title: Synthesis of novel azo compounds containing 5(4H)-oxazolone ring as potent tyrosinase inhibitors.
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.
authors: Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran. h_hamidian@pnu.ac.ir
authors: Hooshang
authors: H
authors: Hamidian
authors: Roya
authors: R
authors: Tagizadeh
authors: Samieh
authors: S
authors: Fozooni
authors: Vahid
authors: V
authors: Abbasalipour
authors: Ali
authors: A
authors: Taheri
authors: Mohadeseh
authors: M
authors: Namjou
mesh_terms: D000363:Agaricales / Q000201:enzymology*; D000818:Animals; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D008543:Melanins / Q000378:metabolism; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010081:Oxazolone / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D001391:Azo Compounds; D008543:Melanins; D010081:Oxazolone; D014442:Monophenol Monooxygenase