Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1
Identifieur interne : 000866 ( Istex/Corpus ); précédent : 000865; suivant : 000867Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1
Auteurs : Esra Tatar ; Lkay Küçükgüzel ; Dirk Daelemans ; Tanaji T. Talele ; Neerja Kaushik-Basu ; Erik De Clercq ; Christophe PannecouqueSource :
- Archiv der Pharmazie [ 0365-6233 ] ; 2013-02.
English descriptors
- Teeft :
- Acid hydrazide, Acylhydrazone, Acylhydrazones, Alkyl, Amide, Amino acid side chains, Anal, Antiviral, Antiviral activity, Assay, Biol, Bioorg, Calcd, Cell culture, Chem, Clercq, Compound, Crude product, Default parameters, Derivative, Dextran sulfate, Docking, Gmbh, Hplc, Hydrazide, Hydrazine hydrate, Hydrazone, Hydrazone derivatives, Hydrazones, Iiib, Iiib nnrtir, Information table, Inhibitor, Kgaa, Ltered, Marmara university, Moiety, Nnrti, Nnrti mode, Novel site, Online version, Petroleum ether, Pharm, Reaction medium, Stereoselective, Stereoselective inhibitors, Tatar, Test compound, Test compounds, Transcriptase, Verlag, Verlag gmbh, Weinheim, Weinheim arch, Weinheim hydrazones, Wild type.
Abstract
In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC50) = 123.8 µM (selectivity index, SI > 3), IC50 = 12.1 µM (SI > 29), IC50 = 17.4 µM (SI > 19), respectively. Enantiomers 8R, 11R, and 12R were inactive against the HIV‐1 strain IIIB. Hydrazones 8S, 11S, and 12S which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.
Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. 8 S, 11 S, and 12 S showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers 8R, 11R, and 12 R were inactive against HIV‐1 strain IIIB. Molecular docking calculations of the R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.
Url:
DOI: 10.1002/ardp.201200311
Links to Exploration step
ISTEX:7F0B79C3003E6A746C16DD9A4FBEC596D1488B8DLe document en format XML
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Talele</name><affiliation><mods:affiliation>Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, St. John's University, Queens, NY, USA</mods:affiliation></affiliation></author><author><name sortKey="Kaushik Asu, Neerja" sort="Kaushik Asu, Neerja" uniqKey="Kaushik Asu N" first="Neerja" last="Kaushik-Basu">Neerja Kaushik-Basu</name><affiliation><mods:affiliation>Department of Biochemistry and Molecular Biology, UMDNJ‐New Jersey Medical School, Newark, NJ, USA</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, KU Leuven, Leuven, Belgium</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, KU Leuven, Leuven, Belgium</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">346</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="140">140</biblScope><biblScope unit="page" to="153">153</biblScope><biblScope unit="page-count">14</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2013-02">2013-02</date></imprint><idno type="ISSN">0365-6233</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0365-6233</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Acid hydrazide</term><term>Acylhydrazone</term><term>Acylhydrazones</term><term>Alkyl</term><term>Amide</term><term>Amino acid side chains</term><term>Anal</term><term>Antiviral</term><term>Antiviral activity</term><term>Assay</term><term>Biol</term><term>Bioorg</term><term>Calcd</term><term>Cell culture</term><term>Chem</term><term>Clercq</term><term>Compound</term><term>Crude product</term><term>Default parameters</term><term>Derivative</term><term>Dextran sulfate</term><term>Docking</term><term>Gmbh</term><term>Hplc</term><term>Hydrazide</term><term>Hydrazine hydrate</term><term>Hydrazone</term><term>Hydrazone derivatives</term><term>Hydrazones</term><term>Iiib</term><term>Iiib nnrtir</term><term>Information table</term><term>Inhibitor</term><term>Kgaa</term><term>Ltered</term><term>Marmara university</term><term>Moiety</term><term>Nnrti</term><term>Nnrti mode</term><term>Novel site</term><term>Online version</term><term>Petroleum ether</term><term>Pharm</term><term>Reaction medium</term><term>Stereoselective</term><term>Stereoselective inhibitors</term><term>Tatar</term><term>Test compound</term><term>Test compounds</term><term>Transcriptase</term><term>Verlag</term><term>Verlag gmbh</term><term>Weinheim</term><term>Weinheim arch</term><term>Weinheim hydrazones</term><term>Wild type</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC50) = 123.8 µM (selectivity index, SI > 3), IC50 = 12.1 µM (SI > 29), IC50 = 17.4 µM (SI > 19), respectively. Enantiomers 8R, 11R, and 12R were inactive against the HIV‐1 strain IIIB. Hydrazones 8S, 11S, and 12S which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</div><div type="abstract" xml:lang="en">Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. 