Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

被引：17

作者：

Thanigaimalai, Pillaiyar ^{[1
,2
]}

Rao, Eeda Venkateswara ^{[1
,2
]}

Lee, Ki-Cheul ^{[1
,2
]}

Sharma, Vinay K. ^{[1
,2
]}

Roh, Eunmiri ^{[3
]}

Kim, Youngsoo ^{[3
]}

Jung, Sang-Hun ^{[1
,2
]}

机构：

[1] Chungnam Natl Univ, Coll Pharm, Taejon 305764, South Korea

[2] Chungnam Natl Univ, Inst Drug Res & Dev, Taejon 305764, South Korea

[3] Chungbuk Natl Univ, Coll Pharm, Cheongju 361763, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 02期

基金：

新加坡国家研究基金会;

关键词：

Melanogenesis inhibitor; 2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide; Skin whitening agent; Thiosemicarbazone; TYROSINASE; THIOSEMICARBAZONES; MECHANISM; OXYRESVERATROL; DERIVATIVES;

D O I：

10.1016/j.bmcl.2011.12.035

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC50 = 1.1 mu M) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of alpha-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：886 / 889

页数：4

共 43 条

[1] Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid [J].