Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202646 |
Resumo: | A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, and the derivative (±)-11-methoxy-5,6,6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1,2-a]naphthalene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt0, 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. |
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Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activitytetrahydroquinoline alkaloidsWittig reactionsolvolytic N-methylationantibacterial activityA novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, and the derivative (±)-11-methoxy-5,6,6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1,2-a]naphthalene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt0, 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.Sociedade Brasileira de Química2018-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202646Journal of the Brazilian Chemical Society v.29 n.12 2018reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180145info:eu-repo/semantics/openAccessDiaz-Muñoz,GasparMiranda,Izabel L.Sartori,Suélen K.Dias,Gabriel N. S.Kohlhoff,MarkusPurgato,Gislaine A.Diaz,Marisa A. N.eng2018-11-26T00:00:00Zoai:scielo:S0103-50532018001202646Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2018-11-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.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 L. Sartori,Suélen K. Dias,Gabriel N. S. Kohlhoff,Markus Purgato,Gislaine A. Diaz,Marisa A. N. |
author_role |
author |
author2 |
Miranda,Izabel L. Sartori,Suélen K. Dias,Gabriel N. S. Kohlhoff,Markus Purgato,Gislaine A. Diaz,Marisa A. N. |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Diaz-Muñoz,Gaspar Miranda,Izabel L. Sartori,Suélen K. Dias,Gabriel N. S. Kohlhoff,Markus Purgato,Gislaine A. Diaz,Marisa A. N. |
dc.subject.por.fl_str_mv |
tetrahydroquinoline alkaloids Wittig reaction solvolytic N-methylation antibacterial activity |
topic |
tetrahydroquinoline alkaloids Wittig reaction solvolytic N-methylation antibacterial activity |
description |
A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, and the derivative (±)-11-methoxy-5,6,6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1,2-a]naphthalene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt0, 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. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202646 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202646 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20180145 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
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 |
Journal of the Brazilian Chemical Society v.29 n.12 2018 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318181299257344 |