Síntese e atividade antitumoral e antioxidante de calcogeno-amino timidinas (CAT)
Ano de defesa: | 2016 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | |
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: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
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 |
id |
UFSM_17ca29aa56510bdd39a54cdfa245f175 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/18064 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
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; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/18064/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/18064/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD53ORIGINALDIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdfDIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdfDissertação de Mestradoapplication/pdf4640699http://repositorio.ufsm.br/bitstream/1/18064/1/DIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf03e51d92500824507fee4e84f58d107bMD51TEXTDIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.txtDIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.txtExtracted texttext/plain118306http://repositorio.ufsm.br/bitstream/1/18064/4/DIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.txtf70b03cca0f64cbe813d10bc1f62b451MD54THUMBNAILDIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.jpgDIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.jpgIM Thumbnailimage/jpeg4500http://repositorio.ufsm.br/bitstream/1/18064/5/DIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.jpged73df84b6386814882a9b5317e07a69MD551/180642019-08-30 03:01:57.282oai: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:2019-08-30T06:01:57Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
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 |
dc.relation.authority.fl_str_mv |
09fef019-ac43-4d8b-83d3-3565e4686d7b 4a6e574e-e65d-4245-ac5a-e1efd444ca8f 6190e59b-afb1-46bf-8172-0091c1964025 |
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 |
http://repositorio.ufsm.br/bitstream/1/18064/2/license_rdf http://repositorio.ufsm.br/bitstream/1/18064/3/license.txt http://repositorio.ufsm.br/bitstream/1/18064/1/DIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf http://repositorio.ufsm.br/bitstream/1/18064/4/DIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.txt http://repositorio.ufsm.br/bitstream/1/18064/5/DIS_PPGQUIMICA_2016_ROSA_RAQUEL.pdf.jpg |
bitstream.checksum.fl_str_mv |
4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df 03e51d92500824507fee4e84f58d107b f70b03cca0f64cbe813d10bc1f62b451 ed73df84b6386814882a9b5317e07a69 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
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_ |
1793240079937830912 |