Chemical feasibility studies of a potential coumarin-based prodrug system

By using model amines, several amides of coumarinic acid with the phenolic hydroxyl group protected as an ester were prepared. These model amides underwent a facile (t1/2 1.5–31 min) lactonization to release the original amine compounds upon esterase catalyzed hydrolysis of the phenolic ester. Such a system can be used for the preparation of esterase-sensitive prodrugs of amine-containing compounds or peptides.