Cargando…

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

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 antip...

Descripción completa

Detalles Bibliográficos
Autores principales: Carvalho, Samir Aquino, Kaiser, Marcel, Brun, Reto, da Silva, Edson Ferreira, Fraga, Carlos Alberto Manssour
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271834/
https://www.ncbi.nlm.nih.gov/pubmed/25490429
http://dx.doi.org/10.3390/molecules191220374
_version_ 1783377018567524352
author Carvalho, Samir Aquino
Kaiser, Marcel
Brun, Reto
da Silva, Edson Ferreira
Fraga, Carlos Alberto Manssour
author_facet Carvalho, Samir Aquino
Kaiser, Marcel
Brun, Reto
da Silva, Edson Ferreira
Fraga, Carlos Alberto Manssour
author_sort Carvalho, Samir Aquino
collection PubMed
description 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 (IC(50) = 6.27 µM) when compared to miltefosine, the reference drug (IC(50) = 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 (IC(50) = 1.93 µM), was cytotoxic against mammalian L-6 cells.
format Online
Article
Text
id pubmed-6271834
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62718342018-12-28 Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives Carvalho, Samir Aquino Kaiser, Marcel Brun, Reto da Silva, Edson Ferreira Fraga, Carlos Alberto Manssour Molecules Article 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 (IC(50) = 6.27 µM) when compared to miltefosine, the reference drug (IC(50) = 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 (IC(50) = 1.93 µM), was cytotoxic against mammalian L-6 cells. MDPI 2014-12-05 /pmc/articles/PMC6271834/ /pubmed/25490429 http://dx.doi.org/10.3390/molecules191220374 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Carvalho, Samir Aquino
Kaiser, Marcel
Brun, Reto
da Silva, Edson Ferreira
Fraga, Carlos Alberto Manssour
Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives
title Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives
title_full Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives
title_fullStr Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives
title_full_unstemmed Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives
title_short Antiprotozoal Activity of (E)-Cinnamic N-Acylhydrazone Derivatives
title_sort antiprotozoal activity of (e)-cinnamic n-acylhydrazone derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271834/
https://www.ncbi.nlm.nih.gov/pubmed/25490429
http://dx.doi.org/10.3390/molecules191220374
work_keys_str_mv AT carvalhosamiraquino antiprotozoalactivityofecinnamicnacylhydrazonederivatives
AT kaisermarcel antiprotozoalactivityofecinnamicnacylhydrazonederivatives
AT brunreto antiprotozoalactivityofecinnamicnacylhydrazonederivatives
AT dasilvaedsonferreira antiprotozoalactivityofecinnamicnacylhydrazonederivatives
AT fragacarlosalbertomanssour antiprotozoalactivityofecinnamicnacylhydrazonederivatives