Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações do UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/12413 |
Resumo: | The present thesis describes the synthesis and pharmacological evaluation of new tacrine structural analogues, as well as N-derivation reactions and C-C and C-N coupling on these compounds. By this way, a series of 7-amino-spiro[chromeno[4,3-b]quinolone-6,1’-cycloalkanes], where [cycloalkanes = cyclopentane, cyclohexane, cycloheptane, 2-methyl-, 3-methyl-, 4-methyl-, and 4-t-butyl-cyclohexane] were synthesized with yields of 30 – 65 % through a cyclocondensation between 2-amino-benzonitriles and seven exemples of spiro[chromano-2,1’-cycloalkan]-4-ones, using AlCl3 as catalyst, in a solventless conventional thermal heating. Later, aiming at the study of the influence of chlorine and bromine as substituents in the biologic activity of these systems, and the possibility of insertion of new groups using one bromine substituted compound in coupling reactions, this methodology was extended to obtain halo substituted 7-amino-spiro[chromeno[4.3-b]quinolone-6,1’-cycloalkanes]. Subsequently, theses spirochromeno-quinolines (tacrine hybrids) where evaluated for they AChE and BChE in vitro activities as well as complementary molecular docking studies. Both results for these new tacrine analogues were correlated with their structural characteristics for these compounds. The spirochromeno-quinolines were also evaluated for they cytotoxicity using healthy human leukocytes. In the sequence, N-derivation reactions in 7-amino-spiro[chromeno[4,3-b]quinolone-6,1’-cycloalkanes] were made, allowing the insertion of a pyrrole heterocycles by Clauson-Kass reaction, with yields of 52-78 %. These new compounds were evaluated for they antitumor and antimicrobial activities. Lastly, the C-C and C-N coupling reactions employing sonogashira, Suzuki-Myaura and Buchwald-Hartwig techniques for the 7-amino-9-bromo-spiro[chromeno[4,3-b]quinolone-6,1’cyclohexane] furnished products of future interest in a synthetic and biologic points of view. |
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2018-02-14T12:46:48Z2018-02-14T12:46:48Z2017http://repositorio.ufsm.br/handle/1/12413The present thesis describes the synthesis and pharmacological evaluation of new tacrine structural analogues, as well as N-derivation reactions and C-C and C-N coupling on these compounds. By this way, a series of 7-amino-spiro[chromeno[4,3-b]quinolone-6,1’-cycloalkanes], where [cycloalkanes = cyclopentane, cyclohexane, cycloheptane, 2-methyl-, 3-methyl-, 4-methyl-, and 4-t-butyl-cyclohexane] were synthesized with yields of 30 – 65 % through a cyclocondensation between 2-amino-benzonitriles and seven exemples of spiro[chromano-2,1’-cycloalkan]-4-ones, using AlCl3 as catalyst, in a solventless conventional thermal heating. Later, aiming at the study of the influence of chlorine and bromine as substituents in the biologic activity of these systems, and the possibility of insertion of new groups using one bromine substituted compound in coupling reactions, this methodology was extended to obtain halo substituted 7-amino-spiro[chromeno[4.3-b]quinolone-6,1’-cycloalkanes]. Subsequently, theses spirochromeno-quinolines (tacrine hybrids) where evaluated for they AChE and BChE in vitro activities as well as complementary molecular docking studies. Both results for these new tacrine analogues were correlated with their structural characteristics for these compounds. The spirochromeno-quinolines were also evaluated for they cytotoxicity using healthy human leukocytes. In the sequence, N-derivation reactions in 7-amino-spiro[chromeno[4,3-b]quinolone-6,1’-cycloalkanes] were made, allowing the insertion of a pyrrole heterocycles by Clauson-Kass reaction, with yields of 52-78 %. These new compounds were evaluated for they antitumor and antimicrobial activities. Lastly, the C-C and C-N coupling reactions employing sonogashira, Suzuki-Myaura and Buchwald-Hartwig techniques for the 7-amino-9-bromo-spiro[chromeno[4,3-b]quinolone-6,1’cyclohexane] furnished products of future interest in a synthetic and biologic points of view.A presente tese descreve a síntese e avaliação farmacológica de novos análogos estruturais da tacrina, assim como as reações de N-derivatização e de acoplamento C-C e C-N desses compostos. Assim, uma série de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos], onde [cicloalcanos = ciclopentano, ciclohexano, cicloheptano, 2-metil-, 3-metil-, 4-metil-, e 4-t-butil-ciclohexano] foi sintetizada com rendimentos de 30 – 65 % através de uma reação de ciclocondensação entre 2-amino-benzonitrilas e sete exemplos de espiro[cromano-2,1'-cicloalcan]-4-onas, utilizando AlCl3 como catalisador, na ausência de solvente e sob aquecimento térmico convencional. Posteriormente, visando o estudo da influência dos substituintes cloro e bromo na atividade biológica desse sistema, além da possibilidade de inserção de novos grupos a partir de um composto bromo substituído em reações de acoplamento, estendeu-se essa metodologia para a obtenção dos 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] halo substituídos. Subsequentemente, essas espirocromeno-quinolinas (tacrinas híbridas) foram avaliadas quanto a atividade de AChE e BChE in vitro e foram realizados estudos complementares de docking molecular. Ambos os resultados para esses novos análogos da tacrina foram correlacionados com as características estruturais desses compostos. Ainda, essas espirocromeno-quinolinas foram submetidos a testes de citotoxicidade em células sadias de leucócitos humanos. Em sequência, foram realizadas inicialmente reações de N-derivatização em 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos], possibilitando a inserção do heterociclo pirrol via reação de Clauson-Kass, com rendimentos de 52 – 78 %. Esses novos compostos foram avaliados quanto a atividade antitumoral e antimicrobiana. Por fim, reações de acoplamento C-C e C-N tipo Sonogashira, Suzuki-Myaura e Buchwald-Hartwig para o exemplar 7-amino-9-bromo-espiro[cromeno[4,3-b]quinolina-6,1’-ciclohexano] conduziram a produtos de futuro interesse sob o ponto de vista sintético e biológico.