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Journal articles on the topic 'Click chemistry; Azide-alkyne cycloaddition 1'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Bera, Smritilekha, and Dhananjoy Mondal. "Click-Chemistry-Assisted Alteration of Glycosaminoglycans for Biological Applications." SynOpen 07, no. 02 (2023): 277–89. http://dx.doi.org/10.1055/s-0040-1720072.

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AbstractThis short review describes the assistance of click chemistry in the chemical modification of glycosaminoglycans. Through an alkyne-azide 1,3-dipolar cycloaddition reaction, the chemically and physiologically stable triazole unit connects glycosaminoglycans with other labelled or attached functionalities. The synthesized glycosaminoglycan (GAG) conjugates act as drug carriers, forming hydrogels or nanohydrogels for localized drug delivery or injectable GAGs and so on. These are used in research on antithrombotic agents, protein binding, and hepatocyte growth factors, as well as in mech

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2

Kore, Nitin, and Pavel Pazdera. "New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine." Current Organic Synthesis 15, no. 4 (2018): 552–65. http://dx.doi.org/10.2174/1570179415666180110152642.

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Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic,

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3

Svete, Jurij, Uroš Grošelj, Franc Požgan, and Bogdan Štefane. "Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)." Synthesis 50, no. 23 (2018): 4501–24. http://dx.doi.org/10.1055/s-0037-1610284.

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Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected e

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4

Rakotoarivelo, Nambinina V., Ennaji Najahi, and Pierre Perio. "ISOINDOLINOTRIAZOLE DERIVATIVES: SYNTHESIS BY THE AZIDE-ALKYNE CYCLOADDITION CLICK CHEMISTRY." JOURNAL OF ADVANCES IN CHEMISTRY 10, no. 7 (2014): 2937–43. http://dx.doi.org/10.24297/jac.v10i7.6797.

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A novel series of isoindolinotriazole derivatives with different substituents in the triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 2-(meta- or para-ethynylphenyl)-4,6-dimethoxyisoindolin-1-ones and several azides. The synthesized triazoles were characterized by IR, 1H NMR, 13C NMR and mass spectral techniques.

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5

Szafrański, Przemysław W., Patryk Kasza, Mariusz Kępczyński, and Marek T. Cegła. "Fluorescent 1,2,3-triazole derivative of 3′-deoxy-3-azidothymidine: synthesis and absorption/emission spectra." Heterocyclic Communications 21, no. 5 (2015): 263–67. http://dx.doi.org/10.1515/hc-2015-0195.

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Abstract3′-Deoxy-3-azidothymidine (AZT, zidovudine) is a nucleoside-analog reverse transcriptase inhibitor, successfully used against the human immunodeficiency virus (HIV). Its structure contains an azide function, which makes it a useful substrate for 1,2,3-triazole synthesis, using the copper-catalyzed azide-alkyne cycloaddition, the flagship reaction of ‘click chemistry’. Herein we present the synthesis and spectral characterization of its 1,2,3-triazole derivative containing a fluorenylmethyloxycarbonyl (fmoc) fluorescent fragment. The preparation and characteristics of a novel fluorescen

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6

Gasser, Gilles, Anna M. Sosniak, Anna Leonidova, Henrik Braband, and Nils Metzler-Nolte. "Towards the Preparation of Novel Re/99mTc Tricarbonyl-Containing Peptide Nucleic Acid Bioconjugates." Australian Journal of Chemistry 64, no. 3 (2011): 265. http://dx.doi.org/10.1071/ch11010.

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A novel azido derivative of the di-(2-picolyl)amide (Dpam) ligand, namely 3-azido-N,N-bis-pyridin-2-ylmethyl-propionamide (3), was prepared from 3-bromo-N,N-bis(pyridin-2-ylmethyl)propanamide (2) with an excess of sodium azide in DMSO. 3 was then reacted, by CuI-catalyzed [3 + 2] cycloaddition (often referred to as ‘Click Chemistry’), with the previously reported alkyne-containing peptide nucleic acid (PNA) monomer Fmoc-1-OtBu to give the Dpam-containing PNA monomer (Fmoc-4-OtBu) in 44% yield. It was also demonstrated that 3 could be reacted by Click Chemistry, on the solid phase, to an alkyne

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7

Novakova, Veronika, Kamil Kopecky, Miroslav Miletin, Jana Ivincova, and Petr Zimcik. "Photodynamically active phthalocyanine building blocks for click chemistry." Journal of Porphyrins and Phthalocyanines 15, no. 09n10 (2011): 1062–69. http://dx.doi.org/10.1142/s1088424611003987.

