Synthesis of New Conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and Evaluation against Leishmania amazonensis
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=S0103-50532018000100159 |
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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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 |
_version_ |
1750318180377559040 |