Prodrugs - Part 1. Formylphenyl esters of aspirin

Article abstract of DOI:10.1016/S0223-5234(97)89642-0

The synthesis and study of a novel series of potential prodrugs of aspirin is reported. 2-, 3- and 4-formylphenyl aspirins, as well as a series of 4-substituted 2-formylphenyl aspirins, have been prepared. A study of their alkaline hydrolysis indicates that these compounds act as true prodrugs of aspirin which hydrolyse to aspirin and the formylphenol. The rates of hydrolysis and activation parameters indicate that hydrolysis of the 2-formylphenyl esters employs an intramolecular catalytic route.