Bioorganic & Medicinal Chemistry 2013-04-01

Synthesis of novel azo compounds containing 5(4H)-oxazolone ring as potent tyrosinase inhibitors.

Hooshang Hamidian, Roya Tagizadeh, Samieh Fozooni, Vahid Abbasalipour, Ali Taheri, Mohadeseh Namjou

Index: Bioorg. Med. Chem. 21(7) , 2088-92, (2013)

Full Text: HTML

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.Copyright © 2013 Elsevier Ltd. All rights reserved.