Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

被引：21

作者：

Brotzman, Nicholas ^{[1
]}

Xu, Yiming ^{[2
]}

Graybill, Allison ^{[1
]}

Cocolas, Alexander ^{[1
]}

Ressler, Andrew ^{[1
]}

Seeram, Navindra P. ^{[2
]}

Ma, Hang ^{[2
]}

Henry, Geneive E. ^{[1
]}

机构：

[1] Susquehanna Univ, Dept Chem, 514 Univ Ave, Selinsgrove, PA 17870 USA

[2] Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Bioact Bot Res Lab, Kingston, RI 02881 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2019年 / 29卷 / 01期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

Carvacrol; Thymol; Alkyl; 4-oxobutanoates; Tyrosinase inhibition;

D O I：

10.1016/j.bmcl.2018.11.013

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Carvacrol (1) and thymol (2) were converted to their alkyl 4-oxobutanoate derivatives (7-20) in three steps, and evaluated for tyrosinase inhibitory activity. The compounds showed structure-dependent activity, with all alkyl 4-oxobutanoates, except 7 and 20, showing better inhibitory activity than the precursor 4-oxobutanoic acids (5 and 6). In general, thymol derivatives exhibited a higher percent inhibitory activity than carvacrol derivatives at 500 mu M. Derivatives containing three-carbon and four-carbon alkyl groups gave the strongest activity (carvacrol derivatives 9-12, IC50 = 128.8-244.1 mu M; thymol derivatives 16-19, IC50 = 102.3-191.4 mu M).

引用

页码：56 / 58

页数：3