A semiempirical AM1 conformational study of 3'-substituted deoxythymidines
Identifieur interne : 001023 ( Istex/Corpus ); précédent : 001022; suivant : 001024A semiempirical AM1 conformational study of 3'-substituted deoxythymidines
Auteurs : Carlos M. Estévez ; Ana M. Gra A ; Miguel A. RíosSource :
- Journal of Molecular Structure: THEOCHEM [ 0166-1280 ] ; 1993.
English descriptors
- Teeft :
- Agents chemother, Chem, Conformation, Conformer, Conformers, Derivative, Exocyclic sugar moiety, Hydrogen bond lengths, Intramolecular hydrogen, Kcal, Kilocalorie, Other molecules, Parametersb, Parametersb conformer, Relative energies, Sabio, Stable conformer, Stationary points, Struct, Sugar ring, Theochem, Thymidine, Topiol, Torsion.
Abstract
Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.
Url:
DOI: 10.1016/0166-1280(93)87051-E
Links to Exploration step
ISTEX:54E570944271D1F6BA8496D7353B705799445576Le document en format XML
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Estévez</name><affiliation><mods:affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</mods:affiliation></affiliation></author><author><name sortKey="Gra A, Ana M" sort="Gra A, Ana M" uniqKey="Gra A A" first="Ana M." last="Gra A">Ana M. Gra A</name><affiliation><mods:affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</mods:affiliation></affiliation></author><author><name sortKey="Rios, Miguel A" sort="Rios, Miguel A" uniqKey="Rios M" first="Miguel A." last="Ríos">Miguel A. 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The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>conformers</json:string><json:string>conformer</json:string><json:string>sabio</json:string><json:string>thymidine</json:string><json:string>sugar ring</json:string><json:string>relative energies</json:string><json:string>chem</json:string><json:string>topiol</json:string><json:string>hydrogen bond lengths</json:string><json:string>parametersb conformer</json:string><json:string>parametersb</json:string><json:string>kilocalorie</json:string><json:string>struct</json:string><json:string>theochem</json:string><json:string>stable conformer</json:string><json:string>kcal</json:string><json:string>conformation</json:string><json:string>intramolecular hydrogen</json:string><json:string>derivative</json:string><json:string>torsion</json:string><json:string>stationary points</json:string><json:string>exocyclic sugar moiety</json:string><json:string>agents chemother</json:string><json:string>other molecules</json:string></teeft></keywords><author><json:item><name>Carlos M. Estévez</name><affiliations><json:string>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</json:string></affiliations></json:item><json:item><name>Ana M. Graña</name><affiliations><json:string>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</json:string></affiliations></json:item><json:item><name>Miguel A. Ríos</name><affiliations><json:string>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</json:string></affiliations></json:item></author><arkIstex>ark:/67375/6H6-MZVK61FP-H</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><abstract>Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.</abstract><qualityIndicators><refBibsNative>true</refBibsNative><abstractWordCount>132</abstractWordCount><abstractCharCount>934</abstractCharCount><keywordCount>0</keywordCount><score>6.572</score><pdfWordCount>2988</pdfWordCount><pdfCharCount>20932</pdfCharCount><pdfVersion>1.2</pdfVersion><pdfPageCount>8</pdfPageCount><pdfPageSize>540 x 720 pts</pdfPageSize></qualityIndicators><title>A semiempirical AM1 conformational study of 3'-substituted deoxythymidines</title><pii><json:string>0166-1280(93)87051-E</json:string></pii><genre><json:string>research-article</json:string></genre><host><title>Journal of Molecular Structure: THEOCHEM</title><language><json:string>unknown</json:string></language><publicationDate>1993</publicationDate><issn><json:string>0166-1280</json:string></issn><pii><json:string>S0166-1280(00)X0290-4</json:string></pii><volume>288</volume><issue>3</issue><pages><first>207</first><last>214</last></pages><genre><json:string>journal</json:string></genre></host><namedEntities><unitex><date><json:string>1993</json:string></date><geogName></geogName><orgName><json:string>Theochem</json:string></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName><json:string>Ana M. 