75514-34-0Relevant academic research and scientific papers
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.
3,5,2′,4′-Tetrahydroxychalcone, a new non-purine xanthine oxidase inhibitor
Niu, Yanfen,Zhu, Huajie,Liu, Jia,Fan, Huafang,Sun, Ling,Lu, Wei,Liu, Xu,Li, Ling
, p. 161 - 166 (2012/01/11)
Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid and the overproduction of uric acid will lead to hyperuricemia which is an important cause of gout. In the present study, three chalcone derivatives were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds, only Compound 1, 3,5,2′,4′-tetrahydroxychalcone, exhibited a significant inhibitory activity on xanthine oxidase with an IC50 value of 22.5 μM. Lineweaver-Burk transformation of the inhibition kinetics data demonstrated that it was a competitive inhibitor of xanthine oxidase and Ki value was 17.4 μM. In vivo, intragastric administration of Compound 1 was able to significantly reduce serum uric acid levels and inhibited hepatic xanthine oxidase activities of hyperuricemic mice in a dose-dependent manner. Acute toxicity study in mice showed that Compound 1 was very safe at a dose of up to 5 g/kg. These results suggest that Compound 1 is a novel competitive xanthine oxidase inhibitor and is worthy of further development.
Synthesis and complete assignment of NMR data of 20 chalcones
Hwang, Doseok,Hyun, Jiye,Jo, Geunhyeong,Koh, Dongsoo,Lim, Yoongho
scheme or table, p. 41 - 45 (2011/09/14)
Chalcones, intermediates in flavonoid biosynthesis, can exhibit antibacterial, antiproliferative, and anti-inflammatory properties. Chalcones contain two benzene rings and both hydroxylated and methoxylated analogs are frequently produced by hydroxylases and O-methyltransferases in plant biosynthetic pathways. Assignments of NMR peaks in the spectra of hydroxylated and/or methoxylated chalcones can help in identifying novel chalcone derivatives isolated from natural sources by referencing these data against NMR spectra obtained from known chalcones. We report here the syntheses of 20 chalcones and complete assignments of 1H and 13C NMR spectra. Copyright
