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Open AccessArticle

Alkyl and Aryl Derivatives Based on p-Coumaric Acid Modification and Inhibitory Action against Leishmania braziliensis and Plasmodium falciparum

1
PostGraduation Program in Technological Development and Innovation in Medicines, Federal University of Paraíba, João Pessoa CEP 58051-970, Brazil
2
PECET-Facultad de Medicina, Universidad de Antioquia, Medellín Calle 70 # 52-21, Colombia
3
Escuela de Ciencias Físicas y Matemáticas, Universidad de Las Américas, Quito 170504, Ecuador
4
Department of Pharmaceutical Sciences, Federal University of Paraíba, João Pessoa CEP 58051-970, Brazil
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(14), 3178; https://doi.org/10.3390/molecules25143178
Received: 22 May 2020 / Revised: 12 June 2020 / Accepted: 17 June 2020 / Published: 11 July 2020
In low-income populations, neglected diseases are the principal cause of mortality. Of these, leishmaniasis and malaria, being parasitic, protozoan infections, affect millions of people worldwide and are creating a public health problem. The present work evaluates the leishmanicidal and antiplasmodial action of a series of twelve p-coumaric acid derivatives. Of the tested derivatives, eight presented antiparasitic activities 13, 812. The hexyl p-coumarate derivative (9) (4.14 ± 0.55 μg/mL; selectivity index (SI) = 2.72) showed the highest leishmanicidal potency against the Leishmania braziliensis amastigote form. The results of the molecular docking study suggest that this compound inhibits aldehyde dehydrogenase (ALDH), mitogen-activated kinase protein (MPK4), and DNA topoisomerase 2 (TOP2), all of which are key enzymes in the development of Leishmania braziliensis. The data indicate that these enzymes interact via Van der Waals bonds, hydrophobic interactions, and hydrogen bonds with phenolic and aliphatic parts of this same compound. Of the other compounds analyzed, methyl p-coumarate (64.59 ± 2.89 μg/mL; IS = 0.1) demonstrated bioactivity against Plasmodium falciparum. The study reveals that esters presenting a p-coumarate substructure are promising for use in synthesis of derivatives with good antiparasitic profiles. View Full-Text
Keywords: hydroxycinnamic acids; natural products; leishmanicidal activity; antiplasmodial activity; cytotoxicity; neglected diseases hydroxycinnamic acids; natural products; leishmanicidal activity; antiplasmodial activity; cytotoxicity; neglected diseases
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Lopes, S.P.; Yepes, L.M.; Pérez-Castillo, Y.; Robledo, S.M.; de Sousa, D.P. Alkyl and Aryl Derivatives Based on p-Coumaric Acid Modification and Inhibitory Action against Leishmania braziliensis and Plasmodium falciparum. Molecules 2020, 25, 3178.

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