Synthesis of potentially bioactive PABA-related N -(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions
Identifieur interne : 001063 ( Istex/Corpus ); précédent : 001062; suivant : 001064Synthesis of potentially bioactive PABA-related N -(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions
Auteurs : Renato S. Gonçalves ; Patrícia V. Abdelnur ; Vanessa G. Santos ; Rosineide C. Simas ; Marcos N. Eberlin ; Alviclér Magalhães ; Eduardo R. Pérez GonzálezSource :
- Amino Acids [ 0939-4451 ] ; 2011-01-01.
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Abstract
Abstract: Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition–elimination SNAr mechanism was confirmed by NMR and MS measurements. Graphical Abstract:
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DOI: 10.1007/s00726-010-0634-z
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Gonçalves</name><affiliation><mods:affiliation>Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Universidade Estadual Paulista, São Paulo, Brazil</mods:affiliation></affiliation><affiliation><mods:affiliation>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</mods:affiliation></affiliation></author><author><name sortKey="Abdelnur, Patricia V" sort="Abdelnur, Patricia V" uniqKey="Abdelnur P" first="Patrícia V." last="Abdelnur">Patrícia V. Abdelnur</name><affiliation><mods:affiliation>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</mods:affiliation></affiliation></author><author><name sortKey="Santos, Vanessa G" sort="Santos, Vanessa G" uniqKey="Santos V" first="Vanessa G." last="Santos">Vanessa G. 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Gonçalves</name><affiliation><mods:affiliation>Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Universidade Estadual Paulista, São Paulo, Brazil</mods:affiliation></affiliation><affiliation><mods:affiliation>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</mods:affiliation></affiliation></author><author><name sortKey="Abdelnur, Patricia V" sort="Abdelnur, Patricia V" uniqKey="Abdelnur P" first="Patrícia V." last="Abdelnur">Patrícia V. Abdelnur</name><affiliation><mods:affiliation>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</mods:affiliation></affiliation></author><author><name sortKey="Santos, Vanessa G" sort="Santos, Vanessa G" uniqKey="Santos V" first="Vanessa G." last="Santos">Vanessa G. 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Pérez González</name><affiliation><mods:affiliation>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: eperez@fct.unesp.br</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Amino Acids</title><title level="j" type="sub">The Forum for Amino Acid, Peptide and Protein Research</title><title level="j" type="abbrev">Amino Acids</title><idno type="ISSN">0939-4451</idno><idno type="eISSN">1438-2199</idno><imprint><publisher>Springer Vienna</publisher><pubPlace>Vienna</pubPlace><date type="published" when="2011-01-01">2011-01-01</date><biblScope unit="volume">40</biblScope><biblScope unit="issue">1</biblScope><biblScope unit="page" from="197">197</biblScope><biblScope unit="page" to="204">204</biblScope></imprint><idno type="ISSN">0939-4451</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0939-4451</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Lactams</term><term>PABA derivatives</term><term>Potential bio-activity</term><term>SNAr reaction</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition–elimination SNAr mechanism was confirmed by NMR and MS measurements. Graphical Abstract:</div></front></TEI><istex><corpusName>springer-journals</corpusName><author><json:item><name>Renato S. Gonçalves</name><affiliations><json:string>Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Universidade Estadual Paulista, São Paulo, Brazil</json:string><json:string>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</json:string></affiliations></json:item><json:item><name>Patrícia V. Abdelnur</name><affiliations><json:string>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</json:string></affiliations></json:item><json:item><name>Vanessa G. Santos</name><affiliations><json:string>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</json:string></affiliations></json:item><json:item><name>Rosineide C. Simas</name><affiliations><json:string>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</json:string></affiliations></json:item><json:item><name>Marcos N. Eberlin</name><affiliations><json:string>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</json:string></affiliations></json:item><json:item><name>Alviclér Magalhães</name><affiliations><json:string>Departamento de Química Inorgânica, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</json:string></affiliations></json:item><json:item><name>Eduardo R. Pérez