Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/18709 |
Resumo: | In the present work two new series of 1,2,3-triazoles-1,4-disubstituted 20-33 obtained by the reaction of 1,3-dipolar cycloaddition, Click-type, were synthesized between the alkaloids derived from benzocalcogenoanilines and the azides of 1,3-chalcogenazoles-2-substituted with the objective of joining three classes of interesting heterocyclic compounds and to explore the biological properties of these molecules in question. Compounds 17-19 were obtained from the bimolecular nucleophilic substitution reaction (SN2) in yields ranging from 55-90% and the alkynes 7, 8 and 26, 27 were also synthesized by SN2 reaction and demonstrated yields ranging from 30-55%. For the synthesis of 1,2,3-triazoles-1,4-disubstituted 25-33, the 1,3-dipolar cycloaddition reaction, which involves azides 17-19 and alkynes in the presence of copper catalyst (CuI) and a mixture of solvents t-BuOH/H2O to obtain the triazole 20-25, whereas for the synthesis of the triazoles 28-33 water was used as the solvent. Yields for the obtained compounds ranged from 75-98% and 72-98%, respectively. According to the tests of antimicrobial activity, a considerable number of compounds were active against the tested microorganisms. The compounds were evaluated for in vitro antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as antifungal activity, with 25a-d compounds showing promising results both in terms of antimicrobial and antioxidant activity. |
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2019-10-30T12:12:35Z2019-10-30T12:12:35Z2019-01-31http://repositorio.ufsm.br/handle/1/18709In the present work two new series of 1,2,3-triazoles-1,4-disubstituted 20-33 obtained by the reaction of 1,3-dipolar cycloaddition, Click-type, were synthesized between the alkaloids derived from benzocalcogenoanilines and the azides of 1,3-chalcogenazoles-2-substituted with the objective of joining three classes of interesting heterocyclic compounds and to explore the biological properties of these molecules in question. Compounds 17-19 were obtained from the bimolecular nucleophilic substitution reaction (SN2) in yields ranging from 55-90% and the alkynes 7, 8 and 26, 27 were also synthesized by SN2 reaction and demonstrated yields ranging from 30-55%. For the synthesis of 1,2,3-triazoles-1,4-disubstituted 25-33, the 1,3-dipolar cycloaddition reaction, which involves azides 17-19 and alkynes in the presence of copper catalyst (CuI) and a mixture of solvents t-BuOH/H2O to obtain the triazole 20-25, whereas for the synthesis of the triazoles 28-33 water was used as the solvent. Yields for the obtained compounds ranged from 75-98% and 72-98%, respectively. According to the tests of antimicrobial activity, a considerable number of compounds were active against the tested microorganisms. The compounds were evaluated for in vitro antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as antifungal activity, with 25a-d compounds showing promising results both in terms of antimicrobial and antioxidant activity.No presente trabalho foram sintetizadas duas novas séries de 1,2,3-triazóis-1,4-dissubstituídos 20-33 obtidas através da reação de cicloadição 1,3-dipolar, tipo Click, entre os alcinos derivados de benzocalcogenoanilinas e as azidas provenientes de 1,3-calcogenazóis-2-substituídos com o objetivo de unir três classes de compostos heterocíclicos interessantes e explorar as propriedades biológicas destas moléculas em questão. Os compostos 17-19 foram obtidos a partir de reação de substituição nucleofílica bimolecular (SN2) em rendimentos que variaram de 55-90% e os alcinos 7, 8 e 26, 27 foram também sintetizados por reação de SN2 e demonstraram rendimentos que variaram de 30-55%. Para a síntese de 1,2,3-triazóis-1,4-dissubstituídos 25-33, utilizou-se a reação de cicloadição 1,3-dipolar, que envolve azidas 17-19 e alcinos na presença de catalisador de cobre (CuI) adequado e uma mistura de solventes t-BuOH/H2O para obtenção dos triazóis 20-25, enquanto que para a síntese dos triazóis 28-33 utilizou-se água como solvente. Os rendimentos para os compostos obtidos variaram de 75-98% e 72-98%, respectivamente. De acordo com os testes de atividade antimicrobiana, um número considerável de compostos apresentaram-se ativos frente aos microrganismos testados. Os compostos foram avaliados quanto à atividade antibacteriana in vitro contra bactérias Gram-positivas e Gram-negativas, e também com relação à atividade antifúngica, merecendo destaque os compostos 25a-d os quais demonstraram resultados promissores tanto em termos de atividade antimicrobiana quanto antioxidante.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/openAccess1,2,3-triazóis-1,4-substituídosCicloadição 1,3-dipolarBenzocalcogenoanilinas1,3-calcogenazóisAtividade antimicrobianaAvaliação do potencial antioxidante1,2,3-triazoles-1,4-substituted1,3-dipolar cycloadditionBenzocalcogenoanilines1,3-chalcogenazolesAntimicrobian activityEvaluation of antioxidant potentialCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóisSynthesis and biological evaluation of 1,2,3-triazoles-1,4-disubstituted derived from benzochalcogenoanilines and 2-aryl-4- (azidomethyl) -1,3-chalcogenazolesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisDornelles, Lucianohttp://lattes.cnpq.br/7629319262073140Fantinel, Leonardohttp://lattes.cnpq.br/3934644027018397Ilha, Viniciushttp://lattes.cnpq.br/3882671719676564Dalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Schumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135http://lattes.cnpq.br/3329083517926813Rodrigues, Mariele Borkowski1006000000006006b4b1c8a-fdd1-49f0-a8ce-2d891b6579b676d7ae34-6524-4bc4-8ed4-12e5ed6d0124b0e1e2a5-71c6-4a3f-9161-9fa6805b8b497478688e-3aa2-4a32-9f0a-d2b661267e8311b367fb-0eed-426e-9ab5-e42e52a8d0986c8d4d2c-6e7a-4fa7-8f85-f8e27a24863breponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2019_RODRIGUES_MARIELE.pdfTES_PPGQUIMICA_2019_RODRIGUES_MARIELE.pdfTese de Doutoradoapplication/pdf8717270http://repositorio.ufsm.br/bitstream/1/18709/1/TES_PPGQUIMICA_2019_RODRIGUES_MARIELE.pdf8e76bd8432140e806247ab6b3a93becbMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
