1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea derivatives as small molecule heparanase inhibitors.

Abstract A novel class of 1-[4-(1 H -benzoimidazol-2-yl)-phenyl]-3-[4-(1 H -benzoimidazol-2-yl)-phenyl]-ureas are described as potent inhibitors of heparanase. Among them are 1,3-bis-[4-(1 H -benzoimidazol-2-yl)-phenyl]-urea ( 7a ) and 1,3-bis-[4-(5,6-dimethyl-1 H -benzoimidazol-2-yl)-phenyl]-urea ( 7d ), which displayed good heparanase inhibitory activity (IC 50 0.075–0.27 μM). Compound 7a showed good efficacy in a B16 metastasis model.