title: Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase.
abstract: Two series of novel kojic acid analogues (4a-j) and (5a-d) were designed and synthesized, and their mushroom tyrosinase inhibitory activities was evaluated. The result indicated that all the synthesized derivatives exhibited excellent tyrosinase inhibitory properties having IC50values in the range of 1.35±2.15-17.50±2.75μM, whereas standard inhibitor kojic acid have IC50values 20.00±1.08μM. Specifically, 5-phenyl-3-[5-hydroxy-4-pyrone-2-yl-methylmercap-to]-4-(2,4-dihydroxyl-benzylamino)-1,2,4-triazole (4f) exhibited the most potent tyrosinase inhibitory activity with IC50value of 1.35±2.15μM. The kinetic studies of the compound (4f) demonstrated that the inhibitory effects of the compound on the tyrosinase were belonging to competitive inhibitors. Meanwhile, the structure-activity relationship was discussed.
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China; Key Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, China; Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, Xiangtan 411201, China. Electronic address: xwl99zsu@163.com.
authors.forename: Wenlin
authors.initials: W
authors.lastname: Xie
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Huilin
authors.initials: H
authors.lastname: Zhang
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Jingjing
authors.initials: J
authors.lastname: He
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Jingai
authors.initials: J
authors.lastname: Zhang
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Qiuyan
authors.initials: Q
authors.lastname: Yu
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Chunxiang
authors.initials: C
authors.lastname: Luo
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Shangru
authors.initials: S
authors.lastname: Li
mesh_terms: D000363:Agaricales / Q000201:enzymology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C000620854:5-phenyl-3-(5-hydroxy-4-pyrone-2-yl-methylmercapto)-4-(2,4-dihydroxylbenzylamino)-1,2,4-triazole; D004791:Enzyme Inhibitors; D011753:Pyrones; D014230:Triazoles; C011890:kojic acid; D014442:Monophenol Monooxygenase
keywords: 1,2,4-Triazole; Benzaldehyde; Kojic acid; Tyrosinase inhibitors