Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4‐triazole as Potent Tyrosinase Inhibitors |
| |
| Authors: | Wenlin Xie Jingai Zhang Xiaojing Ma Wenqian Yang Ying Zhou Xufu Tang Yan Zou Hui Li Jingjing He Shimin Xie Yunhui Zhao Fengping Liu |
| |
| Affiliation: | 1. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, China;2. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan University of Science and Technology, Xiangtan, China;3. Hunan Provincial University Key Laboratory of QSAR/QSPR, Xiangtan, China;4. Hunan University of Humanities, Science and Technology, Loudi, China |
| |
| Abstract: | A series of 5‐substituted‐3‐[5‐hydroxy‐4‐pyrone‐2‐yl‐methymercapto]‐4‐amino‐1,2,4‐triazole derivatives were synthesized by nucleophilic substitution reaction of 5‐hydroxy‐2‐chloromethyl ‐4H‐pyran‐4‐one with 5‐substituted‐3‐mercapto‐4‐amino‐1,2,4‐triazole, and their inhibitory effects on mushroom tyrosinase were evaluated. The results indicated that most of the synthesized compounds exhibited significant inhibitory activity. Specifically, 5‐(4‐chlorophenyl)‐3‐[5‐hydroxy‐4‐pyrone‐2‐yl‐methymercapto]‐4‐amino‐1,2,4‐triazole ( 6j ) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 4.50 ± 0.34 μm . The kinetic studies of the compound ( 6j ) demonstrated that the inhibitory effects of the compound on the tyrosinase were belonging to competitive inhibitors. Meanwhile, the structure–activity relationship was also discussed. |
| |
| Keywords: | 1,2,4‐triazole kojic acid derivatives mushroom tyrosinase tyrosinase inhibitors |
|
|
