Abstract
The β-N,N-dimethylaminoethyl ester of diethylmalonuric acid was prepared and evaluated as a water-soluble pro-drug of barbital. The ester was found to undergo a rapid and quantitative cyclization in neutral and alkaline aqueous solution to barbital, the half-time of conversion being 2.8 min at pH 7.4 and 37°C. The kinetics of cyclization were studied in the pH range 4–10.2 and it was found that protonation of the dimethylamino moiety resulted in a 9-fold greater reactivity compared with the free base form. This rate-accelerating effect was attributed to electrostatic stabilization of a negatively charged reaction center. The solubility of the hydrochloride salt of the ester in water was found to be greater than 75% w/v. The results suggested that β-N,N-dimethylaminoethyl esters of malonuric acids may be potentially useful water-soluble pro-drugs of the respective barbituric acids with improved delivery properties for parenteral use.
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