445284-59-3Relevant academic research and scientific papers
Correlating experimental electrochemistry and theoretical calculations in 2′-hydroxy chalcones: The role of the intramolecular hydrogen bond
Martínez-Cifuentes, Maximiliano,Salazar, Ricardo,Escobar, Carlos A.,Weiss-López, Boris E.,Santos, Leonardo S.,Araya-Maturana, Ramiro
, p. 50929 - 50937 (2015)
In this work we present a study on the molecular structure and electrochemical behavior of a series of methoxylated 2′-hydroxychalcones, whose antitumor activity has been previously described. Cyclic voltammetry was used to quantitatively characterize the
A synthetic chalcone as a potent inducer of glutathione biosynthesis
Kachadourian, Remy,Day, Brian J.,Pugazhenti, Subbiah,Franklin, Christopher C.,Genoux-Bastide, Estelle,Mahaffey, Gregory,Gauthier, Charlotte,Di Pietro, Attilio,Boumendjel, Ahcène
experimental part, p. 1382 - 1388 (2012/04/04)
Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2′,5′-dihydroxychalcone (2′,5′-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F and Cl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4′,6′-dimethoxy-2′- hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.
Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: Critical role of methoxylation in both inhibition potency and cytotoxicity
Valdameri, Glaucio,Gauthier, Charlotte,Terreux, Rapha?l,Kachadourian, Rémy,Day, Brian J.,Winnischofer, Sheila M. B.,Rocha, Maria E. M.,Frachet, Véronique,Ronot, Xavier,Di Pietro, Attilio,Boumendjel, Ahcène
scheme or table, p. 3193 - 3200 (2012/06/01)
ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 μM and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6′-hydroxyl-2′,4′-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.
