Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)

Detalhes bibliográficos
Ano de defesa: 2016
Autor(a) principal: Rosa, Raquel Mello da lattes
Orientador(a): Rodrigues, Oscar Endrigo Dorneles lattes
Banca de defesa: Mostardeiro, Marco Aurelio lattes
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:
Nucleosídeos
Calcogeno-amino Timidina (CAT)
Atividade antioxidante e antitumoral
Antioxidant and antitumoral activity
Palavras-chave em Inglês:
Nucleosides
Chalcogeno-aminothymidine
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/18064
Resumo: This work aims the synthesis of new 5'-arilchalcogenil-3-animo-thymidine (5a-m) derivative containing chalcogenium or thymidines nucleosides derivatives (3-azidothymidine 1) with potential antioxidant and antitumor evaluation. The development of a synthetic route involving two transformations in a single reaction step was planned. The compounds exhibit changes at specific positions consisting in adding organochalcogenium at position 5 of 3-azidothymidine 1. The cleavage reaction of the corresponding aryl dichalcogenetes (4a-j) in THF followed by the addition of the reducing agent NaBH4 and EtOH, leading to the formation of nucleophilic species to react chalcogen through a bimolecular nucleophilic substitution reaction, these nucleophiles reacted with 3-azidothymidine mesilada 3 and along this same protocol, the reduction of the azide grouping of 3-azidothymidine mesilada 3 to their desired amines was performed forming the 5'-arilchalcogenil-3-animo-thymidine (5a-m) in yields in the range 20 -82%. The studies of reaction time and the amount of reducing agent were performed in order to optimize for the two desired reaction steps, which allowed quick access to a range of novel compounds. With properly characterized compounds, they have undergone as its antioxidant and anti-tumor potential
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spelling 2019-08-29T11:03:28Z2019-08-29T11:03:28Z2016-07-29http://repositorio.ufsm.br/handle/1/18064This work aims the synthesis of new 5'-arilchalcogenil-3-animo-thymidine (5a-m) derivative containing chalcogenium or thymidines nucleosides derivatives (3-azidothymidine 1) with potential antioxidant and antitumor evaluation. The development of a synthetic route involving two transformations in a single reaction step was planned. The compounds exhibit changes at specific positions consisting in adding organochalcogenium at position 5 of 3-azidothymidine 1. The cleavage reaction of the corresponding aryl dichalcogenetes (4a-j) in THF followed by the addition of the reducing agent NaBH4 and EtOH, leading to the formation of nucleophilic species to react chalcogen through a bimolecular nucleophilic substitution reaction, these nucleophiles reacted with 3-azidothymidine mesilada 3 and along this same protocol, the reduction of the azide grouping of 3-azidothymidine mesilada 3 to their desired amines was performed forming the 5'-arilchalcogenil-3-animo-thymidine (5a-m) in yields in the range 20 -82%. The studies of reaction time and the amount of reducing agent were performed in order to optimize for the two desired reaction steps, which allowed quick access to a range of novel compounds. With properly characterized compounds, they have undergone as its antioxidant and anti-tumor potentialO presente trabalho tem como finalidade apresentar a síntese de uma nova classe de 5’-arilcalcogenil-3-animo-timidina (5a-m) contendo derivados de organocalcogênios do nucleosídeo timidina (3-azidotimidina 1) via processo one-pot envolvendo avaliação antioxidante e antitumoral. Planejou-se a elaboração de uma rota sintética que envolveu duas transformações em uma única etapa reacional. Os compostos apresentaram variações em posições específicas, derivadas da adição de organocalcogênios na posição 5 da 3-azidotimidina 1. A reação consiste na clivagem dos respectivos dicalcogenetos arílicos (4a-j) em THF seguido pela adição da agente redutor de NaBH4 e EtOH, levando a formação das espécies nucleofílicas de calcogênio que levou a introdução da porção organocalcogênio. Adicionalmente nesta mesma etapa, foi realizada a redução da azida do grupamento da 3-azidotimidina mesilada 3 para as respectivas aminas desejadas, formando as 5’-arilcalcogenil-3-animo-timidina (5a-m) em rendimentos na faixa de 20-82%. Os estudos do tempo reacional e a quantidade do agente redutor foram realizados visando a otimização para as duas etapas reacionais desejadas, o que propiciou o acesso rápido a uma gama de compostos inéditos. Com os compostos devidamente caracterizados, estes foram submetidos a avaliações quanto sua potencialidade antioxidante e antitumoral.