Imidazolidin-4-one peptidomimetic derivatives of primaquine: Synthesis and antimalarial activity

Nuno Vale, Joana Matos, Jiri Gut, Fátima Nogueira, Virgílio do Rosário, Philip J. Rosenthal, Rui Moreira, Paula Gomes

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

The synthesis of imidazolidin-4-one derivatives of primaquine containing the five-membered ring at the C-terminus of a dipeptide backbone coupled to the parent drug is described. These peptidomimetic derivatives were active against a chloroquine-resistant Plasmodium falciparum strain and inhibited the development of the sporogonic cycle of Plasmodium berghei, affecting the appearance of oocysts in the midguts of the mosquitoes. The novel imidazolidin-4-ones are extremely stable, both in human plasma and in pH 7.4 buffer, as a result of N1-acylation. Thus, 'internal' imidazolidin-4-ones derived from dipeptidyl 8-aminoquinolines represent a new entry in antimalarial structure-activity relationships.

Original languageEnglish
Pages (from-to)4150-4153
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number14
DOIs
Publication statusPublished - 15 Jul 2008

Keywords

  • Antimalarial
  • Gametocytocidal
  • Imidazolidin-4-one
  • Malaria
  • Peptidomimetic
  • Primaquine

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