Themed collection A Decade of Progress in Click Reactions Based on CuAAC

53 items
Communication

1,2,3-Triazoles derived from olanzapine: their synthesis via an ultrasound assisted CuAAC method and evaluation as inhibitors of PDE4B

An ultrasound assisted CuAAC method afforded novel 1,2,3-triazoles derived from olanzapine as inhibitors of PDE4B.

Graphical abstract: 1,2,3-Triazoles derived from olanzapine: their synthesis via an ultrasound assisted CuAAC method and evaluation as inhibitors of PDE4B
Communication

Zebrafish based strategy for the identification of a potential pharmacophore for apoptosis: a greener CuAAC approach for novel 1,2,3-triazoles derived from mefenamic acid

A novel pharmacophore for apoptosis has been identified via a screening strategy in zebrafish.

Graphical abstract: Zebrafish based strategy for the identification of a potential pharmacophore for apoptosis: a greener CuAAC approach for novel 1,2,3-triazoles derived from mefenamic acid
Open Access Paper

[3+2] click chemistry approach to tetrazine containing polymers

We report a [3+2] cycloaddition using 3,6-bis-propargyloxy-1,2,4,5-tetrazine and azides to synthesize energetic polymers containing 1,2,4,5-tetrazine within the scaffold.

Graphical abstract: [3+2] click chemistry approach to tetrazine containing polymers
Open Access Paper

Structure-based design of 5′-substituted 1,2,3-triazolylated oseltamivir derivatives as potent influenza neuraminidase inhibitors

Exploring influenza neuraminidase inhibitors by targeting the charged residues near the entrance of the 150-cavity.

Graphical abstract: Structure-based design of 5′-substituted 1,2,3-triazolylated oseltamivir derivatives as potent influenza neuraminidase inhibitors
Open Access Paper

A click-based modular approach to introduction of peroxides onto molecules and nanostructures

Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials.

Graphical abstract: A click-based modular approach to introduction of peroxides onto molecules and nanostructures
Open Access Paper

Cu(II)-alginate-based superporous hydrogel catalyst for click chemistry azide–alkyne cycloaddition type reactions in water

The Cu(II)-alginate-based superporous hydrogel was prepared and used as a heterogenous catalyst in the regioselective click of 1,4-disubstituted-1,2,3-triazoles by CuAAC reactions.

Graphical abstract: Cu(ii)-alginate-based superporous hydrogel catalyst for click chemistry azide–alkyne cycloaddition type reactions in water
Open Access Paper

Design, synthesis, biological evaluation and molecular docking study of novel pyridoxine–triazoles as anti-Alzheimer's agents

A series of multi-target natural product-pyridoxine based derivatives were designed, synthesized, characterized and evaluated as anti-Alzheimer agents. Out of all the molecules of the series, 5i was found to be best.

Graphical abstract: Design, synthesis, biological evaluation and molecular docking study of novel pyridoxine–triazoles as anti-Alzheimer's agents
Open Access Paper

Microwave-assisted synthesis, biological evaluation and molecular docking studies of new coumarin-based 1,2,3-triazoles

Coumarin-based 1,4-disubstituted 1,2,3-triazole derivatives were synthesized using a highly efficient, eco-friendly protocol via a copper(I)-catalyzed click reaction between various substituted arylazides and terminal alkynes.

Graphical abstract: Microwave-assisted synthesis, biological evaluation and molecular docking studies of new coumarin-based 1,2,3-triazoles
Open Access Paper

Quinoline-triazole hybrids inhibit falcipain-2 and arrest the development of Plasmodium falciparum at the trophozoite stage

The present study involves development of novel quinoline triazole-containing cysteine protease inhibitors which arrest the development of P. falciparum at the trophozoite stage.

Graphical abstract: Quinoline-triazole hybrids inhibit falcipain-2 and arrest the development of Plasmodium falciparum at the trophozoite stage
Open Access Paper

Clickable poly-L-lysine for the formation of biorecognition surfaces

The fast and stable adsorption of modified PLL on activated surfaces was combined with the versatile catalyst-free click chemistry for the fast and selective functionalization of substrates with DNA.

Graphical abstract: Clickable poly-l-lysine for the formation of biorecognition surfaces
Open Access Paper

Discovery of novel 1,4-disubstituted 1,2,3-triazole phenylalanine derivatives as HIV-1 capsid inhibitors

Novel phenylalanine derivatives were discovered as HIV-1 capsid protein inhibitors via “click reaction”. Most of them exhibited remarkable anti-HIV-1 activity.