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Synthesis of symmetrical and unsymmetrical zinc phthalocyanines from two different precursors 4,5-bis(tert-butylsulfanyl)phthalonitrile (A) and N-(3-azidopropyl)-2,3-dicyanoquinoxaline-6-carboxamide (B) is described. Congeners of AAAA, AAAB, ABAB and AABB type were isolated by a chromatographic technique, however, the congener of BBBB type had to be prepared in a separate reaction. The adjacent and opposite isomers were also separated and fully characterized. Isolated phthalocyanines contained different number of azide groups, a substrate for highly efficient Cu(I) -catalyzed azide-alkyne 1,3-

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8

Bahsis, Lahoucine, Meryem Hrimla, Hicham Ben El Ayouchia, Hafid Anane, Miguel Julve, and Salah-Eddine Stiriba. "2-Aminobenzothiazole-Containing Copper(II) Complex as Catalyst in Click Chemistry: An Experimental and Theoretical Study." Catalysts 10, no. 7 (2020): 776. http://dx.doi.org/10.3390/catal10070776.

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The reaction of copper(II) acetate with the 2-aminobenzothiazole (abt) heterocycle affords the new copper(II) complex of formula [Cu(abt)2(OOCCH3)2] (1) in a straightforward manner. Compound 1 served as a precatalyst for azide/alkyne cycloaddition reactions (CuAAC) in water, leading to 1,4-disubstituted-1,2,3-triazole derivatives in a regioselective manner and with excellent yields at room temperature. The main advantages of the coordination of such a heterocyclic ligand in 1 are its strong σ-donating ability (N-Cu), nontoxicity and biological properties. In addition, the click chemistry react

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9

Dolan, Ciarán, Briar Naysmith, Simon F. R. Hinkley, et al. "Synthesis of Novel Triazole-Containing Phosphonate Polymers." Australian Journal of Chemistry 68, no. 4 (2015): 680. http://dx.doi.org/10.1071/ch14513.

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The objective of this research was to develop novel phosphonate-containing polymers as they remain a relatively under researched area of polymer chemistry. Herein, we report the synthesis and characterization of 2-(1-(2-(diethoxyphosphoryl)ethyl)-1H-1,2,3-triazol-4-yl)ethyl acrylate (M1) and diethyl (2-(4-(2-acrylamidoethyl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate (M2) monomers using the copper-catalyzed azide–alkyne cycloaddition (CuAAC) ‘click’ reaction, and their subsequent polymerization via both uncontrolled and reversible addition–fragmentation chain transfer (RAFT) polymerization techni

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10

Saraiva, Nuno M., Ana Alves, Ana Isabel Barbosa, et al. "Click on Click: Click-Flavone Glycosides Encapsulated in Click-Functionalised Polymersomes for Glioblastoma Therapy." Pharmaceutics 17, no. 6 (2025): 771. https://doi.org/10.3390/pharmaceutics17060771.

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In this study, three new 3,7-dihydroxyflavone (1) derivatives with different sugars were designed and synthesised by click chemistry. Click chemistry requires the previously modification of building blocks with azide and alkyne groups and therefore, the 3,7-dihydroxyflavone (1) was first converted in 3,7-(prop-2-yn-yloxy)flavone (2) and acetobromo-α-D-glucose (3) was converted into 2,3,4,6-tetra-O-acetyl-β-glucopyranosyl azide (4). Subsequently, a click reaction was performed via copper-catalysed cycloaddition (CuAAC) between 2 and 4, as well as between 2 and 2-acetamido-3,4,6-tetra-O-acetyl-2

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11

Bahsis, Lahoucine, Hicham Ben El Ayouchia, Hafid Anane, et al. "Clicking Azides and Alkynes with Poly(pyrazolyl)borate-Copper(I) Catalysts: An Experimental and Computational Study." Catalysts 9, no. 8 (2019): 687. http://dx.doi.org/10.3390/catal9080687.

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The synthesis of 1,4-disubstituted-1,2,3-triazoles under a copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) regime was accomplished in high yields and a regioselective manner by using two homoscorpionate poly(pyrazolyl)borate anions: tris(pyrazolyl)hydroborate (HB(pz)3−) and bis(pyrazolyl)hydroborate (H2B(pz)2−), which stabilized in situ the catalytically active copper (I) center. The [3+2] cycloaddition (32CA) reactions took place under strict click conditions, including room temperature and a mixture of environmentally benign solvents such as water/ethanol in a 1:1 (v/v) ratio. These c

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12

Ferreira, Marcos V., Poliana Ricci, Henrique A. Sobreira, et al. "Optimization of the Heterogeneous Synthesis Conditions for Cellulose Tosylation and Synthesis of a Propargylamine Cellulosic Derivative." Polymers 17, no. 1 (2024): 58. https://doi.org/10.3390/polym17010058.

