Síntese de N-dióxidos derivados de piperazinas e zidovudinas

Detalhes bibliográficos
Ano de defesa: 2022
Autor(a) principal: Wendt, Marcelo lattes
Orientador(a): Rodrigues, Oscar Endrigo Dorneles lattes
Banca de defesa: Morel, Ademir Farias, Godoi, Benhur de
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
Calcogenonucleosídeos
N,N-dióxidos
Piperazinas
Metodologia sintética
Covid-19
Palavras-chave em Inglês:
Chalcogen-nucleoside
N,N-dioxides
Piperazines
Synthetic methodology
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/26691
Resumo: Chalcogenonucleosides has been the object on studies because of its biological potential and their pharmaceutical properties, with prominence antitumor, antiviral and antioxidant properties. In addition, piperazine structures are present in compounds of pharmacological application showing antimicrobial, anticancer, antidepressant properties, among others. Finally, compounds derived from 2H-benzimidazole N,N-dioxides, despite being less studied when compared to the previous classes, have shown results that point to their potential, being used as an antiparasitic agent, in addition to having antitumor and antioxidant properties.With this in mind, the present work sought to develop a synthetic methodology to obtain new compounds of 1-(aryl-sulfonyl)-4-(1,3-dioxide-2,2-dimethyl-2H-benzimidazole)-acetylpiperazines 3a-c and 5'-arylcalcogenyl-3'-(1,3-dioxide-2,2-dimethyl-2H-benzimidazo-amido)- thymidines 5a-m, in order to make it possible to obtain 16 new compounds through , using DCC and DCM in open atmosphere and at room temperature, with good yields (49% to 90%). Additionally, in silico and in vitro tests, it was found that the compounds obtained showed favorable molecular anchoring results for interaction with the active site of the main protease of SARS-CoV-2, as well as an inhibitory action against it, indicating the possibility of acting as an inhibitor of SARS-COV-2
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spelling 2022-10-27T16:48:15Z2022-10-27T16:48:15Z2022-09-30http://repositorio.ufsm.br/handle/1/26691Chalcogenonucleosides has been the object on studies because of its biological potential and their pharmaceutical properties, with prominence antitumor, antiviral and antioxidant properties. In addition, piperazine structures are present in compounds of pharmacological application showing antimicrobial, anticancer, antidepressant properties, among others. Finally, compounds derived from 2H-benzimidazole N,N-dioxides, despite being less studied when compared to the previous classes, have shown results that point to their potential, being used as an antiparasitic agent, in addition to having antitumor and antioxidant properties.With this in mind, the present work sought to develop a synthetic methodology to obtain new compounds of 1-(aryl-sulfonyl)-4-(1,3-dioxide-2,2-dimethyl-2H-benzimidazole)-acetylpiperazines 3a-c and 5'-arylcalcogenyl-3'-(1,3-dioxide-2,2-dimethyl-2H-benzimidazo-amido)- thymidines 5a-m, in order to make it possible to obtain 16 new compounds through , using DCC and DCM in open atmosphere and at room temperature, with good yields (49% to 90%). Additionally, in silico and in vitro tests, it was found that the compounds obtained showed favorable molecular anchoring results for interaction with the active site of the main protease of SARS-CoV-2, as well as an inhibitory action against it, indicating the possibility of acting as an inhibitor of SARS-COV-2Calcogenonucleosídeos vem sendo alvo de estudo devido ao seu potencial biológico e suas propriedades farmacêuticas, das quais podem-se destacar propriedades antitumorais, antivirais, antioxidantes, entre outras. Também, estruturas de piperazinas apresentam-se presentes em compostos de aplicação farmacológica apresentando propriedades antimicrobianas, anticancerígenas, antidepressivas, entre outras. Por fim, os compostos derivados de N,N-dióxidos de 2H-benzimidazóis, apesar de menos estudados quando comparados as classes anteriores, vem apresentando resultados apontando seu potencial, sendo utilizado como agente antiparasitário, além de apresentar propriedades antitumorais e antioxidantes. Tendo isto em vista, o presente trabalho buscou desenvolver uma metodologia sintética para a obtenção de novos compostos de 1-(aril-sulfonil)-4-(1,3-dióxido-2,2-dimetil2H-benzimidazol)-acetil-piperazinas 3a-c e 5’-arilcalcogenil-3’-(1,3-dióxido-2,2-dimetil-2Hbenzimidazo-amido)-timidinas 5a-m, de modo a possibilitar a obtenção de 16 novos compostos através de condições brandas, empregando DCC e DCM em atmosfera aberta e temperatura ambiente, com bons rendimentos (49% a 90%). Adicionalmente, verificou-se, em testes in sílico e in vitro, que os compostos obtidos apresentavam resultados de ancoragem molecular favoráveis para interação com o sítio ativo da protease principal do SARS-CoV-2, bem como, ação inibitória frente ao mesmo, indicando possibilidade de atuação como inibidor do SARS-COV-2.porUniversidade 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/openAccessCalcogenonucleosídeosN,N-dióxidosPiperazinasMetodologia sintéticaCovid-19Chalcogen-nucleosideN,N-dioxidesPiperazinesSynthetic methodologyCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de N-dióxidos derivados de piperazinas e zidovudinasSynthesis of N-dioxides derived from piperazines and zidovudinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisRodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Dornelles, LucianoMorel, Ademir FariasGodoi, Benhur dehttp://lattes.cnpq.br/2234330730171169Wendt, Marcelo10060000000060060060060060060009fef019-ac43-4d8b-83d3-3565e4686d7b0e3d0a07-3d28-4edf-9e6f-01d65ada384688ff8616-1678-47c5-b3c5-9a8e5085844f22df5f67-c304-4742-b982-4d1e6d30aeccc30fcd74-7708-48d5-ba10-655685fff806reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUÍMICA_2022_WENDT_MARCELO.pdfDIS_PPGQUÍMICA_2022_WENDT_MARCELO.pdfDissertação de mestradoapplication/pdf6213178http://repositorio.ufsm.br/bitstream/1/26691/1/DIS_PPGQU%c3%8dMICA_2022_WENDT_MARCELO.pdf1999d1b4f136c5fb9efe5ccf6ab5d922MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/26691/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/26691/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/266912022-10-27 13:48:15.833oai:repositorio.ufsm.br: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 Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-10-27T16:48:15Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Síntese de N-dióxidos derivados de piperazinas e zidovudinas
dc.title.alternative.eng.fl_str_mv Synthesis of N-dioxides derived from piperazines and zidovudines
title Síntese de N-dióxidos derivados de piperazinas e zidovudinas
spellingShingle Síntese de N-dióxidos derivados de piperazinas e zidovudinas
Wendt, Marcelo
Calcogenonucleosídeos
N,N-dióxidos
Piperazinas
Metodologia sintética
Covid-19
Chalcogen-nucleoside
N,N-dioxides
Piperazines
Synthetic methodology
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de N-dióxidos derivados de piperazinas e zidovudinas
title_full Síntese de N-dióxidos derivados de piperazinas e zidovudinas
title_fullStr Síntese de N-dióxidos derivados de piperazinas e zidovudinas
title_full_unstemmed Síntese de N-dióxidos derivados de piperazinas e zidovudinas
title_sort Síntese de N-dióxidos derivados de piperazinas e zidovudinas
author Wendt, Marcelo
author_facet Wendt, Marcelo
author_role author
dc.contributor.advisor1.fl_str_mv Rodrigues, Oscar Endrigo Dorneles
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/6536519955416085
dc.contributor.advisor-co1.fl_str_mv Dornelles, Luciano
dc.contributor.referee1.fl_str_mv Morel, Ademir Farias
dc.contributor.referee2.fl_str_mv Godoi, Benhur de
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/2234330730171169
dc.contributor.author.fl_str_mv Wendt, Marcelo
contributor_str_mv Rodrigues, Oscar Endrigo Dorneles
Dornelles, Luciano
Morel, Ademir Farias
Godoi, Benhur de
dc.subject.por.fl_str_mv Calcogenonucleosídeos
N,N-dióxidos
Piperazinas
Metodologia sintética
Covid-19
topic Calcogenonucleosídeos
N,N-dióxidos
Piperazinas
Metodologia sintética
Covid-19
Chalcogen-nucleoside
N,N-dioxides
Piperazines
Synthetic methodology
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Chalcogen-nucleoside
N,N-dioxides
Piperazines
Synthetic methodology
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description Chalcogenonucleosides has been the object on studies because of its biological potential and their pharmaceutical properties, with prominence antitumor, antiviral and antioxidant properties. In addition, piperazine structures are present in compounds of pharmacological application showing antimicrobial, anticancer, antidepressant properties, among others. Finally, compounds derived from 2H-benzimidazole N,N-dioxides, despite being less studied when compared to the previous classes, have shown results that point to their potential, being used as an antiparasitic agent, in addition to having antitumor and antioxidant properties.With this in mind, the present work sought to develop a synthetic methodology to obtain new compounds of 1-(aryl-sulfonyl)-4-(1,3-dioxide-2,2-dimethyl-2H-benzimidazole)-acetylpiperazines 3a-c and 5'-arylcalcogenyl-3'-(1,3-dioxide-2,2-dimethyl-2H-benzimidazo-amido)- thymidines 5a-m, in order to make it possible to obtain 16 new compounds through , using DCC and DCM in open atmosphere and at room temperature, with good yields (49% to 90%). Additionally, in silico and in vitro tests, it was found that the compounds obtained showed favorable molecular anchoring results for interaction with the active site of the main protease of SARS-CoV-2, as well as an inhibitory action against it, indicating the possibility of acting as an inhibitor of SARS-COV-2
publishDate 2022
dc.date.accessioned.fl_str_mv 2022-10-27T16:48:15Z
dc.date.available.fl_str_mv 2022-10-27T16:48:15Z
dc.date.issued.fl_str_mv 2022-09-30
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/26691
url http://repositorio.ufsm.br/handle/1/26691
dc.language.iso.fl_str_mv por
language por
dc.relation.cnpq.fl_str_mv 100600000000
dc.relation.confidence.fl_str_mv 600
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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
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reponame_str Biblioteca Digital de Teses e Dissertações do UFSM
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