Graphical abstract: Discovery of novel 1,4-disubstituted 1,2,3-triazole phenylalanine derivatives as HIV-1 capsid inhibitors
Open Access Paper

New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation

A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et3NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields.

Graphical abstract: New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation
Open Access Paper

Development of self-stratified antibacterial polymers via click chemistry

A new self-stratified contact-killing antimicrobial polyurethane was synthesized via efficient and orthogonal click-chemistry.

Graphical abstract: Development of self-stratified antibacterial polymers via click chemistry
Open Access Paper

Synthesis of D-glyco-alkynone derivatives via carbonylative Sonogashira reaction

A carbonylative Sonogashira coupling approach to the synthesis of glyco-alkynones is described.

Graphical abstract: Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction
Open Access Paper

Gram scale production of 1-azido-β-D-glucose via enzyme catalysis for the synthesis of 1,2,3-triazole-glucosides

The retaining β-glucosidase acid/base mutant TxGH116D593A catalyzed the production of 1-azido-β-D-glucose for synthesis of 15 1,2,3-triazole β-glucosyl derivatives.

Graphical abstract: Gram scale production of 1-azido-β-d-glucose via enzyme catalysis for the synthesis of 1,2,3-triazole-glucosides
Open Access Paper

A new synthetic pathway based on one-pot sequential aza-Michael addition and photoCuAAC click reactions

A solvent-free process is described for the synthesis of tailor-made molecules from a one-pot, two-step approach combining aza-Michael addition and photoinduced copper(I) catalysed azide–alkyne (photo-CuAAC) reactions.

Graphical abstract: A new synthetic pathway based on one-pot sequential aza-Michael addition and photoCuAAC click reactions
Open Access Paper

Preparation of novel 1,2,3-triazole furocoumarin derivatives via click chemistry and their anti-vitiligo activity

A novel 1,2,3-triazole furocoumarin derivatives with anti-vitiligo activity were synthesized via click chemistry.

Graphical abstract: Preparation of novel 1,2,3-triazole furocoumarin derivatives via click chemistry and their anti-vitiligo activity
Open Access Paper

Carbohydrate-conjugated 4-(1,3,2-dithiarsolan-2-yl)aniline as a cytotoxic agent against colorectal cancer

We synthesized a carbohydrate-conjugated 4-(1,3,2-dithiarsolan-2-yl)aniline. It exhibited reduced cytotoxicity to normal cells, suggesting a feasible approach to improve the therapeutic index of arsenic-containing compounds as chemotherapeutic agents.

Graphical abstract: Carbohydrate-conjugated 4-(1,3,2-dithiarsolan-2-yl)aniline as a cytotoxic agent against colorectal cancer
Open Access Paper

Photocatalytic copper-catalyzed azide–alkyne cycloaddition click reaction with Cu(II) coordination polymer

Cu(II) coordination polymers as photocatalysts for the copper-catalyzed azide–alkyne cycloaddition click reaction under household light irradiation in air.

Graphical abstract: Photocatalytic copper-catalyzed azide–alkyne cycloaddition click reaction with Cu(ii) coordination polymer
Open Access Paper

Efficient and straightforward click synthesis of structurally related dendritic triazoles

Structurally related triazolic dendrimers were efficiently synthesized applying CuAAC reaction.

Graphical abstract: Efficient and straightforward click synthesis of structurally related dendritic triazoles
Open Access Paper

Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of N-glycopeptides, pseudo-trisaccharides and an iminosugar

Glycals react with PIFA (or PIDA)–TMSN3 in presence of TMSOTf to form sugar derived 1,2-diazides and vicinal azidoacetates. Synthesis of 2-azido-N-glycopeptides, pseudotrisaccharides, and a piperidine triol derivative is reported.

Graphical abstract: Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of N-glycopeptides, pseudo-trisaccharides and an iminosugar
Open Access Paper

Facile synthesis of novel hybrid POSS biomolecules via “Click” reactions

A novel alkyne-terminated cubic-octameric POSS was synthesised in high yield and click chemistry has been used to attach bio-oligomers.

Graphical abstract: Facile synthesis of novel hybrid POSS biomolecules via “Click” reactions
Open Access Paper

Continuous flow-ultrasonic synergy in click reactions for the synthesis of novel 1,2,3-triazolyl appended 4,5-unsaturated L-ascorbic acid derivatives

A combination of flow chemistry and batch-based synthetic procedures has been successfully applied to the assembly of novel 4,5-unsaturated L-ascorbic acid series 6a–6n with diverse C-6-substituted 1,2,3-triazole moiety.

