Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity

Detalhes bibliográficos
Autor(a) principal: Diaz-Muñoz, Gaspar
Data de Publicação: 2018
Outros Autores: Miranda, Izabel Luzia, Sartori, Suélen Karine, Dias, Gabriel Nunes de Souza, Kohlhoff, Markus, Purgato, Gislaine Aparecida, Diaz, Marisa Alves Nogueira
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/54724
Resumo: FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE MINAS GERAIS
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spelling Diaz-Muñoz, GasparMiranda, Izabel LuziaSartori, Suélen KarineDias, Gabriel Nunes de SouzaKohlhoff, MarkusPurgato, Gislaine AparecidaDiaz, Marisa Alves Nogueira2022-08-18T18:39:20Z2022-08-18T18:39:20Z2018DIAZ-MUÑOZ, Gaspar et al. Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity. J. Braz. Chem. Soc., v. 29, n. 12, p. 2646-2656, 2018. https://doi.org/10.21577/0103-5053.201801450103-5053https://www.arca.fiocruz.br/handle/icict/5472410.21577/0103-5053.20180145FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE MINAS GERAISUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilUniversidade Federal de Minas Gerais. Departamento de Aquacultura. Belo Horizonte, MG, BrazilFundação Oswaldo Cruz. Instituto René Rachou. Química de Produtos Naturais Bioativos. Belo Horizonte, MG, BrazilUniversidade Federal de Viçosa. Departamento de Bioquímica e Biologia Molecular. Viçosa, MG, BrazilUniversidade Federal de Viçosa. Departamento de Bioquímica e Biologia Molecular. Viçosa, MG, BrazilA novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (+/-)-galipinine, (+/-)-cuspareine, (t)-galipeine and (+/-)-angustureine, and the derivative (+/-)-11-methoxy-5,6.6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1.2-a]naphilialene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt-0, generated in situ by reduction of PtO2. The evaluation of biofilm inhibition and antibacterial activity of the compounds against Staphylococcus aureus strains isolated from cows with mastitis revealed that the alkaloid derivative is a promising candidate for an antibiotic drug.engSociedade Brasileira de QuímicaUnprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activityinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articletetrahydroquinoline alkaloidsWittig reactionsolvolytic N-methylationantibacterial activityinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZORIGINALunprecedented one poto sequence.pdfunprecedented one poto sequence.pdfapplication/pdf1620813https://www.arca.fiocruz.br/bitstream/icict/54724/2/unprecedented%20one%20poto%20sequence.pdf6409ff0608a0d30f964744455f410e89MD52LICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/54724/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51icict/547242022-08-18 15:39:20.625oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352022-08-18T18:39:20Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
title Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
spellingShingle Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
Diaz-Muñoz, Gaspar
tetrahydroquinoline alkaloids
Wittig reaction
solvolytic N-methylation
antibacterial activity
title_short Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
title_full Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
title_fullStr Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
title_full_unstemmed Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
title_sort Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
author Diaz-Muñoz, Gaspar
author_facet Diaz-Muñoz, Gaspar
Miranda, Izabel Luzia
Sartori, Suélen Karine
Dias, Gabriel Nunes de Souza
Kohlhoff, Markus
Purgato, Gislaine Aparecida
Diaz, Marisa Alves Nogueira
author_role author
author2 Miranda, Izabel Luzia
Sartori, Suélen Karine
Dias, Gabriel Nunes de Souza
Kohlhoff, Markus
Purgato, Gislaine Aparecida
Diaz, Marisa Alves Nogueira
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Diaz-Muñoz, Gaspar
Miranda, Izabel Luzia
Sartori, Suélen Karine
Dias, Gabriel Nunes de Souza
Kohlhoff, Markus
Purgato, Gislaine Aparecida
Diaz, Marisa Alves Nogueira
dc.subject.en.pt_BR.fl_str_mv tetrahydroquinoline alkaloids
Wittig reaction
solvolytic N-methylation
antibacterial activity
topic tetrahydroquinoline alkaloids
Wittig reaction
solvolytic N-methylation
antibacterial activity
description FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE MINAS GERAIS
publishDate 2018
dc.date.issued.fl_str_mv 2018
dc.date.accessioned.fl_str_mv 2022-08-18T18:39:20Z
dc.date.available.fl_str_mv 2022-08-18T18:39:20Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv DIAZ-MUÑOZ, Gaspar et al. Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity. J. Braz. Chem. Soc., v. 29, n. 12, p. 2646-2656, 2018. https://doi.org/10.21577/0103-5053.20180145
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/54724
dc.identifier.issn.pt_BR.fl_str_mv 0103-5053
dc.identifier.doi.none.fl_str_mv 10.21577/0103-5053.20180145
identifier_str_mv DIAZ-MUÑOZ, Gaspar et al. Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity. J. Braz. Chem. Soc., v. 29, n. 12, p. 2646-2656, 2018. https://doi.org/10.21577/0103-5053.20180145
0103-5053
10.21577/0103-5053.20180145
url https://www.arca.fiocruz.br/handle/icict/54724
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
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reponame_str Repositório Institucional da FIOCRUZ (ARCA)
collection Repositório Institucional da FIOCRUZ (ARCA)
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