CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry

Iniyavan, P.; Balaji, G. L.; Sarveswari, S.; Vijayakumar, V.

doi:10.1016/j.tetlet.2015.07.016

Cited by 21 publications

(10 citation statements)

References 45 publications

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“…The indexed XRD peaks of the CuO nanorods and nanospheres are shown in Figure a. The XRD peaks of the prepared samples were found to match the single‐phase CuO with a monoclinic structure and the diffraction data were in good agreement with JCPDS card of CuO (JCPDS 80–1268) . The absence of any peaks corresponding to Cu(OH) 2 , Cu 2 O, or Cu connoted the purity of CuO phase in two samples.…”

Section: Resultsmentioning

confidence: 99%

Copper (II) Oxide Nanoparticles as an Efficient Catalyst in the Azide–AlkyneCycloaddition

et al. 2016

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Copper (II) oxide nanorods and nanospheres were prepared and their structural, morphological, and electronic properties were investigated by X‐ray diffraction analysis, X‐ray absorption near edge structure, scanning electron microscope and transmission electron microscope.CuO nanoparticles efficiently catalyzes azide‐alkyne 1,3‐dipolar cycloaddition (CuAAC) reaction producing corresponding 1,2,3‐triazole derivatives in excellent yields without use of any additives. The advantages of present protocol are mild reaction conditions, reusability of the catalyst, and applicability to a wide range of substrates.

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Section: Resultsmentioning

confidence: 99%

Copper (II) Oxide Nanoparticles as an Efficient Catalyst in the Azide–AlkyneCycloaddition

et al. 2016

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“…The crude products of phenyl azides 7f’ and 7i’ were further purified by column chromatography (silica gel, hexane). All phenyl azides are known [ 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 ]. The characteristics and spectroscopic data are given in the supporting information .…”

Section: Methodsmentioning

confidence: 99%

The Design and Synthesis of a New Series of 1,2,3-Triazole-Cored Structures Tethering Aryl Urea and Their Highly Selective Cytotoxicity toward HepG2

et al. 2022

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Target cancer drug therapy is an alternative treatment for advanced hepatocellular carcinoma (HCC) patients. However, the treatment using approved targeted drugs has encountered a number of limitations, including the poor pharmacological properties of drugs, therapy efficiency, adverse effects, and drug resistance. As a consequence, the discovery and development of anti-HCC drug structures are therefore still in high demand. Herein, we designed and synthesized a new series of 1,2,3-triazole-cored structures incorporating aryl urea as anti-HepG2 agents. Forty-nine analogs were prepared via nucleophilic addition and copper-catalyzed azide-alkyne cycloaddition (CuAAC) with excellent yields. Significantly, almost all triazole-cored analogs exhibited less cytotoxicity toward normal cells, human embryonal lung fibroblast cell MRC-5, compared to Sorafenib and Doxorubicin. Among them, 2m’ and 2e exhibited the highest selectivity indexes (SI = 14.7 and 12.2), which were ca. 4.4- and 3.7-fold superior to that of Sorafenib (SI = 3.30) and ca. 3.8- and 3.2-fold superior to that of Doxorubicin (SI = 3.83), respectively. Additionally, excellent inhibitory activity against hepatocellular carcinoma HepG2, comparable to Sorafenib, was still maintained. A cell-cycle analysis and apoptosis induction study suggested that 2m’ and 2e likely share a similar mechanism of action to Sorafenib. Furthermore, compounds 2m’ and 2e exhibit appropriate drug-likeness, analyzed by SwissADME. With their excellent anti-HepG2 activity, improved selectivity indexes, and appropriate druggability, the triazole-cored analogs 2m’ and 2e are suggested to be promising candidates for development as targeted cancer agents and drugs used in combination therapy for the treatment of HCC.

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“…Use of acridine derivatives in the synthesis of proteins, peptides, and nucleic acid also reported to show antitumor and binding (DNA) activities . Substituted acridines were synthesized from aromatic aldehydes, dimedone, and nitrogen‐containing reagents such as urea, ammonium acetate and basic alumina catalyst, ammonium bicarbonate, ammonium hydroxide, hydroxyl amine, various anilines, and using different catalysts such as ceric ammonium nitrate, SPNP, ammonium chloride, copper sulfate pentahydrate, SiO 2 ‐I, CuO, dodecyl benzenesulfonic acid (phase transfer catalyst) in hazardous/nonhazardous solvents using microwave, reflux, and traditional heating methods.…”

Section: Introductionmentioning

confidence: 99%

Eco‐friendly, ultrasound‐assisted, and facile synthesis of one‐pot multicomponent reaction of acridine‐1,8(2H,5H)‐diones in an aqueous solvent

Chavan¹,

Pansare

Shelke

2019

J Chinese Chemical Soc

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CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry

Cited by 21 publications

References 45 publications

Copper (II) Oxide Nanoparticles as an Efficient Catalyst in the Azide–AlkyneCycloaddition

Copper (II) Oxide Nanoparticles as an Efficient Catalyst in the Azide–AlkyneCycloaddition

The Design and Synthesis of a New Series of 1,2,3-Triazole-Cored Structures Tethering Aryl Urea and Their Highly Selective Cytotoxicity toward HepG2

Eco‐friendly, ultrasound‐assisted, and facile synthesis of one‐pot multicomponent reaction of acridine‐1,8(2H,5H)‐diones in an aqueous solvent

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