González</name><affiliations><json:string>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</json:string><json:string>E-mail: eperez@fct.unesp.br</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>PABA derivatives</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Lactams</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Potential bio-activity</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>SNAr reaction</value></json:item></subject><articleId><json:string>634</json:string><json:string>s00726-010-0634-z</json:string></articleId><arkIstex>ark:/67375/VQC-9K808BK0-X</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>OriginalPaper</json:string></originalGenre><abstract>Abstract: Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition–elimination SNAr mechanism was confirmed by NMR and MS measurements. 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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 Aff2"><AuthorName DisplayOrder="Western"><GivenName>Renato</GivenName><GivenName>S.</GivenName><FamilyName>Gonçalves</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff3"><AuthorName DisplayOrder="Western"><GivenName>Patrícia</GivenName><GivenName>V.</GivenName><FamilyName>Abdelnur</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff3"><AuthorName DisplayOrder="Western"><GivenName>Vanessa</GivenName><GivenName>G.</GivenName><FamilyName>Santos</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff3"><AuthorName DisplayOrder="Western"><GivenName>Rosineide</GivenName><GivenName>C.</GivenName><FamilyName>Simas</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff3"><AuthorName DisplayOrder="Western"><GivenName>Marcos</GivenName><GivenName>N.</GivenName><FamilyName>Eberlin</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff4"><AuthorName DisplayOrder="Western"><GivenName>Alviclér</GivenName><FamilyName>Magalhães</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff2" CorrespondingAffiliationID="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Eduardo</GivenName><GivenName>R.</GivenName><FamilyName>Pérez González</FamilyName></AuthorName><Contact><Phone>+55-18-3229535</Phone><Fax>+55-18-32215682</Fax><Email>eperez@fct.unesp.br</Email></Contact></Author><Affiliation ID="Aff1"><OrgDivision>Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT)</OrgDivision><OrgName>Universidade Estadual Paulista</OrgName><OrgAddress><City>São Paulo</City><Country Code="BR">Brazil</Country></OrgAddress></Affiliation><Affiliation ID="Aff2"><OrgDivision>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia</OrgDivision><OrgName>Universidade Estadual Paulista</OrgName><OrgAddress><Street>Campus de Presidente Prudente</Street><Postbox>C.P. 467</Postbox><City>Presidente Prudente</City><State>SP</State><Postcode>19060-900</Postcode><Country Code="BR">Brazil</Country></OrgAddress></Affiliation><Affiliation ID="Aff3"><OrgDivision>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química</OrgDivision><OrgName>Universidade de Campinas UNICAMP</OrgName><OrgAddress><City>Campinas</City><State>SP</State><Country Code="BR">Brazil</Country></OrgAddress></Affiliation><Affiliation ID="Aff4"><OrgDivision>Departamento de Química Inorgânica</OrgDivision><OrgName>Instituto de Química, Universidade de Campinas UNICAMP</OrgName><OrgAddress><City>Campinas</City><State>SP</State><Country Code="BR">Brazil</Country></OrgAddress></Affiliation></AuthorGroup><Abstract ID="Abs1" Language="En" OutputMedium="All"><AbstractSection ID="ASec1"><Heading>Abstract</Heading><Para>Potentially bioactive <Emphasis Type="Italic">N</Emphasis>-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by S<Subscript>N</Subscript>Ar reactions of aromatic acids with <Emphasis Type="Italic">N</Emphasis>-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition–elimination S<Subscript>N</Subscript>Ar mechanism was confirmed by NMR and MS measurements.</Para></AbstractSection><AbstractSection ID="ASec2" OutputMedium="Online"><Heading>Graphical Abstract</Heading><Para><Figure Category="Standard" Float="No" ID="Figa"><MediaObject ID="MO1"><ImageObject Color="BlackWhite" Format="GIF" Rendition="HTML" Type="Linedraw" FileRef="MediaObjects/726_2010_634_Figa_HTML.gif"></ImageObject></MediaObject></Figure></Para></AbstractSection></Abstract><KeywordGroup Language="En" OutputMedium="All"><Heading>Keywords</Heading><Keyword>PABA derivatives</Keyword><Keyword>Lactams</Keyword><Keyword>Potential bio-activity</Keyword><Keyword>S<Subscript>N</Subscript>Ar reaction</Keyword></KeywordGroup><ArticleNote Type="ESMHint"><Heading>Electronic supplementary material</Heading><SimplePara>The online version of this article (doi:<ExternalRef><RefSource>10.1007/s00726-010-0634-z</RefSource><RefTarget Address="10.1007/s00726-010-0634-z" TargetType="DOI"></RefTarget></ExternalRef>) contains supplementary material, which is available to authorized users.