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
More filters
Journal ArticleDOI
Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition
Ute F. Röhrig,Ute F. Röhrig,Somi Reddy Majjigapu,Somi Reddy Majjigapu,Aurélien Grosdidier,Sylvian Bron,Sylvian Bron,Vincent Stroobant,Luc Pilotte,Didier Colau,Pierre Vogel,Pierre Vogel,Benoît Van den Eynde,Vincent Zoete,Olivier Michielin,Olivier Michielin,Olivier Michielin +16 more
TL;DR: A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.
Journal ArticleDOI
“Click” reactions in polysaccharide modification
Xiangtao Meng,Kevin J. Edgar +1 more
TL;DR: Application in polysaccharide modification of six groups of click reactions are reviewed, including CuAAC, metal-free [3+2] cycloaddition, Diels–Alder reaction, oxime click, Thiol-Michael reaction, and thiol-ene reaction, as well as one click-like reaction that is the subject of the authors' own research, olefin cross-metathesis.
Journal ArticleDOI
Rational Design of Multitarget-Directed Ligands: Strategies and Emerging Paradigms
TL;DR: This article discusses the systematic establishment of target combination, lead generation, and optimization of multitarget-directed ligands (MTDLs), and analyzes some MTDLs research cases for several complex diseases in recent years and the physicochemical properties of 117 clinical multitarget drugs, with the aim of revealing the trends and insights of the potential use of MT DLs.
Journal ArticleDOI
CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review
TL;DR: The review lays emphasis on the significance of 1,2,3-triazoles synthesized via CuAAC reaction having potential to act as anti-microbial, anti-cancer, anti’viral,Anti-inflammatory,anti-tuberculosis, pro-diabetic, and anti-Alzheimer drugs.
Journal ArticleDOI
Bioorthogonal labelling of biomolecules: new functional handles and ligation methods
TL;DR: This review provides a literature overview of bioorthogonal ligation methods for protein modification, which have largely evolved over the last 15 years.
References
More filters
Journal ArticleDOI
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.