title: Microwave-assisted synthesis and tyrosinase inhibitory activity of chalcone derivatives.
abstract: 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 0.274 μM. 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.
authors: Department of Biology and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang, 422100, China. xtliujb@yahoo.com.cn
authors: Jinbing
authors: J
authors: Liu
authors: Changhong
authors: C
authors: Chen
authors: Fengyan
authors: F
authors: Wu
authors: Liangzhong
authors: L
authors: Zhao
mesh_terms: D000363:Agaricales / Q000201:enzymology; D002599:Chalcone / Q000737:chemistry*; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D008872:Microwaves; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011485:Protein Binding; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
chemical_list: C585820:1-(1-(4-methoxyphenyl)-3-phenylallylidene) thiosemicarbazide; D047188:Chalcones; D004791:Enzyme Inhibitors; D013882:Thiosemicarbazones; D002599:Chalcone; D014442:Monophenol Monooxygenase