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessTacrinaEspiro-heterociclosAtividade anti-colinesteraseModelagem molecularCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivadosSynthesis and pharmacological evaluation of 7-amino-spiro[chromeno[4,3-b]quinolin-6,1’-cycloalkanes] and derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Schetinger, Maria Rosa Chitolinahttp://lattes.cnpq.br/4401319386725357Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Cunico Filho, Wilson Joãohttp://lattes.cnpq.br/8974631592328450Severo Filho, Wolmar Alipiohttp://lattes.cnpq.br/1999826579939679http://lattes.cnpq.br/2866422095275149Silva, Letícia Barros da10060000000060006c852ad-d805-43c3-99d6-93a6a86f507c66ee3055-d874-4cd0-a5b8-cd2a0b24d0dbcba4a833-b1c5-4608-8453-7a46f671faf12f7bd6ce-78fa-4968-ac66-2d1407e90f6006be5ca0-0b52-4bca-810f-4481a8bc36e053fe5053-c6ce-42b8-bcd9-a02be9cd75aereponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2017_SILVA_LETICIA.pdfTES_PPGQUIMICA_2017_SILVA_LETICIA.pdfTese de Doutoradoapplication/pdf9352397http://repositorio.ufsm.br/bitstream/1/12413/1/TES_PPGQUIMICA_2017_SILVA_LETICIA.pdfd306e255b5f12efd24612afc6fc2b3f5MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
dc.title.alternative.eng.fl_str_mv |
Synthesis and pharmacological evaluation of 7-amino-spiro[chromeno[4,3-b]quinolin-6,1’-cycloalkanes] and derivatives |
title |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
spellingShingle |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados Silva, Letícia Barros da Tacrina Espiro-heterociclos Atividade anti-colinesterase Modelagem molecular CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
title_full |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
title_fullStr |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
title_full_unstemmed |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
title_sort |
Síntese e avaliação farmacológica de 7-amino-espiro[cromeno[4,3-b]quinolina-6,1’-cicloalcanos] e derivados |
author |
Silva, Letícia Barros da |
author_facet |
Silva, Letícia Barros da |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Schetinger, Maria Rosa Chitolina |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/4401319386725357 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee3.fl_str_mv |
Cunico Filho, Wilson João |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/8974631592328450 |
dc.contributor.referee4.fl_str_mv |
Severo Filho, Wolmar Alipio |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/1999826579939679 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/2866422095275149 |
dc.contributor.author.fl_str_mv |
Silva, Letícia Barros da |
contributor_str_mv |
Bonacorso, Helio Gauze Schetinger, Maria Rosa Chitolina Zanatta, Nilo Cunico Filho, Wilson João Severo Filho, Wolmar Alipio |
dc.subject.por.fl_str_mv |
Tacrina Espiro-heterociclos Atividade anti-colinesterase Modelagem molecular |
topic |
Tacrina Espiro-heterociclos Atividade anti-colinesterase Modelagem molecular CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present thesis describes the synthesis and pharmacological evaluation of new tacrine structural analogues, as well as N-derivation reactions and C-C and C-N coupling on these compounds. By this way, a series of 7-amino-spiro[chromeno[4,3-b]quinolone-6,1’-cycloalkanes], where [cycloalkanes = cyclopentane, cyclohexane, cycloheptane, 2-methyl-, 3-methyl-, 4-methyl-, and 4-t-butyl-cyclohexane] were synthesized with yields of 30 – 65 % through a cyclocondensation between 2-amino-benzonitriles and seven exemples of spiro[chromano-2,1’-cycloalkan]-4-ones, using AlCl3 as catalyst, in a solventless conventional thermal heating. Later, aiming at the study of the influence of chlorine and bromine as substituents in the biologic activity of these systems, and the possibility of insertion of new groups using one bromine substituted compound in coupling reactions, this methodology was extended to obtain halo substituted 7-amino-spiro[chromeno[4.3-b]quinolone-6,1’-cycloalkanes]. Subsequently, theses spirochromeno-quinolines (tacrine hybrids) where evaluated for they AChE and BChE in vitro activities as well as complementary molecular docking studies. Both results for these new tacrine analogues were correlated with their structural characteristics for these compounds. The spirochromeno-quinolines were also evaluated for they cytotoxicity using healthy human leukocytes. In the sequence, N-derivation reactions in 7-amino-spiro[chromeno[4,3-b]quinolone-6,1’-cycloalkanes] were made, allowing the insertion of a pyrrole heterocycles by Clauson-Kass reaction, with yields of 52-78 %. These new compounds were evaluated for they antitumor and antimicrobial activities. Lastly, the C-C and C-N coupling reactions employing sonogashira, Suzuki-Myaura and Buchwald-Hartwig techniques for the 7-amino-9-bromo-spiro[chromeno[4,3-b]quinolone-6,1’cyclohexane] furnished products of future interest in a synthetic and biologic points of view. |
publishDate |
2017 |
dc.date.issued.fl_str_mv |
2017 |
dc.date.accessioned.fl_str_mv |
2018-02-14T12:46:48Z |
dc.date.available.fl_str_mv |
2018-02-14T12:46:48Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/12413 |
url |
http://repositorio.ufsm.br/handle/1/12413 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
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UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1801485257607741440 |