RT Journal Article
T1 Enantioselective synthesis of 4-amino-3,4-dihydrocoumarins and their non-cyclic hydroxyester precursors: Biological evaluation for the treatment of glioblastoma multiforme.
A1 Borrego, Lorenzo G
A1 Recio, Rocío
A1 Moreno, Nazaret
A1 Chelouan, Ahmed
A1 Álvarez, Eleuterio
A1 Sánchez-Coronilla, Antonio
A1 Caro, Carlos
A1 Pearson, John R
A1 García-Martín, Maria Luisa
A1 Khiar, Noureddine
A1 Fernández, Inmaculada
K1 Enantiopure 4-amino-3,4-dihydrocoumarins
K1 Glioblastoma multiforme
K1 N-sulfinylarylimines
K1 β-hydroxyesters
AB 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.
YR 2022
FD 2022-09-01
LK http://hdl.handle.net/10668/22187
UL http://hdl.handle.net/10668/22187
LA en
DS RISalud
RD Aug 31, 2025