Synthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approach

Kuczynska, Kinga; Bończak, Bartłomiej; Rárová, Lucie; Kvasnicová, Marie; Strnad, Miroslav; Pakulski, Zbigniew; Cmoch, Piotr; Fiałkowski, Marcin

doi:10.1016/j.molstruc.2021.131751

Cited by 17 publications

(8 citation statements)

References 40 publications

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“…The cross-linking agent, 4,4′-diethynyl-1,1′-biphenyl (DEBP) (11), was synthesized following the previously published procedure. 35 In short, (4-bromophenylethynyl)trimethylsilane (9) was treated with BuLi, followed y the copper iodide. This caused dimerization of bromide (9) upon heating the solution to room temperature, resulting in biphenyl (10) with a good yield.…”

Section: Methodsmentioning

confidence: 99%

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Donor–Acceptor Stenhouse Adducts for Stimuli-Responsive Self-Assembly of Gold Nanoparticles into Semiconducting Thin Films

Bończak

Fiałkowski

2022

J. Phys. Chem. C

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Recent advancements in materials science and chemistry allowed the creation of intelligent, programmable materials. The stimuli-responsive substances are the most prominent candidates for developing sophisticated nanomachinery. Especially, photo- and thermoresponsive systems have gained much attention in recent years as elegant solutions for drug transportation, information storage, biomaterials, and material engineering. However, to this day, only a limited number of molecular domains display triggered and reversible self-organization at the water–oil interface. Among various substances functionalized with responsive moieties, the donor–acceptor Stenhouse adduct (DASA) stands out as an exciting but poorly explored tool in the toolbox of materials science. After being illuminated with a green light, the compound changes its coloration and polarity. This state can be reversed by increasing the temperature. The study presents the synthesis of gold nanoparticles (AuNPs) decorated with a DASA-containing ligand that can undergo on-demand, light-triggered, and thermoreversible self-organization at the water–oil interface. The layer of the nanoparticles locked at the interface can be successfully cross-linked, either by a dithiol molecule or via copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC). The latter option results in a composite with semiconducting properties. The research has the potential to impact the delivery systems for catalysis and the development of programmable materials with electroactive properties.

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Section: Methodsmentioning

confidence: 99%

“…The cross-linking agent, 4,4′-diethynyl-1,1′-biphenyl (DEBP) ( 11 ), was synthesized following the previously published procedure . In short, (4-bromophenylethynyl)trimethylsilane ( 9 ) was treated with BuLi, followed y the copper iodide.…”

Section: Experimental Sectionmentioning

confidence: 99%

Donor–Acceptor Stenhouse Adducts for Stimuli-Responsive Self-Assembly of Gold Nanoparticles into Semiconducting Thin Films

Bończak

Fiałkowski

2022

J. Phys. Chem. C

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“…This developed technique called imaging phospholipase D activity with clickable alcohols via transphosphatidylation (IM-PACT) was reported as promising many new insights into lipid signalling pathways. Kuczynska et al [73] reported twelve 1,2,3-triazoles derived from a triterpenoid namely betulin showing a broad range of biological activities including antimalarial, anti-inflammatory, antiviral and cytotoxic (Figure 4). Newly synthesized azide derivatives of betulin skeleton were coupled with various phenylalkynes having different substituents via copper-catalyzed 1,3-dipolar cycloaddition (CuAAC) reaction affording the target 1,2,3-triazole scaffolds.…”

Section: Design Synthesis Properties and Applications Of 123-triazolesmentioning

confidence: 99%

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Halay

Açıkbaş

2023

ACE

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Click chemistry is totally an approach consisting of efficient and reliable reactions that bind two molecular building blocks and require no complex purification techniques. The aspire of achieving molecules with the desired characteristics and behaviour is the key to the click chemistry concept. In this concept, in order to obtain 1,2,3-triazole products as diversely functionalized molecules, copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has been widely used for years in the field of materials science, organic synthesis and the biochemistry. This review focusses on the importance of click chemistry for obtaining biologically active triazole molecules and therefore the applications of such 1,2,3-triazole derivatives in medicinal chemistry field are highlighted.

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“…18 1,2,3triazole employed superior antimicrobial, antifungal, 20 antioxidant 21 and cytotoxic activities. 22 Collections of glycoconjugated 1,2,3-triazoles derivatives from different sugars functionalized with alkyne or azide moieties have been synthesized via CuAA-click reaction and their antibacterial were evaluated. [23][24][25] Many factors improve the 1,2,3triazoles biological value such as physical and chemical properties, high stability against oxidant agent, hydrolysis resistant in acid/base conditions, the hydrogen bonds forming and amide bioisoesters.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anticancer and Antibacterial Activity of Mannose-based bis-1,2,3-Triazole Derivatives

Mahdi

Mohammed

2023

Baghdad Sci.J

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In the current work, aromatic amines and alkyl halides have been converted to the corresponding azides 2a‒d and 4a-d by the reaction with sodium nitrite and sodium azide respectively for amines and sodium azide for halides. Then, dipropargyl ether derivative of D-mannose 8 has been synthesized from diacetone mannose that has been obtained by the treatment of D-mannose (5) with dry acetone in the presence of sulfuric acid. Then, aldol condensation has been used to prepare diol 7 from the mannose diacetonide 6. The reaction of compound 7 with propargyl bromide in alkaline media has been afforded dipropargyl derivative 8. In a parallel step, both dialkyne with aromatic and aliphatic azide have been coupled to produce 1,2,3-triazole derivatives 9a‒d in the presence of Cu(I) salts. All synthesized compounds have been characterized by 1D and 2D NMR spectra alongside with HRMS data. The antibacterial activity against both gram-positive and gram-negative has been tested. Moreover, the anticancer activity has also been evaluated against AMJ13 cell line.

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Synthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approach

Cited by 17 publications

References 40 publications

Donor–Acceptor Stenhouse Adducts for Stimuli-Responsive Self-Assembly of Gold Nanoparticles into Semiconducting Thin Films

Donor–Acceptor Stenhouse Adducts for Stimuli-Responsive Self-Assembly of Gold Nanoparticles into Semiconducting Thin Films

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Synthesis, Anticancer and Antibacterial Activity of Mannose-based bis-1,2,3-Triazole Derivatives

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