Chlorogenic Acid Derivatives with Alkyl Chains of Different Lengths and Orientations: Potent α-Glucosidase Inhibitors

α-Glucosidases play important roles in the digestion of carbohydrates and biosynthesis of viral envelope glycoproteins. Inhibitors of α-glucosidase are promising candidates for the development of antitype II diabetics and anti-AIDS drugs. Here, we report the synthesis and α-glucosidase inhibitory ac...

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Bibliographic Details
Published in:Journal of medicinal chemistry 2008-10, Vol.51 (19), p.6188-6194
Main Authors: Ma, Chao-Mei, Hattori, Masao, Daneshtalab, Mohsen, Wang, Lili
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Alkylation
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Binding Sites
Biological and medical sciences
Chlorogenic Acid - analogs & derivatives
Chlorogenic Acid - chemical synthesis
Chlorogenic Acid - pharmacology
Dose-Response Relationship, Drug
Drug Stability
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Gastric Juice - chemistry
General and cellular metabolism. Vitamins
Geobacillus stearothermophilus - enzymology
Glycoside Hydrolase Inhibitors
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Saccharomyces cerevisiae - enzymology
Stereoisomerism
Structure-Activity Relationship
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Summary:α-Glucosidases play important roles in the digestion of carbohydrates and biosynthesis of viral envelope glycoproteins. Inhibitors of α-glucosidase are promising candidates for the development of antitype II diabetics and anti-AIDS drugs. Here, we report the synthesis and α-glucosidase inhibitory activity of mono- and diketal/acetal derivatives of chlorogenic acid. The diketal derivatives showed more potent inhibitory activity than the monoketals. The 1,7-(5-nonanone) 3,4-(5-nonanone)-chlorogenic acid diketal showed remarkable inhibitory activity against α-glucosidases with potency better than that of 1-deoxynojirimycin hydrochloride. Four diasteremers of pelargonaldehyde diacetal and two of monoacetal derivatives of chlorogenic acid were synthesized in this study. They showed significant potent inhibition similar to or more potent than the ketal counterparts. Acetals with the alkyl chain oriented toward position 2 of chlorogenic acid showed more potent activity than those oriented toward position 6.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm800621x