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Elsevier, Bioorganic and Medicinal Chemistry Letters, 6(15), p. 1595-1598

DOI: 10.1016/j.bmcl.2005.01.065

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

Journal article published in 2005 by C. Santos ORCID, Cledir Santos, Ml Mateus, Ap dos Santos, Ana Paula dos Santos, Rui Moreira ORCID, Eliandre de Oliveira ORCID, Paula Gomes
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This paper is available in a repository.

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Abstract

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 ° 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 did not affect the levels of hepatic glutathione. Thus, dipeptides seem promising candidates as carriers for cyclization-activated prodrugs. © 2005 Elsevier Ltd. All rights reserved.