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[15]</json:string><json:string>[19]</json:string></ref_bibl><bibl></bibl></unitex></namedEntities><ark><json:string>ark:/67375/6H6-MZVK61FP-H</json:string></ark><categories><wos></wos><scienceMetrix></scienceMetrix><scopus><json:string>1 - Physical Sciences</json:string><json:string>2 - Chemistry</json:string><json:string>3 - Physical and Theoretical Chemistry</json:string><json:string>1 - Physical Sciences</json:string><json:string>2 - Physics and Astronomy</json:string><json:string>3 - Condensed Matter Physics</json:string><json:string>1 - Life Sciences</json:string><json:string>2 - Biochemistry, Genetics and Molecular Biology</json:string><json:string>3 - Biochemistry</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 biologiques fondamentales et appliquees. psychologie</json:string><json:string>4 - industries agroalimentaires</json:string></inist></categories><publicationDate>1993</publicationDate><copyrightDate>1993</copyrightDate><doi><json:string>10.1016/0166-1280(93)87051-E</json:string></doi><id>54E570944271D1F6BA8496D7353B705799445576</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/ark:/67375/6H6-MZVK61FP-H/fulltext.pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/ark:/67375/6H6-MZVK61FP-H/bundle.zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/ark:/67375/6H6-MZVK61FP-H/fulltext.tei"><teiHeader><fileDesc><titleStmt><title level="a">A semiempirical AM1 conformational study of 3'-substituted deoxythymidines</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher scheme="https://scientific-publisher.data.istex.fr">ELSEVIER</publisher><availability><licence><p>elsevier</p></licence></availability><p scheme="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-HKKZVM7B-M"></p><date>1993</date></publicationStmt><notesStmt><note type="research-article" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</note><note type="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a">A semiempirical AM1 conformational study of 3'-substituted deoxythymidines</title><author xml:id="author-0000"><persName><forename type="first">Carlos M.</forename><surname>Estévez</surname></persName><affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</affiliation></author><author xml:id="author-0001"><persName><forename type="first">Ana M.</forename><surname>Graña</surname></persName><affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</affiliation></author><author xml:id="author-0002"><persName><forename type="first">Miguel A.</forename><surname>Ríos</surname></persName><note type="correspondence"><p>Corresponding author.</p></note><affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</affiliation></author><idno type="istex">54E570944271D1F6BA8496D7353B705799445576</idno><idno type="ark">ark:/67375/6H6-MZVK61FP-H</idno><idno type="DOI">10.1016/0166-1280(93)87051-E</idno><idno type="PII">0166-1280(93)87051-E</idno></analytic><monogr><title level="j">Journal of Molecular Structure: THEOCHEM</title><title level="j" type="abbrev">THEOCH</title><idno type="pISSN">0166-1280</idno><idno type="PII">S0166-1280(00)X0290-4</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1993"></date><biblScope unit="volume">288</biblScope><biblScope unit="issue">3</biblScope><biblScope unit="page" from="207">207</biblScope><biblScope unit="page" to="214">214</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1993</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. 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The series examined included high-activity derivatives with N<ce:inf>3</ce:inf> or F as the 3'-substituent, low-activity derivatives with CN or NH<ce:inf>2</ce:inf>, and the moderately active 3'-<ce:italic>H</ce:italic> and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.</ce:simple-para></ce:abstract-sec></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>A semiempirical AM1 conformational study of 3'-substituted deoxythymidines</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>A semiempirical AM1 conformational study of 3'-substituted deoxythymidines</title></titleInfo><name type="personal"><namePart type="given">Carlos M.</namePart><namePart type="family">Estévez</namePart><affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Ana M.</namePart><namePart type="family">Graña</namePart><affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Miguel A.</namePart><namePart type="family">Ríos</namePart><affiliation>Departamento de Química Fisica, Facultade de Química, Universidade de Santiago, 15706 Santiago de Compostela, Spain</affiliation><description>Corresponding author.</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" 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>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1993</dateIssued><copyrightDate encoding="w3cdtf">1993</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. 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