8 S, 11 S, and 12 S showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers 8R, 11R, and 12 R were inactive against HIV‐1 strain IIIB. Molecular docking calculations of the R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</div></front></TEI><istex><corpusName>wiley</corpusName><keywords><teeft><json:string>hydrazone</json:string><json:string>chem</json:string><json:string>hplc</json:string><json:string>amide</json:string><json:string>anal</json:string><json:string>calcd</json:string><json:string>iiib</json:string><json:string>hydrazones</json:string><json:string>pharm</json:string><json:string>kgaa</json:string><json:string>weinheim</json:string><json:string>verlag gmbh</json:string><json:string>gmbh</json:string><json:string>verlag</json:string><json:string>nnrti</json:string><json:string>docking</json:string><json:string>bioorg</json:string><json:string>antiviral</json:string><json:string>acylhydrazones</json:string><json:string>stereoselective</json:string><json:string>ltered</json:string><json:string>moiety</json:string><json:string>stereoselective inhibitors</json:string><json:string>clercq</json:string><json:string>alkyl</json:string><json:string>tatar</json:string><json:string>transcriptase</json:string><json:string>hydrazide</json:string><json:string>acylhydrazone</json:string><json:string>biol</json:string><json:string>assay</json:string><json:string>petroleum ether</json:string><json:string>novel site</json:string><json:string>crude product</json:string><json:string>inhibitor</json:string><json:string>derivative</json:string><json:string>test compounds</json:string><json:string>weinheim arch</json:string><json:string>reaction medium</json:string><json:string>weinheim hydrazones</json:string><json:string>wild type</json:string><json:string>antiviral activity</json:string><json:string>compound</json:string><json:string>hydrazine hydrate</json:string><json:string>amino acid side chains</json:string><json:string>marmara university</json:string><json:string>nnrti mode</json:string><json:string>hydrazone derivatives</json:string><json:string>acid hydrazide</json:string><json:string>online version</json:string><json:string>cell culture</json:string><json:string>test compound</json:string><json:string>default parameters</json:string><json:string>dextran sulfate</json:string><json:string>iiib nnrtir</json:string><json:string>information table</json:string></teeft></keywords><author><json:item><name>Esra Tatar</name><affiliations><json:string>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, İstanbul, Turkey</json:string></affiliations></json:item><json:item><name>İlkay Küçükgüzel</name><affiliations><json:string>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, İstanbul, Turkey</json:string><json:string>E-mail: ikucukguzel@marmara.edu.tr</json:string><json:string>Correspondence address: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, 34668 İstanbul, Turkey. Fax: +90 216 345 29 52</json:string></affiliations></json:item><json:item><name>Dirk Daelemans</name><affiliations><json:string>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</json:string></affiliations></json:item><json:item><name>Tanaji T. Talele</name><affiliations><json:string>Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, St. John's University, Queens, NY, USA</json:string></affiliations></json:item><json:item><name>Neerja Kaushik‐Basu</name><affiliations><json:string>Department of Biochemistry and Molecular Biology, UMDNJ‐New Jersey Medical School, Newark, NJ, USA</json:string></affiliations></json:item><json:item><name>Erik De Clercq</name><affiliations><json:string>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</json:string></affiliations></json:item><json:item><name>Christophe Pannecouque</name><affiliations><json:string>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Acylhydrazones</value></json:item><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>Molecular modeling</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Non‐nucleoside