SYNTHESIS AND ANTI-TYROSINASE ACTIVITY EVALUATION OF FLUORINATED CHALCONE AND PHENYL BENZYL ETHER DERIVATIVES
Pigmentation is a common skin disorder caused by several factors including UV exposure, skin aging, hormonal imbalance and skin irritation. Ascorbic acid, alpha-arbutin, tranexamic acid, kojic acid, and niacinamide have all been used in skin lightening treatments. This study aimed to develop a new active compound for skin lightening. Ten chalcone and nine phenyl benzyl ether analogues of bibenzyl compounds and bifluranol (9) were synthesized using aldol condensation reaction and Williamson ether synthesis, respectively. Their activity in vitro against tyrosinase, the rate-determining enzyme in melanogenesis, was evaluated at 500 µM. The results revealed that the chalcone analogues were more active than the phenyl benzyl ethers. The p-fluorinated analogues for both chalcone 12d (p-F) and ether 15d (p-F) inhibited tyrosinase in vitro to the highest extent for each series with inhibitory percentages of 38 and 32 at 500 µM respectively. These findings might provide useful guidance for further structural development of the more potent tyrosinase inhibitors used in whitening agents.
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