Structural requirement of phenylthiourea analogs for their inhibitory activity of melanogenesis and tyrosinase

被引：30

作者：

Thanigaimalai, Pillaiyar ^{[1
,2
]}

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

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

Joo, Cheonik ^{[1
,2
]}

Cho, Won-Jea ^{[3
]}

Roh, Eunmiri ^{[4
]}

Kim, Youngsoo ^{[4
]}

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] Chonnam Natl Univ, Coll Pharm, Kwangju, South Korea

[4] Chungbuk Natl Univ, Cheongju 361763, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 22期

基金：

新加坡国家研究基金会;

关键词：

1-Phenylthioureas; 1,3-Disubstituted thioureas; Melaninogenic inhibitor; Tyrosinase inhibitor; Docking study; CRYSTAL-STRUCTURE; CATECHOL OXIDASE; MECHANISM; ACID; OXYRESVERATROL; BENZOTHIAZOLES; HYDROQUINONE; THIOUREAS; REAGENT; CELLS;

D O I：

10.1016/j.bmcl.2011.09.024

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Effect of a series of 1-phenylthioureas 1a-k and 1,3-disubstituted thioureas 2a-k were evaluated against melanin formation in melanoma B16 cell line and mushroom tyrosinase. Inhibitory activity of tyrosinase of 1-phenylthioureas 1a-k is parallel to their melanogenic inhibition. Thus, the melanogenic inhibition in melanoma B16 cells of 1-phenylthioureas could be the result of inhibition of tyrosinase. However, 1,3-diaryl or 1-phenyl-3-alkylthioureas, 2a-k, appears as melanogenic inhibitor without inhibition of tyrosinase. The molecular docking study of 1e and 2b to binding pocket of tyrosinase provided convincing explanation regarding the necessity of direct connection of planar phenyl to thiourea unit without N'-substitution of phenylthioureas 1 as tyrosinase inhibitor and 2 as non-tyrosinase inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6824 / 6828

页数：5

共 36 条

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