reverse transcriptase inhibitors</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Stereoselective activity</value></json:item></subject><articleId><json:string>ARDP201200311</json:string></articleId><arkIstex>ark:/67375/WNG-XDF0L29D-B</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC50) = 123.8 µM (selectivity index, SI > 3), IC50 = 12.1 µM (SI > 29), IC50 = 17.4 µM (SI > 19), respectively. Enantiomers 8R, 11R, and 12R were inactive against the HIV‐1 strain IIIB. Hydrazones 8S, 11S, and 12S which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</abstract><qualityIndicators><score>8.308</score><pdfWordCount>9134</pdfWordCount><pdfCharCount>52414</pdfCharCount><pdfVersion>1.4</pdfVersion><pdfPageCount>14</pdfPageCount><pdfPageSize>595 x 794 pts</pdfPageSize><pdfWordsPerPage>652</pdfWordsPerPage><pdfText>true</pdfText><refBibsNative>true</refBibsNative><abstractWordCount>109</abstractWordCount><abstractCharCount>793</abstractCharCount><keywordCount>5</keywordCount></qualityIndicators><title>Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1</title><pmid><json:string>23280502</json:string></pmid><genre><json:string>article</json:string></genre><host><title>Archiv der Pharmazie</title><language><json:string>unknown</json:string></language><doi><json:string>10.1002/(ISSN)1521-4184</json:string></doi><issn><json:string>0365-6233</json:string></issn><eissn><json:string>1521-4184</json:string></eissn><publisherId><json:string>ARDP</json:string></publisherId><volume>346</volume><issue>2</issue><pages><first>140</first><last>153</last><total>14</total></pages><genre><json:string>journal</json:string></genre><subject><json:item><value>Full Paper</value></json:item><json:item><value>Full Papers</value></json:item></subject></host><namedEntities><unitex><date><json:string>2013</json:string><json:string>8400S</json:string><json:string>12s</json:string><json:string>12S</json:string><json:string>11s</json:string><json:string>11S</json:string></date><geogName></geogName><orgName><json:string>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</json:string><json:string>Agilent Technologies</json:string><json:string>Rudolph Research Analytical</json:string><json:string>Marmara University</json:string><json:string>Beckman Instruments</json:string><json:string>Schrodinger, Inc.</json:string><json:string>Department of Pharmaceutical Sciences, College of Pharmacy and Health</json:string><json:string>Department of Biochemistry and Molecular Biology</json:string></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName><json:string>Erik De Clercq</json:string><json:string>K. 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Tatar et al.</json:string><json:string>[2]</json:string><json:string>[46]</json:string><json:string>[30, 36]</json:string></ref_bibl><bibl></bibl></unitex></namedEntities><ark><json:string>ark:/67375/WNG-XDF0L29D-B</json:string></ark><categories><wos><json:string>1 - science</json:string><json:string>2 - pharmacology & pharmacy</json:string><json:string>2 - chemistry, multidisciplinary</json:string><json:string>2 - chemistry, medicinal</json:string></wos><scienceMetrix><json:string>1 - natural sciences</json:string><json:string>2 - chemistry</json:string><json:string>3 - medicinal & biomolecular chemistry</json:string></scienceMetrix><scopus><json:string>1 - Life Sciences</json:string><json:string>2 - Pharmacology, Toxicology and Pharmaceutics</json:string><json:string>3 - Drug Discovery</json:string><json:string>1 - Life Sciences</json:string><json:string>2 - Pharmacology, Toxicology and Pharmaceutics</json:string><json:string>3 - Pharmaceutical Science</json:string></scopus><inist><json:string>1 - sciences appliquees, technologies et medecines</json:string><json:string>2 - sciences biologiques et medicales</json:string><json:string>3 - sciences medicales</json:string></inist></categories><publicationDate>2013</publicationDate><copyrightDate>2013</copyrightDate><doi><json:string>10.1002/ardp.201200311</json:string></doi><id>7F0B79C3003E6A746C16DD9A4FBEC596D1488B8D</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-XDF0L29D-B/fulltext.pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-XDF0L29D-B/bundle.zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/ark:/67375/WNG-XDF0L29D-B/fulltext.tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main">Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1</title><title