Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.11.282 ◽

2015 ◽

Vol 11 ◽

pp. 2631-2640 ◽

Cited By ~ 9

Author(s):

Camilla Matassini ◽

Stefania Mirabella ◽

Andrea Goti ◽

Inmaculada Robina ◽

Antonio J Moreno-Vargas ◽

...

Keyword(s):

Click Chemistry ◽

Terminal Alkyne ◽

Biological Investigation

The synthesis of new multivalent architectures based on a trihydroxypiperidine α-fucosidase inhibitor is reported herein. Tetravalent and nonavalent dendrimers were obtained by means of the click chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive moiety. A preliminary biological investigation is also reported towards commercially available and human glycosidases.

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Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Synthesis ◽

10.1055/s-0037-1610781 ◽

2021 ◽

Author(s):

Felipe C. Demidoff ◽

Leandro L. de Carvalho ◽

Eduardo José P. Rodrigues Filho ◽

Andréa Luzia F. de Souza ◽

Chaquip D. Netto

Keyword(s):

Click Chemistry ◽

Organic Synthesis ◽

Biological Activities ◽

Cross Coupling ◽

Coupling Reactions ◽

Large Array ◽

Terminal Alkyne ◽

Co Catalyst ◽

Cross Coupling Reactions ◽

Convenient Synthesis

AbstractFunctionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free CuI-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.

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Clay-Supported Cu(II) Catalyst: An Efficient, Heterogeneous, and Recyclable Catalyst for Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Alloxan-Derived Terminal Alkyne and Substituted Azides Using Click Chemistry

Synthetic Communications ◽

10.1080/00397911.2015.1099675 ◽

2015 ◽

Vol 45 (22) ◽

pp. 2608-2626 ◽

Cited By ~ 9

Author(s):

Nitin Dubey ◽

Pratibha Sharma ◽

Ashok Kumar

Keyword(s):

Click Chemistry ◽

Recyclable Catalyst ◽

Terminal Alkyne

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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 ◽

10.2174/1570179415666180110152642 ◽

2018 ◽

Vol 15 (4) ◽

pp. 552-565 ◽

Cited By ~ 2

Author(s):

Nitin Kore ◽

Pavel Pazdera

Keyword(s):

Click Chemistry ◽

Nucleophilic Substitution ◽

Cyano Group ◽

Catalytic Action ◽

Cycloaddition Reactions ◽

Terminal Alkynes ◽

Terminal Alkyne ◽

Aryl Azide ◽

Catalytic Application ◽

Novel Synthesis

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, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting α-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable, and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.

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CuAAC click chemistry for the enhanced detection of novel alkyne-based natural product toxins

Chemical Communications ◽

10.1039/c8cc05113e ◽

2018 ◽

Vol 54 (86) ◽

pp. 12234-12237 ◽

Cited By ~ 5

Author(s):

Edward S. Hems ◽

Ben A. Wagstaff ◽

Gerhard Saalbach ◽

Robert A. Field

Keyword(s):

Natural Products ◽

Click Chemistry ◽

Natural Product ◽

Harmful Algal Blooms ◽

Algal Blooms ◽

Terminal Alkyne

In the context of discovering and quantifying terminal alkyne-based natural products, here we report the combination of CuAAC click chemistry with LC-MS for the detection of polyether toxins (prymnesins) associated with harmful algal blooms.

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Visual detection of Cu(ii) ions based on a simple pyrene derivative using click chemistry

Analytical Methods ◽

10.1039/c4ay00880d ◽

2014 ◽

Vol 6 (14) ◽

pp. 4977-4981 ◽

Cited By ~ 7

Author(s):

Yanbo Yang ◽

Zhiyi Yao ◽

Baiyang Tang ◽

Junhua Yu ◽

Xiaolin Bi ◽

...

Keyword(s):

Click Chemistry ◽

Fluorescent Probe ◽

Visual Detection ◽

Click Reaction ◽

Aqueous Media ◽

Terminal Alkyne ◽

Positively Charged ◽

Ratiometric Fluorescent Probe

A ratiometric fluorescent probe for the visual detection of Cu2+in aqueous media has been developed based on a “click” reaction between a pyrene azide and a positively charged terminal alkyne.

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