Synthesis and Biological Evaluation of Piperic Acid Amides as Free Radical Scavengers and α-Glucosidase Inhibitors

被引：13

作者：

Takao, Koichi ^{[1
]}

Miyashiro, Takaki ^{[1
]}

Sugita, Yoshiaki ^{[1
]}

机构：

[1] Josai Univ, Fac Pharmaceut Sci, Dept Pharmaceut & Hlth Sci, Bioorgan Chem Lab, Sakado, Saitama 3500295, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2015年 / 63卷 / 05期

关键词：

piperine; alpha-glucosidase inhibitor; antioxidant; structure-activity relationship; ANTIOXIDANT ACTIVITY; OXIDATIVE STRESS; BLACK PEPPER; SEROTONIN; DERIVATIVES;

D O I：

10.1248/cpb.c14-00874

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of piperic acid amides (4-24, 29, 30) were synthesized and their 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and a-glucosidase inhibitory activities were evaluated. Among the synthesized compounds, the amides 11, 13 and 15, which contain o-methoxyphenol, catechol or 5-hydroxyindole moieties, showed potent DPPH free radical scavenging activity (11: EC50 140,mu m; 13: EC50 28 mu m; 15: EC50 20 mu m). The amides 10, 18 and 23 showed higher inhibitory activity of a-glucosidase (10: IC50 21 mu m; 18: IC50 21 mu m; 23: IC50 12 mu m). These data suggest that the hydrophobicity of the conjugated amines is an important determinant of alpha-glucosidase inhibitory activity. In addition, the amides 13 and 15 showed both potent DPPH free radical scavenging activity and a-glucosidase inhibitory activity (13: IC50 46 mu m; 15: IC50 46 mu m). This is the first report identifying the DPPH free radical scavenging and a-glucosidase inhibitory activities of piperic acid amides and suggests that these amides may serve as lead compounds for the development of novel a-glucosidase inhibitors with antioxidant activity.

引用

页码：326 / 333

页数：8

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