Abstract
Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated beta-C-d-glucosyl and beta-C-D-galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding beta-C-D-glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated beta-C-D-glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC(50): 0.62-0.88 miroM), with no significant difference between gluco and galacto derivatives.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzoquinones / chemical synthesis*
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Benzoquinones / chemistry
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Benzoquinones / pharmacology
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Diabetes Mellitus, Type 2 / drug therapy
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Dimerization
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Glycosides / chemical synthesis*
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Glycosides / chemistry
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Glycosides / pharmacology
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Hypoglycemic Agents / chemical synthesis*
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Hypoglycemic Agents / chemistry
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Hypoglycemic Agents / pharmacology
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Inhibitory Concentration 50
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Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
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Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
Substances
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Benzoquinones
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Enzyme Inhibitors
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Glycosides
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Hypoglycemic Agents
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Protein Tyrosine Phosphatase, Non-Receptor Type 1