Adamantyl N-benzylbenzamide: New series of depigmentation agents with tyrosinase inhibitory activity

被引：28

作者：

Baek, Heung Soo ^{[1
]}

Hong, Yong Deog ^{[1
]}

Lee, Chang Seok ^{[1
]}

Rho, Ho Sik ^{[1
]}

Shin, Song Seok ^{[1
]}

Park, Young-Ho ^{[1
]}

Joo, Yung Hyup ^{[1
]}

机构：

[1] AmorePacific Corp R&D Ctr, Med Beauty Res Inst, Dermatol Drug Res, Yongin 446729, Kyounggi Do, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 05期

关键词：

Depigmentation; Tyrosinase inhibitor; Adamantane moiety; MUSHROOM TYROSINASE; MOIETY; DERIVATIVES; ACID;

D O I：

10.1016/j.bmcl.2011.12.144

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new series of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety has been synthesized, and the depigmenting and tyrosinase inhibitory activities of the molecules were evaluated. The lipophilic character of the adamantyl moiety appeared to confer greater depigmentation power on the benzamide derivatives as compared to those lacking adamantyl substitution. Molecular modeling was applied in order to elucidate the interactions between ligands and tyrosinase that led to inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2110 / 2113

页数：4

共 20 条

[1] Tyrosinase inhibitory effects of 1,3-diphenylpropanes from Broussonetia kazinoki [J].

Baek, Yoon Su ;

Ryu, Young Bae ;

Curtis-Long, Marcus J. ;

Ha, Tae Joung ;

Rengasamy, Rajesh ;

Yang, Min Suk ;

Park, Ki Hun .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (01) :35-41

[2] Chemical and instrumental approaches to treat hyperpigmentation [J].

Briganti, S ;

Camera, E ;

Picardo, M .

PIGMENT CELL RESEARCH, 2003, 16 (02) :101-110

[3] N-benzylbenzamides: A new class of potent tyrosinase inhibitors [J].

Cho, SJ ;

Roh, JS ;

Sun, WS ;

Kim, SH ;

Park, KD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) :2682-2684

[4] Contiguous lesions in lentigo maligna [J].

Dalton, SR ;

Gardner, TL ;

Libow, LF ;

Elston, DM .

JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 2005, 52 (05) :859-862

[5] Benzyl benzoates: New phlorizin analogs as mushroom tyrosinase inhibitors [J].

Fang, Yuntai ;

Chen, Yaozong ;

Feng, Guanfeng ;

Ma, Lin .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (03) :1167-1171

[6] The treatment of melasma: A review of clinical trials [J].

Gupta, Aditya K. ;

Gover, Melissa D. ;

Nouri, Keyvan ;

Taylor, Susan .

JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 2006, 55 (06) :1048-1065

[7] Surflex: Fully automatic flexible molecular docking using a molecular similarity-based search engine [J].

Jain, AN .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (04) :499-511

[8] 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

[9] Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future [J].

Kim, YJ ;

Uyama, H .

CELLULAR AND MOLECULAR LIFE SCIENCES, 2005, 62 (15) :1707-1723

[10]

Marmol V., 1996, FEBS LETT, V381, P165

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