Antileishmanial activity of amides from Piper amalago and synthetic analogs

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ID: 92555
2013
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Abstract
Two natural amides isolated from the chloroform extract of Piper amalago L., Piperaceae, leaves, a hydrogenated derivative and seven synthetic analogs were tested against the promastigote and intracellular amastigote forms of Leishmania amazonensis. The antileishmanial activity was evaluated in terms of growth inhibitory concentration for 50% of protozoa (IC50). The cytotoxicity toward the J774A1 macrophages was evaluated in terms of the cytotoxic concentrations for 50% of macrophages (CC50). The ability to induce nitric oxide production was also investigated for all compounds. The saturated amide 7-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)- 1-heptanone was obtained by hydrogenation of the natural compound N-[7-(3’,4’- methylenedioxyphenyl)-2(Z),4(Z)-heptadienoyl]pyrrolidine. Synthetic amides were prepared by addition of the appropriate amine to the corresponding acyl chloride. The natural compound, N-[7-(3’,4’-methylenedioxyphenyl)-2(E),4(E)-heptadienoyl] pyrrolidine, was the most active of all tested compounds against the promastigote and intracellular amastigote forms with IC50 values of 15 μM and 14.5 μM, respectively. None of the compounds modulated the production of nitric oxide. Keywords: amides, antileishmanial activity, Piper amalago, synthetic analogs
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Authors Carrara, Vanessa da Silva;Cunha-Júnior, Edézio Ferreira;Torres-Santos, Eduardo Caio;Corrêa, Arlene Gonçalves;Monteiro, Júlia L.;Demarchi, Izabel Galhardo;Lonardoni, Maria Valdrinez Campana;Cortez, Diógenes Aparício Garcia;
Journal revista brasileira de farmacognosia
Year 2013
DOI DOI not found
URL
http://www.sciencedirect.com/science/article/pii/S0102695X13700590
Keywords
chemistry Pharmacy and materia medica Therapeutics. Pharmacology Medicine Materials of engineering and construction. Mechanics of materials Chemical technology Science anesthesiology environmental engineering earthwork. foundations

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