Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B

Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated β-C- d -glucosyl and β-C- d -galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding β-C- d -glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated β-C- d -glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC50: 0.62–0.88 μM), with no significant difference between gluco and galacto derivatives.