level="a" type="short" xml:lang="en">L‐Valine Hydrazones as Stereoselective Inhibitors of HIV‐1 RT</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><availability><licence>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</licence></availability><date type="published" when="2013-02"></date></publicationStmt><notesStmt><note type="content-type" subtype="article" source="article" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</note><note type="publication-type" subtype="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="article"><analytic><title level="a" type="main">Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1</title><title level="a" type="short" xml:lang="en">L‐Valine Hydrazones as Stereoselective Inhibitors of HIV‐1 RT</title><author xml:id="author-0000"><persName><forename type="first">Esra</forename><surname>Tatar</surname></persName><affiliation><orgName type="department">Faculty of Pharmacy</orgName><orgName type="division">Department of Pharmaceutical Chemistry</orgName><orgName type="institution">Marmara University</orgName><address><addrLine>Haydarpaşa</addrLine><addrLine>İstanbul, Turkey</addrLine><country key="TR" xml:lang="en">TURKEY</country></address></affiliation></author><author xml:id="author-0001" role="corresp"><persName><forename type="first">İlkay</forename><surname>Küçükgüzel</surname></persName><email>ikucukguzel@marmara.edu.tr</email><affiliation><orgName type="department">Faculty of Pharmacy</orgName><orgName type="division">Department of Pharmaceutical Chemistry</orgName><orgName type="institution">Marmara University</orgName><address><addrLine>Haydarpaşa</addrLine><addrLine>İstanbul, Turkey</addrLine><country key="TR" xml:lang="en">TURKEY</country></address></affiliation></author><author xml:id="author-0002"><persName><forename type="first">Dirk</forename><surname>Daelemans</surname></persName><affiliation><orgName type="institution">Rega Institute for Medical Research</orgName><address><addrLine>KU Leuven</addrLine><addrLine>Leuven, Belgium</addrLine><country key="BE" xml:lang="en">BELGIUM</country></address></affiliation></author><author xml:id="author-0003"><persName><forename type="first">Tanaji T.</forename><surname>Talele</surname></persName><affiliation><orgName type="division">Department of Pharmaceutical Sciences</orgName><orgName type="institution">College of Pharmacy and Health Sciences</orgName><orgName type="institution">St. John's University</orgName><address><addrLine>Queens</addrLine><addrLine>NY, USA</addrLine><country key="US" xml:lang="en">UNITED STATES</country></address></affiliation></author><author xml:id="author-0004"><persName><forename type="first">Neerja</forename><surname>Kaushik‐Basu</surname></persName><affiliation><orgName type="laboratory">Department of Biochemistry and Molecular Biology</orgName><orgName type="department">UMDNJ‐New Jersey Medical School</orgName><address><addrLine>Newark</addrLine><addrLine>NJ, USA</addrLine><country key="US" xml:lang="en">UNITED STATES</country></address></affiliation></author><author xml:id="author-0005"><persName><forename type="first">Erik</forename><surname>De Clercq</surname></persName><affiliation><orgName type="institution">Rega Institute for Medical Research</orgName><address><addrLine>KU Leuven</addrLine><addrLine>Leuven, Belgium</addrLine><country key="BE" xml:lang="en">BELGIUM</country></address></affiliation></author><author xml:id="author-0006"><persName><forename type="first">Christophe</forename><surname>Pannecouque</surname></persName><affiliation><orgName type="institution">Rega Institute for Medical Research</orgName><address><addrLine>KU Leuven</addrLine><addrLine>Leuven, Belgium</addrLine><country key="BE" xml:lang="en">BELGIUM</country></address></affiliation></author><idno type="istex">7F0B79C3003E6A746C16DD9A4FBEC596D1488B8D</idno><idno type="ark">ark:/67375/WNG-XDF0L29D-B</idno><idno type="DOI">10.1002/ardp.201200311</idno><idno type="unit">ARDP201200311</idno><idno type="toTypesetVersion">file:ARDP.ARDP201200311.pdf</idno></analytic><monogr><title level="j" type="main">Archiv der Pharmazie</title><title level="j" type="alt">ARCHIV DER PHARMAZIE</title><idno type="pISSN">0365-6233</idno><idno type="eISSN">1521-4184</idno><idno type="book-DOI">10.1002/(ISSN)1521-4184</idno><idno type="book-part-DOI">10.1002/ardp.v346.2</idno><idno type="product">ARDP</idno><imprint><biblScope unit="vol">346</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="140">140</biblScope><biblScope unit="page" to="153">153</biblScope><biblScope unit="page-count">14</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2013-02"></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" 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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>In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, <hi rend="bold">8</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">S</hi></hi></hi>, <hi rend="bold">11</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">S</hi></hi></hi>, and <hi rend="bold">12</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">S</hi></hi></hi> showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC<hi rend="subscript">50</hi>) = 123.8 µM (selectivity index, SI > 3), IC<hi rend="subscript">50</hi> = 12.1 µM (SI > 29), IC<hi rend="subscript">50</hi> = 17.4 µM (SI > 19), respectively. Enantiomers <hi rend="bold">8</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">R</hi></hi></hi>, <hi rend="bold">11</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">R</hi></hi></hi>, and <hi rend="bold">12</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">R</hi></hi></hi> were inactive against the HIV‐1 strain III<hi rend="subscript">B</hi>. Hydrazones <hi rend="bold">8</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">S</hi></hi></hi>, <hi rend="bold">11</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">S</hi></hi></hi>, and <hi rend="bold">12</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">S</hi></hi></hi> which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of <hi rend="italic">R‐</hi> and <hi rend="italic">S</hi>‐enantiomers of <hi rend="bold">8</hi>, <hi rend="bold">11</hi>, and <hi rend="bold">12</hi> were performed using the hydrazone‐bound novel site of HIV‐1 RT.</p></abstract><abstract xml:lang="en" style="graphical"><p>Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. <hi rend="bold">8</hi><hi rend="subscript">
<hi rend="bold"><hi rend="italic">S</hi></hi></hi>, <hi rend="bold">11</hi><hi rend="subscript">
<hi rend="bold"><hi rend="italic">S</hi></hi></hi>, and <hi rend="bold">12</hi><hi rend="subscript">
<hi rend="bold"><hi rend="italic">S</hi></hi></hi> showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers <hi rend="bold">8</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">R</hi></hi></hi>, <hi rend="bold">11</hi><hi rend="subscript"><hi rend="bold"><hi rend="italic">R</hi></hi></hi>, and <hi rend="bold">12</hi><hi rend="subscript">
<hi rend="bold"><hi rend="italic">R</hi></hi></hi> were inactive against HIV‐1 strain III<hi rend="subscript">B</hi>. Molecular docking calculations of the <hi rend="italic">R‐</hi> and <hi rend="italic">S</hi>‐enantiomers of <hi rend="bold">8</hi>, <hi rend="bold">11</hi>, and <hi rend="bold">12</hi> were performed using the hydrazone‐bound novel site of HIV‐1 RT. <figure type="box"><media mimeType="image" url="urn:x-wiley:03656233:media:ARDP201200311:content"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">Acylhydrazones</term><term xml:id="kwd2">HIV‐1</term><term xml:id="kwd3">Molecular modeling</term><term xml:id="kwd4">Non‐nucleoside reverse transcriptase inhibitors</term><term xml:id="kwd5">Stereoselective activity</term></keywords><keywords rend="articleCategory"><term>Full Paper</term></keywords><keywords rend="tocHeading1"><term>Full Papers</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc><revisionDesc><change when="2019-12-20" who="#istex" xml:id="pub2tei">formatting</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-XDF0L29D-B/fulltext.txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>WILEY‐VCH Verlag</publisherName><publisherLoc>Weinheim</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1521-4184</doi><issn type="print">0365-6233</issn><issn type="electronic">1521-4184</issn><idGroup><id type="product" value="ARDP"></id></idGroup><titleGroup><title type="main" xml:lang="en" sort="ARCHIV DER PHARMAZIE">Archiv der Pharmazie</title><title type="short">Arch. Pharm. Pharm. Med. Chem.