Abstract:
Chalcones have drawn attention due to the simple structures and wide spectra of biological activities. Their core structure bearing diaryl rings with α,β-unsaturated ketone was generated easily using Claisen-Schmidt condensation. In this study, one hundred and eight chalcones and their derivatives were synthesized; among them, twenty-five were disclosed as new compounds. All synthesized chalcones were well-characterized by means of spectroscopy and evaluated for their anti-cancer (A549) and anti-inflammatory activities, and α-glucosidase inhibition. For anti-cancer activity, 3',4',5'-trimethoxyphenyl on the A ring, and hydroxy and methoxy groups on the B ring exhibited high potent inhibitory activity against A549 with three best potent compounds (4, 6, and 7). For anti-inflammatory activity, lead compounds including 2'-hydroxychalcone (34, 35, 42, 43, 45, and 48) and six 4'-aminochalcones (54, 55, 57, 58, 59, 70) showed high potent NO inhibitory activity without toxicity in LPS-induced RAW 264.7 macrophage cells. For α-glucosidase inhibitors, N-monoalkyl-4'-aminochalcones with the hydroxy group at meta and the methoxy at para position on the B ring (89, 91, 92) exhibited high α-glucosidase inhibitory activity with an uncompetitive inhibition mode. Moreover, E-arylidene steroids were investigated and three compounds (107, 108, 110) exhibited high potency as α-glucosidase inhibitors with mixed, noncompetitive, and competitive inhibition mode, respectively.
