Substituted <i>N</i>‐Benzylbenzamide: A New Series of Depigmentation Agents with Tyrosinase Inhibitory Activity

Yoo, Jae Won; Hong, Yong Deog; Baek, Hye Jin; Choi, Soo Jeong; Lee, Chang Seok; Byoun, Kyoung Hee; Rho, Ho Sik; Lee, John Hwan; Joo, Yung Hyup

doi:10.1002/bkcs.10931

Bulletin Korean Chem Soc

2016

DOI: 10.1002/bkcs.10931

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Substituted N‐Benzylbenzamide: A New Series of Depigmentation Agents with Tyrosinase Inhibitory Activity

Jae Won Yoo

Yong Deog Hong

Hye Jin Baek

et al.

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Cited by 2 publications

References 14 publications

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Tyrosinase Inhibition and Antimelanogenic Effects of Resorcinol‐Containing Compounds

Beaumet,

Lazinski,

Maresca

et al. 2024

ChemMedChem

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Tyrosinases (TYRs) are copper‐containing metalloenzymes present in a large diversity of species. In human, hTYR is responsible for pivotal steps in melanogenesis, catalysing the oxidation of l‐tyrosine to l‐DOPA and further to dopaquinone. While numerous TYR inhibitors have been reported, polyphenolic compounds tend to dominate the literature. However, many of these compounds, particularly monophenols and catechols, have been identified as alternative substrates rather than true inhibitors, given their structural similarity to natural substrates. Resorcinol‐containing compounds have emerged as promising candidates to address this challenge, as the meta‐dihydroxy moiety in resorcinol demonstrates resistance to TYR‐mediated oxidation, while retaining the favourable interactions with copper ions provided by the hydroxy groups. Although their precise mechanism of action remains debated, resorcinol derivatives have yielded some of the most active compounds against isolated mushroom and human TYRs, as well as clinically used dermocosmetic agents like rucinol and thiamidol, which exhibited very promising effects in patients with facial melasma. This review outlines the development of resorcinol‐containing TYR inhibitors, categorized by scaffold type, ranging from simple alkyl analogues to intricate synthetic derivatives. Mechanistic insights about the resorcinol–TYR interaction are also presented and debated.

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Tyrosinase Inhibition and Antimelanogenic Effects of Resorcinol‐Containing Compounds

Beaumet,

Lazinski,

Maresca

et al. 2024

ChemMedChem

View full text Add to dashboard Cite

show abstract

Medicinal Prospects of Targeting Tyrosinase: A Feature Review

Wang

Xiong

Xing

et al. 2023

CMC

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Tyrosinase is a bifunctional polyphenol oxidase (PPO), catalyzing two oxidative reactions: monophenols to o-quinones (monophenolase activity) and o-diphenols to o-quinones (diphenolase activity). As tyrosinase is the rate-limiting enzyme for the melanogenesis process, it is an attractive target for melanogenesis inhibition. Aiming at skin whitening, anticancer, Parkinson’s disease (PD) treatment, antibacterial, fruit and vegetable preservation and other anti-pigmentation effect, medicinal chemists have exploited diverse tyrosinase inhibitors through various approaches. In addition to discovering inhibitors with novel scaffold, good activity and high safety, researchers also focused on developing strategies for synergistic effects of multiple inhibitors and simultaneously regulating multiple targets to treat cancer or neurodegenerative diseases. This review focused on multiple natural and synthetic tyrosinase inhibitors which could contribute to preventing fruit and vegetable browning, skin whitening, antibacterial, anticancer, Parkinson's Disease etc.

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Substituted N‐Benzylbenzamide: A New Series of Depigmentation Agents with Tyrosinase Inhibitory Activity

Cited by 2 publications

References 14 publications

Tyrosinase Inhibition and Antimelanogenic Effects of Resorcinol‐Containing Compounds

Tyrosinase Inhibition and Antimelanogenic Effects of Resorcinol‐Containing Compounds

Medicinal Prospects of Targeting Tyrosinase: A Feature Review

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