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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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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 |
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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 |
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