Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity

Autores
Castro, Sebastián Jorge; Padrón, José M.; Darses, Benjamin; Nicotra, Viviana Estela; Dauban, Philippe
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A set of new guaianolide derivatives (1–9) was obtained from ludartin, achalensolide, and 11,13-dihydroachalensolide by application of catalytic nitrene transfer reactions. Intermolecular nitrene C(sp3)−H insertions led to the amination of C-1, C-2, and C-10 positions, while alkene aziridination was also observed under these reaction conditions. The antiproliferative activity of natural compounds and their derivatives was evaluated against a panel of human solid tumor cell lines. The results show that an increase in the biological activity was observed following amination at the C-2 position of Ludartin, thereby demonstrating the interest in late-stage C−H amination to improve the bioactivity of natural products.
Fil: Castro, Sebastián Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Padrón, José M.. Universidad de La Laguna; España
Fil: Darses, Benjamin. Université Paris-Saclay; Francia. Universite Grenoble Alpes; Francia
Fil: Nicotra, Viviana Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Dauban, Philippe. Université Paris-Saclay; Francia
Materia
ANTIPROLIFERATIVE ACTIVITY
C−H AMINATION
LATE-STAGE FUNCTIONALIZATION
NITRENES
SESQUITERPENES
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:11336/136028
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/136028
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activityCastro, Sebastián JorgePadrón, José M.Darses, BenjaminNicotra, Viviana EstelaDauban, PhilippeANTIPROLIFERATIVE ACTIVITYC−H AMINATIONLATE-STAGE FUNCTIONALIZATIONNITRENESSESQUITERPENEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A set of new guaianolide derivatives (1–9) was obtained from ludartin, achalensolide, and 11,13-dihydroachalensolide by application of catalytic nitrene transfer reactions. Intermolecular nitrene C(sp3)−H insertions led to the amination of C-1, C-2, and C-10 positions, while alkene aziridination was also observed under these reaction conditions. The antiproliferative activity of natural compounds and their derivatives was evaluated against a panel of human solid tumor cell lines. The results show that an increase in the biological activity was observed following amination at the C-2 position of Ludartin, thereby demonstrating the interest in late-stage C−H amination to improve the bioactivity of natural products.Fil: Castro, Sebastián Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Padrón, José M.. Universidad de La Laguna; EspañaFil: Darses, Benjamin. Université Paris-Saclay; Francia. Universite Grenoble Alpes; FranciaFil: Nicotra, Viviana Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Dauban, Philippe. Université Paris-Saclay; FranciaWiley VCH Verlag2021-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/136028Castro, Sebastián Jorge; Padrón, José M.; Darses, Benjamin; Nicotra, Viviana Estela; Dauban, Philippe; Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity; Wiley VCH Verlag; European Journal of Organic Chemistry; 2021; 12; 3-2021; 1859-18631434-193X1099-0690CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/ejoc.202100074info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202100074info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:01:36Zoai:ri.conicet.gov.ar:11336/136028instacron: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:34982025-09-03 10:01:36.565CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
title Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
spellingShingle Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
Castro, Sebastián Jorge
ANTIPROLIFERATIVE ACTIVITY
C−H AMINATION
LATE-STAGE FUNCTIONALIZATION
NITRENES
SESQUITERPENES
title_short Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
title_full Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
title_fullStr Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
title_full_unstemmed Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
title_sort Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity
dc.creator.none.fl_str_mv Castro, Sebastián Jorge
Padrón, José M.
Darses, Benjamin
Nicotra, Viviana Estela
Dauban, Philippe
author Castro, Sebastián Jorge
author_facet Castro, Sebastián Jorge
Padrón, José M.
Darses, Benjamin
Nicotra, Viviana Estela
Dauban, Philippe
author_role author
author2 Padrón, José M.
Darses, Benjamin
Nicotra, Viviana Estela
Dauban, Philippe
author2_role author
author
author
author
dc.subject.none.fl_str_mv ANTIPROLIFERATIVE ACTIVITY
C−H AMINATION
LATE-STAGE FUNCTIONALIZATION
NITRENES
SESQUITERPENES
topic ANTIPROLIFERATIVE ACTIVITY
C−H AMINATION
LATE-STAGE FUNCTIONALIZATION
NITRENES
SESQUITERPENES
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 set of new guaianolide derivatives (1–9) was obtained from ludartin, achalensolide, and 11,13-dihydroachalensolide by application of catalytic nitrene transfer reactions. Intermolecular nitrene C(sp3)−H insertions led to the amination of C-1, C-2, and C-10 positions, while alkene aziridination was also observed under these reaction conditions. The antiproliferative activity of natural compounds and their derivatives was evaluated against a panel of human solid tumor cell lines. The results show that an increase in the biological activity was observed following amination at the C-2 position of Ludartin, thereby demonstrating the interest in late-stage C−H amination to improve the bioactivity of natural products.
Fil: Castro, Sebastián Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Padrón, José M.. Universidad de La Laguna; España
Fil: Darses, Benjamin. Université Paris-Saclay; Francia. Universite Grenoble Alpes; Francia
Fil: Nicotra, Viviana Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Dauban, Philippe. Université Paris-Saclay; Francia
description A set of new guaianolide derivatives (1–9) was obtained from ludartin, achalensolide, and 11,13-dihydroachalensolide by application of catalytic nitrene transfer reactions. Intermolecular nitrene C(sp3)−H insertions led to the amination of C-1, C-2, and C-10 positions, while alkene aziridination was also observed under these reaction conditions. The antiproliferative activity of natural compounds and their derivatives was evaluated against a panel of human solid tumor cell lines. The results show that an increase in the biological activity was observed following amination at the C-2 position of Ludartin, thereby demonstrating the interest in late-stage C−H amination to improve the bioactivity of natural products.
publishDate 2021
dc.date.none.fl_str_mv 2021-03
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/11336/136028
Castro, Sebastián Jorge; Padrón, José M.; Darses, Benjamin; Nicotra, Viviana Estela; Dauban, Philippe; Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity; Wiley VCH Verlag; European Journal of Organic Chemistry; 2021; 12; 3-2021; 1859-1863
1434-193X
1099-0690
CONICET Digital
CONICET
url http://hdl.handle.net/11336/136028
identifier_str_mv Castro, Sebastián Jorge; Padrón, José M.; Darses, Benjamin; Nicotra, Viviana Estela; Dauban, Philippe; Late‐stage Rh(II)‐catalyzed titrene transfer for the synthesis of guaianolide analogs with enhanced antiproliferative activity; Wiley VCH Verlag; European Journal of Organic Chemistry; 2021; 12; 3-2021; 1859-1863
1434-193X
1099-0690
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/ejoc.202100074
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202100074
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
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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
_version_ 1842269706782769152
score 13.13397

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