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  • Title: Synthesis of novel azo compounds containing 5(4H)-oxazolone ring as potent tyrosinase inhibitors.
    Author: Hamidian H, Tagizadeh R, Fozooni S, Abbasalipour V, Taheri A, Namjou M.
    Journal: Bioorg Med Chem; 2013 Apr 01; 21(7):2088-92. PubMed ID: 23411395.
    Abstract:
    Six new azo dyes containing of 5(4H)-oxazolone ring were prepared by diazotization of 4-aminohippuric acid and coupling with N,N-dimethylaniline, 1-naphthol and 2-naphthol and condensation with 4-fluoro benzaldehyde or 4-trifluoromethoxy benzaldehyde. The new compounds were fully characterized by spectroscopic techniques. All synthesized compounds exhibited high tyrosinase inhibitory behavior. The results of mushroom tyrosinase inhibition assays indicate that the 4-trifluoromethoxy derivatives have high degrees of inhibition and N,N-dimethylaniline derivatives are better for tyrosinase inhibition than 1-naphthol and 2-naphthol derivatives. All synthesized azo compounds (4a-4f) showed the most potent mushroom tyrosinase inhibition, comparable to that of Kojic acid and l-mimosine, as reference standard inhibitors.
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