</SimplePara></ArticleNote></ArticleHeader><NoBody></NoBody></Article></Issue></Volume></Journal></Publisher></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis of potentially bioactive PABA-related N -(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Synthesis of potentially bioactive PABA-related N -(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions</title></titleInfo><name type="personal"><namePart type="given">Renato</namePart><namePart type="given">S.</namePart><namePart type="family">Gonçalves</namePart><affiliation>Programa de Pós-Graduação em Ciência e Tecnologia de Materiais (POSMAT), Universidade Estadual Paulista, São Paulo, Brazil</affiliation><affiliation>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Patrícia</namePart><namePart type="given">V.</namePart><namePart type="family">Abdelnur</namePart><affiliation>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Vanessa</namePart><namePart type="given">G.</namePart><namePart type="family">Santos</namePart><affiliation>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Rosineide</namePart><namePart type="given">C.</namePart><namePart type="family">Simas</namePart><affiliation>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Marcos</namePart><namePart type="given">N.</namePart><namePart type="family">Eberlin</namePart><affiliation>Laboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Alviclér</namePart><namePart type="family">Magalhães</namePart><affiliation>Departamento de Química Inorgânica, Instituto de Química, Universidade de Campinas UNICAMP, Campinas, SP, Brazil</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal" displayLabel="corresp"><namePart type="given">Eduardo</namePart><namePart type="given">R.</namePart><namePart type="family">Pérez González</namePart><affiliation>Laboratório de Química Orgânica Fina, Departamento de Física, Química e Biologia, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista, Campus de Presidente Prudente, C.P. 467, 19060-900, Presidente Prudente, SP, Brazil</affiliation><affiliation>E-mail: eperez@fct.unesp.br</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>Springer Vienna</publisher><place><placeTerm type="text">Vienna</placeTerm></place><dateCreated encoding="w3cdtf">2010-03-07</dateCreated><dateIssued encoding="w3cdtf">2011-01-01</dateIssued><copyrightDate encoding="w3cdtf">2010</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><abstract lang="en">Abstract: Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition–elimination SNAr mechanism was confirmed by NMR and MS measurements. Graphical Abstract:</abstract><note>Original Article</note><subject lang="en"><genre>Keywords</genre><topic>PABA derivatives</topic><topic>Lactams</topic><topic>Potential bio-activity</topic><topic>SNAr reaction</topic></subject><relatedItem type="host"><titleInfo><title>Amino Acids</title><subTitle>The Forum for Amino Acid, Peptide and Protein Research</subTitle></titleInfo><titleInfo type="abbreviated"><title>Amino Acids</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">2010-12-31</dateIssued><copyrightDate encoding="w3cdtf">2011</copyrightDate></originInfo><subject><genre>Life Sciences</genre><topic>Neurobiology</topic><topic>Proteomics</topic><topic>Life Sciences, general</topic><topic>Biochemical Engineering</topic><topic>Analytical Chemistry</topic><topic>Biochemistry, general</topic></subject><identifier type="ISSN">0939-4451</identifier><identifier type="eISSN">1438-2199</identifier><identifier type="JournalID">726</identifier><identifier type="IssueArticleCount">23</identifier><identifier type="VolumeIssueCount">5</identifier><part><date>2011</date><detail type="issue"><title>Peptides as Toxins/Defensins</title></detail><detail type="volume"><number>40</number><caption>vol.</caption></detail><detail type="issue"><number>1</number><caption>no.</caption></detail><extent unit="pages"><start>197</start><end>204</end></extent></part><recordInfo><recordOrigin>Springer-Verlag, 2011</recordOrigin></recordInfo></relatedItem><identifier type="istex">397E488740446D9579A0D5D2244EC7E92D690A66</identifier><identifier type="ark">ark:/67375/VQC-9K808BK0-X</identifier><identifier type="DOI">10.1007/s00726-010-0634-z</identifier><identifier type="ArticleID">634</identifier><identifier type="ArticleID">s00726-010-0634-z</identifier><accessCondition type="use and reproduction" contentType="copyright">Springer-Verlag, 2010</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>Springer-Verlag, 2010</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/ark:/67375/VQC-9K808BK0-X/record.json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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