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Cellulose tosylate (MCC-Tos) is a key derivative for surface modification and a crucial precursor for cellulose compatibilization in click reactions, enabling its functionalization for advanced applications. Replacing tosyl groups with alkyne groups broadens cellulose’s potential in biocompatible reactions, such as thiol-yne click chemistry and protein/enzyme immobilization. To achieve this, we optimized the heterogeneous synthesis of MCC-Tos using a Doehlert matrix statistical design, evaluating the influence and interaction of the reaction conditions. The optimized conditions—144 h reaction

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13

Díaz, David D., Sreenivas Punna, Philipp Holzer, et al. "Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition." Journal of Polymer Science Part A: Polymer Chemistry 42, no. 17 (2004): 4392–403. http://dx.doi.org/10.1002/pola.20330.

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14

Arumugam, Selvanathan, Sara V. Orski, Ngalle Eric Mbua, et al. "Photo-click chemistry strategies for spatiotemporal control of metal-free ligation, labeling, and surface derivatization." Pure and Applied Chemistry 85, no. 7 (2013): 1499–513. http://dx.doi.org/10.1351/pac-con-13-01-08.

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Three photo-click ligation strategies described in this account provide scientists with efficient and selective tools for derivatization of various molecules, polymers, and surfaces. Fast photochemical reactions that are utilized in these techniques permit spatiotemporal control of the process. The absence of activating reagents and catalysts, as well as compatibility with aqueous media, makes photo-click ligations suitable for biomedical applications. The first of these approaches relies on the photochemical decarbonylation of cyclopropenones to produce cyclooctynes. The latter undergo rapid

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15

Timmers, Matt, Andi Kipper, Raphael Frey, et al. "Exploring the Chemical Properties and Medicinal Applications of Tetramethylthiocycloheptyne Sulfoximine Used in Strain-Promoted Azide–Alkyne Cycloaddition Reactions." Pharmaceuticals 16, no. 8 (2023): 1155. http://dx.doi.org/10.3390/ph16081155.

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The recently developed compound, tetramethylthiocycloheptyne sulfoximine (TMTHSI), has shown to be a promising strained alkyne for strain-promoted azide–alkyne cycloaddition (SPAAC), metal-free click chemistry. This research explores the properties of TMTHSI-based compounds via three aspects: (1) large-scale production, (2) unique stability in acidic conditions and its subsequent use in peptide synthesis, and (3) the functionalization of antibodies. Here, it is shown that (1) scale-up is achieved on a scale of up to 100 g. (2) TMTHSI is remarkably stable against TFA allowing for the site-speci

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16

Wang, Yu, Yudong Wang, Sushant Sahu, August A. Gallo, and Xiao-Dong Zhou. "Efficient Synthesis of High-Performance Anion Exchange Membranes by Applying Clickable Tetrakis(dialkylamino)phosphonium Cations." Polymers 15, no. 2 (2023): 352. http://dx.doi.org/10.3390/polym15020352.

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Tetrakis(dialkylamino)phosphonium (TKDAAP) compounds exhibit extraordinary base resistance, a prerequisite feature for high-performance anion exchange membranes (AEMs). It is, however, challenging to synthesize a TKDAAP compound with reactive functionality that can be used to link the cation to a polymer backbone. In this study, two TKDAAP compounds with alkyne functionality were synthesized and incorporated into an azide-modified SBS triblock copolymer backbone via Cu(I)-catalyzed alkyne–azide cycloaddition (CuAAC) “click” chemistry. The properties of the resulting AEMs were characterized. It

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17

Marchenko, Roman D., and Andrei S. Potapov. "Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions." Molbank 2023, no. 1 (2023): M1551. http://dx.doi.org/10.3390/m1551.

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Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or cata

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18

Jin, Yijie, Manjusha Joshi, Takuma Araki, et al. "Click Synthesis of Triazole Polymers Based on Lignin-Derived Metabolic Intermediate and Their Strong Adhesive Properties to Cu Plate." Polymers 15, no. 6 (2023): 1349. http://dx.doi.org/10.3390/polym15061349.

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2-Pyrone-4,6-dicarboxylic acid (PDC) is a chemically stable metabolic intermediate of lignin that can be produced on a large scale by transforming bacteria. Novel biomass-based polymers based on PDC were synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and fully characterized by nuclear magnetic resonance, infrared spectroscopies, thermal analysis, and tensile lap shear strength measurements. The onset decomposition temperatures of these PDC-based polymers were all above 200 °C. In addition, the PDC-based polymers exhibited strong adhesive properties to various metal plates, w

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19

Reissig, Hans-Ulrich, and Fei Yu. "One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives." Beilstein Journal of Organic Chemistry 19 (September 18, 2023): 1399–407. http://dx.doi.org/10.3762/bjoc.19.101.

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The nucleophilic substitution of benzylic bromides with sodium azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis(bromomethyl)benzene furnished geometrically differing bis(1,2,3-triazole) derivatives. The use of tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) as ligand for the click step turned out to be very advantageous. The compounds

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Dondoni, Alessandro. "Selected Research Topics of the Dondoni Group over the Last Two Decades (2000–2020)." Synlett 31, no. 14 (2020): 1361–71. http://dx.doi.org/10.1055/s-0040-1707107.

