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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates
Sandra Oramas-Royo1, Priscila López-Rojas2, Ángel Amesty3
1Instituto Universitario de Bio-Orgánica (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, 38206 Tenerife, Spain. soramas@ull.edu.es.
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 μM, respectively. Molecular dockings were also carried on Plasmodium falciparum enzyme dihydroorotate dehydrogenase (PfDHODH) in order to rationalize the results.
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