Synthesis and anti-HIV activity evaluation of novel N ′-arylidene-2-[1-(naphthalen-1-yl)-1 H -tetrazol-5-ylthio]acetohydrazides
Identifieur interne : 001930 ( Istex/Corpus ); précédent : 001929; suivant : 001931Synthesis and anti-HIV activity evaluation of novel N ′-arylidene-2-[1-(naphthalen-1-yl)-1 H -tetrazol-5-ylthio]acetohydrazides
Auteurs : Peng Zhan ; Hongbing Liu ; Xinyong Liu ; Yan Wang ; Christophe Pannecouque ; Myriam Witvrouw ; Erik De ClercqSource :
- Medicinal Chemistry Research [ 1054-2523 ] ; 2010-09-01.
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Abstract
Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides was synthesized and evaluated, as nonnucleoside reverse transcriptase inhibitors (NNRTIs), for their in vitro HIV-1 and HIV-2 activity using the IIIB strain and ROD strain, respectively. The activity was monitored by the inhibition of the virus-induced cytopathic effect in the human T-lymphocyte (MT-4) cells. All of the new compounds were structurally confirmed by spectral analyses. Compounds 5q and 5r showed EC50 of 29.62 μM (CC50 of 169.24 ± 23.83μM) and 31.62 μM (CC50 > 309.06 μM), and resulting in selectivity index of 6 and >9, respectively. However, all newly synthesized derivatives were not active against HIV-2 replication. Graphical Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides were synthesized and evaluated for their anti-HIV activities in MT-4 cell culture. Two compounds exhibited potent inhibitory activity specifically against HIV-1 replication.
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DOI: 10.1007/s00044-009-9220-x
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People’s Republic of China</mods:affiliation></affiliation></author><author><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><affiliation><mods:affiliation>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: xinyongl@sdu.edu.cn</mods:affiliation></affiliation></author><author><name sortKey="Wang, Yan" sort="Wang, Yan" uniqKey="Wang Y" first="Yan" last="Wang">Yan Wang</name><affiliation><mods:affiliation>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</mods:affiliation></affiliation></author><author><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name><affiliation><mods:affiliation>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</mods:affiliation></affiliation></author><author><name sortKey="Witvrouw, Myriam" sort="Witvrouw, Myriam" uniqKey="Witvrouw M" first="Myriam" last="Witvrouw">Myriam Witvrouw</name><affiliation><mods:affiliation>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</mods:affiliation></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation><mods:affiliation>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Medicinal Chemistry Research</title><title level="j" type="abbrev">Med Chem Res</title><idno type="ISSN">1054-2523</idno><idno 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transcriptase inhibitors (NNRTIs), for their in vitro HIV-1 and HIV-2 activity using the IIIB strain and ROD strain, respectively. The activity was monitored by the inhibition of the virus-induced cytopathic effect in the human T-lymphocyte (MT-4) cells. All of the new compounds were structurally confirmed by spectral analyses. Compounds 5q and 5r showed EC50 of 29.62 μM (CC50 of 169.24 ± 23.83μM) and 31.62 μM (CC50 > 309.06 μM), and resulting in selectivity index of 6 and >9, respectively. However, all newly synthesized derivatives were not active against HIV-2 replication. Graphical Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides were synthesized and evaluated for their anti-HIV activities in MT-4 cell culture. Two compounds exhibited potent inhibitory activity specifically against HIV-1 replication.