Studies on prodrugs. I. Preparation and characterization of acyloxyallylester of ampicillin.

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Abstract
The use of prodrugs as a method to improve oral absorption has been carried out widely in the case of penicillins. To investigate a new type of promoiety for ampicillin prodrugs, acyloxyallyl esters were prepared and their oral absorbabilities, stabilities and hydrolyzabilities to parent ampicillin were studied. As starting materials for (3-phthalidylidene)ethyl esters, ethylidenephthalide and its derivatives were regiospecifically prepared by a new method using the Wittig reaction. (3-Phthalidylidene)ethyl esters (14a-c [ampicillin(3-phthalidylidene)ethyl ester hydrochloride, ampicillin(3-(6-chlorophthalidylidene))ethyl ester hydrochloride and ampicillin(3-(6-methoxyphthalidylidene))ethyl ester hydrochloride, respectively]) given orally were well absorbed in mice, but (thiophthalidylidene)ethyl ester (14d [ampicillin(3-(2-thiophthalidylidene))ethyl ester hydrochloride]) and (isocoumarin-4-yl)methyl ester (14e [ampicillin(5,7-dimethoxyisocoumarin-4-yl)methyl ester hydrochloride]) were poorly absorbed.

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