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From a selection of research topics carried out in our laboratory during the last twenty years it becomes apparent that our main target was the discovery of new or improved synthetic methods together with new properties. Our efforts were made with the aim of being of some utility to other fields of research, with particular emphasis to glycobiology and heterocyle-based bioorganic chemistry. We performed new chemistry mainly in the field of carbohydrate manipulations taking as a primary rule the simplicity and efficiency manners. Toward this end, modern synthetic tools and approaches were emplo

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Shehzadi, Syeda Aaliya. "Synthesis and Biological Evaluation of Novel 1,4-Disubstituted 1,2,3-Triazoles and Bis 1,2,3-Triazoles as Anti-Bacterial Agents." Medicinal Chemistry 9, no. 1 (2019): 6. https://doi.org/10.4172/2161-0444.1000527.

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A library of novel 1,4-disbustituted 1,2,3-triazoles 3a-3k was prepared by using Click-chemistry concept. In this 1,3-dipolar cycloaddition, the 3-methoxy-4-(prop-2-yn-1-yloxy)benzaldehyde (1) was used as alkyne partner which was synthesized from vanillin and propargyl bromide and was reacted with differently substituted arylpropoxy azides to furnish series of mono and bis 1,4-disubstituted-1,2,3-triazoles. All the synthesized compounds were characterized spectroscopically and were evaluated for their antimicrobial activity. Preliminary results of antibacterial screening revealed that various

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22

Neumajer, Gábor, Gergő Tóth, Szabolcs Béni, and Béla Noszál. "Novel ion-binding C3 symmetric tripodal triazoles: synthesis and characterization." Open Chemistry 12, no. 1 (2014): 115–25. http://dx.doi.org/10.2478/s11532-013-0351-z.

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AbstractNovel C3 symmetric tripodal molecules were synthesized from cyclohexane 1,3,5-tricarboxylic acid. Utilizing click and Sonogashira reactions, ion-binding triazole and pyridazin-3(2H)-one units were incorporated to form polydentate ligands for ion complexation. The structures of the novel C3 symmetric derivatives were extensively characterized by 1H, 13C and 2D NMR techniques along with HRMS and IR. The copper(I)-binding potentials of these ligands were investigated by using them as additives in model copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The copper(I) complex

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23

Ahmed, Essam Kh, and Mohamed A. Ameen. "A Straightforward and Mild Method of Tethering Monosaccharides to Thieno[2,3-d]pyrimidinones via the Copper(I)-catalyzed Azide-Alkyne ‘Click Chemistry’." Zeitschrift für Naturforschung B 67, no. 12 (2012): 1282–88. http://dx.doi.org/10.5560/znb.2012-0193.

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A mild and versatile method based on Cu(I)-catalyzed [3+2] cycloaddition (Meldal-Sharpless reaction) was developed to tether biomolecules, such as monosacharides or lipophylic azides, to alkyne functions of spirobenzo[b]thieno[2,3-d]pyrimidine-1´-cyclohexane. The reactions are highlighted by their modularity and high efficiency with excellent yields in most cases. The products are interesting precursors for a variety of applications.

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Odrobińska, Justyna, Magdalena Skonieczna, and Dorota Neugebauer. "Micellar Carriers of Active Substances Based on Amphiphilic PEG/PDMS Heterograft Copolymers: Synthesis and Biological Evaluation of Safe Use on Skin." International Journal of Molecular Sciences 22, no. 3 (2021): 1202. http://dx.doi.org/10.3390/ijms22031202.

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Amphiphilic copolymers containing polydimethylsiloxane (PDMS) and polyethylene glycol methyl ether (MPEG) were obtained via an azide-alkyne cycloaddition reaction between alkyne-functionalized copolymer of MPEG methacrylate and azide-functionalized PDMS. “Click” reactions were carried out with an efficiency of 33–47% increasing grafting degrees. The grafted copolymers were able to carry out the micellization and encapsulation of active substances, such as vitamin C (VitC), ferulic acid (FA) and arginine (ARG) with drug loading content (DLC) in the range of 2–68% (VitC), and 51–89% (FA or ARG).

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Gbadegesin, Omotola D., and Simeon K. Adesina. "Gemcitabine–Doxorubicin Combination Polymer-Drug Conjugate Prepared by SPAAC Click Chemistry: In Vitro Characterization." International Journal of Molecular Sciences 26, no. 6 (2025): 2798. https://doi.org/10.3390/ijms26062798.

