Abstract
BackgroundBased on some previous research, the chalcone derivatives exhibited potent xanthine oxidase inhibitory activity, e.g. sappanchalcone (7), with IC50 value of 3.9 μM, was isolated from Caesalpinia sappan. Therefore, objectives of this research are design and synthesis of 7 and other chalcone derivatives by Claisen–Schmidt condensation and then evaluate their XO inhibitory activity.ResultsFifteen chalcone derivatives were synthesized by Claisen–Schmidt condensation, and were evaluated for XO inhibitory activity. Nine out of 15 synthetic chalcones showed inhibitory activity (3; 5–8; 10–13). Sappanchalcone derivatives (11) (IC50, 2.5 μM) and a novel chalcone (13) (IC50, 2.4 μM) displayed strong xanthine oxidase inhibitory activity that is comparable to allopurinol (IC50, 2.5 μM). The structure–activity relationship of these chalcone derivatives was also presented.ConclusionsIt is the first research on synthesis sappanchalcone (7) by Claisen–Schmidt condensation. The overall yield of this procedure was 6.6 %, higher than that of reported procedure (4 %). Design, synthesis, and evaluation of chalcone derivatives were carried out. This result suggests that the chalcone derivative can be used as potential non-purine XO inhibitors.Graphical abstractThe chalcone derivatives as potential non-purine xanthine oxidase inhibitors Electronic supplementary materialThe online version of this article (doi:10.1186/s40064-016-3485-6) contains supplementary material, which is available to authorized users.
Highlights
Based on some previous research, the chalcone derivatives exhibited potent xanthine oxidase inhibitory activity, e.g. sappanchalcone (7), with IC50 value of 3.9 μM, was isolated from Caesalpinia sappan
The reaction was monitored by thinlayer chromatography (TLC)
Pure chalcone was purified by recrystallization and structure elucidation was determined by NMR spectroscopy
Summary
Based on some previous research, the chalcone derivatives exhibited potent xanthine oxidase inhibitory activity, e.g. sappanchalcone (7), with IC50 value of 3.9 μM, was isolated from Caesalpinia sappan. Objectives of this research are design and synthesis of 7 and other chalcone derivatives by Claisen–Schmidt condensation and evaluate their XO inhibitory activity. Xanthine oxidase (XO) is a key enzyme in purine metabolic pathway. This complex metalloflavoprotein catalyzes the oxidation of hypoxanthine into xanthine and into uric acid (Massey et al 1969). Overproduction or under excretion of uric acid leads to hyperuricemia, a key cause of gout (Scott and Agudelo 2003).
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