Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides
Identifieur interne : 000A62 ( Main/Exploration ); précédent : 000A61; suivant : 000A63Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides
Auteurs : Magdalena Łysakowska [Pologne] ; Jan Balzarini [Belgique] ; Dorota G. Piotrowska [Pologne]Source :
- 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).
Url:
DOI: 10.1002/ardp.201300382
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 000856
- to stream Istex, to step Curation: 000836
- to stream Istex, to step Checkpoint: 000031
- to stream Main, to step Merge: 000A64
- to stream Main, to step Curation: 000A62
Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides</title><author><name sortKey="Lysakowska, Magdalena" sort="Lysakowska, Magdalena" uniqKey="Lysakowska M" first="Magdalena" last="Łysakowska">Magdalena Łysakowska</name></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></author><author><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:81623B75D2E813127AAE28534F4481C7633E4EF4</idno><date when="2014" year="2014">2014</date><idno type="doi">10.1002/ardp.201300382</idno><idno type="url">https://api.istex.fr/ark:/67375/WNG-MRMBVVF2-T/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">000856</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000856</idno><idno type="wicri:Area/Istex/Curation">000836</idno><idno type="wicri:Area/Istex/Checkpoint">000031</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000031</idno><idno type="wicri:doubleKey">0365-6233:2014:Lysakowska M:design:synthesis:antiviral</idno><idno type="wicri:Area/Main/Merge">000A64</idno><idno type="wicri:Area/Main/Curation">000A62</idno><idno type="wicri:Area/Main/Exploration">000A62</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides</title><author><name sortKey="Lysakowska, Magdalena" sort="Lysakowska, Magdalena" uniqKey="Lysakowska M" first="Magdalena" last="Łysakowska">Magdalena Łysakowska</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź</wicri:regionArea><wicri:noRegion>Łódź</wicri:noRegion></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="1"><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Leuven</wicri:regionArea><wicri:noRegion>Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Pharmacy, Bioorganic Chemistry Laboratory, Medical University of Łódź, Łódź</wicri:regionArea><wicri:noRegion>Łódź</wicri:noRegion></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Pologne</country></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><affiliations><list><country><li>Belgique</li><li>Pologne</li></country></list><tree><country name="Pologne"><noRegion><name sortKey="Lysakowska, Magdalena" sort="Lysakowska, Magdalena" uniqKey="Lysakowska M" first="Magdalena" last="Łysakowska">Magdalena Łysakowska</name></noRegion><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name></country><country name="Belgique"><noRegion><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Sante/explor/CovidV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000A62 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000A62 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Sante
|area= CovidV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= ISTEX:81623B75D2E813127AAE28534F4481C7633E4EF4
|texte= Design, Synthesis, Antiviral, and Cytostatic Evaluation of Novel Isoxazolidine Analogs of Homonucleotides
}}
| This area was generated with Dilib version V0.6.33. |  |