Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues
Identifieur interne : 001271 ( Main/Exploration ); précédent : 001270; suivant : 001272Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues
Auteurs : Rosa Miralles-Llumà [Espagne] ; Antoni Figueras [Espagne] ; Félix Busqué [Espagne] ; Angel Alvarez-Larena [Espagne] ; Jan Balzarini [Belgique] ; Marta Figueredo [Espagne] ; Josep Font [Espagne] ; Ramon Alibés [Espagne, Canada] ; Jean-Didier Maréchal [Espagne, Canada]Source :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2013-12.
English descriptors
- Teeft :
- Acid monohydrate, Activation process, Agents chemother, Analogue, Antiviral, Antiviral activity, Aqueous phase, Argon atmosphere, Best binding mode, Binding modes, Binding site, Calcd, Cdcl3, Cell cultures, Chcl3, Chem, Column chromatography, Comprehensive screening, Cyclobutane, Cyclobutane moiety, Cyclobutene, Cyclobutene analogues, Dddd, Derivative, Diethyl ether, Diol, Docking, Docking calculations, Dowex, Dropwise, Entry code, Ether, Etoac, Etoh, Flash column chromatography, Full paper, Further purification, Gmbh, Gmpk, Guanine, Guanine derivatives, Hrms, Kgaa, Kinase, Lett, Meoh, Methylene spacer, Mitsunobu reaction, Mmol, Moiety, Natural nucleosides, Nucleoside, Nucleoside analogues, Original solution, Oxidative cleavage, Phosphorylation, Purine, Reaction mixture, Reflux, Reflux temperature, Relative configuration, Room temp, Target nucleoside analogue, Temp, Tetrahedron, Tetrahedron lett, Thymine, Thymine nucleoside, Verlag, Verlag gmbh, Vesicular stomatitis virus, Weinheim, White foam.
Abstract
This paper describes the stereoselective synthesis of a series of functionalized cyclobutane and cyclobutene L‐nucleoside analogues featuring a methylene spacer between the carbocycle and the nucleobase. These L‐nucleoside analogues were subjected to comprehensive screening for antiviral activity. To obtain knowledge at the molecular structural level relevant for designing future analogues, the mechanism of action of these L‐nucleoside analogues as anti‐herpes simplex virus agents was investigated by computational approaches. In particular, protein–ligand docking calculations were used to rationalize the ability of the prodrug candidates to be activated. Docking experiments were performed on the three kinases involved in the activation process of thymine and guanine derivatives.
Cyclobutane and cyclobutene L‐nucleoside analogues have been synthesized and screened for antiviral activity. The mechanism of action of their activation process as anti‐herpes simplex virus agents has been investigated by computational approaches.
Url:
DOI: 10.1002/ejoc.201301097
Affiliations:
- Belgique, Canada, Espagne
- Catalogne, Province du Brabant flamand
- Barcelone, Louvain
- Université autonome de Barcelone
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 000898
- to stream Istex, to step Curation: 000864
- to stream Istex, to step Checkpoint: 000038
- to stream Main, to step Merge: 001273
- to stream Main, to step Curation: 001271
Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues</title><author><name sortKey="Miralles Luma, Rosa" sort="Miralles Luma, Rosa" uniqKey="Miralles Luma R" first="Rosa" last="Miralles-Llumà">Rosa Miralles-Llumà</name></author><author><name sortKey="Figueras, Antoni" sort="Figueras, Antoni" uniqKey="Figueras A" first="Antoni" last="Figueras">Antoni Figueras</name></author><author><name sortKey="Busque, Felix" sort="Busque, Felix" uniqKey="Busque F" first="Félix" last="Busqué">Félix Busqué</name></author><author><name sortKey="Alvarez Arena, Angel" sort="Alvarez Arena, Angel" uniqKey="Alvarez Arena A" first="Angel" last="Alvarez-Larena">Angel Alvarez-Larena</name></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></author><author><name sortKey="Figueredo, Marta" sort="Figueredo, Marta" uniqKey="Figueredo M" first="Marta" last="Figueredo">Marta Figueredo</name></author><author><name sortKey="Font, Josep" sort="Font, Josep" uniqKey="Font J" first="Josep" last="Font">Josep Font</name></author><author><name sortKey="Alibes, Ramon" sort="Alibes, Ramon" uniqKey="Alibes R" first="Ramon" last="Alibés">Ramon Alibés</name></author><author><name sortKey="Marechal, Jean Idier" sort="Marechal, Jean Idier" uniqKey="Marechal J" first="Jean-Didier" last="Maréchal">Jean-Didier Maréchal</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:99BB5044A3372764643CA72CF269D1EBFD5ECA74</idno><date when="2013" year="2013">2013</date><idno