114277-21-3Relevant academic research and scientific papers
Synthesis and evaluation of 5-benzylidene(thio)barbiturate-β-d-glycosides as mushroom tyrosinase inhibitors
Yan, Qin,Cao, Rihui,Yi, Wei,Yu, Liang,Chen, Zhiyong,Ma, Lin,Song, Huacan
supporting information; experimental part, p. 4055 - 4058 (2010/04/02)
A series of 5-benzylidene(thio)barbiturate-β-d-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that most of compounds had more potent inhibitory activities than arbutin (IC50 8.4 mmol/L). Compound 12b was found to be the most potent inhibitor with IC50 value of 0.05 mmol/L. SARs analysis suggested that (1) 5-benzylidenethiobarbiturate substructures were efficacious for the inhibitory activity; (2) the lipophilic property of acetylated sugar moiety facilitated the inhibitory potency; (3) the hydroxyl group of 3′-configuration contributed to the increase of inhibitory effects. In addition, the inhibition mechanism study revealed that 5-benzylidene(thio)barbiturate-β-d-glycosides were irreversible inhibitors.
