Rapid hydrolysis of amides under physiological conditions: influence of the microenvironment on the stability of the amide bond.

A new class of bicyclic carboxyamides 1a-9a differing with respect to substitution patterns and exo-endo geometry has been synthesized. These amides are characterized by a structure-dependent unusual rapid hydrolysis rate at physiological conditions. The corresponding bicyclic anhydrides might be used as tools for masking and modifying therapeutic agents containing amine functionalities.