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

Hamidian, H. and Tagizadeh, R. and Fozooni, S. and Abbasalipour, V. and Taheri, A. and Namjou, M. (2013) Synthesis of novel azo compounds containing 5(4H)-oxazolone ring as potent tyrosinase inhibitors. Bioorganic and Medicinal Chemistry, 21 (7). pp. 2088-2092.

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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. © 2013 Elsevier Ltd. All rights reserved.

Item Type: Article
Additional Information: cited By 16
Uncontrolled Keywords: 1 2 4 4 1 (4 fluorophenyl)methylidene] 5 oxo 4,5 dihydro 1,3 oxazol 2 yl]phenyl] 1 diazenyl] 2 naphthyl acetate; 1 2 4 5 oxo 4 1 4 (trifluoromethoxy)phenylmethylidene 4,5 dihydro 1,3 oxazol 2 ylphenyl 1 diazenyl 2 naphthyl acetate; 1 naphthol; 2 2 4 4 1 (4 fluorophenyl)methylidene 5 oxo 4,5 dihydro 1,3 oxazol 2 ylphenyl 1 diazenyl 2 naphthyl acetate; 2 2 4 5 oxo 4 1 4 (trifluoromethoxy)phenylmethylidene 4,5 dihydro 1,3 oxazol 2 ylphenyl 1 diazenyl 1 naphthyl acetate; 2 4 2 4 (dimethylamino)phenyl 1 diazenylphenyl 4 1 (4 fluorophenyl)methylidene 1,3 oxazol 5 one; 2 4 2 4 (dimethylamino)phenyl 1 diazenylphenyl 4 1 (4 trifluoromethoxy)phenylmethylidene 1,3 oxazol 5 one; 2 naphthol; 4 aminohippuric acid; 4 fluoro benzaldehyde; 4 trifluoromethoxy benzaldehyde; azo compound; azo dye; benzaldehyde derivative; enzyme inhibitor; kojic acid; mimosine; monophenol monooxygenase; n,n dimethylaniline; unclassified drug, animal cell; article; cancer inhibition; diazotization; drug determination; drug structure; drug synthesis; enzyme inhibition; melanoma cell; mouse; mushroom; nonhuman; polymerization; spectroscopy; structure analysis, Agaricales; Animals; Azo Compounds; Cell Line, Tumor; Cell Survival; Melanins; Mice; Monophenol Monooxygenase; Oxazolone, Basidiomycota
Subjects: مقالات نمایه شده محققین دانشگاه در سایت ,Web of Science ,Scopus
Divisions: معاونت تحقیقات و فناوری
Depositing User: GOUMS
Date Deposited: 13 Aug 2017 03:38
Last Modified: 13 Aug 2017 03:40
URI: http://eprints.goums.ac.ir/id/eprint/9360

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