Synthesis and Biological Evaluation of Piperic Acid Amides as Free Radical Scavengers and α-Glucosidase Inhibitors
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- Takao Koichi
- Laboratory of Bioorganic Chemistry, Department of Pharmaceutical and Health Sciences, Faculty of Pharmaceutical Sciences, Josai University
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- Miyashiro Takaki
- Laboratory of Bioorganic Chemistry, Department of Pharmaceutical and Health Sciences, Faculty of Pharmaceutical Sciences, Josai University
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- Sugita Yoshiaki
- Laboratory of Bioorganic Chemistry, Department of Pharmaceutical and Health Sciences, Faculty of Pharmaceutical Sciences, Josai University
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Abstract
A series of piperic acid amides (4–24, 29, 30) were synthesized and their 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and α-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 µM; 13: EC50 28 µM; 15: EC50 20 µM). The amides 10, 18 and 23 showed higher inhibitory activity of α-glucosidase (10: IC50 21 µM; 18: IC50 21 µM; 23: IC50 12 µM). These data suggest that the hydrophobicity of the conjugated amines is an important determinant of α-glucosidase inhibitory activity. In addition, the amides 13 and 15 showed both potent DPPH free radical scavenging activity and α-glucosidase inhibitory activity (13: IC50 46 µM; 15: IC50 46 µM). This is the first report identifying the DPPH free radical scavenging and α-glucosidase inhibitory activities of piperic acid amides and suggests that these amides may serve as lead compounds for the development of novel α-glucosidase inhibitors with antioxidant activity.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 63 (5), 326-333, 2015
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679153268352
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- NII Article ID
- 130005067242
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 026355168
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- PubMed
- 25948326
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed