BIOMAT Database Logo BIOMAT Database Logo

Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4-triazole as potent tyrosinase inhibitors. 2015

Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201, China.

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.

UI MeSH Term Description Entries
D011753 Pyrones Keto-pyrans.
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D000363 Agaricales An extensive order of basidiomycetous fungi whose fruiting bodies are commonly called mushrooms. Agaricaceae,Mushrooms,Agaricale,Mushroom
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D014442 Monophenol Monooxygenase An enzyme of the oxidoreductase class that catalyzes the reaction between L-tyrosine, L-dopa, and oxygen to yield L-dopa, dopaquinone, and water. It is a copper protein that acts also on catechols, catalyzing some of the same reactions as CATECHOL OXIDASE. EC 1.14.18.1. Dopa Oxidase,Phenoloxidase,Tyrosinase,Cresolase,Phenol Oxidase,Phenoloxidase A,Phenoloxidase B,Monooxygenase, Monophenol,Oxidase, Dopa,Oxidase, Phenol

Related Publications

Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors: Design, synthesis and biological evaluation.
February 2019, Bioorganic chemistry,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Design, synthesis, molecular modeling, and biological evaluation of novel kojic acid derivatives containing bioactive heterocycle moiety as inhibitors of tyrosinase and antibrowning agents.
November 2021, Food chemistry,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Design, synthesis, and biological evaluation of pleuromutilin derivatives containing 1,2,4-triazole linker.
June 2023, Drug development research,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Design, synthesis and biological evaluation of tacrine-1,2,3-triazole derivatives as potent cholinesterase inhibitors.
January 2018, MedChemComm,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Synthesis, Biological Evaluation and Molecular Docking of Deferasirox and Substituted 1,2,4-Triazole Derivatives as Novel Potent Urease Inhibitors: Proposing Repositioning Candidate.
May 2020, Chemistry & biodiversity,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Design, synthesis, and biological evaluation of 1,5-diaryl-1,2,4-triazole derivatives as selective cyclooxygenase-2 inhibitors.
September 2010, Archiv der Pharmazie,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Evaluation of Biological Activity of New 1,2,4-Triazole Derivatives Containing Propionic Acid Moiety.
April 2023, Molecules (Basel, Switzerland),
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Design, synthesis and biological evaluation of 1,3,4-triazole-3-acetamide derivatives as potent neuraminidase inhibitors.
April 2022, Bioorganic & medicinal chemistry letters,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Novel kojic acid-1,2,4-triazine hybrids as anti-tyrosinase agents: Synthesis, biological evaluation, mode of action, and anti-browning studies.
September 2023, Food chemistry,
Wenlin Xie, and Jingai Zhang, and Xiaojing Ma, and Wenqian Yang, and Ying Zhou, and Xufu Tang, and Yan Zou, and Hui Li, and Jingjing He, and Shimin Xie, and Yunhui Zhao, and Fengping Liu
Spirohydantoins and 1,2,4-triazole-3-carboxamide derivatives as inhibitors of histone deacetylase: Design, synthesis, and biological evaluation.
February 2018, European journal of medicinal chemistry,
Copied contents to your clipboard!