Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure

Aza-analogue of the basic disaccharide unit of heparane sulfate was designed as a potent inhibitor against heparanase produced by solid tumors cell, and synthesized via a coupling reaction of phenyl 2-azide-1-thio-d-glucopyranoside derivatives with a partially protected 1-deoxynojirimycin derived from d-glucose. The azapseudodisaccharide inhibited tumor cell heparanase with IC50 value of 58–63 μM.