Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.

Autores
Porta, Exequiel Oscar Jesús; Carvalho, Paulo B.; Avery, Mitchell A.; Tekwani, Babu L.; Labadie, Guillermo Roberto
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of 1,2,3-triazolylsterols was prepared from pregnenolone through reductive amination and copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). The newly generated stereocenter of the key propargylamino intermediate provided a mixture of diastereomers which were separated chromatographically, and the configuration of the R isomer was determined by X-ray crystallography. Ten triazolyl sterols were prepared, and the products and intermediates were screened in vitro against different parasites, with some compounds presenting IC50 values in the low micromolar range against Leishmania donovani
Fil: Porta, Exequiel Oscar Jesús. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Carvalho, Paulo B.. University of Maryland; Estados Unidos
Fil: Avery, Mitchell A.. University Of Mississippi; Estados Unidos
Fil: Tekwani, Babu L.. University Of Mississippi; Estados Unidos
Fil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
Pregnenolone
Reductive Amination
Click Chemistry
Triazolylsterols
Antimalarial
Antileishmanial
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/29755
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.Porta, Exequiel Oscar JesúsCarvalho, Paulo B.Avery, Mitchell A.Tekwani, Babu L.Labadie, Guillermo RobertoPregnenoloneReductive AminationClick ChemistryTriazolylsterolsAntimalarialAntileishmanialhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of 1,2,3-triazolylsterols was prepared from pregnenolone through reductive amination and copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). The newly generated stereocenter of the key propargylamino intermediate provided a mixture of diastereomers which were separated chromatographically, and the configuration of the R isomer was determined by X-ray crystallography. Ten triazolyl sterols were prepared, and the products and intermediates were screened in vitro against different parasites, with some compounds presenting IC50 values in the low micromolar range against Leishmania donovaniFil: Porta, Exequiel Oscar Jesús. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Carvalho, Paulo B.. University of Maryland; Estados UnidosFil: Avery, Mitchell A.. University Of Mississippi; Estados UnidosFil: Tekwani, Babu L.. University Of Mississippi; Estados UnidosFil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaElsevier Science Inc2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/29755Porta, Exequiel Oscar Jesús; Carvalho, Paulo B.; Avery, Mitchell A.; Tekwani, Babu L.; Labadie, Guillermo Roberto; Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.; Elsevier Science Inc; Steroids; 79; 1-2014; 28-360039-128XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.steroids.2013.10.010info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0039128X13002341info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:14:45Zoai:ri.conicet.gov.ar:11336/29755instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:14:45.929CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
title Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
spellingShingle Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
Porta, Exequiel Oscar Jesús
Pregnenolone
Reductive Amination
Click Chemistry
Triazolylsterols
Antimalarial
Antileishmanial
title_short Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
title_full Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
title_fullStr Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
title_full_unstemmed Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
title_sort Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.
dc.creator.none.fl_str_mv Porta, Exequiel Oscar Jesús
Carvalho, Paulo B.
Avery, Mitchell A.
Tekwani, Babu L.
Labadie, Guillermo Roberto
author Porta, Exequiel Oscar Jesús
author_facet Porta, Exequiel Oscar Jesús
Carvalho, Paulo B.
Avery, Mitchell A.
Tekwani, Babu L.
Labadie, Guillermo Roberto
author_role author
author2 Carvalho, Paulo B.
Avery, Mitchell A.
Tekwani, Babu L.
Labadie, Guillermo Roberto
author2_role author
author
author
author
dc.subject.none.fl_str_mv Pregnenolone
Reductive Amination
Click Chemistry
Triazolylsterols
Antimalarial
Antileishmanial
topic Pregnenolone
Reductive Amination
Click Chemistry
Triazolylsterols
Antimalarial
Antileishmanial
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of 1,2,3-triazolylsterols was prepared from pregnenolone through reductive amination and copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). The newly generated stereocenter of the key propargylamino intermediate provided a mixture of diastereomers which were separated chromatographically, and the configuration of the R isomer was determined by X-ray crystallography. Ten triazolyl sterols were prepared, and the products and intermediates were screened in vitro against different parasites, with some compounds presenting IC50 values in the low micromolar range against Leishmania donovani
Fil: Porta, Exequiel Oscar Jesús. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Carvalho, Paulo B.. University of Maryland; Estados Unidos
Fil: Avery, Mitchell A.. University Of Mississippi; Estados Unidos
Fil: Tekwani, Babu L.. University Of Mississippi; Estados Unidos
Fil: Labadie, Guillermo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description A series of 1,2,3-triazolylsterols was prepared from pregnenolone through reductive amination and copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). The newly generated stereocenter of the key propargylamino intermediate provided a mixture of diastereomers which were separated chromatographically, and the configuration of the R isomer was determined by X-ray crystallography. Ten triazolyl sterols were prepared, and the products and intermediates were screened in vitro against different parasites, with some compounds presenting IC50 values in the low micromolar range against Leishmania donovani
publishDate 2014
dc.date.none.fl_str_mv 2014-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/29755
Porta, Exequiel Oscar Jesús; Carvalho, Paulo B.; Avery, Mitchell A.; Tekwani, Babu L.; Labadie, Guillermo Roberto; Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.; Elsevier Science Inc; Steroids; 79; 1-2014; 28-36
0039-128X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/29755
identifier_str_mv Porta, Exequiel Oscar Jesús; Carvalho, Paulo B.; Avery, Mitchell A.; Tekwani, Babu L.; Labadie, Guillermo Roberto; Click chemistry decoration of amino sterols as promising strategy to developed new leishmanicidal drugs.; Elsevier Science Inc; Steroids; 79; 1-2014; 28-36
0039-128X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.steroids.2013.10.010
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0039128X13002341
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Inc
publisher.none.fl_str_mv Elsevier Science Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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