Click Chemistry: 1,2,3‐Triazoles as Pharmacophores
TLDR
The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.Abstract:
The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of 'click chemistry' due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.read more
Citations
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New mono- and bidentate P-ligands using one-pot click-chemistry: synthesis and application in Rh-catalyzed hydroformylation
Natalia V. Dubrovina,Lutz Domke,Ivan A. Shuklov,Anke Spannenberg,Robert Franke,Alexander Villinger,Armin Börner +6 more
TL;DR: In this article, three families of new phosphorus ligands have been prepared using the click-chemistry approach, proceeding in only two steps and without intermediate P-protection, allowing the high yield production of mono- and bidentate P-ligands, bearing at least one P-O bond.
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Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.
TL;DR: The approach is scalable and offers an expeditious route to the enantioselective synthesis of versatile and otherwise difficult to access aldehydes that bear an α-halo-substituted quaternary carbon stereogenic center as well as an assortment of 2,2-disubstituting epoxides that contain an easily modifiable alkene.
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Copper(I)‐Catalyzed Interrupted Click/Sulfenylation Cascade: One‐Pot Synthesis of Sulfur Cycle Fused 1,2,3‐Triazoles
Weiguo Wang,Weiguo Wang,Shuai Huang,Shikun Yan,Xuejun Sun,Chen-Ho Tung,Zhenghu Xu,Zhenghu Xu +7 more
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A pyrene-functionalized triazole-linked hexahomotrioxacalix[3]arene as a fluorescent chemosensor for Zn²⁺ ions
Chong Wu,Yusuke Ikejiri,Jiang-Lin Zhao,Xue-Kai Jiang,Xin-Long Ni,Xi Zeng,Carl Redshaw,Takehiko Yamato +7 more
TL;DR: A pyrenyl appended hexahomotrioxacalix[3]arene L featuring 1,2,3-triazole linkers was synthesized as a fluorescent chemosensor for Zn2+ in mixed aqueous media.
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1,2,3-Triazoles from carbonyl azides and alkynes: filling the gap
TL;DR: This work reports the first example of this class of reaction, with a copper-based system that efficiently enables the synthesis of N-carbamoyl 1,2,3-triazoles by [3+2] cycloaddition ofN-carbonoyl azides and alkynes.
References
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A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
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Click Chemistry: Diverse Chemical Function from a Few Good Reactions.
TL;DR: In this paper, a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach called click chemistry is defined, enabled, and constrained by a handful of nearly perfect "springloaded" reactions.
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Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
TL;DR: A novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported, and the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1, 3-dipoles entering the reaction.
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Cu-catalyzed azide-alkyne cycloaddition.
TL;DR: The basis for the unique properties and rate enhancement for triazole formation under Cu(1) catalysis should be found in the high ∆G of the reaction in combination with the low character of polarity of the dipole of the noncatalyzed thermal reaction, which leads to a considerable activation barrier.
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The growing impact of click chemistry on drug discovery.
TL;DR: The copper-(I)-catalyzed 1,2,3-triazole formation from azides and terminal acetylenes is a particularly powerful linking reaction, due to its high degree of dependability, complete specificity, and the bio-compatibility of the reactants.