Aza-ortho-Quinone Methide and Its Conjugated Acid: Reactivity, Stability and Acidity

Abstract

Aza-o-quinone methides and their conjugated acids are reactive drug metabolites that might react with nucleophilic sites of DNAs and proteins to cause cancer or immune responses, and their reactivity with water is the key information to judge if these metabolites are harmful in living systems. For the first time, aza-o-quinone methide (1) and its conjugated acid (2) are observed by laser flash photolysis, and their reactivity, stability and acidity in water are determined.

Keywords: acidity; aza-o-quinone methide; cycloaddition; drug metabolite; reactivity.