Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis

Detalhes bibliográficos
Autor(a) principal: Medeiros,Antonia C. R. F.
Data de Publicação: 2018
Outros Autores: Borges,Julio C., Becker,Klaus M., Rodrigues,Raquel F., Leon,Leonor L., Canto-Cavalheiro,Marilene, Bernardino,Alice M. R., Souza,Marcos C. de, Pedrosa,Leandro F.
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=S0103-50532018000100159
Resumo: In this research three series of substituted 1H-pyrazolo[3,4-b]pyridine phosphoramidates were synthesized and characterized by infrared, 1H, 13C, and 31P nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The products were obtained in good yields (67-83%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chloro-1H-pyrazolo[3,4-b]pyridines. These compounds were evaluated as antileishmanials against Leishmania amazonensis promastigotes in vitro. Among all, compounds of a series showed expressive antileishmanial activity. Two of them emerged as the most active, with IC50 values of 6.44 ± 1.49 and 12.25 ± 0.68 µM. The cytotoxicity of this series was assessed on murine cells and presented values similar to the reference drug pentamidine.
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spelling Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensisantileishmanial activity1H-pyrazolo[3,4-b]pyridinephosphoramidateIn this research three series of substituted 1H-pyrazolo[3,4-b]pyridine phosphoramidates were synthesized and characterized by infrared, 1H, 13C, and 31P nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The products were obtained in good yields (67-83%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chloro-1H-pyrazolo[3,4-b]pyridines. These compounds were evaluated as antileishmanials against Leishmania amazonensis promastigotes in vitro. Among all, compounds of a series showed expressive antileishmanial activity. Two of them emerged as the most active, with IC50 values of 6.44 ± 1.49 and 12.25 ± 0.68 µM. The cytotoxicity of this series was assessed on murine cells and presented values similar to the reference drug pentamidine.Sociedade Brasileira de Química2018-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100159Journal of the Brazilian Chemical Society v.29 n.1 2018reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20170126info:eu-repo/semantics/openAccessMedeiros,Antonia C. R. F.Borges,Julio C.Becker,Klaus M.Rodrigues,Raquel F.Leon,Leonor L.Canto-Cavalheiro,MarileneBernardino,Alice M. R.Souza,Marcos C. dePedrosa,Leandro F.eng2018-02-08T00:00:00Zoai:scielo:S0103-50532018000100159Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2018-02-08T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
title Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
spellingShingle Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
Medeiros,Antonia C. R. F.
antileishmanial activity
1H-pyrazolo[3,4-b]pyridine
phosphoramidate
title_short Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
title_full Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
title_fullStr Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
title_full_unstemmed Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
title_sort Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
author Medeiros,Antonia C. R. F.
author_facet Medeiros,Antonia C. R. F.
Borges,Julio C.
Becker,Klaus M.
Rodrigues,Raquel F.
Leon,Leonor L.
Canto-Cavalheiro,Marilene
Bernardino,Alice M. R.
Souza,Marcos C. de
Pedrosa,Leandro F.
author_role author
author2 Borges,Julio C.
Becker,Klaus M.
Rodrigues,Raquel F.
Leon,Leonor L.
Canto-Cavalheiro,Marilene
Bernardino,Alice M. R.
Souza,Marcos C. de
Pedrosa,Leandro F.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Medeiros,Antonia C. R. F.
Borges,Julio C.
Becker,Klaus M.
Rodrigues,Raquel F.
Leon,Leonor L.
Canto-Cavalheiro,Marilene
Bernardino,Alice M. R.
Souza,Marcos C. de
Pedrosa,Leandro F.
dc.subject.por.fl_str_mv antileishmanial activity
1H-pyrazolo[3,4-b]pyridine
phosphoramidate
topic antileishmanial activity
1H-pyrazolo[3,4-b]pyridine
phosphoramidate
description In this research three series of substituted 1H-pyrazolo[3,4-b]pyridine phosphoramidates were synthesized and characterized by infrared, 1H, 13C, and 31P nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The products were obtained in good yields (67-83%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chloro-1H-pyrazolo[3,4-b]pyridines. These compounds were evaluated as antileishmanials against Leishmania amazonensis promastigotes in vitro. Among all, compounds of a series showed expressive antileishmanial activity. Two of them emerged as the most active, with IC50 values of 6.44 ± 1.49 and 12.25 ± 0.68 µM. The cytotoxicity of this series was assessed on murine cells and presented values similar to the reference drug pentamidine.
publishDate 2018
dc.date.none.fl_str_mv 2018-01-01
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=S0103-50532018000100159
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100159
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20170126
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.1 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
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