Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases

Autores
Testero, Sebastian Andres; Bouley, Renee; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The copper-mediated and non-basic oxidative cross-coupling of organotrifluoroborates with phenols was applied to elaboration of the structures of thiirane-based inhibitors of matrix metalloproteinases. By revision of the synthetic sequence to allow this cross-coupling as the final step, and taking advantage of the neutral nature of organotrifluoroborate cross-coupling, a focussed series of inhibitors showing aryloxy and alkenyloxy replacement of the phenoxy substituent was prepared. This reaction shows exceptional promise as an alternative to the classic copper-mediated but strongly basic Ullmann reaction, for the diversification of ether segments within base-labile lead structures.
Fil: Testero, Sebastian Andres. 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. University of Notre Dame; Estados Unidos
Fil: Bouley, Renee. University of Notre Dame; Estados Unidos
Fil: Fisher, Jed F.. University of Notre Dame; Estados Unidos
Fil: Chang, Mayland. University of Notre Dame; Estados Unidos
Fil: Mobashery, Shahriar. University of Notre Dame; Estados Unidos
Materia
CROSS-COUPLING
DIARYL ETHER SYNTHESIS
ORGANOTRIFLUOROBORATE SALT
THIIRANE
ULLMANN REACTION
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:11336/133267
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinasesTestero, Sebastian AndresBouley, ReneeFisher, Jed F.Chang, MaylandMobashery, ShahriarCROSS-COUPLINGDIARYL ETHER SYNTHESISORGANOTRIFLUOROBORATE SALTTHIIRANEULLMANN REACTIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The copper-mediated and non-basic oxidative cross-coupling of organotrifluoroborates with phenols was applied to elaboration of the structures of thiirane-based inhibitors of matrix metalloproteinases. By revision of the synthetic sequence to allow this cross-coupling as the final step, and taking advantage of the neutral nature of organotrifluoroborate cross-coupling, a focussed series of inhibitors showing aryloxy and alkenyloxy replacement of the phenoxy substituent was prepared. This reaction shows exceptional promise as an alternative to the classic copper-mediated but strongly basic Ullmann reaction, for the diversification of ether segments within base-labile lead structures.Fil: Testero, Sebastian Andres. 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. University of Notre Dame; Estados UnidosFil: Bouley, Renee. University of Notre Dame; Estados UnidosFil: Fisher, Jed F.. University of Notre Dame; Estados UnidosFil: Chang, Mayland. University of Notre Dame; Estados UnidosFil: Mobashery, Shahriar. University of Notre Dame; Estados UnidosPergamon-Elsevier Science Ltd2011-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/133267Testero, Sebastian Andres; Bouley, Renee; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar; Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry Letters; 21; 9; 5-2011; 2675-26780960-894XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0960894X10018408info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2010.12.076info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:24:12Zoai:ri.conicet.gov.ar:11336/133267instacron: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 10:24:13.078CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
title Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
spellingShingle Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
Testero, Sebastian Andres
CROSS-COUPLING
DIARYL ETHER SYNTHESIS
ORGANOTRIFLUOROBORATE SALT
THIIRANE
ULLMANN REACTION
title_short Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
title_full Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
title_fullStr Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
title_full_unstemmed Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
title_sort Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
dc.creator.none.fl_str_mv Testero, Sebastian Andres
Bouley, Renee
Fisher, Jed F.
Chang, Mayland
Mobashery, Shahriar
author Testero, Sebastian Andres
author_facet Testero, Sebastian Andres
Bouley, Renee
Fisher, Jed F.
Chang, Mayland
Mobashery, Shahriar
author_role author
author2 Bouley, Renee
Fisher, Jed F.
Chang, Mayland
Mobashery, Shahriar
author2_role author
author
author
author
dc.subject.none.fl_str_mv CROSS-COUPLING
DIARYL ETHER SYNTHESIS
ORGANOTRIFLUOROBORATE SALT
THIIRANE
ULLMANN REACTION
topic CROSS-COUPLING
DIARYL ETHER SYNTHESIS
ORGANOTRIFLUOROBORATE SALT
THIIRANE
ULLMANN REACTION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The copper-mediated and non-basic oxidative cross-coupling of organotrifluoroborates with phenols was applied to elaboration of the structures of thiirane-based inhibitors of matrix metalloproteinases. By revision of the synthetic sequence to allow this cross-coupling as the final step, and taking advantage of the neutral nature of organotrifluoroborate cross-coupling, a focussed series of inhibitors showing aryloxy and alkenyloxy replacement of the phenoxy substituent was prepared. This reaction shows exceptional promise as an alternative to the classic copper-mediated but strongly basic Ullmann reaction, for the diversification of ether segments within base-labile lead structures.
Fil: Testero, Sebastian Andres. 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. University of Notre Dame; Estados Unidos
Fil: Bouley, Renee. University of Notre Dame; Estados Unidos
Fil: Fisher, Jed F.. University of Notre Dame; Estados Unidos
Fil: Chang, Mayland. University of Notre Dame; Estados Unidos
Fil: Mobashery, Shahriar. University of Notre Dame; Estados Unidos
description The copper-mediated and non-basic oxidative cross-coupling of organotrifluoroborates with phenols was applied to elaboration of the structures of thiirane-based inhibitors of matrix metalloproteinases. By revision of the synthetic sequence to allow this cross-coupling as the final step, and taking advantage of the neutral nature of organotrifluoroborate cross-coupling, a focussed series of inhibitors showing aryloxy and alkenyloxy replacement of the phenoxy substituent was prepared. This reaction shows exceptional promise as an alternative to the classic copper-mediated but strongly basic Ullmann reaction, for the diversification of ether segments within base-labile lead structures.
publishDate 2011
dc.date.none.fl_str_mv 2011-05
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/11336/133267
Testero, Sebastian Andres; Bouley, Renee; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar; Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry Letters; 21; 9; 5-2011; 2675-2678
0960-894X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/133267
identifier_str_mv Testero, Sebastian Andres; Bouley, Renee; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar; Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry Letters; 21; 9; 5-2011; 2675-2678
0960-894X
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://www.sciencedirect.com/science/article/abs/pii/S0960894X10018408
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2010.12.076
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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_ 1844614238595710976
score 13.070432

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