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

• Type: Article in International Scientific Journal
• Date: 2008

Authors

Nuno Vale (Author) FCUP; Joana Matos (Author) Other; Jiri Gut (Author) Other; Fatima Nogueira (Author) Other; Virgilio do Rosario (Author) Other; Philip J Rosenthal (Author) Other; Rui Moreira (Author) Other; Paula Gomes (Author) FCUP

Journal

Title: Bioorganic and Medicinal Chemistry Letters

Vol. 18

Pages: 4150-4153

ISSN: 0960-894X

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 31 Citations

Scopus - 32 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-XRA

DOI: 10.1016/j.bmcl.2008.05.076

Abstract (EN): 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 N(1)-acylation. Thus, 'internal' imidazolidin-4-ones derived from dipeptidyl 8-aminoquinolines represent a new entry in antimalarial structure-activity relationships.

Language: English

Type (Professor's evaluation): Scientific