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 and against three different tumor cell lines (SKBr-3, MCF-7, HEL). The most activ...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (21), p.3917
Hauptverfasser:	Oramas-Royo, Sandra, López-Rojas, Priscila, Amesty, Ángel, Gutiérrez, David, Flores, Ninoska, Martín-Rodríguez, Patricia, Fernández-Pérez, Leandro, Estévez-Braun, Ana
Format:	Artikel
Sprache:	eng
Schlagworte:	1,2,3-triazole-naphthoquinones Antifungal agents Antimalarial activity Antimalarial agents Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antiprotozoal agents Binding sites Biosynthesis Cell Line, Tumor Chloroquine Conjugates copper-catalyzed cycloaddition Cycloaddition Dehydrogenases Dihydroorotate dehydrogenase docking Drugs Enzymes Humans Hybridization Hydrogen bonds Inhibitory Concentration 50 Malaria Models, Molecular Naphthoquinones - chemical synthesis Naphthoquinones - chemistry Naphthoquinones - pharmacology Natural products Parasites Pharmaceutical sciences Plasmodium falciparum Plasmodium falciparum - drug effects Triazoles Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology Tumor cell lines
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Zusammenfassung:	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 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 and having IC of 0.8 and 1.2 μM, respectively. Molecular dockings were also carried on Plasmodium falciparum enzyme dihydroorotate dehydrogenase ( DHODH) in order to rationalize the results.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules24213917