Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações do UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/16546 |
Resumo: | The present work presents the synthesis and spectroscopic study of new oxadiazaborinine derivatives from 2-amino substituted azaheterocycles systems, subdivided into four different classes of azaheterocycles, these are comprised of naphthyridine, pyridine, pyrimidine and quinoxaline systems. The four substituted 2-amino systems were initially converted to the respective amides from the N-acylation reactions and then used for the conversion to the difluoro-organoboron heterocyclic systems derived in reactions with BF3.Et2O. Initially, the novel N-(1,8-naphthyridinyl) benzamide precursor blocks were obtained n yields of 65 – 92 %. From these systems and N-(1,8-naphthyridinyl) acetamides analogous derivatives, reactions were carried out with BF3.Et2O to obtain the respective difluororganoboro derivative heterocycles in yields of from 50 – 66 %. Subsequently, reactions of (N-pyridinyl) benzamides and (N-pyrimidinyl) benzamides with BF3.Et2O provided the isolation of two new analogous series in yields of 51– 70 % and 50 – 68 %, respectively. Finally, novel benzamides derived from 2-aminoquinoxalines systems were obtained in yields of 62 – 82 % and were sequentially used as precursor blocks for the synthesis of novel difluoro-organoboro heterocycles by reaction with BF3.Et 2O. In the course of the synthesis of the four series of difluoro-organoboron heterocycles, the structural characterization of the unpublished molecules was performed by 1H, 13C, 19F and 11B NMR, two-dimensional experiments HMBC 1H-15N, GC-MS, X-ray diffraction in monocrystals and analysis elementar CHN. In parallel, photophysical properties such as absorption, emission, fluorescence quantum yield, Stokes shifts and cyclic voltammetry properties were performed, presented and discussed. Interaction assays of these heterocycles with ct-DNA and BSA, as well as molecular docking and theoretical calculations complemented the present study. |
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2019-05-13T19:02:37Z2019-05-13T19:02:37Z2018-07-11http://repositorio.ufsm.br/handle/1/16546The present work presents the synthesis and spectroscopic study of new oxadiazaborinine derivatives from 2-amino substituted azaheterocycles systems, subdivided into four different classes of azaheterocycles, these are comprised of naphthyridine, pyridine, pyrimidine and quinoxaline systems. The four substituted 2-amino systems were initially converted to the respective amides from the N-acylation reactions and then used for the conversion to the difluoro-organoboron heterocyclic systems derived in reactions with BF3.Et2O. Initially, the novel N-(1,8-naphthyridinyl) benzamide precursor blocks were obtained n yields of 65 – 92 %. From these systems and N-(1,8-naphthyridinyl) acetamides analogous derivatives, reactions were carried out with BF3.Et2O to obtain the respective difluororganoboro derivative heterocycles in yields of from 50 – 66 %. Subsequently, reactions of (N-pyridinyl) benzamides and (N-pyrimidinyl) benzamides with BF3.Et2O provided the isolation of two new analogous series in yields of 51– 70 % and 50 – 68 %, respectively. Finally, novel benzamides derived from 2-aminoquinoxalines systems were obtained in yields of 62 – 82 % and were sequentially used as precursor blocks for the synthesis of novel difluoro-organoboro heterocycles by reaction with BF3.Et 2O. In the course of the synthesis of the four series of difluoro-organoboron heterocycles, the structural characterization of the unpublished molecules was performed by 1H, 13C, 19F and 11B NMR, two-dimensional experiments HMBC 1H-15N, GC-MS, X-ray diffraction in monocrystals and analysis elementar CHN. In parallel, photophysical properties such as absorption, emission, fluorescence quantum yield, Stokes shifts and cyclic voltammetry properties were performed, presented and discussed. Interaction assays of these