Research into the anti-tumor properties of chalcones has received significant attention over the last few years. Two novel large series of .alpha.-bromoacryloylamidochalcones contg. a pair of Michael acceptors in their structures, corresponding to the .alpha.-bromoacryloyl moiety and the .alpha.,.beta.-unsatd. ketone system of the chalcone framework, were synthesized and evaluated for antiproliferative activity against five cancer cell lines. Such hybrid derivs. demonstrated significantly increased anti-tumor activity compared with the corresponding amino chalcones. The most promising lead mols. were 4-BrC(:CH2)CONHC6H4CH:CHCOR[ R = C6H4OEt-4 (I), 2-thienyl] and 4-BrC(:CH2)CONHC6H4COCH:CHC6H2(OMe)3-2,3,4, which had the highest activity toward the five cell lines. Flow cytometry with K562 cells showed that the most active compds. resulted in a large proportion of the cells entering in the apoptotic sub-G0-G1 peak. Moreover, I induced apoptosis through the mitochondrial pathway and activated caspase-3.

Hybrid alpha-bromoacryloylamido chalcones. Design, synthesis and biological evaluation

ROMAGNOLI, Romeo;BARALDI, Pier Giovanni;CANELLA, Alessandro;GAMBARI, Roberto;
2009

Abstract

Research into the anti-tumor properties of chalcones has received significant attention over the last few years. Two novel large series of .alpha.-bromoacryloylamidochalcones contg. a pair of Michael acceptors in their structures, corresponding to the .alpha.-bromoacryloyl moiety and the .alpha.,.beta.-unsatd. ketone system of the chalcone framework, were synthesized and evaluated for antiproliferative activity against five cancer cell lines. Such hybrid derivs. demonstrated significantly increased anti-tumor activity compared with the corresponding amino chalcones. The most promising lead mols. were 4-BrC(:CH2)CONHC6H4CH:CHCOR[ R = C6H4OEt-4 (I), 2-thienyl] and 4-BrC(:CH2)CONHC6H4COCH:CHC6H2(OMe)3-2,3,4, which had the highest activity toward the five cell lines. Flow cytometry with K562 cells showed that the most active compds. resulted in a large proportion of the cells entering in the apoptotic sub-G0-G1 peak. Moreover, I induced apoptosis through the mitochondrial pathway and activated caspase-3.
2009
Romagnoli, Romeo; Baraldi, Pier Giovanni; Carrion, M. D.; Cruz Lopez, O.; Lopez Cara, C.; Balzarini, J.; Hamel, E.; Canella, Alessandro; Fabbri, E.; G...espandi
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1377634
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact