The tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold

A comprehensive review on tyrosinase inhibitors

“…So far, several azole derivatives (Figure 13) have been studied for their tyrosinase inhibitory activity 388 . The discovered new types of inhibitors included DL-3(5-benzazolyl) alanines and alpha-methyldopa analogs 389 , aryl pyrazoles 390 , heterocyclic hybrids based on pyrazole and thiazolidinone scaffolds 391 , 3,5-diaryl-4,5-dihydro-1H 392 and 3,5-diaryl pyrazole derivatives 393 , pyrazolo[4,3-e][1,2,4]triazine sulfonamides and sildenafil 394–396 , 1,3-oxazine-tetrazole 397 , indole-spliced thiadiazole 398 , benzimidazole-1,2,3-triazole hybrids 399 , 1,2,3-triazole-linked coumarinopyrazole conjugates 400 , isoxazolone derivatives 401 5(4H)-oxazolone derivative 402 , imidazolium ionic liquids 403 , thiazolyl resorcinols 404 have demonstrated the inhibitory effect on tyrosinase. Furthermore, some thiazolidine derivatives have been evaluated for their tyrosinase inhibitory activity including azo-hydrazone tautomeric dyes substituted by thiazolidinone moiety 405 , (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione 406 , 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives 407 , (2RS,4R)-2-(2,4-dihydroxyphenyl)thiazolidine-4-carboxylic acid 408 , 2-(substituted phenyl) thiazolidine-4-carboxylic acid derivatives 409 and (Z)-5-(3-hydroxy-4-methoxybenzylidene)-2-iminothiazolidin-4-one 410 .…”

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

“…In the last years several studies have been directed to the development of novel tyrosinase inhibitors inspired by natural scaffolds, which should overcome stability, efficacy, and isolation yield issues. One of the main exploited scaffolds is hydroxycinnamic acid: indeed several hydroxycinnamic acid analogues have been synthesized through the most disparate approaches [123][124][125][126][127][128][129][130][131][132][133][134][135][136][137][138][139][140][141], leading in some cases to very potent mushroom tyrosinase inhibitors (Figure 17), such as 2,4-dihydroxycinnamides (IC 50 = 0.0112-0.16 µM) [132,133]. A thiophenyl derivative of 2,4-dihydroxycinnamic acid has also exhibited a very low IC 50 value (0.013 µM) against the monophenolase activity of the enzyme [134].…”

A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells

“…Moreover, biological activities of chalcone-like derivatives are significantly determined based on the position and numbers of functional groups attached to benzene ring. In spite of diverse structural moiety of natural tyrosinase inhibitors and available methodology to reasonably design effective synthetic derivatives, many synthetic tyrosinase inhibitors with novel skeletons have been studied [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. Especially, Hwang et al [ 27 ] reported the effects of heterocyclic chalcone derivatives containing heterocycles, such as thiophene or furan ring as an isostere of benzene ring on free radical scavenging activity.…”

“…Recently, our laboratory discovered and reported several tyrosinase inhibitors [ 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 29 ]. In particular, Kim et al [ 22 , 23 ] and Lee et al [ 24 ] demonstrated the importance of a thiazolidine derivative bearing 2,4-dihydroxy phenyl moiety (MHY498) which attributed to the inhibitory activity against tyrosinase.…”