Abstract
A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 µM; 13: EC50 14 µM; 18: EC50 13 µM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 µM; 14: IC50 25 µM; 18: IC50 28 µM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.
MeSH terms
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Antioxidants / chemical synthesis
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Antioxidants / chemistry
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Antioxidants / pharmacology
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Biphenyl Compounds / chemical synthesis
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Biphenyl Compounds / chemistry
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Biphenyl Compounds / pharmacology
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Free Radical Scavengers / chemical synthesis*
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Free Radical Scavengers / chemistry
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Free Radical Scavengers / pharmacology*
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Free Radicals / metabolism
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Glycoside Hydrolase Inhibitors / chemical synthesis*
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Glycoside Hydrolase Inhibitors / chemistry
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Glycoside Hydrolase Inhibitors / pharmacology*
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Isoflavones / chemical synthesis*
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Isoflavones / chemistry
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Isoflavones / pharmacology*
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Molecular Structure
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Picrates / chemical synthesis
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Picrates / chemistry
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Picrates / pharmacology
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alpha-Glucosidases / metabolism*
Substances
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Antioxidants
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Biphenyl Compounds
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Free Radical Scavengers
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Free Radicals
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Glycoside Hydrolase Inhibitors
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Isoflavones
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Picrates
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1,1-diphenyl-2-picrylhydrazyl
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alpha-Glucosidases