Synthesis and activity of N-Benzyl pseudopeptides HIV protease inhibitors

Mauro Marastoni, Martina Bazzaro, Fabrizio Bortolotti, Roberto Tomatis

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A series of N-benzyl pseudopeptides was designed, synthesized and tested as HIV-1 protease inhibitors. The ability of the new compounds containing N-benzyl hydroxyalkylamino acid core structure to inhibit HIV replication in cell culture is comparable to their capacity to inhibit the isolated enzyme, a result compatible with good pharmacokinetic properties of these derivatives. The pseudotripeptide Fmoc-Leu-N(Bzl)Hse-Met-NH-tBu was the best inhibitor of the series (IC50=170 nM) showing promising inhibition of viral replication (ED50=52 nM). All new compounds exhibit high enzymatic resistance and stability against cell cultures and plasma enzymes.

Original languageEnglish (US)
Pages (from-to)2477-2483
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume11
Issue number11
DOIs
StatePublished - May 29 2003

Bibliographical note

Funding Information:
Financial support of this work by University of Ferrara and by Ministero dell'Università e della Ricerca Scientifica e Tecnologica (MURST) is gratefully acknowledged.

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