10.1021/acscombsci.8b00118
The research focuses on the synthesis and evaluation of a small library of triazolyl polyphenols, correlating their antioxidant activity and stability with the number and position of hydroxyl groups on the aromatic rings. The study involves the synthesis of 1,2,3-triazoles disubstituted with polyphenol groups at 1,4-positions using a metal-free method, with subsequent demethylation to yield polyphenolic compounds. The antioxidant activity of these compounds was assessed using in vitro assays, namely the oxygen radical absorbance capacity (ORAC) and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS) tests, while their in vivo effects were evaluated using a Saccharomyces cerevisiae model organism assay. The stability of the compounds in aqueous solutions was also monitored over a two-month period. Reactants included various anilines, acetophenones, and tosylhydrazide, while analyses utilized fluorescence spectrometry for ORAC, spectrophotometry for ABTS, and colony forming units for the yeast assay.
10.1002/jccs.201700129
The research focuses on the design, synthesis, and antifungal evaluation of 17 novel benzoxazole derivatives containing a 1,2,3-triazole moiety. These compounds were synthesized through a copper(II) acetylacetonate-catalyzed cyclization reaction between 2-aminophenol derivatives and 1H-1,2,3-triazole-4-carbaldehyde derivatives, which were prepared in three steps starting from aromatic amine. The antifungal activities of these compounds were evaluated against two plant pathogenic fungi, Botrytis cinerea (BC) and Fusarium Verticillium (FV), using hymexazol as the standard drug. The synthesized compounds were characterized using NMR, IR, and high-resolution mass spectroscopy (HRMS), and their structures were confirmed through these analyses. The antifungal activity was assessed by preparing a stock solution of each compound in DMSO, diluting it in potato dextrose agar, inoculating with fungal cakes, and measuring the inhibition of fungal growth after incubation at 28°C for 48 hours. The inhibition ratios were calculated by comparing the average diameter of fungal spread in the presence of the compounds to that of the control.
10.1080/00397911.2020.1843178
The study presents a one-pot, two-step synthesis method for the creation of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives, which are important heterocyclic compounds with applications in pharmaceuticals and other industries. The process involves an N-allylation reaction using N-propargylated amines, 2,3-dibromopropene, and K2CO3 in DMSO, followed by a CuI-catalyzed [3+2] cycloaddition reaction with sodium azide. These chemicals serve as starting materials and catalysts to facilitate the formation of the desired triazole derivatives with high efficiency and good product yield (80–91%). The study's purpose is to develop a simple, efficient method for synthesizing these compounds, which could be practically useful given their potential broad bioactivities.
10.1002/anie.201309855
This research presents the first iridium-catalyzed azide-alkyne cycloaddition (IrAAC) of electron-rich internal thioalkynes, aiming to develop a mild and efficient method for synthesizing fully substituted 1,2,3-triazoles. The study demonstrates that using [{Ir(cod)Cl}2] as a catalyst allows for high efficiency and regioselectivity under mild conditions, compatible with various solvents and functional groups. The process successfully utilizes thioalkynes and azides, such as benzyl azide, in dichloromethane solvent, yielding triazole products with excellent yields. The findings highlight the advantages of IrAAC over traditional copper- and ruthenium-catalyzed methods, paving the way for broader applications in organic synthesis and materials science.
10.3762/bjoc.14.270
The study presents a novel copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction for synthesizing 1,4-disubstituted 1,2,3-triazoles using alkyl diacyl peroxides, azidotrimethylsilane (TMSN3), and terminal alkynes. The alkyl diacyl peroxides, derived from aliphatic carboxylic acids, serve as alkyl azide precursors, decomposing in the presence of the Cu(I) catalyst to form alkyl radicals and azido–Cu(II) species. TMSN3 acts as a safer azide source, reacting with the alkyl radicals to form alkyl azides. The terminal alkynes participate in the subsequent CuAAC reaction, catalyzed by the regenerated Cu(I), to produce the desired 1,2,3-triazoles. This method simplifies the process by generating organic azides in situ, avoiding the handling of unstable organic azides, and offers a wide substrate scope, high yields, and excellent regioselectivity.
10.1039/d1gc02002a
The research focuses on developing hypercrosslinked polymers (HCPs) containing dimethylformamide (DMF) moieties as alternatives to DMF solvent for azide-based synthesis. The study synthesized HCP-DMF and HCP-DMF-SO3H, which have flexible DMF-like moieties that provide a polar microenvironment for catalysis. The research aimed to replace hazardous DMF solvent with ethanol (EtOH) in the synthesis of benzylic azides and 1,2,3-triazoles, common structures in bioactive molecules. The experiments involved the conversion of NaN3 to benzylic azides and the synthesis of 1,2,3-triazoles using these HCP catalysts in EtOH, avoiding the use of DMF. Analyses included Fourier-transform infrared spectroscopy (FT-IR), fluorescence spectroscopy using Nile red as a probe, thermogravimetric analysis (TGA), solid-state 13C NMR, X-ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM) to characterize the HCP materials. The catalytic performance of the materials was evaluated by monitoring the reaction yields and recyclability of the catalysts.
10.5935/0103-5053.20160017
This research focuses on the synthesis and antitrypanosomastid activity of 1,4-diaryl-1,2,3-triazole compounds derived from natural products veraguensin, grandisin, and machilin G. The study aims to develop new bioactive compounds to combat neglected diseases such as Chagas disease and Leishmaniases, which are caused by protozoan parasites. The researchers synthesized sixteen 1,4-diaryl-1,2,3-triazole compounds using click chemistry, a method that allows for the efficient synthesis of diverse compounds. The key chemicals used in the synthesis include terminal acetylenes and aromatic azides, which were combined through a 1,3-dipolar cycloaddition reaction to form the triazole core. The compounds were tested for their biological activity against Leishmania amazonensis, Leishmania infantum, and Trypanosoma cruzi. The results showed that three compounds exhibited significant antileishmanial activity, with IC50 values as low as 1.1 μM, and one compound showed high activity against Leishmania infantum with an IC50 of 5.2 μM. Additionally, one derivative had an IC50 of 28.6 μM against T. cruzi. The study concludes that the 1,2,3-triazole compounds, particularly those containing a methylenedioxy group, demonstrated promising antitrypanosomatid activity and low cytotoxicity, making them potential candidates for further in vivo studies.
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