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Aryl piperazine and pyrrolidine as antimalarial agents. Synthesis and investigation of structure-activity relationships
Authors: Mendoza, A. (Adela)
Perez-Silanes, S. (Silvia)
Quiliano, M. (Miguel)
Pabon, A. (Adriana)
Gonzalez, G. (Germán)
Garavito, G. (G.)
Zimic, M. (Mirko)
Vaisberg, A. (Abrahm)
Aldana, I. (Ignacio)
Monge, A. (Antonio)
Deharo, E. (Eric)
Keywords: Piperazine
Antimalarial agents
Docking studies
Issue Date: 2011
Publisher: Elsevier
Publisher version:
ISSN: 0014-4894
Citation: Mendoza A, Perez-Silanes S, Quiliano M, Pabon A, Galiano S, Gonzalez G, et al. Aryl piperazine and pyrrolidine as antimalarial agents. Synthesis and investigation of structure-activity relationships. Exp Parasitol 2011 Jun;128(2):97-103.
Piperazine and pyrrolidine derivatives were synthesized and evaluated for their capacity to inhibit the growth of Plasmodium falciparum chloroquine-resistant (FCR-3) strain in culture. The combined presence of a hydroxyl group, a propane chain and a fluor were shown to be crucial for the antiplasmodial activity. Five compounds of the aryl-alcohol series inhibited 50% of parasite growth at doses ≤ 10 µM. The most active compound 1-(4-fluoronaphthyl)-3-[4-(4-nitro-2-trifluoromethylphenyl)piperazin-1-yl]propan-1-ol was almost 20 to 40 times more active on Plasmodium falciparum (IC50: 0.5 µM) than on tumorogenic and non tumorogenic cells. Calculated physicochemical parameters showed a good potential for intestinal absorption, but due to difficulty in being solubilised prior to oral administration, it was weakly active against Plasmodium berghei infected mice (ED50: 35%). In silico molecular docking study and molecular electrostatic potential calculation revealed that this compound bound to the active site of Plasmodium plasmepsin II enzyme.
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Appears in Collections:DA - Farmacia - Orgánica - Artículos de revista
DA - CIFA - I+D de medicamentos - Artículos de revistas

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