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Synthesis and Evaluation of 2',4',6'-trihydroxychalcones as a New Class of Tyrosinase Inhibitors

Synthesis and Evaluation of 2',4',6'-trihydroxychalcones as a New Class of Tyrosinase Inhibitors

Nishida Jun, Gao Hong, Kawabata Jun

Bioorg Med Chem. 2007 Mar 15;15(6):2396-402.

PMID: 17267225

Abstract:

In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 2',4',6'-trihydroxychalcone (1), 2,2',3,4',6'-pentahydroxychalcone (4), 2',3,4,4',5,6'-hexahydroxychalcone (5), 2',4',6'-trihydroxy- 3,4-dimethoxychalcone (9) and 2,2',4,4',6'-pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to l-tyrosine as a substrate. By the structure-activity relationship study, it was suggested that the 2',4',6'-trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC(50)=1microM) was found to show the highest activity out of a set of 15 hydroxychalcones, even better than both 2,2',4,4'-tetrahydroxychalcone (13, IC(50)=5microM) and kojic acid (16, IC(50)=12microM), which were known as potent tyrosinase inhibitors. Kinetic study revealed that 15 acts as a competitive inhibitor of tyrosinase with K(i) value of 3.1microM.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1009934	2,2,4,4,6,6-Hexamethylcyclotrisilazane		1009-93-4	Price

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