Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases
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 a...
| Autores: | ; ; ; ; |
|---|---|
| Tipo de documento: | Artículo |
| Estado: | Published version |
| Fecha de publicación: | 2011 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Lenguaje: | Inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/133267 |
| Acceso en línea: | http://hdl.handle.net/11336/133267 |
| Nivel de acceso: | Acceso abierto |
| Palabra clave: | CROSS-COUPLING DIARYL ETHER SYNTHESIS ORGANOTRIFLUOROBORATE SALT THIIRANE ULLMANN REACTION https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| _version_ | 1878403914502504448 |
|---|---|
| author | Testero, Sebastian Andres |
| author2 | Bouley, Renee Fisher, Jed F. Chang, Mayland Mobashery, Shahriar |
| author2_role | author author author author |
| author_browse | Bouley, Renee Chang, Mayland Fisher, Jed F. Mobashery, Shahriar Testero, Sebastian Andres |
| author_facet | Testero, Sebastian Andres Bouley, Renee Fisher, Jed F. Chang, Mayland Mobashery, Shahriar |
| author_role | author |
| collection | CONICET Digital (CONICET) |
| 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. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | AR_d7db6facee8f75b58f0f9270e7e2138a |
| 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 |
| institution | Consejo Nacional de Investigaciones Científicas y Técnicas |
| instname_str | Consejo Nacional de Investigaciones Científicas y Técnicas |
| language | eng |
| network_acronym_str | AR |
| network_name_str | Argentina |
| oai_identifier_str | oai:ri.conicet.gov.ar:11336/133267 |
| publishDate | 2011 |
| publishDateSort | 2011 |
| publisher | Pergamon-Elsevier Science Ltd |
| publisherStr | Pergamon-Elsevier Science Ltd |
| reponame_str | CONICET Digital (CONICET) |
| spelling | Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases Testero, Sebastian Andres Bouley, Renee Fisher, Jed F. Chang, Mayland Mobashery, Shahriar CROSS-COUPLING DIARYL ETHER SYNTHESIS ORGANOTRIFLUOROBORATE SALT THIIRANE ULLMANN REACTION https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 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 Pergamon-Elsevier Science Ltd 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 |
| 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 https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| status_str | publishedVersion |
| title | 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_short | 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 |
| topic | CROSS-COUPLING DIARYL ETHER SYNTHESIS ORGANOTRIFLUOROBORATE SALT THIIRANE ULLMANN REACTION https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| topic_facet | CROSS-COUPLING DIARYL ETHER SYNTHESIS ORGANOTRIFLUOROBORATE SALT THIIRANE ULLMANN REACTION https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| url | http://hdl.handle.net/11336/133267 |