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Combination chemotherapy is preferred for the treatment of ovarian cancer (OC). Systemic toxicity, however, frequently limits the effectiveness of treatment. Polymer–drug conjugates (PDCs) containing synergistic combinations of chemotherapeutic drugs can be used to enhance therapeutic efficacy. We earlier reported the use of a strain-promoted [3 + 2] azide–alkyne cycloaddition (SPAAC)-mediated polymerization method for the preparation of single-drug PDCs. In this report, the polymerization method was used to prepare gemcitabine–doxorubicin combination PDC. The PDC had a high molecular weight (

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Mahmoud, Abdallah, Piotr Smoleński, M. Guedes da Silva, and Armando Pombeiro. "Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition." Molecules 25, no. 22 (2020): 5479. http://dx.doi.org/10.3390/molecules25225479.

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The 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) derivatives, viz. the already reported 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane 5-oxide (DAPTA=O, 1), the novel 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-sulfide (DAPTA=S, 2), and 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-selenide (DAPTA=Se, 3), have been synthesized under mild conditions. They are soluble in water and most common organic solvents and have been characterized using 1H and 31P NMR spectroscopy and, for 2 and 3, also by single crystal X-ray diffraction. The effect of

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Sultana, Jasmin, and Diganta Sarma. "Tetraamminecopper(II) Sulfate Monohydrate in Oxidative Azide-olefin Cyclo-addition and Three-component Click Reaction." Current Organic Synthesis 17, no. 1 (2020): 65–72. http://dx.doi.org/10.2174/1570179417666191223152643.

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Introduction: An effective Cu-complex, [Cu(NH3)4SO4 • H2O] was prepared conveniently from the inexpensive and easily available starting reagents in a simple route. Materials and Methods: Excellent reactivity of the catalyst was observed towards two competent clickcycloadditions: (a) oxidative cycloaddition of azides with electron-poor olefins and (b) one-pot cycloaddition of alkynes with boronic acid and sodium azide under “click-appropriate” conditions. Results: No external oxidant, short reaction time, high product yield, wide substrate scope, and aqueous solvent media make the azide-olefin

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Canseco-González, Daniel, José Luis Rodríguez de la O, and José Enrique Herbert-Pucheta. "Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case." Heterocyclic Communications 25, no. 1 (2019): 98–106. http://dx.doi.org/10.1515/hc-2019-0018.

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AbstractCopper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been scarcely discussed. Herein we present a strategy that combines X-Ray Diffraction (XRD) with 13C- paramagnetic Nuclear Magnetic Resonance spectroscopy, in order to demonstrate the presence of parama

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Kashina, Anna V., Tamara K. Meleshko, Natalia N. Bogorad, Viktor K. Lavrentyev та Alexander V. Yakimansky. "Molecular Brushes with a Polyimide Backbone and Poly(ε-Caprolactone) Side Chains by the Combination of ATRP, ROP, and CuAAC". Polymers 13, № 19 (2021): 3312. http://dx.doi.org/10.3390/polym13193312.

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An approach to the synthesis of the novel molecular brushes with a polyimide (PI) backbone and poly(ε-caprolactone) (PCL) side chains was developed. To obtain such copolymers, a combination of various synthesis methods was used, including polycondensation, atom transfer radical polymerization (ATRP), ring opening polymerization (ROP), and Cu (I)-catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). ATRP of 2-hydroxyethyl methacrylate (HEMA) on PI macroinitiator followed by ROP of ε-caprolactone (CL) provided a “brush on brush” structure PI-g-(PHEMA-g-PCL). For the synthesis of PI-g-PCL two syn

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Khadir Fall, Serigne Abdou, Saïd Achamlale, Younas Aouine, Asmae Nakkabi, Hassane Faraj, and Anouar Alami. "Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate." Molbank 2020, no. 4 (2020): M1167. http://dx.doi.org/10.3390/m1167.

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The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performe

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Shen, Yechen, and Younghwan Kwon. "Synthesis and Characterization of Reactive Energetic Plasticizers for Poly(glycidyl azide-co-tetramethylene glycol)-Based Polyurethane Binders." Journal of Nanoscience and Nanotechnology 21, no. 7 (2021): 4110–15. http://dx.doi.org/10.1166/jnn.2021.19184.

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Two reactive energetic plasticizers, 3-((2,2-dinitropropoxy)methoxy)prop-1-yne and 4-((2,2-dinitropropoxy)methoxy)but-1-yne which can react with an azido-containing poly(glycidyl azide-co-tetramethylene glycol) prepolymer by cupper-free 1,3-dipolor cycloaddition (“Click”) reaction, were synthesized and characterized, in order to investigate their plasticizing performance and catalyst-free 1,3-dipolar cycloaddition reactivity on energetic polyurethane binders. Two reactive energetic plasticizers showed better plasticizing performance than commercial energetic plasticizers. In the reactivity poi

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Wu, Jiayi, Ming Wang, Huanhuan Hong, Jianyuan Lin, Ning Gan, and Wenchao Bi. "A Novel Truncated DNAzyme Modified Paper Analytical Device for Point-of-Care Test of Copper Ions in Natural Waters." Chemosensors 10, no. 2 (2022): 72. http://dx.doi.org/10.3390/chemosensors10020072.

