RESUMEN
A series of N-glycosyl- 6BrCaQ conjugates was synthesized through a Pd-catalyzed cross-coupling reaction between brominated N-glycosyl quinolin-2-one derivatives and various nitrogen nucleophiles. Antiproliferative assays revealed that this new series of analogues represents a promising class of antitumor compounds as illustrated by the high biological activity observed for several derivatives towards different cancer cell lines compared to the non-glycosylated congeners.
Asunto(s)
Amidas , Antineoplásicos , Proliferación Celular , Ensayos de Selección de Medicamentos Antitumorales , Paladio , Humanos , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Catálisis , Paladio/química , Amidas/química , Amidas/farmacología , Amidas/síntesis química , Proliferación Celular/efectos de los fármacos , Línea Celular Tumoral , Relación Estructura-Actividad , Estructura Molecular , Quinolonas/química , Quinolonas/farmacología , Quinolonas/síntesis química , Relación Dosis-Respuesta a Droga , Quinolinas/química , Quinolinas/farmacología , Quinolinas/síntesis químicaRESUMEN
An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.
Asunto(s)
Oxindoles/síntesis química , Paladio/química , Azúcares/química , Catálisis , Estructura Molecular , Oxindoles/químicaRESUMEN
Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with α- or ß-3-iodo-N-glycosylquinolin-2-ones has been accomplished under mild and operationally simple reaction conditions through the use of a Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or ß-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of α- or ß-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods.
