Borrego Sánchez de la Cuesta, Lorenzo GabrielRecio Jiménez, RocíoMoreno Rodríguez, NazaretChelouan, AhmedÁlvarez, EleuterioSánchez Coronilla, AntonioCaro Salazar, CarlosPearson, John R.García-Martín, María LuisaKhiar, NoureddineFernández Fernández, Inmaculada2023-05-122023-05-122022Borrego 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.2022.114730.0223-52341768-3254https://hdl.handle.net/11441/145962The 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.application/pdf17 p.engAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/Enantiopure 4-amino-3,4-dihydrocoumarinsGlioblastoma multiformeN-sulfinylaryliminesβ-hydroxyestersinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccesshttps://doi.org/10.1016/j.ejmech.2022.114730