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On-site determination of trace copper ions in natural waters is of great significance to environmental monitoring, and how to develop accurate and specific point-of-care test methods is one critical issue. In the study, a paper-based analytical device (PAD) being modified with a new truncated DNAzyme (CLICK-T, which was derived from a reported DNAzyme-CLICK-17) was developed for Cu ions detection. The detection mechanism was based on Cu(II)-catalyzed azide-alkyne cycloaddition (Cu(II)AAC) reaction. It can directly conduct on-site analysis of Cu(II) ions based on fluorescent signals detected us

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Jiaranaikulwanitch, Jutamas, Hataichanok Pandith, Sarin Tadtong, et al. "Novel Multifunctional Ascorbic Triazole Derivatives for Amyloidogenic Pathway Inhibition, Anti-Inflammation, and Neuroprotection." Molecules 26, no. 6 (2021): 1562. http://dx.doi.org/10.3390/molecules26061562.

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Alzheimer’s disease (AD) is a common neurodegenerative disorder. The number of patients with AD is projected to reach 152 million by 2050. Donepezil, rivastigmine, galantamine, and memantine are the only four drugs currently approved by the United States Food and Drug Administration for AD treatment. However, these drugs can only alleviate AD symptoms. Thus, this research focuses on the discovery of novel lead compounds that possess multitarget regulation of AD etiopathology relating to amyloid cascade. The ascorbic acid structure has been designated as a core functional domain due to several

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Tale, Rajesh H., Venkatesh B. Gopula, and Gopal K. Toradmal. "‘Click’ ligand for ‘click’ chemistry: (1-(4-methoxybenzyl)-1-H-1,2,3-triazol-4-yl)methanol (MBHTM) accelerated copper-catalyzed [3+2] azide–alkyne cycloaddition (CuAAC) at low catalyst loading." Tetrahedron Letters 56, no. 43 (2015): 5864–69. http://dx.doi.org/10.1016/j.tetlet.2015.09.010.

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Holzer, Isabelle, Oksana Desiatkina, Nicoleta Anghel, et al. "Synthesis and Antiparasitic Activity of New Trithiolato-Bridged Dinuclear Ruthenium(II)-arene-carbohydrate Conjugates." Molecules 28, no. 2 (2023): 902. http://dx.doi.org/10.3390/molecules28020902.

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Eight novel carbohydrate-tethered trithiolato dinuclear ruthenium(II)-arene complexes were synthesized using CuAAC ‘click’ (Cu(I)-catalyzed azide-alkyne cycloaddition) reactions, and there in vitro activity against transgenic T. gondii tachyzoites constitutively expressing β-galactosidase (T. gondii β-gal) and in non-infected human foreskin fibroblasts, HFF, was determined at 0.1 and 1 µM. When evaluated at 1 µM, seven diruthenium-carbohydrate conjugates strongly impaired parasite proliferation by >90%, while HFF viability was retained at 50% or more, and they were further subjected to the

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Amarasiri, Madushani, Yen Vo, Michael G. Gardiner, et al. "The Synthesis and Biological Evaluation of Some C-9 and C-10 Substituted Derivatives of the RNA Polymerase I Transcription Inhibitor CX-5461." Australian Journal of Chemistry 74, no. 7 (2021): 540. http://dx.doi.org/10.1071/ch21049.

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The regio-isomeric alkynyl-substituted derivatives, 2 and 3, of the RNA Polymerase I (Pol I) transcription inhibitor CX-5461 (1) were prepared and the active one (compound 3) subjected to click reactions ([3+2]-cycloaddition reactions) with certain alkyl azides bearing biotin or fluorescent tags. Compounds 2 and 3, as well as four [3+2]-cycloadducts of the latter, were subjected to biological evaluation in a human acute myeloid leukemia cell line model. Among the six compounds tested only alkyne 3 remained active but this was less potent than parent 1.

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Tang, Tinghong, Cuiting Chen, Xin Fu, Huilan Xu, Luyong Wu, and Wenhao Chen. "Copper-Catalyzed Synthesis of 4-CF3-1,2,3-Triazoles: An Efficient and Facile Approach via Click Reaction." Molecules 29, no. 6 (2024): 1191. http://dx.doi.org/10.3390/molecules29061191.