type="doi">10.1002/ejoc.201301097</idno><idno type="url">https://api.istex.fr/ark:/67375/WNG-W30SRTHN-1/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">000898</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000898</idno><idno type="wicri:Area/Istex/Curation">000864</idno><idno type="wicri:Area/Istex/Checkpoint">000038</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000038</idno><idno type="wicri:doubleKey">1434-193X:2013:Miralles Luma R:synthesis:antiviral:evaluation</idno><idno type="wicri:Area/Main/Merge">001273</idno><idno type="wicri:Area/Main/Curation">001271</idno><idno type="wicri:Area/Main/Exploration">001271</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues</title><author><name sortKey="Miralles Luma, Rosa" sort="Miralles Luma, Rosa" uniqKey="Miralles Luma R" first="Rosa" last="Miralles-Llumà">Rosa Miralles-Llumà</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation></author><author><name sortKey="Figueras, Antoni" sort="Figueras, Antoni" uniqKey="Figueras A" first="Antoni" last="Figueras">Antoni Figueras</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation></author><author><name sortKey="Busque, Felix" sort="Busque, Felix" uniqKey="Busque F" first="Félix" last="Busqué">Félix Busqué</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation></author><author><name sortKey="Alvarez Arena, Angel" sort="Alvarez Arena, Angel" uniqKey="Alvarez Arena A" first="Angel" last="Alvarez-Larena">Angel Alvarez-Larena</name><affiliation wicri:level="4"><country xml:lang="fr">Espagne</country><wicri:regionArea>Servei de Cristallografia, Universitat Autònoma de Barcelona, 08193 Bellaterra</wicri:regionArea><placeName><region nuts="2" type="communauté">Catalogne</region><settlement type="city">Barcelone</settlement></placeName><orgName type="university">Université autonome de Barcelone</orgName></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="3"><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author><author><name sortKey="Figueredo, Marta" sort="Figueredo, Marta" uniqKey="Figueredo M" first="Marta" last="Figueredo">Marta Figueredo</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation></author><author><name sortKey="Font, Josep" sort="Font, Josep" uniqKey="Font J" first="Josep" last="Font">Josep Font</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation></author><author><name sortKey="Alibes, Ramon" sort="Alibes, Ramon" uniqKey="Alibes R" first="Ramon" last="Alibés">Ramon Alibés</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Canada</country></affiliation></author><author><name sortKey="Marechal, Jean Idier" sort="Marechal, Jean Idier" uniqKey="Marechal J" first="Jean-Didier" last="Maréchal">Jean-Didier Maréchal</name><affiliation wicri:level="4"><orgName type="university">Université autonome de Barcelone</orgName><country>Espagne</country><placeName><settlement type="city">Barcelone</settlement><region nuts="2" type="region">Catalogne</region></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Canada</country></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">European Journal of Organic Chemistry</title><title level="j" type="alt">EUROPEAN JOURNAL OF ORGANIC CHEMISTRY</title><idno type="ISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><imprint><biblScope unit="vol">2013</biblScope><biblScope unit="issue">34</biblScope><biblScope unit="page" from="7761">7761</biblScope><biblScope unit="page" to="7775">7775</biblScope><biblScope unit="page-count">15</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2013-12">2013-12</date></imprint><idno type="ISSN">1434-193X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1434-193X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Acid monohydrate</term><term>Activation process</term><term>Agents chemother</term><term>Analogue</term><term>Antiviral</term><term>Antiviral activity</term><term>Aqueous phase</term><term>Argon atmosphere</term><term>Best binding mode</term><term>Binding modes</term><term>Binding site</term><term>Calcd</term><term>Cdcl3</term><term>Cell cultures</term><term>Chcl3</term><term>Chem</term><term>Column chromatography</term><term>Comprehensive screening</term><term>Cyclobutane</term><term>Cyclobutane moiety</term><term>Cyclobutene</term><term>Cyclobutene analogues</term><term>Dddd</term><term>Derivative</term><term>Diethyl ether</term><term>Diol</term><term>Docking</term><term>Docking calculations</term><term>Dowex</term><term>Dropwise</term><term>Entry