Synthesis, Characterization and Cytotoxic Activity of Novel β-hydroxy-1,2,3-Triazoles Derived from Eugenol
DOI:
https://doi.org/10.29356/jmcs.v70i1.2541Keywords:
Eugenol, 1,2,3-triazole derivatives, β-hydroxy-1,2,3-triazole, cytotoxic activity, MCF-7 cellsAbstract
Phenylpropanoids and their semisynthetic derivatives are an important class of compounds with diverse biological applications. Herein, a series of β-hydroxy-1,2,3-triazole derivatives of eugenol were synthetized via ring opening of eugenol epoxide and the subsequent copper-catalyzed azide-alkyne cycloaddition reaction (CuAAC). The novel eugenol derivatives were characterized by 1D and 2D NMR spectroscopy and HR-MS. The cytotoxic activity of eugenol and 1,2,3-triazole derivatives against the human breast cancer cell line MCF-7 was investigated. Compounds 3a and 3b displayed a similar cytotoxic activity than eugenol, whereas derivatives 3c and 3d showed a slight lower cytotoxic than the natural phenylpropanoid.
Resumen. Los fenilpropanoides y sus derivados semisintéticos son una importante clase de compuestos con diversas aplicaciones biológicas. En este trabajo, una serie de derivados β-hidroxi-1,2,3-triazoles de eugenol fueron sintetizados mediante la apertura del anillo del epóxido de eugenol y la subsecuente reacción de cicloadición de azida-alquino catalizada por cobre (CuAAC). Los nuevos derivados de eugenol fueron caracterizados por RMN en 1D y 2D y EM-AR. La actividad citotóxica del eugenol y de los derivados 1,2,3-triazoles fue investigada contra la línea celular de cáncer de mama humano MCF-7. Los compuestos 3a y 3b mostraron una actividad citotóxica similar al eugenol, mientras que los derivados 3c y 3d mostraron una citotoxicidad ligeramente menor que el fenilpropanoide de origen natural.
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Copyright (c) 2026 Evelin Martínez-Benavidez, Alma K. Tzec-Nahuat, Carlos Alavez-Ek, Roger G. Cauich-Kumul, Juan M. Martínez-Alejo, Gumersindo Mirón-López, Gonzalo J. Mena-Rejón, Angel D. Herrera-España
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