycloadducts. The cis‐ and trans‐isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33–100 µM.</abstract><abstract type="graphical">Cycloadditions between N‐methyl‐C‐(diethoxyphosphoryl)nitrone and N‐allyl nucleobases led to isoxazolidine homonucleotides, with trans‐isoxazolidines predominating. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but compounds cis‐11 and trans‐11 (B = 5,6‐dimethylbenzo[d]imidazole, 3‐acetylindole, N3‐benzoylbenzuracil) were found to inhibit the proliferation of L1210 cells (IC50 = 33–100 µM).</abstract><note type="funding">Medical University of Łódź - No. 503/3‐014‐1/503‐06‐300; No. 502‐03‐/3‐014‐01/502‐34‐030; </note><note type="funding">KU Leuven - No. GOA 10/014; </note><subject lang="en"><genre>keywords</genre><topic>Antiproliferative agents</topic><topic>Cycloaddition</topic><topic>Isoxazolidines</topic></subject><relatedItem type="host"><titleInfo><title>Archiv der Pharmazie</title></titleInfo><titleInfo type="abbreviated"><title>Arch. Pharm. Chem. 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