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Incorporation of a trifluoromethyl group with 1,2,3-triazoles motifs was described. We explored a click reaction approach for regioselective synthesis of 1-susbstituted-4-trifluoromethyl-1,2,3-triazoles in which 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) reacts with commercial 2-bromo-3,3,3-trifluoropropene (BTP) to form 3,3,3-trifloropropyne (TFP) in situ. Arising from merits associated with the availability and stability of BTP, and the high efficiencies of CuI/1,10-Phenanthroline (Phen)-catalyzed cycloaddition reactions of azides with alkynes, this readily performed click process takes place

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Tale, Rajesh H., Venkatesh B. Gopula, and Gopal K. Toradmal. "ChemInform Abstract: ′Click′ Ligand for ′Click′ Chemistry: (1-(4-Methoxybenzyl)-1-H-1,2,3-triazol-4-yl)methanol (MBHTM) Accelerated Copper-Catalyzed [3 + 2] Azide-Alkyne Cycloaddition (CuAAC) at Low Catalyst Loading." ChemInform 47, no. 15 (2016): no. http://dx.doi.org/10.1002/chin.201615136.

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Ivanskaya, E. V., M. I. Meschaninova, M. A. Vorobyeva, D. O. Zharkov, and D. S. Novopashina. "The approach to the preparation of cyclic photocleavable RNA for photoactivatable CRISPR/Cas9 System." Биоорганическая химия 50, no. 5 (2024): 622–35. https://doi.org/10.31857/s0132342324050051.

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The development of controllable gene editing systems on the base of CRISPR/Cas is an actually problem of modern molecular biology and genetic enginery. Interesting variant of solution of this problem is modification of guide RNA by introduction of photocleavable linkers. We developed the approach to the synthesis of cyclic photocleavable guide crRNA for the CRISPR/Cas9 system with photolinker on the base of 1-(2-nitrophenyl)-1,2-ethanediol (PL). Upon irradiation by UV-light these guide RNA are linearized and CRISPR/Cas9 system is activated. Two chemical methods to the cyclization of RNA were t

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Ismaili, Hossein, Abdolhamid Alizadeh, Kristen E. Snell, and Mark S. Workentin. "Remarkable high-yielding chemical modification of gold nanoparticles using uncatalyzed click-type 1,3-dipolar cycloaddition chemistry and hyperbaric conditions." Canadian Journal of Chemistry 87, no. 12 (2009): 1708–15. http://dx.doi.org/10.1139/v09-138.

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Azide-terminated alkyl thiolate monolayer-protected gold nanoparticles (1-C12MPN) with a core size of 1.8 ± 0.2 nm were prepared. 1-C12MPN was modified in high yields via an uncatalyzed 1,3-dipolar cycloaddition (click-type reaction) with a variety of terminal acyl–alkynes under hyperbaric conditions at 11 000 atm. The resulting 1,2,3-triazole modified MPNs (2-C12MPN) were characterized using 1H NMR spectroscopy and were verified by comparison of the spectra to those obtained for the products of the model reactions of 1-azidododecane with the same alkynes. TEM analysis showed that the high-pre

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Mushtaq, Yun, and Jeon. "Recent Advances in Bioorthogonal Click Chemistry for Efficient Synthesis of Radiotracers and Radiopharmaceuticals." Molecules 24, no. 19 (2019): 3567. http://dx.doi.org/10.3390/molecules24193567.

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In recent years, several catalyst-free site-specific reactions have been investigated for the efficient conjugation of biomolecules, nanomaterials, and living cells. Representative functional group pairs for these reactions include the following: (1) azide and cyclooctyne for strain-promoted cycloaddition reaction, (2) tetrazine and trans-alkene for inverse-electron-demand-Diels–Alder reaction, and (3) electrophilic heterocycles and cysteine for rapid condensation/addition reaction. Due to their excellent specificities and high reaction rates, these conjugation methods have been utilized for t

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Vereecke, Guy, Haroen Debruyn, Quinten de Keyser, Rita Vos, Abhishek Dutta, and Frank Holsteyns. "Effect of 1-D Nano-Confinement on the Kinetics of a Click-Chemistry Surface Reaction Used in Biosensors." Solid State Phenomena 282 (August 2018): 182–89. http://dx.doi.org/10.4028/www.scientific.net/ssp.282.182.

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In semiconductor manufacturing of 3-D nano-structures, modified kinetics have been encountered for the aqueous chemical etching of thin films in nano-confined spaces. A popular explanation relies on changes in reactant concentration from the overlap of electrostatic double layers (EDL) on opposite walls of the nano-structures. In this study, the cycloaddition of dibenzylcyclooctyne-PEG3-alcohol (DBCO) to a linear azide-terminated SAM was performed in nanochannels of width varying from 62 to 32 nm. ATR-FTIR was used to monitor the reaction kinetics, characterize water structuring and determine

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Rono, Charles K., James Darkwa, Debra Meyer, and Banothile C. E. Makhubela. "A Novel Series of N-aryltriazole and N-acridinyltriazole Hybrids as Potential Anticancer Agents." Current Organic Synthesis 16, no. 6 (2019): 900–912. http://dx.doi.org/10.2174/1570179416666190704112904.

