Microwave-Assisted Synthesis and Tyrosinase Inhibitory Activity of Chalcone Derivatives

被引：25

作者：

Liu, Jinbing ^{[1
]}

Chen, Changhong ^{[1
]}

Wu, Fengyan ^{[1
]}

Zhao, Liangzhong ^{[1
]}

机构：

[1] Shaoyang Univ, Dept Biol & Chem Engn, Shaoyang 422100, Peoples R China

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2013年 / 82卷 / 01期

关键词：

chalcone derivatives; inhibition mechanism; microwave-assisted synthesis; tyrosinase inhibitors; HUMAN EPIDERMAL MELANOCYTES; MUSHROOM TYROSINASE; BIOLOGICAL EVALUATION; CRYSTAL-STRUCTURE; CATECHOL OXIDASE; MELANOGENESIS; PIGMENTATION; KINETICS; CELLS; ACID;

D O I：

10.1111/cbdd.12126

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of chalcones and their derivatives were synthesized, and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activity, and four compounds exhibited more potent tyrosinase inhibitory activity than the reference standard inhibitor kojic acid (5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one). Specifically, 1-(-1-(4-methoxyphen- yl)-3-phenylallylidene)thiosemicarbazide (18) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 0.274m. The inhibition mechanism analysis of 1-(-1-(2,4-dihydroxyphenyl)-3-phenylallylidene) thiosemicarbazide (16) and 1-(-1-(4-methoxyphenyl)-3-phenylallylidene) thiosemicarbazide (18) demonstrated that the inhibitory effects of the two compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' analysis suggested that further development of such compounds might be of interest.

引用

页码：39 / 47

页数：9

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