Cyclization-activated Prodrugs

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Cyclization-activated prodrugs.

Many drugs suffer from an extensive first-pass metabolism leading to drug inactivation and/or production of toxic metabolites, which makes them attractive targets for prodrug design. The classical prodrug approach, which involves enzyme-sensitive covalent linkage between the parent drug and a carrier moiety, is a well established strategy to overcome bioavailability/toxicity issues. However, th...

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Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol.

Dipeptide esters of paracetamol were prepared in high yields. These compounds are quantitatively hydrolyzed to paracetamol and corresponding 2,5-diketopiperazines at pH 7.4 and 37 degrees C. The reactivity is increased in sarcosine and proline peptides and decreased by bulky side chains at both the N- and C-terminal residues of the dipeptide carrier. Moreover, dipeptide esters of paracetamol di...

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ژورنال

عنوان ژورنال: Molecules

سال: 2007

ISSN: 1420-3049

DOI: 10.3390/12112484