title: Synthesis and biological evaluation of piperic acid amides as free radical scavengers and α-glucosidase inhibitors.
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.
authors.affiliation: Laboratory of Bioorganic Chemistry, Department of Pharmaceutical and Health Sciences, Faculty of Pharmaceutical Sciences, Josai University.
authors.forename: Koichi
authors.initials: K
authors.lastname: Takao
authors.forename: Takaki
authors.initials: T
authors.lastname: Miyashiro
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Sugita
mesh_terms: D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis*; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D015394:Molecular Structure; D000520:alpha-Glucosidases / Q000378:metabolism*
chemical_list: D005231:Fatty Acids, Unsaturated; D016166:Free Radical Scavengers; D065089:Glycoside Hydrolase Inhibitors; D000520:alpha-Glucosidases; C017637:piperic acid