Graphical abstract: Continuous flow-ultrasonic synergy in click reactions for the synthesis of novel 1,2,3-triazolyl appended 4,5-unsaturated l-ascorbic acid derivatives
Paper

A recyclable and water soluble copper(I)-catalyst: one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation

A protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component reaction by a water soluble copper(I) complex has been developed.

Graphical abstract: A recyclable and water soluble copper(i)-catalyst: one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation
Paper

Copper-free click chemistry for microdroplet's W/O interface engineering

Microdroplets surface engineering using an azide fluorosurfactant prone to react with various functional heads conjugated beforehand to a strained alkyne.

Graphical abstract: Copper-free click chemistry for microdroplet's W/O interface engineering
Open Access Paper

Attachment of antimicrobial peptides to reverse osmosis membranes by Cu(I)-catalyzed 1,3-dipolar alkyne–azide cycloaddition

Optimized polymer membrane surface modification with antimicrobial properties.

Graphical abstract: Attachment of antimicrobial peptides to reverse osmosis membranes by Cu(i)-catalyzed 1,3-dipolar alkyne–azide cycloaddition
Paper

π-Stacking assisted redox active peptide–gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

We have synthesized, via click-chemistry, a redox-active peptide–gallol conjugate which facilitates rapid formation of antimicrobial silver nanoparticles with prominent antifungal activity.

Graphical abstract: π-Stacking assisted redox active peptide–gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles
Paper

Design and synthesis of novel dual-target agents for HDAC1 and CK2 inhibition

Drug entities able to address multiple targets can be more effective than those directed to just one biological target.

Graphical abstract: Design and synthesis of novel dual-target agents for HDAC1 and CK2 inhibition
Paper

Tao-Phos-controlled desymmetrization of succinimide-based bisalkynes via asymmetric copper-catalyzed Huisgen alkyne–azide click cycloaddition: substrate scope and mechanism

The Cu(II)/Tao-Phos-catalyzed Huisgen cycloaddition of succinimide-derived bisalkynes resulted in chiral triazoles bearing a quaternary carbon-stereogenic center with good yields and chemoselectivity as well as moderate to high enantioselectivities (up to 97% ee).

Graphical abstract: Tao-Phos-controlled desymmetrization of succinimide-based bisalkynes via asymmetric copper-catalyzed Huisgen alkyne–azide click cycloaddition: substrate scope and mechanism
Paper

Synthesis of benzimidazole-based 1,3,4-oxadiazole-1,2,3-triazole conjugates as glycogen synthase kinase-3β inhibitors with antidepressant activity in in vivo models

Synthesized benzimidazole based 1,3,4-oxadiazole-1,2,3-triazole conjugates were found to inhibit GSK-3β activity in vitro and exhibit antidepressant-like activity in in vivo studies.

Graphical abstract: Synthesis of benzimidazole-based 1,3,4-oxadiazole-1,2,3-triazole conjugates as glycogen synthase kinase-3β inhibitors with antidepressant activity in in vivo models
Paper

Design, synthesis and biological evaluation of novel triazole-core reversal agents against P-glycoprotein-mediated multidrug resistance

We designed and synthesized a novel series of P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) inhibitors bearing a triazolphenethyl–tetrahydroisoquinoline scaffold through click chemistry.

Graphical abstract: Design, synthesis and biological evaluation of novel triazole-core reversal agents against P-glycoprotein-mediated multidrug resistance
Paper

Design, synthesis, biological evaluation and molecular docking of amide and sulfamide derivatives as Escherichia coli pyruvate dehydrogenase complex E1 inhibitors

Optimal binding mode of novel E. coli PDHc E1 inhibitor 9d.

Graphical abstract: Design, synthesis, biological evaluation and molecular docking of amide and sulfamide derivatives as Escherichia coli pyruvate dehydrogenase complex E1 inhibitors
Paper

Facile preparation and properties of multifunctional polyacetylene via highly efficient click chemistry

A series of novel multifunctional polyacetylenes bearing oxadiazole and azo groups as molecular pendants were designed and synthesized via highly effective click chemistry.