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/openAccessNucleosídeosCalcogeno-amino Timidina (CAT)Atividade antioxidante e antitumoralAntioxidant and antitumoral activityNucleosidesChalcogeno-aminothymidineCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)Synthesis, antioxidant and antitumoral activities of chalcogeno-amino thymidine derivatiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisRodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Mostardeiro, Marco Aureliohttp://lattes.cnpq.br/6195396264565980http://lattes.cnpq.br/3966179889958769Rosa, Raquel Mello da10060000000060009fef019-ac43-4d8b-83d3-3565e4686d7b4a6e574e-e65d-4245-ac5a-e1efd444ca8f6190e59b-afb1-46bf-8172-0091c1964025reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
dc.title.alternative.eng.fl_str_mv Synthesis, antioxidant and antitumoral activities of chalcogeno-amino thymidine derivaties
title Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
spellingShingle Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
Rosa, Raquel Mello da
Nucleosídeos
Calcogeno-amino Timidina (CAT)
Atividade antioxidante e antitumoral
Antioxidant and antitumoral activity
Nucleosides
Chalcogeno-aminothymidine
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
title_full Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
title_fullStr Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
title_full_unstemmed Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
title_sort Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
author Rosa, Raquel Mello da
author_facet Rosa, Raquel Mello da
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.referee1.fl_str_mv Mostardeiro, Marco Aurelio
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/6195396264565980
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/3966179889958769
dc.contributor.author.fl_str_mv Rosa, Raquel Mello da
contributor_str_mv Rodrigues, Oscar Endrigo Dorneles
Mostardeiro, Marco Aurelio
dc.subject.por.fl_str_mv Nucleosídeos
Calcogeno-amino Timidina (CAT)
Atividade antioxidante e antitumoral
Antioxidant and antitumoral activity
topic Nucleosídeos
Calcogeno-amino Timidina (CAT)
Atividade antioxidante e antitumoral
Antioxidant and antitumoral activity
Nucleosides
Chalcogeno-aminothymidine
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Nucleosides
Chalcogeno-aminothymidine
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description This work aims the synthesis of new 5'-arilchalcogenil-3-animo-thymidine (5a-m) derivative containing chalcogenium or thymidines nucleosides derivatives (3-azidothymidine 1) with potential antioxidant and antitumor evaluation. The development of a synthetic route involving two transformations in a single reaction step was planned. The compounds exhibit changes at specific positions consisting in adding organochalcogenium at position 5 of 3-azidothymidine 1. The cleavage reaction of the corresponding aryl dichalcogenetes (4a-j) in THF followed by the addition of the reducing agent NaBH4 and EtOH, leading to the formation of nucleophilic species to react chalcogen through a bimolecular nucleophilic substitution reaction, these nucleophiles reacted with 3-azidothymidine mesilada 3 and along this same protocol, the reduction of the azide grouping of 3-azidothymidine mesilada 3 to their desired amines was performed forming the 5'-arilchalcogenil-3-animo-thymidine (5a-m) in yields in the range 20 -82%. The studies of reaction time and the amount of reducing agent were performed in order to optimize for the two desired reaction steps, which allowed quick access to a range of novel compounds. With properly characterized compounds, they have undergone as its antioxidant and anti-tumor potential
publishDate 2016
dc.date.issued.fl_str_mv 2016-07-29
dc.date.accessioned.fl_str_mv 2019-08-29T11:03:28Z
dc.date.available.fl_str_mv 2019-08-29T11:03:28Z
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/1/18064
url http://repositorio.ufsm.br/handle/1/18064
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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institution UFSM
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