N-benzylbenzamides: A new class of potent tyrosinase inhibitors

被引:48
作者
Cho, SJ
Roh, JS
Sun, WS
Kim, SH
Park, KD [1 ]
机构
[1] Korea Res Inst Biosci & Biotechnol, Lab Cellular Funct Modulator, Taejon 305333, South Korea
[2] Seoul Natl Univ, Sch Earth & Environm Sci, Marine Biotechnol Lab, Seoul 151747, South Korea
[3] HAITAI Confectionary R&D Ctr, Seoul, South Korea
[4] SK Chem, Life Sci R&D Ctr, Div Life Sci, Suwon, South Korea
[5] Nutrex Technol, Seoul 137864, South Korea
关键词
tyrosinase inhibitor; N-benzylbenzamides; 4-substituted resorcinol; SAR;
D O I
10.1016/j.bmcl.2006.02.018
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of potent inhibitors of tyrosinase and their structure-activity relationships are described. N-Benzylbenzamide derivatives (1-21) with hydroxyl(s) were synthesized and tested for their tyrosinase inhibitory activity. With this series, compound 15 provided a potent tyrosinase inhibition: it effectively inhibited the oxidation Of L-DOPA catalyzed by mushroom tyrosinase with an IC50 of 2.2 mu M. (C) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2682 / 2684
页数:3
相关论文
共 10 条
[1]   Chemical and instrumental approaches to treat hyperpigmentation [J].
Briganti, S ;
Camera, E ;
Picardo, M .
PIGMENT CELL RESEARCH, 2003, 16 (02) :101-110
[2]   Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety [J].
Khatib, S ;
Nerya, O ;
Musa, R ;
Shmuel, M ;
Tamir, S ;
Vaya, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (02) :433-441
[3]   Flavonols from Heterotheca inuloides:: Tyrosinase inhibitory activity and structural criteria [J].
Kubo, I ;
Kinst-Hori, I ;
Chaudhuri, SK ;
Kubo, Y ;
Sánchez, Y ;
Ogura, T .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (07) :1749-1755
[4]  
MAEDA K, 1991, J SOC COSMET CHEM, V42, P361
[5]   Mushroom tyrosinase inhibitory activity of esculetin isolated from seeds of Euphorbia lathyris L. [J].
Masamoto, Y ;
Ando, H ;
Murata, Y ;
Shimoishi, Y ;
Tada, M ;
Takahata, K .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2003, 67 (03) :631-634
[6]  
MOSHER DB, 1983, UPDATE DERMATOLOGY G, V1, P205
[7]   Dimethyl sulfide, a volatile flavor constituent, is a slow-binding inhibitor of tyrosinase [J].
Pérez-Gilabert, M ;
García-Carmona, F .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2001, 285 (02) :257-261
[8]   Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesis [J].
Roh, JS ;
Han, JY ;
Kim, JH ;
Hwang, JK .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2004, 27 (12) :1976-1978
[9]   Mushroom tyrosinase: Recent prospects [J].
Seo, SY ;
Sharma, VK ;
Sharma, N .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (10) :2837-2853
[10]   Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: Structure-activity investigations [J].
Shimizu, K ;
Kondo, R ;
Sakai, K .
PLANTA MEDICA, 2000, 66 (01) :11-15