dc.title.alternative.eng.fl_str_mv |
Synthesis and biological evaluation of 1,2,3-triazoles-1,4-disubstituted derived from benzochalcogenoanilines and 2-aryl-4- (azidomethyl) -1,3-chalcogenazoles |
title |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
spellingShingle |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis Rodrigues, Mariele Borkowski 1,2,3-triazóis-1,4-substituídos Cicloadição 1,3-dipolar Benzocalcogenoanilinas 1,3-calcogenazóis Atividade antimicrobiana Avaliação do potencial antioxidante 1,2,3-triazoles-1,4-substituted 1,3-dipolar cycloaddition Benzocalcogenoanilines 1,3-chalcogenazoles Antimicrobian activity Evaluation of antioxidant potential CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
title_full |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
title_fullStr |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
title_full_unstemmed |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
title_sort |
Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis |
author |
Rodrigues, Mariele Borkowski |
author_facet |
Rodrigues, Mariele Borkowski |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Dornelles, Luciano |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7629319262073140 |
dc.contributor.referee1.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.referee2.fl_str_mv |
Ilha, Vinicius |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/3882671719676564 |
dc.contributor.referee3.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/9769548819312192 |
dc.contributor.referee4.fl_str_mv |
Schumacher, Ricardo Frederico |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/7856034546434135 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3329083517926813 |
dc.contributor.author.fl_str_mv |
Rodrigues, Mariele Borkowski |
contributor_str_mv |
Dornelles, Luciano Fantinel, Leonardo Ilha, Vinicius Dalcol, Ionara Irion Schumacher, Ricardo Frederico |
dc.subject.por.fl_str_mv |
1,2,3-triazóis-1,4-substituídos Cicloadição 1,3-dipolar Benzocalcogenoanilinas 1,3-calcogenazóis Atividade antimicrobiana Avaliação do potencial antioxidante |
topic |
1,2,3-triazóis-1,4-substituídos Cicloadição 1,3-dipolar Benzocalcogenoanilinas 1,3-calcogenazóis Atividade antimicrobiana Avaliação do potencial antioxidante 1,2,3-triazoles-1,4-substituted 1,3-dipolar cycloaddition Benzocalcogenoanilines 1,3-chalcogenazoles Antimicrobian activity Evaluation of antioxidant potential CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
1,2,3-triazoles-1,4-substituted 1,3-dipolar cycloaddition Benzocalcogenoanilines 1,3-chalcogenazoles Antimicrobian activity Evaluation of antioxidant potential |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In the present work two new series of 1,2,3-triazoles-1,4-disubstituted 20-33 obtained by the reaction of 1,3-dipolar cycloaddition, Click-type, were synthesized between the alkaloids derived from benzocalcogenoanilines and the azides of 1,3-chalcogenazoles-2-substituted with the objective of joining three classes of interesting heterocyclic compounds and to explore the biological properties of these molecules in question. Compounds 17-19 were obtained from the bimolecular nucleophilic substitution reaction (SN2) in yields ranging from 55-90% and the alkynes 7, 8 and 26, 27 were also synthesized by SN2 reaction and demonstrated yields ranging from 30-55%. For the synthesis of 1,2,3-triazoles-1,4-disubstituted 25-33, the 1,3-dipolar cycloaddition reaction, which involves azides 17-19 and alkynes in the presence of copper catalyst (CuI) and a mixture of solvents t-BuOH/H2O to obtain the triazole 20-25, whereas for the synthesis of the triazoles 28-33 water was used as the solvent. Yields for the obtained compounds ranged from 75-98% and 72-98%, respectively. According to the tests of antimicrobial activity, a considerable number of compounds were active against the tested microorganisms. The compounds were evaluated for in vitro antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as antifungal activity, with 25a-d compounds showing promising results both in terms of antimicrobial and antioxidant activity. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-10-30T12:12:35Z |
dc.date.available.fl_str_mv |
2019-10-30T12:12:35Z |
dc.date.issued.fl_str_mv |
2019-01-31 |
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/1/18709 |
url |
http://repositorio.ufsm.br/handle/1/18709 |
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 |
6b4b1c8a-fdd1-49f0-a8ce-2d891b6579b6 76d7ae34-6524-4bc4-8ed4-12e5ed6d0124 b0e1e2a5-71c6-4a3f-9161-9fa6805b8b49 7478688e-3aa2-4a32-9f0a-d2b661267e83 11b367fb-0eed-426e-9ab5-e42e52a8d098 6c8d4d2c-6e7a-4fa7-8f85-f8e27a24863b |
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:Repositório Institucional Manancial 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 |
Repositório Institucional Manancial UFSM |
collection |
Repositório Institucional Manancial UFSM |
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