Recent advances in click chemistry reactions mediated by transition metal based systems

Tăbăcaru, Aurel; Furdui, Bianca; Ghinea, Ioana Otilia; Cârâc, Geta; Dinică, Rodica Mihaela

doi:10.1016/j.ica.2016.07.029

Cited by 47 publications

(24 citation statements)

References 141 publications

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“…Functionalization of surfaces and materials through the covalent attachment of organic monolayers has become the focus of much research in the last decade because of numerous applications in chemical/biological sensing, drug delivery, selective gas separation, cancer detection, etc. In this regard, click chemistry reactions – which were introduced by Kolb et al in 2001 – are excellent candidates due to having unique characteristics such as mild reaction conditions, high efficiency, compatibility with different kinds of solvents specially water, high reaction rate, and easy post‐treatment and are thus used for many applications …”

Section: Introductionmentioning

confidence: 99%

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Dadfar

Sekula-Neuner

Bog

et al. 2018

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Different types of click chemistry reactions are proposed and used for the functionalization of surfaces and materials, and covalent attachment of organic molecules. In the present work, two different catalyst-free click approaches, namely azide-alkyne and thiol-alkyne click chemistry are studied and compared for the immobilization of microarrays of azide or thiol inks on functionalized glass surfaces. For this purpose, the surface of glass is first functionalized with dibenzocyclooctyne-acid (DBCO-acid), a cyclooctyne with a carboxyl group. Then, the DBCO-terminated surfaces are functionalized via microchannel cantilever spotting with different fluorescent and nonfluorescent azide and thiol inks. Although both routes work reliably for surface functionalization, the protein binding experiments reveal that using a thiol-alkyne route will obtain the highest surface density of molecular immobilization in such spotting approaches. The obtained achievements and results from this work can be used for design and manufacturing of microscale patterns suitable for biomedical and biological applications.

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Section: Introductionmentioning

confidence: 99%

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Dadfar

Sekula-Neuner

Bog

et al. 2018

Small

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“…The click chemistry reaction that has been used in this study was introduced for first time by Kolb et al This reaction is in fact cyclo‐addition of alkynes to azides to form 1,4‐disubsituted‐1,2,3‐triazoles. The copper(I)‐catalyzed click reaction is simple, high‐speed with mild condition that extensively is applied in different fields especially in pharmaceuticals …”

Section: Resultsmentioning

confidence: 99%

“…One‐pot procedure for radiolabeling of compound I was performed by using 2‐ethynylpyridine due to excellent results of disubstituted 1,2,3‐triazole through a click reaction …”

Section: Resultsmentioning

confidence: 99%

New ^99mTc(CO)₃‐radiolabeled arylpiperazine pharmacophore as potent 5HT_1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation

Erfani

Malek

Ebrahimi

et al. 2019

Labelled Comp Radiopharmac

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In spite of previous efforts, there is lack of a radiotracer for imaging the 5HT 1A receptor density in human brain, which is involved in several neurological brain disorders. The aim of this study was to prepare a new derivative of 1-(2-methoxyphenyl)piperazine (MPP) as a main chemical structure of 5HT 1A receptor antagonist with 3-carbon linker and radiolabeled by [ 99m Tc][Tc(CO) 3 (H 2 O) 3 ] + precursor. Docking studies before chemical synthesis showed similar fashion of interaction for both WAY100635 (potent 5HT 1A receptor antagonist) and new designed ligand, despite of addition of 99m Tc(CO) 3 group in the structure of new ligand. MPP-(CH 2 ) 3 -N 3 was synthesized via three efficient and reliable chemical synthesis steps (more than 80% yield) then radiolabeled by addition of 2-ethynylpyridine and [ 99m Tc] [Tc(CO) 3 (H 2 O) 3 ] + precursor in one pot procedure (more than 95% radiochemical efficiency) through click chemistry method. After incubation, radiotracer was found stable in vitro up to 2 hours. Binding assays showed about 33% specific binding of radiotracer to the 5HT 1A receptors. Brain biodistribution studies indicated (0.26 ± 0.05)% ID/g hippocampus uptake at 30 minutes post injection, which its specificity was verified through blocking studies. These results suggested that new designed radioligand might serve as a potent SPECT imaging agent to estimate status of 5HT 1A receptors. KEYWORDS 1-(2-methoxyphenyl)piperazine (MPP), 2-ethynylpyridine, 5HT 1A homology model, click chemistry, docking, WAY100635