</title></titleGroup></publicationMeta><publicationMeta level="part" position="20"><doi origin="wiley" registered="yes">10.1002/ardp.v346.2</doi><numberingGroup><numbering type="journalVolume" number="346">346</numbering><numbering type="journalIssue">2</numbering></numberingGroup><coverDate startDate="2013-02">February 2013</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="8" status="forIssue"><doi origin="wiley" registered="yes">10.1002/ardp.201200311</doi><idGroup><id type="unit" value="ARDP201200311"></id></idGroup><countGroup><count type="pageTotal" number="14"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title><title type="tocHeading1">Full Papers</title></titleGroup><copyright ownership="publisher">Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2012-08-22"></event><event type="manuscriptRevised" date="2012-10-10"></event><event type="manuscriptAccepted" date="2012-10-17"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:3.2.0 mode:FullText" date="2013-03-11"></event><event type="publishedOnlineEarlyUnpaginated" date="2012-12-20"></event><event type="publishedOnlineFinalForm" date="2013-02-08"></event><event type="firstOnline" date="2012-12-20"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-05"></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">140</numbering><numbering type="pageLast">153</numbering></numberingGroup><correspondenceTo>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, 34668 İstanbul, Turkey. Fax: +90 216 345 29 52</correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ARDP.ARDP201200311.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="6"></count><count type="tableTotal" number="2"></count><count type="referenceTotal" number="57"></count><count type="wordTotal" number="9449"></count></countGroup><titleGroup><title type="main" xml:lang="en">Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1</title><title type="short" xml:lang="en"><sc>L</sc>‐Valine Hydrazones as Stereoselective Inhibitors of HIV‐1 RT</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Esra</givenNames><familyName>Tatar</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1" corresponding="yes"><personName><givenNames>İlkay</givenNames><familyName>Küçükgüzel</familyName></personName><contactDetails><email>ikucukguzel@marmara.edu.tr</email></contactDetails></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Dirk</givenNames><familyName>Daelemans</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af3"><personName><givenNames>Tanaji T.</givenNames><familyName>Talele</familyName></personName></creator><creator xml:id="au5" creatorRole="author" affiliationRef="#af4"><personName><givenNames>Neerja</givenNames><familyName>Kaushik‐Basu</familyName></personName></creator><creator xml:id="au6" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Erik</givenNames><familyName>De Clercq</familyName></personName></creator><creator xml:id="au7" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Christophe</givenNames><familyName>Pannecouque</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="TR" type="organization"><unparsedAffiliation>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, İstanbul, Turkey</unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="BE" type="organization"><unparsedAffiliation>Rega Institute for Medical Research, KU Leuven, Leuven, Belgium</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="US" type="organization"><unparsedAffiliation>Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, St. John's University, Queens, NY, USA</unparsedAffiliation></affiliation><affiliation xml:id="af4" countryCode="US" type="organization"><unparsedAffiliation>Department of Biochemistry and Molecular Biology, UMDNJ‐New Jersey Medical School, Newark, NJ, USA</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Acylhydrazones</keyword><keyword xml:id="kwd2">HIV‐1</keyword><keyword xml:id="kwd3">Molecular modeling</keyword><keyword xml:id="kwd4">Non‐nucleoside reverse transcriptase inhibitors</keyword><keyword xml:id="kwd5">Stereoselective activity</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:03656233:media:ardp201200311:ardp_201200311_sm_suppdata"></mediaResource><caption>suppdata</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, <b>8</b><sub><b><i>S</i></b></sub>, <b>11</b><sub><b><i>S</i></b></sub>, and <b>12</b><sub><b><i>S</i></b></sub> showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC<sub>50</sub>) = 123.8 µM (selectivity index, SI > 3), IC<sub>50</sub> = 12.1 µM (SI > 29), IC<sub>50</sub> = 17.4 µM (SI > 19), respectively. Enantiomers <b>8</b><sub><b><i>R</i></b></sub>, <b>11</b><sub><b><i>R</i></b></sub>, and <b>12</b><sub><b><i>R</i></b></sub> were inactive against the HIV‐1 strain III<sub>B</sub>. Hydrazones <b>8</b><sub><b><i>S</i></b></sub>, <b>11</b><sub><b><i>S</i></b></sub>, and <b>12</b><sub><b><i>S</i></b></sub> which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of <i>R‐</i> and <i>S</i>‐enantiomers of <b>8</b>, <b>11</b>, and <b>12</b> were performed using the hydrazone‐bound novel site of HIV‐1 RT.