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Molecules 2014, 19(12), 20374-20381; doi:10.3390/molecules191220374

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

1
Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, Rio de Janeiro, RJ 21041-250, Brazil
2
Swiss Tropical and Public Health Institute (Swiss TPH), Socinstrasse 57, Basel CH-4002, Switzerland
3
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
4
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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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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