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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Journal ArticleDOI
Iridium-Catalyzed Intermolecular Azide–Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions†
TL;DR: An iridium-catalyzed azide-alkyne cycloaddition reaction (IrAAC) of electron-rich internal alkynes is described, which is the first efficient intermolecular AAC of internal thioalkynes.
Journal ArticleDOI
Functional Carbon Quantum Dots as Medical Countermeasures to Human Coronavirus
Aleksandra Łoczechin,Aleksandra Łoczechin,Karin Seron,Alexandre Barras,Emerson Giovanelli,Sandrine Belouzard,Yen-Ting Chen,Nils Metzler-Nolte,Rabah Boukherroub,Jean Dubuisson,Sabine Szunerits +10 more
TL;DR: The underlying mechanism of action of these CQDs was revealed to be inhibition of HCoV-229E entry that could be due to interaction of the functional groups of the C QDs with HCoVs entry receptors; surprisingly, an equally large inhibition activity was observed at the viral replication step.
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Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agents.
TL;DR: Flow cytometry analysis demonstrated that treatment of MGC-803 with 3c led to cell cycle arrest at G2/M phase accompanied by an increase in apoptotic cell death after 12 h, and compound 3a was more potent than 5-fluorouracil against all tested human cancer cell lines.
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Design, Synthesis, and Structure–Activity Correlations of Novel Dibenzo[b,d]furan, Dibenzo[b,d]thiophene, and N-Methylcarbazole Clubbed 1,2,3-Triazoles as Potent Inhibitors of Mycobacterium tuberculosis
Santhosh Reddy Patpi,Lokesh Pulipati,Perumal Yogeeswari,Dharmarajan Sriram,Nishant Jain,Balasubramanian Sridhar,Ramalinga Murthy,Anjana Devi T,Shasi V. Kalivendi,Srinivas Kantevari +9 more
TL;DR: The results together provided the potential importance of molecular hybridization and the development of triazole clubbed dibenzo[b,d]thiophene-based lead candidates to treat mycobacterial infections.
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Copper(I)‐Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5‐Hetero‐Functionalized Triazoles
TL;DR: A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported, which features a broad substrate scope and good functional group compatibility.
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.