Synthesis and evaluation of α-, β-glucosidase inhibition of 1-N-carboxamide-1-azafagomines and 5-epi-1-azafagomines

• Synthesis of 1-N-sp2 derivatives of 1-azafagomine and 5-epi-1-azafagomine.
• α-, β-Glucosidase inhibition measurements of both 1-azafagomine frameworks.
• High α-glucosidase inhibition activity of a 5-epi-1-azafagomine derivative.
• Good inhibition β-glucosidase activity of both 1-azafagomine frameworks.

1-N-Carboxamide 1-azafagomines and 5-epi-1-azafagomines were obtained from 1-azafagomine and 5-epi-1-azafagomine. The hydroxyl groups and the N-2 pyridazine position were protected prior to reaction with different isocyanates to form ureas. Protective groups were removed leading to the target compounds in 18–23% global yields. Final compounds were tested towards α- and β-glucosidases.

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