Santos, CMateus, MLdos Santos, APMoreira, Rde Oliveira, EGomes, P2015-12-302015-12-302005BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - Vol. 15, n. 6 (2005), p. 1595-15980960-894Xhttp://hdl.handle.net/10451/20946Dipeptide 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.application/pdfengChemistry, MedicinalChemistry, Organicjournal articlehttp://dx.doi.org/10.1016/j.bmcl.2005.01.065