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
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/133267
Ver los metadatos del registro completo
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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 Técnicas2025-10-22T11:56:59Zoai: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:34982025-10-22 11:57:00.182CONICET 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 |
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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 |
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info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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openAccess |
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https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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application/pdf application/pdf |
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Pergamon-Elsevier Science Ltd |
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Pergamon-Elsevier Science Ltd |
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reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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