Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates

A series of 34 1,2,3-triazole-naphthoquinone conjugates were synthesized via copper-catalyzed cycloaddition (CuAAC). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and against three different tumor cell lines (SKBr-3, MCF-7...

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Autores principales: Oramas-Royo, Sandra, López-Rojas, Priscila, Amesty, Ángel, Gutiérrez, David, Flores, Ninoska, Martín-Rodríguez, Patricia, Fernández-Pérez, Leandro, Estévez-Braun, Ana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864696/
https://www.ncbi.nlm.nih.gov/pubmed/31671684
http://dx.doi.org/10.3390/molecules24213917
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author Oramas-Royo, Sandra
López-Rojas, Priscila
Amesty, Ángel
Gutiérrez, David
Flores, Ninoska
Martín-Rodríguez, Patricia
Fernández-Pérez, Leandro
Estévez-Braun, Ana
author_facet Oramas-Royo, Sandra
López-Rojas, Priscila
Amesty, Ángel
Gutiérrez, David
Flores, Ninoska
Martín-Rodríguez, Patricia
Fernández-Pérez, Leandro
Estévez-Braun, Ana
author_sort Oramas-Royo, Sandra
collection PubMed
description A series of 34 1,2,3-triazole-naphthoquinone conjugates were synthesized via copper-catalyzed cycloaddition (CuAAC). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and against three different tumor cell lines (SKBr-3, MCF-7, HEL). The most active antimalarial compounds showed a low antiproliferative activity. Simplified analogues were also obtained and some structure–activity relationships were outlined. The best activity was obtained by compounds 3s and 3j, having IC(50) of 0.8 and 1.2 μM, respectively. Molecular dockings were also carried on Plasmodium falciparum enzyme dihydroorotate dehydrogenase (PfDHODH) in order to rationalize the results.
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spelling pubmed-68646962019-12-23 Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates Oramas-Royo, Sandra López-Rojas, Priscila Amesty, Ángel Gutiérrez, David Flores, Ninoska Martín-Rodríguez, Patricia Fernández-Pérez, Leandro Estévez-Braun, Ana Molecules Article A series of 34 1,2,3-triazole-naphthoquinone conjugates were synthesized via copper-catalyzed cycloaddition (CuAAC). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and against three different tumor cell lines (SKBr-3, MCF-7, HEL). The most active antimalarial compounds showed a low antiproliferative activity. Simplified analogues were also obtained and some structure–activity relationships were outlined. The best activity was obtained by compounds 3s and 3j, having IC(50) of 0.8 and 1.2 μM, respectively. Molecular dockings were also carried on Plasmodium falciparum enzyme dihydroorotate dehydrogenase (PfDHODH) in order to rationalize the results. MDPI 2019-10-30 /pmc/articles/PMC6864696/ /pubmed/31671684 http://dx.doi.org/10.3390/molecules24213917 Text en © 2019 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 (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Oramas-Royo, Sandra
López-Rojas, Priscila
Amesty, Ángel
Gutiérrez, David
Flores, Ninoska
Martín-Rodríguez, Patricia
Fernández-Pérez, Leandro
Estévez-Braun, Ana
Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
title Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
title_full Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
title_fullStr Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
title_full_unstemmed Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
title_short Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
title_sort synthesis and antiplasmodial activity of 1,2,3-triazole-naphthoquinone conjugates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864696/
https://www.ncbi.nlm.nih.gov/pubmed/31671684
http://dx.doi.org/10.3390/molecules24213917
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