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In an effort to develop esterase-sensitive pro-prodrugs for amines, an amide derivative of 3-(2′-acetoxy-4′,6′-dimethylphenyl)-3,3- dimethylpropionic acid (4-methoxyaniline amide (8) was synthesized and its stability investigated. This esterifled hydroxy amide was found under all conditions to degrade via a two-step process initiated by acetyl ester hydrolysis generating the hydroxy amide intermediate...
Several amides of 3-(3′,6′-dioxo-2′,4′-dimethylcyclohexa-l′,4′-diene)-3,3-diniethylpropionic acid (2) have been synthesized and tested as model redox-sensitive pro-prodrugs of amines. The reduction of these model pro-prodrugs generated hydroxy amide intermediates 4a-4h, the lactonization of which resulted in amine release. The rates of lactonization of 4a-4h were investigated at pH 7.4 and 37°C. The...
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