code</term><term>Ether</term><term>Etoac</term><term>Etoh</term><term>Flash column chromatography</term><term>Full paper</term><term>Further purification</term><term>Gmbh</term><term>Gmpk</term><term>Guanine</term><term>Guanine derivatives</term><term>Hrms</term><term>Kgaa</term><term>Kinase</term><term>Lett</term><term>Meoh</term><term>Methylene spacer</term><term>Mitsunobu reaction</term><term>Mmol</term><term>Moiety</term><term>Natural nucleosides</term><term>Nucleoside</term><term>Nucleoside analogues</term><term>Original solution</term><term>Oxidative cleavage</term><term>Phosphorylation</term><term>Purine</term><term>Reaction mixture</term><term>Reflux</term><term>Reflux temperature</term><term>Relative configuration</term><term>Room temp</term><term>Target nucleoside analogue</term><term>Temp</term><term>Tetrahedron</term><term>Tetrahedron lett</term><term>Thymine</term><term>Thymine nucleoside</term><term>Verlag</term><term>Verlag gmbh</term><term>Vesicular stomatitis virus</term><term>Weinheim</term><term>White foam</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">This paper describes the stereoselective synthesis of a series of functionalized cyclobutane and cyclobutene L‐nucleoside analogues featuring a methylene spacer between the carbocycle and the nucleobase. These L‐nucleoside analogues were subjected to comprehensive screening for antiviral activity. To obtain knowledge at the molecular structural level relevant for designing future analogues, the mechanism of action of these L‐nucleoside analogues as anti‐herpes simplex virus agents was investigated by computational approaches. In particular, protein–ligand docking calculations were used to rationalize the ability of the prodrug candidates to be activated. Docking experiments were performed on the three kinases involved in the activation process of thymine and guanine derivatives.</div><div type="abstract" xml:lang="en">Cyclobutane and cyclobutene L‐nucleoside analogues have been synthesized and screened for antiviral activity. The mechanism of action of their activation process as anti‐herpes simplex virus agents has been investigated by computational approaches.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Canada</li><li>Espagne</li></country><region><li>Catalogne</li><li>Province du Brabant flamand</li></region><settlement><li>Barcelone</li><li>Louvain</li></settlement><orgName><li>Université autonome de Barcelone</li></orgName></list><tree><country name="Espagne"><region name="Catalogne"><name sortKey="Miralles Luma, Rosa" sort="Miralles Luma, Rosa" uniqKey="Miralles Luma R" first="Rosa" last="Miralles-Llumà">Rosa Miralles-Llumà</name></region><name sortKey="Alibes, Ramon" sort="Alibes, Ramon" uniqKey="Alibes R" first="Ramon" last="Alibés">Ramon Alibés</name><name sortKey="Alvarez Arena, Angel" sort="Alvarez Arena, Angel" uniqKey="Alvarez Arena A" first="Angel" last="Alvarez-Larena">Angel Alvarez-Larena</name><name sortKey="Busque, Felix" sort="Busque, Felix" uniqKey="Busque F" first="Félix" last="Busqué">Félix Busqué</name><name sortKey="Figueras, Antoni" sort="Figueras, Antoni" uniqKey="Figueras A" first="Antoni" last="Figueras">Antoni Figueras</name><name sortKey="Figueredo, Marta" sort="Figueredo, Marta" uniqKey="Figueredo M" first="Marta" last="Figueredo">Marta Figueredo</name><name sortKey="Font, Josep" sort="Font, Josep" uniqKey="Font J" first="Josep" last="Font">Josep Font</name><name sortKey="Marechal, Jean Idier" sort="Marechal, Jean Idier" uniqKey="Marechal J" first="Jean-Didier" last="Maréchal">Jean-Didier Maréchal</name></country><country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></region></country><country name="Canada"><noRegion><name sortKey="Alibes, Ramon" sort="Alibes, Ramon" uniqKey="Alibes R" first="Ramon" last="Alibés">Ramon Alibés</name></noRegion><name sortKey="Marechal, Jean Idier" sort="Marechal, Jean Idier" uniqKey="Marechal J" first="Jean-Didier" last="Maréchal">Jean-Didier Maréchal</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Sante/explor/CovidV2/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001271 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 001271 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Sante
|area= CovidV2
|flux= Main
|étape= Exploration
|type= RBID
|clé= ISTEX:99BB5044A3372764643CA72CF269D1EBFD5ECA74
|texte= Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues
}}
| This area was generated with Dilib version V0.6.33. |  |