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

被引：36

作者：

Hamidian, Hooshang ^{[1
]}

Tagizadeh, Roya ^{[1
]}

Fozooni, Samieh ^{[2
]}

Abbasalipour, Vahid ^{[1
]}

Taheri, Ali ^{[3
]}

Namjou, Mohadeseh ^{[4
]}

机构：

[1] PNU, Dept Chem, Tehran, Iran

[2] Shahid Bahonar Univ, Zarand High Educ Ctr, Min Engn Dept, Kerman, Iran

[3] Golestan Univ Med Sci, Sch Adv Med Sci, Gorgan, Iran

[4] Golestan Univ Med Sci, Dept Lab Med, Gorgan, Iran

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2013年 / 21卷 / 07期

关键词：

Anti-tyrosinase effect; Diazotization; 5(4H)-Oxazolones; Azo compounds; DERIVATIVES; DYES;

D O I：

10.1016/j.bmc.2013.01.014

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2088 / 2092

页数：5

共 25 条

[1] Synthesis, biological evaluation, and molecular docking of N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives as xanthine oxidase and tyrosinase inhibitors [J].