Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues
Identifieur interne : 000898 ( Istex/Corpus ); précédent : 000897; suivant : 000899Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues
Auteurs : Rosa Miralles-Llumà ; Antoni Figueras ; Félix Busqué ; Angel Alvarez-Larena ; Jan Balzarini ; Marta Figueredo ; Josep Font ; Ramon Alibés ; Jean-Didier MaréchalSource :
- 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
Links to Exploration step
ISTEX:99BB5044A3372764643CA72CF269D1EBFD5ECA74Le document en format XML
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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><mods:affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</mods:affiliation></affiliation></author><author><name sortKey="Figueras, Antoni" sort="Figueras, Antoni" uniqKey="Figueras A" first="Antoni" last="Figueras">Antoni Figueras</name><affiliation><mods:affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</mods:affiliation></affiliation></author><author><name sortKey="Busque, Felix" sort="Busque, Felix" uniqKey="Busque F" first="Félix" last="Busqué">Félix Busqué</name><affiliation><mods:affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, 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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. 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Spain</json:string></affiliations></json:item><json:item><name>Jan Balzarini</name><affiliations><json:string>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium</json:string></affiliations></json:item><json:item><name>Marta Figueredo</name><affiliations><json:string>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</json:string></affiliations></json:item><json:item><name>Josep Font</name><affiliations><json:string>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</json:string></affiliations></json:item><json:item><name>Ramon Alibés</name><affiliations><json:string>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</json:string><json:string>E-mail: ramon.alibes@uab.cat</json:string></affiliations></json:item><json:item><name>Jean‐Didier Maréchal</name><affiliations><json:string>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</json:string><json:string>E-mail: jeandidier.marechal@uab.cat</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Antiviral agents</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Nucleosides</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Carbocycles</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Molecular modeling</value></json:item></subject><articleId><json:string>EJOC201301097</json:string></articleId><arkIstex>ark:/67375/WNG-W30SRTHN-1</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><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. 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Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Antoni</forename><surname>Figueras</surname></persName><affiliation><orgName type="division">Departament de Química</orgName><orgName type="institution">Universitat Autònoma de Barcelona</orgName><address><addrLine>08193 Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0002"><persName><forename type="first">Félix</forename><surname>Busqué</surname></persName><affiliation><orgName type="division">Departament de Química</orgName><orgName type="institution">Universitat Autònoma de Barcelona</orgName><address><addrLine>08193 Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0003"><persName><forename type="first">Angel</forename><surname>Alvarez‐Larena</surname></persName><affiliation><address><addrLine>Servei de Cristallografia</addrLine><addrLine>Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0004"><persName><forename type="first">Jan</forename><surname>Balzarini</surname></persName><affiliation><orgName type="institution">Rega Institute for Medical Research</orgName><address><addrLine>KU Leuven</addrLine><addrLine>Minderbroedersstraat 10, 3000 Leuven, Belgium</addrLine><country key="BE" xml:lang="en">BELGIUM</country></address></affiliation></author><author xml:id="author-0005"><persName><forename type="first">Marta</forename><surname>Figueredo</surname></persName><affiliation><orgName type="division">Departament de Química</orgName><orgName type="institution">Universitat Autònoma de Barcelona</orgName><address><addrLine>08193 Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0006"><persName><forename type="first">Josep</forename><surname>Font</surname></persName><affiliation><orgName type="division">Departament de Química</orgName><orgName type="institution">Universitat Autònoma de Barcelona</orgName><address><addrLine>08193 Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0007"><persName><forename type="first">Ramon</forename><surname>Alibés</surname></persName><email>ramon.alibes@uab.cat</email><affiliation><orgName type="division">Departament de Química</orgName><orgName type="institution">Universitat Autònoma de Barcelona</orgName><address><addrLine>08193 Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><author xml:id="author-0008"><persName><forename type="first">Jean‐Didier</forename><surname>Maréchal</surname></persName><email>jeandidier.marechal@uab.cat</email><affiliation><orgName type="division">Departament de Química</orgName><orgName type="institution">Universitat Autònoma de Barcelona</orgName><address><addrLine>08193 Bellaterra</addrLine><addrLine>Spain, http://grupsderecerca.uab.cat/gr.soe</addrLine><country key="ES" xml:lang="en">SPAIN</country></address></affiliation></author><idno type="istex">99BB5044A3372764643CA72CF269D1EBFD5ECA74</idno><idno type="ark">ark:/67375/WNG-W30SRTHN-1</idno><idno type="DOI">10.1002/ejoc.201301097</idno><idno type="unit">EJOC201301097</idno><idno type="toTypesetVersion">file:EJOC.EJOC201301097.pdf</idno></analytic><monogr><title level="j" type="main">European Journal of Organic Chemistry</title><title level="j" type="alt">EUROPEAN JOURNAL OF ORGANIC CHEMISTRY</title><idno type="pISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><idno type="book-DOI">10.1002/(ISSN)1099-0690</idno><idno type="book-part-DOI">10.1002/ejoc.v2013.34</idno><idno type="product">EJOC</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"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><encodingDesc><schemaRef type="ODD" url="https://xml-schema.delivery.istex.fr/tei-istex.odd"></schemaRef><appInfo><application ident="pub2tei" version="1.0.10" when="2019-12-20"><label>pub2TEI-ISTEX</label><desc>A set of style sheets for converting XML 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<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>This paper describes the stereoselective synthesis of a series of functionalized cyclobutane and cyclobutene <hi rend="smallCaps">L</hi>‐nucleoside analogues featuring a methylene spacer between the carbocycle and the nucleobase. These <hi rend="smallCaps">L</hi>‐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 <hi rend="smallCaps">L</hi>‐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.</p></abstract><abstract xml:lang="en" style="graphical"><p>Cyclobutane and cyclobutene <hi rend="smallCaps">L</hi>‐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.
