香芹酚和麝香草酚 4-氧代丁酸酯衍生物的合成及酪氨酸酶抑制活性。
Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol.
机构信息
Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA.
出版信息
Bioorg Med Chem Lett. 2019 Jan 1;29(1):56-58. doi: 10.1016/j.bmcl.2018.11.013. Epub 2018 Nov 8.
Abstract
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 μM. Derivatives containing three-carbon and four-carbon alkyl groups gave the strongest activity (carvacrol derivatives 9-12, IC = 128.8-244.1 μM; thymol derivatives 16-19, IC = 102.3-191.4 μM).
摘要
香芹酚（1）和百里酚（2）经三步转化为其烷基 4-氧代丁酸酯衍生物（7-20），并评估其对酪氨酸酶抑制活性。这些化合物表现出结构依赖性活性，除 7 和 20 外，所有烷基 4-氧代丁酸酯都显示出比前体 4-氧代丁酸（5 和 6）更好的抑制活性。一般来说，在 500μM 时，百里酚衍生物比香芹酚衍生物表现出更高的抑制百分率。含三碳和四碳烷基的衍生物表现出最强的活性（香芹酚衍生物 9-12，IC=128.8-244.1μM；百里酚衍生物 16-19，IC=102.3-191.4μM）。
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