heterocycles with ct-DNA and BSA, as well as molecular docking and theoretical calculations complemented the present study.O presente trabalho apresenta a síntese e estudo espectroscópico de novos derivados oxadiazaborininos a partir de sistemas azaheterociclos 2-amino substituídos, subdivididos em quatro diferentes classes de azaheterociclos, os quais são compreendidos por sistemas naftiridínicos, piridínicos, pirimidínicos e quinoxalínicos. Os quatro sistemas 2-amino substituídos foram inicialmente convertidos às respectivas amidas a partir de reações de N-acilação e então utilizados para a conversão aos sistemas heterocíclicos diflúor-organoboro derivados em reações com BF3.Et2O. Inicialmente, os blocos precursores inéditos N-(1,8-naftiridinil)benzamidas foram obtidas com rendimentos de 65 – 92 %. A partir desses sistemas e de derivados análogos N-(1,8-naftiridinil)acetamidas, foram realizadas reações com BF3.Et2O para obtenção dos respectivos heterociclos difluororganoboro derivados com rendimentos de 50 – 66 %. Em sequência, reações de (N-piridinil)benzamidas e (N-pirimidinil)benzamidas com BF3.Et2O propiciaram o isolamento de duas novas séries análogas em rendimentos de 51 – 70 % e 50 – 68 %, respectivamente. Finalmente, benzamidas inéditas derivadas de sistemas 2-aminoquinoxalínicos foram obtidas com rendimentos de 62 – 82 % e foram utilizadas, em sequência, como blocos precursores para a síntese de novos heterociclos diflúor-organoboro através de reação com BF3.Et2O. No decorrer da síntese das quatro séries de heterociclos diflúor-organoboro, a caracterização estrutural das moléculas inéditas foi realizada por RMN de 1H, 13C, 19F e 11B, experimentos bidimensionais HMBC 1H-15N, GC-MS, difração de raios-X em monocristais e análise elemenatar CHN. Paralelamente, propriedades fotofísicas como dados de absorção, emissão, rendimento quântico de fluorescência, deslocamento Stokes e voltametria cíclica foram realizados, apresentados e discutidos. Ensaios de interação destes heterocíclos com ct-DNA e BSA, assim como, de docking molecular e cálculos teóricos complementaram o presente estudo.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/openAccessHeterociclos diflúor-organoboroCromóforosPropriedades fotofísicasRMN de ¹⁹F¹¹B e ¹⁵NDifluoro-organoboron heterocyclesChromophoresPhotophysical properties¹⁹F¹¹B and ¹⁵N NMRCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclosSynthesis, structural characterization and phothysical study of difluoro-organoboron chromophors derived from azaheterocyclesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Iglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Rodembusch, Fabiano Severohttp://lattes.cnpq.br/8307866489971127Silva Júnior, Eufrânio Nunes dahttp://lattes.cnpq.br/5627593695811199http://lattes.cnpq.br/1081215659740296Calheiro, Tainara Paulus10060000000060006c852ad-d805-43c3-99d6-93a6a86f507cd903a5c6-ca0d-4051-880c-d7a1c04d9e7f483d6d0c-e419-454b-b413-1a51673258c3f0970438-aab7-4bbe-8d26-13140ae7303afd9e2ee6-b925-4e96-9aa6-bc321b22ca5fe524e828-dff3-443c-9f19-fccc3ca7969areponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2018_CALHEIRO_TAINARA.pdfTES_PPGQUIMICA_2018_CALHEIRO_TAINARA.pdfTese de Doutoradoapplication/pdf15093206http://repositorio.ufsm.br/bitstream/1/16546/1/TES_PPGQUIMICA_2018_CALHEIRO_TAINARA.pdf492ee688032083ef3c519a1ecc514798MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
dc.title.alternative.eng.fl_str_mv |
Synthesis, structural characterization and phothysical study of difluoro-organoboron chromophors derived from azaheterocycles |
title |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
spellingShingle |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos Calheiro, Tainara Paulus Heterociclos diflúor-organoboro Cromóforos Propriedades fotofísicas RMN de ¹⁹F ¹¹B e ¹⁵N Difluoro-organoboron heterocycles Chromophores Photophysical properties ¹⁹F ¹¹B and ¹⁵N NMR CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
title_full |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
