dc.creator | Borrego Sánchez de la Cuesta, Lorenzo Gabriel | es |
dc.creator | Recio Jiménez, Rocío | es |
dc.creator | Moreno Rodríguez, Nazaret | es |
dc.creator | Chelouan, Ahmed | es |
dc.creator | Álvarez, Eleuterio | es |
dc.creator | Sánchez Coronilla, Antonio | es |
dc.creator | Caro Salazar, Carlos | es |
dc.creator | Pearson, John R. | es |
dc.creator | García-Martín, María Luisa | es |
dc.creator | Khiar, Noureddine | es |
dc.creator | Fernández Fernández, Inmaculada | es |
dc.date.accessioned | 2023-05-12T14:28:52Z | |
dc.date.available | 2023-05-12T14:28:52Z | |
dc.date.issued | 2022 | |
dc.identifier.citation | Borrego Sánchez de la Cuesta, L.G., Recio Jiménez, R., Moreno Rodríguez, N., Chelouan, A., Álvarez, E., Sánchez Coronilla, A.,...,Fernández Fernández, I. (2022). Enantioselective synthesis of 4-amino-3,4-dihydrocoumarins and their non-cyclic hydroxyester precursors: Biological evaluation for the treatment of glioblastoma multiforme. European Journal of Medicinal Chemistry, 243. https://doi.org/10.1016/j.ejmech.2022.114730. | |
dc.identifier.issn | 0223-5234 | es |
dc.identifier.issn | 1768-3254 | es |
dc.identifier.uri | https://hdl.handle.net/11441/145962 | |
dc.description.abstract | The stereoselective addition of ethyl acetate enolate to the C═N bond of N-tert-butylsulfinylimines has been investigated in depth. A significant effect of the LHMDS amount and the N-sulfinylimine nature on the stereoselectivity of the process was observed. Conditions were found where sulfinylimines of differently substituted salicylaldehydes derivatives, ethyl acetate, and LHMDS afforded the corresponding addition products as a single diastereomer in good yields. The developed protocol was successfully applied to the first stereoselective synthesis of differently substituted 4-amino-3,4-dihydrocoumarin derivatives. Computational models confirmed the prominent role of the ortho aryl substituent in the stereoselectivity of the process. A significant and selective cytotoxic activity against Glioblastoma Multiforme (GBM) cancer line has been determined for the noncyclic hydroxy ester derivative. | es |
dc.description.sponsorship | Ministerio de Ciencia e Innovación PID2019-104767RB-I00 | es |
dc.description.sponsorship | Junta de Andalucía US- 1381590, FQM-106 | es |
dc.format | application/pdf | es |
dc.format.extent | 17 p. | es |
dc.language.iso | eng | es |
dc.publisher | Elsevier | es |
dc.relation.ispartof | European Journal of Medicinal Chemistry, 243. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | Enantiopure 4-amino-3,4-dihydrocoumarins | es |
dc.subject | Glioblastoma multiforme | es |
dc.subject | N-sulfinylarylimines | es |
dc.subject | β-hydroxyesters | es |
dc.title | Enantioselective synthesis of 4-amino-3,4-dihydrocoumarins and their non-cyclic hydroxyester precursors: Biological evaluation for the treatment of glioblastoma multiforme | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/publishedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química Física | es |
dc.relation.projectID | PID2019-104767RB-I00 | es |
dc.relation.projectID | US-1381590 | es |
dc.relation.projectID | FQM-106 | es |
dc.relation.publisherversion | https://doi.org/10.1016/j.ejmech.2022.114730 | es |
dc.identifier.doi | 10.1016/j.ejmech.2022.114730 | es |
dc.journaltitle | European Journal of Medicinal Chemistry | es |
dc.publication.volumen | 243 | es |
dc.contributor.funder | Ministerio de Ciencia, Innovación y Universidades (MICINN). España | es |
dc.contributor.funder | Junta de Andalucía | es |
dc.description.awardwinning | Premio Mensual Publicación Científica Destacada de la US. Facultad de Farmacia | |