A concise and operationally simple synthesis of enantioenriched Nutlin-3 featuring the desymmetrization of 1,2-bis(4-chlorophenyl)ethane-1,2-diamine as the key step is described. The easy-to-make N-((1R,2R)-2-(3-(3,5-bis(trifluoromethyl) phenyl)thioureido)cyclohexyl)-3,5-bis(trifluoromethyl)benzamide (and N-((1S,2S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido) cyclohexyl)-3,5-bis(trifluoromethyl)benzamide)) involved as anion binding in the key desymmetrization step is the completely recoverable chiral auxiliary. An array of biological tests performed with the 84:16 (-)-Nutlin-3 scalemic mixture showed activities comparable to those of the commercial eutomer.

Expeditious Synthesis and Biological Characterization of Enantio-Enriched (-)-Nutlin-3

FANTINATI, Anna
Primo
;
BIANCO, Sara
Secondo
;
CRISTOFORI, Virginia;CAVAZZINI, Alberto;CATANI, Martina;ZANIRATO, Vinicio;PACIFICO, Salvatore;RIMONDI, Erika;MILANI, Daniela;VOLTAN, Rebecca;SECCHIERO, Paola
Penultimo
;
TRAPELLA, Claudio
Ultimo
2017

Abstract

A concise and operationally simple synthesis of enantioenriched Nutlin-3 featuring the desymmetrization of 1,2-bis(4-chlorophenyl)ethane-1,2-diamine as the key step is described. The easy-to-make N-((1R,2R)-2-(3-(3,5-bis(trifluoromethyl) phenyl)thioureido)cyclohexyl)-3,5-bis(trifluoromethyl)benzamide (and N-((1S,2S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido) cyclohexyl)-3,5-bis(trifluoromethyl)benzamide)) involved as anion binding in the key desymmetrization step is the completely recoverable chiral auxiliary. An array of biological tests performed with the 84:16 (-)-Nutlin-3 scalemic mixture showed activities comparable to those of the commercial eutomer.
Fantinati, Anna; Bianco, Sara; Cristofori, Virginia; Cavazzini, Alberto; Catani, Martina; Zanirato, Vinicio; Pacifico, Salvatore; Rimondi, Erika; Milani, Daniela; Voltan, Rebecca; Secchiero, Paola; Trapella, Claudio
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11392/2374698
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