Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles via 1,3‐Dipolar Cycloaddition/C–N Coupling of Propargyl Alcohols/amines and Aryl Azides

Bakherad, Mohammad; Ghalenoei, Ahmad Kakavand; Keivanloo, Ali

doi:10.1002/jhet.3325

Cited by 2 publications

(1 citation statement)

References 42 publications

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“…The CuAAC reaction of ( 3) with ( 4) was catalyzed by CuBr (0.14 equiv) and triethylamine (7.2 equiv) according to azide or alkyne functionalities in CH 2 Cl 2 at room temperature. Following a previously described procedure, 65 the synthesis of monomer ( 7) was carried out in the presence of 20% of Cu(OAc) 2 .H 2 O and 40% of sodium ascorbate as the catalyst in DMF for 1 h at room temperature. In the synthesis progress of ( 6) the solution was colorless, after the catalyst was added the color became green 10 min later then turned to black after 1 h, and the reaction released heat during the process.…”

Section: Polymer Synthesismentioning

confidence: 99%

Effect of the pendent groups on biobased polymers, obtained from click chemistry suitable, for the adsorption of organic pollutants from water

Brirmi

Chabbah

Chatti

et al. 2022

Polymers for Advanced Techs

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In this work, four triazole-based poly(ether-pyridine)s polymers were synthesized and used as an adsorbent for the removal of phenolic compounds from aqueous solutions. For this purpose, new fluoromonomers containing 1,2,3-triazole units were prepared by the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction and then used for the elaboration of novel poly(ether-pyridine-triazole)s (PEPTs) by direct polycondensation with isosorbide and bisphenol A. Chemical structure of fluorinated pyridinic monomers as well as resulting polymers was confirmed by 1 H and 19 F NMR spectroscopic methods. The thermal behavior of the obtained PEPTs was characterized using differential scanning calorimetry and thermogravimetric analysis. Results of sorption showed that polymers can be effectively used as a sorbent for the removal of polar organic pollutants. The isosorbide-based poly(ether-pyridine-triazole) which contains hydrophilic hydroxyl groups as pendants chains (P4) exhibited the highest sorption efficiencies (78%-100% after 1 h). In order to explain the results an adsorption mechanism mainly based on π-π interactions and hydrogen bonding with the pendent groups is proposed.

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Section: Polymer Synthesismentioning

confidence: 99%

Effect of the pendent groups on biobased polymers, obtained from click chemistry suitable, for the adsorption of organic pollutants from water

Brirmi

Chabbah

Chatti

et al. 2022

Polymers for Advanced Techs

View full text Add to dashboard Cite

show abstract

Antitrypanosomal Activity of 1,2,3-Triazole-Based Hybrids Evaluated Using In Vitro Preclinical Translational Models

Orlando,

Lara,

Lechuga

et al. 2023

Biology

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Chagas disease therapy still relies on two nitroderivatives, nifurtimox and benznidazole (Bz), which have important limitations and serious adverse effects. New therapeutic alternatives for this silent disease, which has become a worldwide public health problem, are essential for its control and elimination. In this study, 1,2,3-triazole analogues were evaluated for efficacy against T. cruzi. Three triazole derivatives, 1d (0.21 µM), 1f (1.23 µM), and 1g (2.28 µM), showed potent activity against trypomastigotes, reaching IC50 values 10 to 100 times greater than Bz (22.79 µM). Promising candidates are active against intracellular amastigotes (IC50 ≤ 6.20 µM). Treatment of 3D cardiac spheroids, a translational in vitro model, significantly reduced parasite load, indicating good drug diffusion and efficacy. Oral bioavailability was predicted for triazole derivatives. Although infection was significantly reduced without drug pressure in a washout assay, the triazole derivatives did not inhibit parasite resurgence. An isobologram analysis revealed an additive interaction when 1,2,3-triazole analogs and Bz were combined in vitro. These data indicate a strengthened potential of the triazole scaffold and encourage optimization based on an analysis of the structure–activity relationship aimed at identifying new compounds potentially active against T. cruzi.

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Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles via 1,3‐Dipolar Cycloaddition/C–N Coupling of Propargyl Alcohols/amines and Aryl Azides

Cited by 2 publications

References 42 publications

Effect of the pendent groups on biobased polymers, obtained from click chemistry suitable, for the adsorption of organic pollutants from water

Effect of the pendent groups on biobased polymers, obtained from click chemistry suitable, for the adsorption of organic pollutants from water

Antitrypanosomal Activity of 1,2,3-Triazole-Based Hybrids Evaluated Using In Vitro Preclinical Translational Models

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