Synthesis of 2-n-benzyl carboxamide derivates of 1-azafagomine

Imino sugars, also known as azasugars, are a group of compounds that have received a lot of attention in recent years because they typically exhibit excellent inhibitory properties over a range of enzymes involved in carbohydrate recognizing receptors, widely found in living organisms. [1] The inhibition of αand β-glucosidases by 1-N-phenyl carboxamide derivatives of 1-azafagomine 1 was studied in our laboratory indicating that they are new leads for the synthesis of glycosidase inhibitors. [2] Our objective now is to synthesise new 1-N-phenyl carboxamide derivates of 1-azafagomine 1 bearing groups at the pposition of the aromatic ring with ability to form extra hydrogen bonds. The interest of this structural modification is based on molecular modelling studies, which predicted a higher inhibitory activity for the final products.