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- Title
Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors.
- Authors
Xie, Wenlin; Zhang, Jingai; Ma, Xiaojing; Yang, Wenqian; Zhou, Ying; Tang, Xufu; Zou, Yan; Li, Hui; He, Jingjing; Xie, Shimin; Zhao, Yunhui; Liu, Fengping
- 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 μ m. 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.
- Subjects
PYRAN synthesis; PYRAN derivatives; TRIAZOLES; PHENOL oxidase; ENZYME inhibitors
- Publication
Chemical Biology & Drug Design, 2015, Vol 86, Issue 5, p1087
- ISSN
1747-0277
- Publication type
Article
- DOI
10.1111/cbdd.12577