Xanthine oxidase, the last enzyme on the breakdown pathway of purine bases, catalyses the conversion of hypoxanthine to xanthine and of xanthine to uric acid. For decades, XO inhibitors have been used for therapy of hyperuricemia, a condition associated with elevated levels of uric acid in the blood. Hyperuricemia has been linked to cardiovascular and chronic kidney disease and is also known to cause gout. In this study, a small library of caffeic acid phenethyl ester (CAPE) derivatives were designed and synthesized as xanthine oxidase inhibitors. The synthesis of CAPE derivatives was carried out in two steps. The first step is the formation of malonic acid monoester from meldrum’s acid and phenethyl alcohol. The second step is the condensation of malonic acid monoester with aldehydes to form CAPE derivatives. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. These CAPE derivatives may be further explored for their therapeutic values of xanthine oxidase inhibitors.

Synthesis and biological evaluation of caffeic acid phenethyl ester (CAPE) derivatives as xanthine oxidase inhibitors

255th National Meeting (2018)

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