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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2013-07-23"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:3.2.6 mode:FullText mathml2tex" date="2013-11-20"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.2.6 mode:FullText" date="2013-11-20"></event><event type="publishedOnlineEarlyUnpaginated" date="2013-10-09"></event><event type="firstOnline" date="2013-10-09"></event><event type="publishedOnlineFinalForm" date="2013-11-20"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.6.4 mode:FullText" date="2015-10-02"></event></eventGroup><numberingGroup><numbering type="pageFirst">7761</numbering><numbering type="pageLast">7775</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:EJOC.EJOC201301097.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="5"></count><count type="tableTotal" number="0"></count><count type="referenceTotal" number="46"></count></countGroup><titleGroup><title type="main" xml:lang="en">Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene <sc>L</sc>‐Nucleoside Analogues</title><title type="short" xml:lang="en">Cyclobutane and Cyclobutene <sc>L</sc>‐Nucleoside Analogues</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Rosa</givenNames><familyName>Miralles‐Llumà</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Antoni</givenNames><familyName>Figueras</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Félix</givenNames><familyName>Busqué</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Angel</givenNames><familyName>Alvarez‐Larena</familyName></personName></creator><creator xml:id="au5" creatorRole="author" affiliationRef="#af3"><personName><givenNames>Jan</givenNames><familyName>Balzarini</familyName></personName></creator><creator xml:id="au6" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Marta</givenNames><familyName>Figueredo</familyName></personName></creator><creator xml:id="au7" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Josep</givenNames><familyName>Font</familyName></personName></creator><creator xml:id="au8" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Ramon</givenNames><familyName>Alibés</familyName></personName><contactDetails><email>ramon.alibes@uab.cat</email></contactDetails></creator><creator xml:id="au9" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Jean‐Didier</givenNames><familyName>Maréchal</familyName></personName><contactDetails><email>jeandidier.marechal@uab.cat</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="ES" type="organization"><unparsedAffiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, <url href="http://grupsderecerca.uab.cat/gr.soe">http://grupsderecerca.uab.cat/gr.soe</url></unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="ES" type="organization"><unparsedAffiliation>Servei de Cristallografia, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="BE" type="organization"><unparsedAffiliation>Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Antiviral agents</keyword><keyword xml:id="kwd2">Nucleosides</keyword><keyword xml:id="kwd3">Carbocycles</keyword><keyword xml:id="kwd4">Molecular modeling</keyword></keywordGroup><supportingInformation><p>As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
</p><supportingInfoItem><mediaResource alt="supporting information" href="urn-x:wiley:1434193X:media:ejoc201301097:ejoc_201301097_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>This paper describes the stereoselective synthesis of a series of functionalized cyclobutane and cyclobutene <sc>L</sc>‐nucleoside analogues featuring a methylene spacer between the carbocycle and the nucleobase. These <sc>L</sc>‐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 <sc>L</sc>‐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.</p></abstract><abstract type="graphical" xml:lang="en"><p>Cyclobutane and cyclobutene <sc>L</sc>‐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.
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:1434193X:media:EJOC201301097:fig000"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Cyclobutane and Cyclobutene L‐Nucleoside Analogues</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues</title></titleInfo><name type="personal"><namePart type="given">Rosa</namePart><namePart type="family">Miralles‐Llumà</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Antoni</namePart><namePart type="family">Figueras</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Félix</namePart><namePart type="family">Busqué</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Angel</namePart><namePart type="family">Alvarez‐Larena</namePart><affiliation>Servei de Cristallografia, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain</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, Minderbroedersstraat 10, 3000 Leuven, Belgium</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Marta</namePart><namePart type="family">Figueredo</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Josep</namePart><namePart type="family">Font</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Ramon</namePart><namePart type="family">Alibés</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><affiliation>E-mail: ramon.alibes@uab.cat</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jean‐Didier</namePart><namePart type="family">Maréchal</namePart><affiliation>Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain, http://grupsderecerca.uab.cat/gr.soe</affiliation><affiliation>E-mail: jeandidier.marechal@uab.cat</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">2013-12</dateIssued><dateCaptured encoding="w3cdtf">2013-07-23</dateCaptured><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">5</extent><extent unit="tables">0</extent><extent unit="references">46</extent></physicalDescription><abstract 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.</abstract><abstract type="graphical" 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.</abstract><subject lang="en"><genre>keywords</genre><topic>Antiviral agents</topic><topic>Nucleosides</topic><topic>Carbocycles</topic><topic>Molecular modeling</topic></subject><relatedItem type="host"><titleInfo><title>European Journal of Organic Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>Eur. J. Org. Chem.</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><note type="content"> As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. 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