Graphical abstract: Facile preparation and properties of multifunctional polyacetylene via highly efficient click chemistry
Paper

Synthesis of novel 1,4-disubstituted 1,2,3-triazolo-bosentan derivatives – evaluation of antimicrobial and anticancer activities and molecular docking

One pot synthesis with good yields. Good antimicrobial activity against 4EMV receptor. Prominent anticancer activity against A549 and SKOV-3 cell lines. Significant in vitro cytotoxicity at 7.81 μg mL−1. Docking mode of 1h with 2XP2 receptor.

Graphical abstract: Synthesis of novel 1,4-disubstituted 1,2,3-triazolo-bosentan derivatives – evaluation of antimicrobial and anticancer activities and molecular docking
Paper

A simple lateral flow biosensor for the rapid detection of copper(II) ions based on click chemistry

A simple and enzyme-free lateral flow biosensor for the rapid detection of Cu2+ based on copper(I) ion (Cu+)-catalyzed click chemistry has been constructed for the first time.

Graphical abstract: A simple lateral flow biosensor for the rapid detection of copper(ii) ions based on click chemistry
Paper

Click synthesis of a polyamidoamine dendrimer-based camptothecin prodrug

In the present work we report on the click synthesis of a new camptothecin (CPT) prodrug based on an anionic polyamidoamine (PAMAM) dendrimer intended for cancer therapy.

Graphical abstract: Click synthesis of a polyamidoamine dendrimer-based camptothecin prodrug
Open Access Paper

Dendron conjugation to graphene oxide using click chemistry for efficient gene delivery

Owing to its large surface area and rapid cellular uptake, graphene oxide (GO) is emerging as an attractive candidate material for delivery of drugs and genes.

Graphical abstract: Dendron conjugation to graphene oxide using click chemistry for efficient gene delivery
Paper

2,4-Bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines: synthesis and tuning of optical properties by polar substituents

Novel D–π–A–π–D type chromophores – 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines were prepared and their photophysical, electrochemical properties in conjunction with quantum chemical calculations were investigated.

Graphical abstract: 2,4-Bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines: synthesis and tuning of optical properties by polar substituents
Paper

Highly efficient synthesis and characterization of multiarm and miktoarm star-long-branched polymers via click chemistry

Two series of 3–12 multiarm star polymers and 4-miktoarm star copolymer of butadiene and styrene, in which the Mn of arm was higher than 20 kg mol−1, were synthesized with high efficiency (from 85.0% to 96.1%) via click chemistry.

Graphical abstract: Highly efficient synthesis and characterization of multiarm and miktoarm star-long-branched polymers via click chemistry
Paper

Functionalizable red emitting calcium sensor bearing a 1,4-triazole chelating moiety

Herein we developed a functionalizable OFF–ON red emitting fluorescent calcium probe based on a new chelating system formed by CuAAC click chemistry (Huisgen cycloaddition).

Graphical abstract: Functionalizable red emitting calcium sensor bearing a 1,4-triazole chelating moiety
Paper

Development of a microfluidic “click chip” incorporating an immobilized Cu(I) catalyst

The development of a microfluidic “click chip” incorporating an immobilized Cu(I) catalyst for click reactions.

Graphical abstract: Development of a microfluidic “click chip” incorporating an immobilized Cu(i) catalyst
Paper

2-Pyrrolecarbaldiminato–Cu(II) complex catalyzed three-component 1,3-dipolar cycloaddition for 1,4-disubstituted 1,2,3-triazoles synthesis in water at room temperature

2-Pyrrolecarbaldiminato–Cu(II) complexes were first established as efficient catalyst for 1,4-disubstituted 1,2,3-triazoles synthesis under green and mild reaction conditions.

Graphical abstract: 2-Pyrrolecarbaldiminato–Cu(ii) complex catalyzed three-component 1,3-dipolar cycloaddition for 1,4-disubstituted 1,2,3-triazoles synthesis in water at room temperature
Paper

Highly efficient click reaction on water catalyzed by a ruthenium complex

Reactivity of ruthenium-catalyzed click reaction has been enhanced greatly by using H2O as the solvent.

Graphical abstract: Highly efficient click reaction on water catalyzed by a ruthenium complex
Paper

Copper immobilized onto a triazole functionalized magnetic nanoparticle: a robust magnetically recoverable catalyst for “click” reactions

A novel magnetic heterogeneous copper catalyst was synthesized by immobilization of copper ions onto triazole functionalized Fe3O4.