</div></front></TEI><istex><corpusName>springer-journals</corpusName><author><json:item><name>Peng Zhan</name><affiliations><json:string>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</json:string></affiliations></json:item><json:item><name>Hongbing Liu</name><affiliations><json:string>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</json:string></affiliations></json:item><json:item><name>Xinyong Liu</name><affiliations><json:string>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</json:string><json:string>E-mail: xinyongl@sdu.edu.cn</json:string></affiliations></json:item><json:item><name>Yan Wang</name><affiliations><json:string>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</json:string></affiliations></json:item><json:item><name>Christophe Pannecouque</name><affiliations><json:string>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</json:string></affiliations></json:item><json:item><name>Myriam Witvrouw</name><affiliations><json:string>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</json:string></affiliations></json:item><json:item><name>Erik De Clercq</name><affiliations><json:string>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>HIV-1</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>AIDS</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>NNRTIs</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Tetrazole</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Acetohydrazides</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Antiviral activity</value></json:item></subject><articleId><json:string>9220</json:string><json:string>s00044-009-9220-x</json:string></articleId><arkIstex>ark:/67375/VQC-VLS8LPLD-S</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>OriginalPaper</json:string></originalGenre><abstract>Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides was synthesized and evaluated, as nonnucleoside reverse transcriptase inhibitors (NNRTIs), for their in vitro HIV-1 and HIV-2 activity using the IIIB strain and ROD strain, respectively. The activity was monitored by the inhibition of the virus-induced cytopathic effect in the human T-lymphocyte (MT-4) cells. All of the new compounds were structurally confirmed by spectral analyses. Compounds 5q and 5r showed EC50 of 29.62 μM (CC50 of 169.24 ± 23.83μM) and 31.62 μM (CC50 > 309.06 μM), and resulting in selectivity index of 6 and >9, respectively. However, all newly synthesized derivatives were not active against HIV-2 replication. Graphical Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides were synthesized and evaluated for their anti-HIV activities in MT-4 cell culture. 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The activity was monitored by the inhibition of the virus-induced cytopathic effect in the human T-lymphocyte (MT-4) cells. All of the new compounds were structurally confirmed by spectral analyses. Compounds 5q and 5r showed EC50 of 29.62 μM (CC50 of 169.24 ± 23.83μM) and 31.62 μM (CC50 > 309.06 μM), and resulting in selectivity index of 6 and >9, respectively. However, all newly synthesized derivatives were not active against HIV-2 replication. Graphical Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides were synthesized and evaluated for their anti-HIV activities in MT-4 cell culture. Two compounds exhibited potent inhibitory activity specifically against HIV-1 replication.</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>Keywords</head><item><term>HIV-1</term></item><item><term>AIDS</term></item><item><term>NNRTIs</term></item><item><term>Tetrazole</term></item><item><term>Acetohydrazides</term></item><item><term>Antiviral activity</term></item></list></keywords></textClass><textClass><keywords scheme="Journal Subject"><list><head>Biomedicine</head><item><term>Cell Biology</term></item><item><term>Biochemistry, general</term></item><item><term>Pharmacology/Toxicology</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2009-02-15">Created</change><change 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Type="Italic">H</Emphasis>-tetrazol-5-ylthio]acetohydrazides</ArticleTitle><ArticleCategory>Original Research</ArticleCategory><ArticleFirstPage>652</ArticleFirstPage><ArticleLastPage>663</ArticleLastPage><ArticleHistory><RegistrationDate><Year>2009</Year><Month>4</Month><Day>22</Day></RegistrationDate><Received><Year>2009</Year><Month>2</Month><Day>15</Day></Received><Accepted><Year>2009</Year><Month>4</Month><Day>21</Day></Accepted><OnlineDate><Year>2009</Year><Month>5</Month><Day>29</Day></OnlineDate></ArticleHistory><ArticleCopyright><CopyrightHolderName>Birkhäuser Boston</CopyrightHolderName><CopyrightYear>2009</CopyrightYear></ArticleCopyright><ArticleGrants Type="Regular"><MetadataGrant Grant="OpenAccess"></MetadataGrant><AbstractGrant Grant="OpenAccess"></AbstractGrant><BodyPDFGrant Grant="Restricted"></BodyPDFGrant><BodyHTMLGrant Grant="Restricted"></BodyHTMLGrant><BibliographyGrant Grant="Restricted"></BibliographyGrant><ESMGrant Grant="Restricted"></ESMGrant></ArticleGrants></ArticleInfo><ArticleHeader><AuthorGroup><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Peng</GivenName><FamilyName>Zhan</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Hongbing</GivenName><FamilyName>Liu</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff1" CorrespondingAffiliationID="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Xinyong</GivenName><FamilyName>Liu</FamilyName></AuthorName><Contact><Email>xinyongl@sdu.edu.cn</Email></Contact></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Yan</GivenName><FamilyName>Wang</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Christophe</GivenName><FamilyName>Pannecouque</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Myriam</GivenName><FamilyName>Witvrouw</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Erik</GivenName><Particle>De</Particle><FamilyName>Clercq</FamilyName></AuthorName></Author><Affiliation ID="Aff1"><OrgDivision>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences</OrgDivision><OrgName>Shandong University</OrgName><OrgAddress><Street>No. 44 Wenhuaxi Road</Street><City>Jinan</City><Postcode>250012</Postcode><Country Code="CN">People’s Republic of China</Country></OrgAddress></Affiliation><Affiliation ID="Aff2"><OrgDivision>Rega Institute for Medical Research</OrgDivision><OrgName>Katholieke Universiteit Leuven</OrgName><OrgAddress><City>Leuven</City><Postcode>B-3000</Postcode><Country Code="BE">Belgium</Country></OrgAddress></Affiliation></AuthorGroup><Abstract ID="Abs1" Language="En" OutputMedium="All"><AbstractSection ID="ASec1"><Heading>Abstract</Heading><Para>A series of novel <Emphasis Type="Italic">N</Emphasis>′-arylidene-2-[1-(naphthalen-1-yl)-1<Emphasis Type="Italic">H</Emphasis>-tetrazol-5-ylthio] acetohydrazides was synthesized and evaluated, as nonnucleoside reverse transcriptase inhibitors (NNRTIs), for their in vitro HIV-1 and HIV-2 activity using the IIIB strain and ROD strain, respectively. The activity was monitored by the inhibition of the virus-induced cytopathic effect in the human T-lymphocyte (MT-4) cells. All of the new compounds were structurally confirmed by spectral analyses. Compounds <Emphasis Type="Bold">5q</Emphasis> and <Emphasis Type="Bold">5r</Emphasis> showed EC<Subscript>50</Subscript> of 29.62 μM (CC<Subscript>50</Subscript> of 169.24 ± 23.83μM) and 31.62 μM (CC<Subscript>50</Subscript> > 309.06 μM), and resulting in selectivity index of 6 and >9, respectively. However, all newly synthesized derivatives were not active against HIV-2 replication.</Para></AbstractSection><AbstractSection ID="ASec2" OutputMedium="Online"><Heading>Graphical Abstract</Heading><Para>A series of novel <Emphasis Type="Italic">N</Emphasis>′-arylidene-2-[1-(naphthalen-1-yl)-1<Emphasis Type="Italic">H</Emphasis>-tetrazol-5-ylthio] acetohydrazides were synthesized and evaluated for their anti-HIV activities in MT-4 cell culture. Two compounds exhibited potent inhibitory activity specifically against HIV-1 replication.<Figure Category="Standard" Float="No" ID="Figa"><MediaObject ID="MO1"><ImageObject Color="BlackWhite" Format="GIF" Rendition="HTML" Type="Linedraw" FileRef="MediaObjects/44_2009_9220_Figa_HTML.gif"></ImageObject></MediaObject></Figure></Para></AbstractSection></Abstract><KeywordGroup Language="En" OutputMedium="All"><Heading>Keywords</Heading><Keyword>HIV-1</Keyword><Keyword>AIDS</Keyword><Keyword>NNRTIs</Keyword><Keyword>Tetrazole</Keyword><Keyword>Acetohydrazides</Keyword><Keyword>Antiviral activity</Keyword></KeywordGroup></ArticleHeader><NoBody></NoBody></Article></Issue></Volume></Journal></Publisher></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis and anti-HIV activity evaluation of novel N ′-arylidene-2-[1-(naphthalen-1-yl)-1 H -tetrazol-5-ylthio]acetohydrazides</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Synthesis and anti-HIV activity evaluation of novel N ′-arylidene-2-[1-(naphthalen-1-yl)-1 H -tetrazol-5-ylthio]acetohydrazides</title></titleInfo><name type="personal"><namePart type="given">Peng</namePart><namePart type="family">Zhan</namePart><affiliation>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Hongbing</namePart><namePart type="family">Liu</namePart><affiliation>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal" displayLabel="corresp"><namePart type="given">Xinyong</namePart><namePart type="family">Liu</namePart><affiliation>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</affiliation><affiliation>E-mail: xinyongl@sdu.edu.cn</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Yan</namePart><namePart type="family">Wang</namePart><affiliation>Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 Wenhuaxi Road, 250012, Jinan, People’s Republic of China</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Christophe</namePart><namePart type="family">Pannecouque</namePart><affiliation>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Myriam</namePart><namePart type="family">Witvrouw</namePart><affiliation>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Erik</namePart><namePart type="family">De Clercq</namePart><affiliation>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="OriginalPaper" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>SP Birkhäuser Verlag Boston</publisher><place><placeTerm type="text">Boston</placeTerm></place><dateCreated encoding="w3cdtf">2009-02-15</dateCreated><dateIssued encoding="w3cdtf">2010-09-01</dateIssued><copyrightDate encoding="w3cdtf">2009</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><abstract lang="en">Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides was synthesized and evaluated, as nonnucleoside reverse transcriptase inhibitors (NNRTIs), for their in vitro HIV-1 and HIV-2 activity using the IIIB strain and ROD strain, respectively. The activity was monitored by the inhibition of the virus-induced cytopathic effect in the human T-lymphocyte (MT-4) cells. All of the new compounds were structurally confirmed by spectral analyses. Compounds 5q and 5r showed EC50 of 29.62 μM (CC50 of 169.24 ± 23.83μM) and 31.62 μM (CC50 > 309.06 μM), and resulting in selectivity index of 6 and >9, respectively. However, all newly synthesized derivatives were not active against HIV-2 replication. Graphical Abstract: A series of novel N′-arylidene-2-[1-(naphthalen-1-yl)-1H-tetrazol-5-ylthio] acetohydrazides were synthesized and evaluated for their anti-HIV activities in MT-4 cell culture. Two compounds exhibited potent inhibitory activity specifically against HIV-1 replication.</abstract><note>Original Research</note><subject lang="en"><genre>Keywords</genre><topic>HIV-1</topic><topic>AIDS</topic><topic>NNRTIs</topic><topic>Tetrazole</topic><topic>Acetohydrazides</topic><topic>Antiviral activity</topic></subject><relatedItem type="host"><titleInfo><title>Medicinal Chemistry Research</title></titleInfo><titleInfo type="abbreviated"><title>Med Chem Res</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><originInfo><publisher>Springer</publisher><dateIssued encoding="w3cdtf">2010-07-29</dateIssued><copyrightDate encoding="w3cdtf">2010</copyrightDate></originInfo><subject><genre>Biomedicine</genre><topic>Cell Biology</topic><topic>Biochemistry, general</topic><topic>Pharmacology/Toxicology</topic></subject><identifier type="ISSN">1054-2523</identifier><identifier type="eISSN">1554-8120</identifier><identifier type="JournalID">44</identifier><identifier type="IssueArticleCount">8</identifier><identifier type="VolumeIssueCount">9</identifier><part><date>2010</date><detail type="volume"><number>19</number><caption>vol.</caption></detail><detail type="issue"><number>7</number><caption>no.</caption></detail><extent unit="pages"><start>652</start><end>663</end></extent></part><recordInfo><recordOrigin>Springer Science+Business Media, LLC, 2010</recordOrigin></recordInfo></relatedItem><identifier type="istex">55A5BEFD982BE6AC58F668CB35500CF60D434AC7</identifier><identifier type="ark">ark:/67375/VQC-VLS8LPLD-S</identifier><identifier type="DOI">10.1007/s00044-009-9220-x</identifier><identifier type="ArticleID">9220</identifier><identifier type="ArticleID">s00044-009-9220-x</identifier><accessCondition type="use and reproduction" contentType="copyright">Birkhäuser Boston, 2009</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-3XSW68JL-F">springer</recordContentSource><recordOrigin>Birkhäuser Boston, 2009</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/ark:/67375/VQC-VLS8LPLD-S/record.json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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