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Molecules 2014, 19(12), 20374-20381;

Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives

Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, Rio de Janeiro, RJ 21041-250, Brazil
Swiss Tropical and Public Health Institute (Swiss TPH), Socinstrasse 57, Basel CH-4002, Switzerland
Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio), Programa de Pesquisa em Desenvolvimento de Fármacos, Instituto de Ciências Biomédicas, Universidade Federal do Rio de Janeiro, P.O. Box 68023, Rio de Janeiro, RJ 21941-902, Brazil
Programa de Pós-Graduação em Química, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21949-900, Brazil
Author to whom correspondence should be addressed.
Received: 28 October 2014 / Revised: 29 November 2014 / Accepted: 1 December 2014 / Published: 5 December 2014
(This article belongs to the Special Issue Cinnamic Acids Hybrids with Biological Interest)
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A series of 14 (E)-cinnamic N-acylhydrazone derivatives, designed through molecular hybridization between the (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazide, were tested for in vitro antiparasitic activity upon axenic amastigote forms of Leishmania donovani and bloodstream forms of Trypamosoma brucei rhodesiense. The derivative (2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-N'-[(1E)-phenylmethylene]acrylohydrazide showed moderate antileishmanial activity (IC50 = 6.27 µM) when compared to miltefosine, the reference drug (IC50 = 0.348 µM). However, the elected compound showed an excellent selectivity index; in one case it was not cytotoxic against mammalian L-6 cells. The most active antitrypanosomal compound, the derivative (E)-N'-(3,4-dihydroxybenzylidene)cinnamohydrazide (IC50 = 1.93 µM), was cytotoxic against mammalian L-6 cells. View Full-Text
Keywords: antiprotozoal activity; Leishmania; Trypanosoma; N-acylhydrazone; (E)-cinnamic acid derivatives; molecular hybridization antiprotozoal activity; Leishmania; Trypanosoma; N-acylhydrazone; (E)-cinnamic acid derivatives; molecular hybridization

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Carvalho, S.A.; Kaiser, M.; Brun, R.; Silva, E.F.; Fraga, C.A.M. Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives. Molecules 2014, 19, 20374-20381.

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