title_fullStr |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
title_full_unstemmed |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
title_sort |
Síntese, caracterização estrutural e estudo fotofísico de cromóforos diflúor-organoboro derivados de azaheterociclos |
author |
Calheiro, Tainara Paulus |
author_facet |
Calheiro, Tainara Paulus |
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 |
Iglesias, Bernardo Almeida |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.referee2.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.referee3.fl_str_mv |
Rodembusch, Fabiano Severo |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/8307866489971127 |
dc.contributor.referee4.fl_str_mv |
Silva Júnior, Eufrânio Nunes da |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/5627593695811199 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/1081215659740296 |
dc.contributor.author.fl_str_mv |
Calheiro, Tainara Paulus |
contributor_str_mv |
Bonacorso, Helio Gauze Iglesias, Bernardo Almeida Rodrigues, Oscar Endrigo Dorneles Rodembusch, Fabiano Severo Silva Júnior, Eufrânio Nunes da |
dc.subject.por.fl_str_mv |
Heterociclos diflúor-organoboro Cromóforos Propriedades fotofísicas RMN de ¹⁹F ¹¹B e ¹⁵N |
topic |
Heterociclos diflúor-organoboro Cromóforos Propriedades fotofísicas RMN de ¹⁹F ¹¹B e ¹⁵N Difluoro-organoboron heterocycles Chromophores Photophysical properties ¹⁹F ¹¹B and ¹⁵N NMR CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Difluoro-organoboron heterocycles Chromophores Photophysical properties ¹⁹F ¹¹B and ¹⁵N NMR |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present work presents the synthesis and spectroscopic study of new oxadiazaborinine derivatives from 2-amino substituted azaheterocycles systems, subdivided into four different classes of azaheterocycles, these are comprised of naphthyridine, pyridine, pyrimidine and quinoxaline systems. The four substituted 2-amino systems were initially converted to the respective amides from the N-acylation reactions and then used for the conversion to the difluoro-organoboron heterocyclic systems derived in reactions with BF3.Et2O. Initially, the novel N-(1,8-naphthyridinyl) benzamide precursor blocks were obtained n yields of 65 – 92 %. From these systems and N-(1,8-naphthyridinyl) acetamides analogous derivatives, reactions were carried out with BF3.Et2O to obtain the respective difluororganoboro derivative heterocycles in yields of from 50 – 66 %. Subsequently, reactions of (N-pyridinyl) benzamides and (N-pyrimidinyl) benzamides with BF3.Et2O provided the isolation of two new analogous series in yields of 51– 70 % and 50 – 68 %, respectively. Finally, novel benzamides derived from 2-aminoquinoxalines systems were obtained in yields of 62 – 82 % and were sequentially used as precursor blocks for the synthesis of novel difluoro-organoboro heterocycles by reaction with BF3.Et 2O. In the course of the synthesis of the four series of difluoro-organoboron heterocycles, the structural characterization of the unpublished molecules was performed by 1H, 13C, 19F and 11B NMR, two-dimensional experiments HMBC 1H-15N, GC-MS, X-ray diffraction in monocrystals and analysis elementar CHN. In parallel, photophysical properties such as absorption, emission, fluorescence quantum yield, Stokes shifts and cyclic voltammetry properties were performed, presented and discussed. Interaction assays of these heterocycles with ct-DNA and BSA, as well as molecular docking and theoretical calculations complemented the present study. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-07-11 |
dc.date.accessioned.fl_str_mv |
2019-05-13T19:02:37Z |
dc.date.available.fl_str_mv |
2019-05-13T19:02:37Z |
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/1/16546 |
url |
http://repositorio.ufsm.br/handle/1/16546 |
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 |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
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