Synthesis of 1,2,3-Triazole Derivatives of N,N-Dimethyltryptamine Isolated From Mimosa tenuiflora Root Bark: Antiplasmodial Activity In Silico and In Vitro.
5 affiliations
- 1Department of Chemistry, Federal University of Piauí, Teresina, Brazil.
- 2Department of Chemistry, Federal University of Espírito Santo, Vitória, Brazil.
- 3Research Center in Biological Chemistry (NQBio), Federal University of São João Del-Rei, Divinópolis, Brazil.
- 4Immunopathology and Tropical Diseases Laboratory, Federal Research and Educational Support Center in Health (NUPADS), Institute of Health Sciences, University of Mato Grosso, Sinop, Brazil.
- 5Department of Biotechnology, SGB Amravati University, Amravati, Maharashtra, India.
Abstract
Malaria is a severe parasitic disease, with Plasmodium falciparum as one of the main etiological agents. The growing resistance to antimalarial drugs underscores the urgent need for the development of new therapeutic agents. This study describes the semisynthesis of eight new 1,4-disubstituted 1,2,3-triazole derivatives (3-10) from N,N-dimethyltryptamine (1), isolated from Mimosa tenuiflora. The derivatives were obtained through copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reactions and characterized by NMR and mass spectrometry. Compound 1 showed low in vitro activity against the W2 strain of P. falciparum (IC₅₀ = 288.4 ± 28.53 µM), whereas compound 4 demonstrated promising activity (IC₅₀ = 4.8 ± 0.32 µM), with higher selectivity toward the TOV-21G cell line. In in silico studies, all derivatives showed more favorable binding energy values compared to compound 1, particularly compound 7 (-9.8 kcal/mol) relative to the crystallographic ligand (-6.9 kcal/mol). These results highlight the importance of structural modifications in the development of new antimalarial agents.
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BibTeX
@article{sousa2026synthesis,
title = {{Synthesis of 1,2,3-Triazole Derivatives of N,N-Dimethyltryptamine Isolated From Mimosa tenuiflora Root Bark: Antiplasmodial Activity In Silico and In Vitro.}},
author = {Renato Pinto de Sousa and William Cezar de Lima Silva and Caíque Lopes Duarte and Ana Claudia de Souza Pinto and Amanda Luisa da Fonseca and Fernanda Alice de Oliveira and Fernando de Pilla Varotti and Bruno Antônio Marinho Sanchez and Mahendra Rai and Maurício Pires de Moura do Amaral and Mariana Helena Chaves and João Sammy Nery de Souza and Warley de Souza Borges and Gerardo Magela Vieira Júnior},
journal = {Chemistry \& biodiversity},
year = {2026},
month = oct,
doi = {10.1002/cbdv.71849},
url = {https://europepmc.org/article/MED/42904838},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - Synthesis of 1,2,3-Triazole Derivatives of N,N-Dimethyltryptamine Isolated From Mimosa tenuiflora Root Bark: Antiplasmodial Activity In Silico and In Vitro.
AU - Renato Pinto de Sousa
AU - William Cezar de Lima Silva
AU - Caíque Lopes Duarte
AU - Ana Claudia de Souza Pinto
AU - Amanda Luisa da Fonseca
AU - Fernanda Alice de Oliveira
AU - Fernando de Pilla Varotti
AU - Bruno Antônio Marinho Sanchez
AU - Mahendra Rai
AU - Maurício Pires de Moura do Amaral
AU - Mariana Helena Chaves
AU - João Sammy Nery de Souza
AU - Warley de Souza Borges
AU - Gerardo Magela Vieira Júnior
PY - 2026
DA - 2026/10/01
JO - Chemistry & biodiversity
DO - 10.1002/cbdv.71849
UR - https://europepmc.org/article/MED/42904838
AB - Malaria is a severe parasitic disease, with Plasmodium falciparum as one of the main etiological agents. The growing resistance to antimalarial drugs underscores the urgent need for the development of new therapeutic agents. This study describes the semisynthesis of eight new 1,4-disubstituted 1,2,3-triazole derivatives (3-10) from N,N-dimethyltryptamine (1), isolated from Mimosa tenuiflora. The derivatives were obtained through copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reactions and characterized by NMR and mass spectrometry. Compound 1 showed low in vitro activity against the W2 strain of P. falciparum (IC₅₀ = 288.4 ± 28.53 µM), whereas compound 4 demonstrated promising activity (IC₅₀ = 4.8 ± 0.32 µM), with higher selectivity toward the TOV-21G cell line. In in silico studies, all derivatives showed more favorable binding energy values compared to compound 1, particularly compound 7 (-9.8 kcal/mol) relative to the crystallographic ligand (-6.9 kcal/mol). These results highlight the importance of structural modifications in the development of new antimalarial agents.
SN - 1612-1872
SN - 1612-1880
ER -