Graphical abstract: Copper immobilized onto a triazole functionalized magnetic nanoparticle: a robust magnetically recoverable catalyst for “click” reactions
Paper

Click synthesis of graphene/poly(N-(2-hydroxypropyl) methacrylamide) nanocomposite via “grafting-onto” strategy at ambient temperature

Well-defined poly(N-(2-hydroxypropyl) methacrylamide) (PHPMA) was grafted onto graphene sheets via click chemistry to afford a PHPMA/graphene nanocomposite with excellent dispersibility in organic solvents and water.

Graphical abstract: Click synthesis of graphene/poly(N-(2-hydroxypropyl) methacrylamide) nanocomposite via “grafting-onto” strategy at ambient temperature
Paper

Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide–alkyne click chemistry

We provide a convenient method to construct photo-responsive poly(carbonate)s via ring-opening polymerization of cyclic carbonates followed by azide–alkyne click chemistry.

Graphical abstract: Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide–alkyne click chemistry
Paper

Modification of graphene oxide by a facile coprecipitation method and click chemistry for use as a drug carrier

A graphene oxide based ternary composite was synthesized for targeted drug carrier.

Graphical abstract: Modification of graphene oxide by a facile coprecipitation method and click chemistry for use as a drug carrier
Paper

Synthesis and electrochemical properties of conducting polyaniline/graphene hybrids by click chemistry

Conducting polyaniline nanofiber-grafted graphene oxide (PANINF-GO) hybrids were prepared by click chemistry reaction and in situ rapid mixing polymerization. The resulting composites exhibited excellent electrochemical properties.

Graphical abstract: Synthesis and electrochemical properties of conducting polyaniline/graphene hybrids by click chemistry
Paper

New clicked thiirane derivatives as gelatinase inhibitors: the relevance of the P1′ segment

A new family of triazolyl thiiranes has been synthesised and characterised as MMP-2 and MMP-9 inhibitors. The hit compound displayed submicromolar inhibition of MMP-2

Graphical abstract: New clicked thiirane derivatives as gelatinase inhibitors: the relevance of the P1′ segment
Paper

Chemoenzymatic synthesis of “click” xylosides and xylobiosides from lignocellulosic biomass

A range of triazole-linked O-xylosides and O-xylobiosides, with potential biological applications, has been prepared by an efficient two-step chemoenzymatic sequence from biomass-derived xylans.

Graphical abstract: Chemoenzymatic synthesis of “click” xylosides and xylobiosides from lignocellulosic biomass
Paper

Copper-catalyzed one-pot synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins

Efficient copper-catalyzed three-component synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins.

Graphical abstract: Copper-catalyzed one-pot synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins
Paper

Diversity oriented approach to triazole based peptidomimetics as mammalian sterile 20 kinase inhibitors

Post assembly peptide modifications – serine/threonine kinase inhibitors.

Graphical abstract: Diversity oriented approach to triazole based peptidomimetics as mammalian sterile 20 kinase inhibitors
Paper

Capping of oligonucleotides with “clickable” m3G-CAPs

Methodology and synthesis of different m3G-CAP constructs equipped with an azide handle and their attachment by “click reaction” with an activated triple bond partner allows efficient formation of oligonucleotide m3G-CAP conjugates.

Graphical abstract: Capping of oligonucleotides with “clickable” m3G-CAPs
53 items

About this collection

Associate Editor Professor Manojit Pal (Dr Reddy’s Institute of Life Sciences, India) is the guest editor for this collection covering a decade of progress in click reactions based on CuAAC.

The Nobel Prize in Chemistry 2022 was awarded jointly to Professor Carolyn R. Bertozzi, Professor Morten Meldal and Professor K. Barry Sharpless for their seminal work in the development of click chemistry and bioorthogonal chemistry. Click chemistry has revolutionized the routes of molecular construction and has applications in drug discovery and development, medicinal and pharmaceutical chemistry, analytical chemistry, materials science, surface science, and more. Additionally, bioorthogonal chemistry has made it possible to monitor the chemical processes occurring in living cells, without interfering with native biochemical systems or causing cellular toxicity.

Click chemistry has not gone unnoticed over the years; many synthetic organic chemists have made contributions (both big and small) to this research area. So, in celebration of the Nobel Prize, we are delighted to launch a new collection comprising of relevant papers published in RSC Advances over last 10 years. The collection predominantly covers the application of click reactions in the areas of bioorganic and medicinal chemistry; papers devoted to the development of methodologies are also included.

RSC Advances welcomes new research papers and reviews focusing on the development and application of CuAAC based click reactions for further inclusion in the collection.

If you are interested in submitting to this collection, please contact the Editorial Office at advances-rsc@rsc.org

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