Design, synthesis and structure-activity relationships of (1H-pyridin-4-ylidene)amines as potential antimalarials

Tiago Rodrigues, Rita C. Guedes, Daniel J.V.A. dos Santos, Marta Carrasco, Jiri Gut, Philip J. Rosenthal, Rui Moreira, Francisca Lopes

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

(1H-Pyridin-4-ylidene)amines containing lipophilic side chains at the imine nitrogen atom were prepared as potential clopidol isosteres in the development of antimalarials. Their antiplasmodial activity was evaluated in vitro against the Plasmodium falciparum W2 (chloroquine-resistant) and FCR3 (atovaquone-resistant) strains. The most active of these derivatives, 4m, had an IC50 of 1 μM against W2 and 3 μM against FCR3. Molecular modeling studies suggest that (1H-pyridin-4-ylidene)amines may bind to the ubiquinol oxidation Qo site of cytochrome bc1.

Original languageEnglish
Pages (from-to)3476-3480
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number13
DOIs
Publication statusPublished - 1 Jul 2009
Externally publishedYes

Keywords

  • (1H-Pyridin-4-ylidene)amines
  • Antiplasmodial

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