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Background: Triazoles are a class of aza-heterocycles with broad spectrum of biological importance. The synthetic tunability of the triazole moiety allows for the development of new pharmacophores with applications as drugs to contend with the burden of cancer. Objective: In this study, we aimed to develop a series of N-aryltriazole and N-acridinyltriazole molecular hybrids and evaluate their potential as anticancer agents. Methods: The triazole derivatives (1-10) were synthesized via a tandem nucleophilic substitution of aryl chlorides with sodium azide followed by 1,3-dipolar cycloaddition o

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Ting, S. R. Simon, Anthony M. Granville, Damien Quémener, Thomas P. Davis, Martina H. Stenzel, and Christopher Barner-Kowollik. "RAFT Chemistry and Huisgen 1,3-Dipolar Cycloaddition: A Route to Block Copolymers of Vinyl Acetate and 6-O-Methacryloyl Mannose?" Australian Journal of Chemistry 60, no. 6 (2007): 405. http://dx.doi.org/10.1071/ch07089.

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The present communication explores a novel avenue to glycopolymer-block-poly(vinyl acetate) polymers by a combination of reversible addition fragmentation chain transfer (RAFT) chemistry and Huisgen 1,3-dipolar cycloaddition (i.e., so-called ‘click’ chemistry) under mild reaction conditions. Such block copolymers are—because of the strongly disparate reactivity of the two monomers—otherwise not obtainable. Poly(vinyl acetate) that has an azide end group (Mn 6800 g mol–1, PDI 1.15) was treated with poly(6-O-methacryloyl mannose) (Mn 7600 g mol–1, PDI 1.11) in the presence of 1,8-diaza[5,4,0]bic

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Terracina, Francesca, Mario Saletti, Marco Paolino, et al. "Cross-Linked Hyaluronan Derivatives in the Delivery of Phycocyanin." Gels 10, no. 2 (2024): 91. http://dx.doi.org/10.3390/gels10020091.

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An easy and viable crosslinking technology, based on the “click-chemistry” reaction copper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click-crosslinking), was applied to graft copolymers of medium molecular weight (i.e., 270 kDa) hyaluronic acid (HA) grafted with ferulic acid (FA) residues bearing clickable propargyl groups, as well as caffeic acid derivatives bearing azido-terminated oligo(ethylene glycol) side chains. The obtained crosslinked materials were characterized from the point of view of their structure and aggregation liability to form hydrogels in a water environment. Th

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Posa, Francesca, Anna Luise Grab, Volker Martin, et al. "Copresentation of BMP-6 and RGD Ligands Enhances Cell Adhesion and BMP-Mediated Signaling." Cells 8, no. 12 (2019): 1646. http://dx.doi.org/10.3390/cells8121646.

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We report on the covalent immobilization of bone morphogenetic protein 6 (BMP-6) and its co-presentation with integrin ligands on a nanopatterned platform to study cell adhesion and signaling responses which regulate the transdifferentiation of myoblasts into osteogenic cells. To immobilize BMP-6, the heterobifunctional linker MU-NHS is coupled to amine residues of the growth factor; this prevents its internalization while ensuring that its biological activity is maintained. Additionally, to allow cells to adhere to such platform and study signaling events arising from the contact to the surfa

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Leier, Samantha, and Frank Wuest. "Innovative Peptide Bioconjugation Chemistry with Radionuclides: Beyond Classical Click Chemistry." Pharmaceuticals 17, no. 10 (2024): 1270. http://dx.doi.org/10.3390/ph17101270.

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Background: The incorporation of radionuclides into peptides and larger biomolecules requires efficient and sometimes biorthogonal reaction conditions, to which click chemistry provides a convenient approach. Methods: Traditionally, click-based radiolabeling techniques have focused on classical click chemistry, such as copper(I)-catalyzed alkyne-azide [3+2] cycloaddition (CuAAC), strain-promoted azide-alkyne [3+2] cycloaddition (SPAAC), traceless Staudinger ligation, and inverse electron demand Diels–Alder (IEDDA). Results: However, newly emerging click-based radiolabeling techniques, includin

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Hou, Zhanfeng, Yuena Wang, Chuan Wan, et al. "Sulfonium Triggered Alkyne–Azide Click Cycloaddition." Organic Letters 24, no. 7 (2022): 1448–53. http://dx.doi.org/10.1021/acs.orglett.2c00021.

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Zhang, Zhongkui, and Chunxiang Kuang. "Easy One-Pot Synthesis of 1-Monosubstituted Aliphatic 1,2,3-Triazoles from Aliphatic Halides, Sodium Azide and Propiolic Acid by a Click Cycloaddition/Decarboxylation Process." Chinese Journal of Chemistry 31, no. 8 (2013): 1011–14. http://dx.doi.org/10.1002/cjoc.201300155.

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Liu, Xifeng, Ping Gong, Pengfei Song, et al. "Fast functionalization of ultrasound microbubbles using strain promoted click chemistry." Biomaterials Science 6, no. 3 (2018): 623–32. http://dx.doi.org/10.1039/c8bm00004b.

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