Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors.

Here a new class of hydroxy- or methoxy-substituted 5-benzylidene(thio)barbiturates were designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that several compounds had more potent tyrosinase inhibitory activities than the widely used tyrosinase inhibitor kojic acid (IC50=18.25μM).

4-[(2-Methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-yl-idene)meth-yl]phenyl acetate.

In the title compound, C(13)H(11)NO(4), an intramolecular C-H⋯N interaction helps to establish the conformation. In the crystal, two C-H⋯O contacts stack adjacent mol-ecules into a one-dimensional double chain running in the a-axis direction.