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Current Organic Synthesis

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General Research Article

Synthesis of Novel Fluoro Phenyl Triazoles Via Click Chemistry with or without Microwave Irradiation and their Evaluation as Anti-proliferative Agents in SiHa Cells

Author(s): Johana Aguilar, Elisa Leyva*, Silvia Elena Loredo-Carrillo, Agobardo Cárdenas-Chaparro, Antonio Martínez-Richa, Hiram Hernández-López, Jorge Gustavo Araujo-Huitrado, Angélica Judith Granados-López, Yamilé López-Hernández and Jesús Adrián López

Volume 21, Issue 4, 2024

Published on: 23 June, 2023

Page: [559 - 570] Pages: 12

DOI: 10.2174/1570179420666230420084000

Price: $65

Abstract

Aims: Perform the synthesis of novel fluoro phenyl triazoles via click chemistry with or without microwave irradiation and their evaluation as anti-proliferative agents in SiHa cells.

Background: Triazoles are heterocyclic compounds containing a five-member ring with two carbon and three nitrogen atoms. They are of great importance since many of them have shown to have biological activity as antifungal, antiviral, antibacterial, anti-HIV, anti-tuberculosis, vasodilator, and anticancer agents.

Objectives: Synthesize novel fluoro phenyl triazoles via click chemistry and evaluate their antiproliferative activity.

Methods: First, several fluorophenyl azides were prepared. Reacting these aryl azides with phenylacetylene in the presence of Cu(I) catalyst, the corresponding fluoro phenyl triazoles were obtained by two methodologies, stirring at room temperature and under microwave irradiation at 40ºC. In addition, their antiproliferative activity was evaluated in cervical cancer SiHa cells.

Results: Fluoro phenyl triazoles were obtained within minutes by means of microwave irradiation. The compound 3f, containing two fluorine atoms next to the carbon connected to the triazole ring, was the most potent among the fluoro phenyl triazoles tested in this study. Interestingly, the addition of a fluorine atom to the phenyl triazole structure in a specific site increases its antiproliferative effect as compared to parent phenyl triazole 3a without a fluorine atom.

Conclusion: Several fluoro phenyl triazoles were obtained by reacting fluoro phenyl azides with phenylacetylene in the presence of copper sulphate, sodium ascorbate and phenanthroline. Preparation of these triazoles with MW irradiation represents a better methodology since they are obtained within minutes and higher yields of cleaner compounds are obtained. In terms of biological studies, the proximity between fluorine atom and triazole ring increases its biological activity.

Keywords: Fluoro phenyl triazoles, click chemistry, microwave, cytotoxic activity, biological, antiproliferative effect.

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