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Keywords:

  • aldehydes;
  • alkylation;
  • biological activity;
  • inhibition;
  • synthesis

Abstract

Alkylation of 1-azafagomine at the 2-N position was achieved by reductive amination of 1-N-acetyl-3,4,6-tri-O-benzyl-1-azafagomine by using aldehydes, palladium hydroxide, and hydrogen in EtOAc/water/acetic acid followed by deprotection. The 2-N-butyl, hexyl, heptyl, nonyl, decyl, and 3-phenylpropyl derivatives were made in this manner, and were tested for inhibition of α-glucosidase from yeast, and of β-glucosidase from almonds. The new compounds were stronger β-glucosidase inhibitors than 1-azafagomine, but weaker α-glucosidase inhibitors.