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Current Bioactive Compounds

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ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

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Research Article

Synthesis of 1,2,3-triazole Compounds by Click Chemistry in Aqueous Medium and Evaluation of Bactericidal and Antitumoral Properties

Author(s): Lucas Lima Zanin, David Esteban Quintero Jimenez, Willian Garcia Birolli, Tiago Venâncio, Talita Alvarenga Valdes, Andrei Leitão and André Luiz Meleiro Porto*

Volume 18, Issue 4, 2022

Published on: 24 January, 2022

Article ID: e191121198117 Pages: 10

DOI: 10.2174/1573407217666211119092038

Price: $65

Abstract

Background: Triazoles are heterocyclic synthetic compounds that have gained relevance after studies by Sharpless on regioselective methodologies for the synthesis of 1,2,3-triazole derivatives. In addition, they have a wide range of biological properties.

Objective: The objective of this study is to develop a synthetic methodology aligned with the principles of click chemistry for the synthesis of 1,2,3-triazole derivatives and verify the profile of these compounds in biological assays.

Methods: Initially, a model reaction was selected and an optimization study involving synthetic conditions was carried out. Using the most efficient condition, a series of compounds was developed by the reactions between 2-azido-1-phenylethan-1-one derivatives and terminal alkynes. In sequence, bactericidal and antitumoral assays were performed.

Results: It was possible to synthesise ten examples using water as a sustainable solvent, in 1 hour, with good yields of 73-99%, including three compounds described for the first time. Two products presented bactericidal activity, one against the gram-negative Escherichia coli ATCC 25922 and other against the gram-positive Paenibacillus alvei CBMAI 2221. Moreover, other two triazole derivatives presented antitumoral activity for prostate and pancreas cancer cells in this screening study with the bioactivity quantified for compound 1-([1,1'-biphenyl]-4-yl)-2-(4-(p-tolyl)- 1H-1,2,3-triazol-1-yl)ethan-1-one (IC50 = 132 μM).

Conclusion: Herein, an efficient methodology for the synthesis of 1,2,3-triazole derivatives with high yields and using water as solvent was developed. Furthermore, some compounds presented positive results to bactericidal and antitumoral assays, justifying further exploration of these novel compounds and their biological properties.

Keywords: Heterocycles, green chemistry, regioselective catalysis, 1, 3-dipolar cycloaddition, antitumoral, bactericidal, biological applications.

Graphical Abstract

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