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

被引:37
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
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
收藏
页码:2088 / 2092
页数:5
相关论文
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].
Bandgar, Babasaheb P. ;
Adsul, Laxman K. ;
Chavan, Hemant V. ;
Shringare, Sadanand N. ;
Korbad, Balaji L. ;
Jalde, Shivkumar S. ;
Lonikar, Shrikant V. ;
Nile, Shivraj H. ;
Shirfule, Amol L. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (18) :5649-5657
[2]  
Catino S.C., 1985, Concise Encyclopedia of Chemical Technology, P142
[3]   Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities [J].
Cho, Jun-Cheol ;
Rho, Ho Sik ;
Joo, Yung Hyup ;
Lee, Chang Seok ;
Lee, Jaekyoung ;
Ahn, Soo Mi ;
Kim, Jung Eun ;
Shin, Song Seok ;
Park, Young-Ho ;
Suh, Kyung-Do ;
Park, Soo Nam .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (12) :4159-4162
[4]  
Cutting W.C., 1967, HDB PHARM, V3rd
[5]   AZO DISPERSE DYES FOR SYNTHETIC-FIBERS .1. 2-METHYLQUINAZOLONE AND 2-PHENYLQUINAZOLONE DERIVATIVES [J].
FADDA, AA ;
ETMAN, HA ;
AMER, FA ;
BARGHOUT, M ;
MOHAMED, KS .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 1994, 61 (04) :343-349
[6]  
Fozooni S, 2008, ARKIVOC, P115
[7]   New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site [J].
Ghani, Usman ;
Ullah, Nisar .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (11) :4042-4048
[8]   The cytotoxicity of γ-secretase inhibitor I to breast cancer cells is mediated by proteasome inhibition, not by γ-secretase inhibition [J].
Han, Jianxun ;
Ma, Ivy ;
Hendzel, Michael J. ;
Allalunis-Turner, Joan .
BREAST CANCER RESEARCH, 2009, 11 (04)
[9]   Design and synthesis of 3-(2-pyridyl)pyrazolo[1,5-α]pyrimidines as potent CRF1 receptor antagonists [J].
Huang, CQ ;
Wilcoxen, KM ;
Grigoriadis, DE ;
McCarthy, JR ;
Chen, C .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (15) :3943-3947
[10]   CORRECTION [J].
IZATT, RM .
CHEMICAL REVIEWS, 1972, 72 (06) :720-&