</p></abstract><abstract type="graphical" xml:lang="en"><p>Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. <b>8</b><sub> <b><i>S</i></b></sub>, <b>11</b><sub> <b><i>S</i></b></sub>, and <b>12</b><sub> <b><i>S</i></b></sub> showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers <b>8</b><sub><b><i>R</i></b></sub>, <b>11</b><sub><b><i>R</i></b></sub>, and <b>12</b><sub> <b><i>R</i></b></sub> were inactive against HIV‐1 strain III<sub>B</sub>. Molecular docking calculations of the <i>R‐</i> and <i>S</i>‐enantiomers of <b>8</b>, <b>11</b>, and <b>12</b> were performed using the hydrazone‐bound novel site of HIV‐1 RT. <blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY‐VCH Verlag" href="urn:x-wiley:03656233:media:ARDP201200311:content"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>L‐Valine Hydrazones as Stereoselective Inhibitors of HIV‐1 RT</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1</title></titleInfo><name type="personal"><namePart type="given">Esra</namePart><namePart type="family">Tatar</namePart><affiliation>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, İstanbul, Turkey</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">İlkay</namePart><namePart type="family">Küçükgüzel</namePart><affiliation>Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, İstanbul, Turkey</affiliation><affiliation>E-mail: ikucukguzel@marmara.edu.tr</affiliation><affiliation>Correspondence address: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Marmara University, Haydarpaşa, 34668 İstanbul, Turkey. Fax: +90 216 345 29 52</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Dirk</namePart><namePart type="family">Daelemans</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">Tanaji T.</namePart><namePart type="family">Talele</namePart><affiliation>Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, St. John's University, Queens, NY, USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Neerja</namePart><namePart type="family">Kaushik‐Basu</namePart><affiliation>Department of Biochemistry and Molecular Biology, UMDNJ‐New Jersey Medical School, Newark, NJ, USA</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, KU Leuven, Leuven, Belgium</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, KU Leuven, Leuven, Belgium</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">2013-02</dateIssued><dateCaptured encoding="w3cdtf">2012-08-22</dateCaptured><dateValid encoding="w3cdtf">2012-10-17</dateValid><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">6</extent><extent unit="tables">2</extent><extent unit="references">57</extent><extent unit="words">9449</extent></physicalDescription><abstract lang="en">In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC50) = 123.8 µM (selectivity index, SI > 3), IC50 = 12.1 µM (SI > 29), IC50 = 17.4 µM (SI > 19), respectively. Enantiomers 8R, 11R, and 12R were inactive against the HIV‐1 strain IIIB. Hydrazones 8S, 11S, and 12S which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</abstract><abstract type="graphical" lang="en">Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. 8 S, 11 S, and 12 S showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers 8R, 11R, and 12 R were inactive against HIV‐1 strain IIIB. Molecular docking calculations of the R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</abstract><subject lang="en"><genre>keywords</genre><topic>Acylhydrazones</topic><topic>HIV‐1</topic><topic>Molecular modeling</topic><topic>Non‐nucleoside reverse transcriptase inhibitors</topic><topic>Stereoselective activity</topic></subject><relatedItem type="host"><titleInfo><title>Archiv der Pharmazie</title></titleInfo><titleInfo type="abbreviated"><title>Arch. Pharm. Pharm. Med. 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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