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

ABSTRACT: 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 IC50 of 0.8 and 1.2 ?M, respectively. Molecular dockings were also carried on Plasmodium falciparum enzyme dihydroorotate dehydrogenase (PfDHODH) in order to rationalize the results.

SUBMITTER: Oramas-Royo S

PROVIDER: S-EPMC6864696 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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

Oramas-Royo Sandra S López-Rojas Priscila P Amesty Ángel Á Gutiérrez David D Flores Ninoska N Martín-Rodríguez Patricia P Fernández-Pérez Leandro L Estévez-Braun Ana A

Molecules (Basel, Switzerland) 20191030 21

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 <i>Plasmodium falciparum</i> 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 ...[more]

PMID: 31671684

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