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“…Several reviews dealing with the pharmacology of triazoles, synthesis of condensed triazoles, carbohydrate triazoles, metal triazoles, ferrocene triazole are present in the literature. However, no single review gives the complete picture of chiral fused 1,2,3 triazoles although the first report appeared in late 90s with Vasella's work on glycosidase inhibitors .…”

Section: Introductionmentioning

confidence: 99%

Chiral Fused 1,2,3‐Triazoles: A Synthetic Overview

2020

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Triazoles have always occupied a pivotal position in the field of medicinal and pharmaceutical chemistry. Recently, the area of chiral fused triazoles has gained attention. The synthetic routes to access chiral fused triazole may involve either a natural or synthetic chiral starting material with a suitably functionalized azide and alkyne component or isomer resolution to achieve chirality. Asymmetric synthesis methods using chiral complexes and organocatalysis have also emerged for obtaining chiral fused triazoles. Herein, we have described an up-to-date overview of different synthetic protocols applied to construct chiral fused 1,2,3-triazoles. Scheme 1. Basic methodologies for triazole construction. 2 3 4 5 6 7 8 . Yanai's stereo-divergent synthesis of ido-triazole ent-6 a and gluco-triazoles 7 a. Scheme 3. Yanai's diastereo-divergent synthesis of manno-, gulo-, galacto-and altro-triazoles. . Konda's synthesis of tricyclic triazolo-oxazepines 62. Scheme 15. Cobb's synthesis of spirocyclic triazolooxazine nucleosides 67. Scheme 16. Sen's synthesis of tetracyclic triazolo-oxazepines 69. to azide group and protected amine was propargylated to access azido-alkynes 122 c-h for triazole formation 124 (Scheme 29). The copper catalyzed version of this step was also carried out that gave almost approximately same yields in lesser Scheme 25. Chrandrasekaran's synthesis of triazolo-pyrazines and pyrazinones from amino acid derived sulfamidates. Scheme 26. Chrandrasekaran's synthesis of triazolo-pyrazinone 110 having pendant amino acid.structural features of triazoles, the authors carried out one pot hydrogenation and insitu Boc-protection of 155 a, followed by azidation and propargylation to afford azido-alkyne 160. Subsequently, thermal azide-alkyne cycloaddition furnished the triazole product 161 in good yield (Scheme 34).Allenyl silanes are extensively used in synthetic organic transformations and provide ready access to enantiopure pyrroles, oxiranes, furans and vinyl silanes. In lewis acid assisted reaction, allenyl silanes work as propargyl anion equivalents. Allenyl silane forms regioselective homopropargylic alcohol when treated with aldehyde and ketone. The stabilization is Scheme 31. Thomas's synthesis of steroidal fused 1,2,3-triazoles.Scheme 32. Thomas's synthesis of steroidal fused NH-1,2,3-triazoles and steroidal 4,5-fused triazolo-alkynes.

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Recent advances in click chemistry reactions mediated by transition metal based systems

Cited by 47 publications

References 141 publications

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

New ^99mTc(CO)₃‐radiolabeled arylpiperazine pharmacophore as potent 5HT_1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation

Chiral Fused 1,2,3‐Triazoles: A Synthetic Overview

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Recent advances in click chemistry reactions mediated by transition metal based systems

Cited by 47 publications

References 141 publications

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

New 99mTc(CO)3‐radiolabeled arylpiperazine pharmacophore as potent 5HT1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation

Chiral Fused 1,2,3‐Triazoles: A Synthetic Overview

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Product

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New ^99mTc(CO)₃‐radiolabeled arylpiperazine pharmacophore as potent 5HT_1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation