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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Medicinal attributes of 1,2,3-triazoles: Current developments
TL;DR: The present work aims to summarize the current approaches adopted for the synthesis of the 1,2,3-triazole and medicinal significance of these architectures as a lead structure for the discovery of drug molecules such as COX-1/COX-2 inhibitors, HIV protease inhibitors, CB1 cannabinoid receptor antagonist and much more which are in the pipeline of clinical trials.
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Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update.
TL;DR: The recent results described in the literature since 2010 are reviewed, classified according to the nature of the catalyst precursor: copper(I) or copper(II) salts or complexes, metallic or nano-particulated copper and several solid-supported copper systems.
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Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications.
TL;DR: The ruthenium-catalyzed azide alkyne cycloaddition affords 1,5-disubstituted 1,2,3-triazoles in one step and complements the more established copper-Catalyzed reaction providing the 1,4-isomer.
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Robust Ruthenium(II)-Catalyzed C–H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers
TL;DR: Ruthenium(II) complexes have emerged as effective catalysts for C-H arylations of tetrazolyl-substituted arenes by chelation assistance.
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Metal-Catalyzed Azide-Alkyne “Click” Reactions: Mechanistic Overview and Recent Trends
TL;DR: In this paper, a review of the mechanistic aspects and recent trends of metal-catalyzed azide-alkyne cycloaddition (MAAC) reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.
References
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Synthesis and biological evaluation of new 2-chloro-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)quinoline derivatives via click chemistry approach
Amol H. Kategaonkar,Pravin V. Shinde,Atul H. Kategaonkar,Sharad K. Pasale,Bapurao B. Shingate,Murlidhar S. Shingare +5 more
TL;DR: Synthesis of new 2-chloro-3-((4-phenyl-1H-1,2, 3-triazol-1-yl)methyl)quinoline derivatives (4a-h) using 1,3-dipolar cycloaddition (click chemistry) has been achieved in very high yield.
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Expanded Utility of the Native Chemical Ligation Reaction
TL;DR: Recent progress of strategies in several areas related to proteomics and chemical biology, namely, in vitro and in vivo protein biotinylation, protein microarray technologies for large-scale protein analysis, and live-cell bioimaging are highlighted.
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New prospects for the grafting of functional groups onto aliphatic polyesters. Ring-opening polymerization of α- or γ-substituted ε-caprolactone followed by chemical derivatization of the substituents
Philippe Lecomte,Raphaël Riva,Stephanie Schmeits,Jutta Rieger,Kathy Van Butsele,Christine Jérôme,Robert Jérôme +6 more
TL;DR: In this paper, two main strategies have been distinguished for the synthesis of aliphatic polyesters, substituted by pendent functional groups: the first route consists of the ring-opening polymerization of e-caprolactone substituted by various functional groups, protected if needed, in α- or γ-position.
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[3]rotaxane-porphyrin conjugate as a novel supramolecular host for fullerenes.
TL;DR: A new supramolecular host with good affinity toward fullerenes has been developed, built on a [3]rotaxane scaffold and contains two free-base porphyrin moieties as recognition units for fullerene.
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Synthesis of DOTA-conjugated multimeric [Tyr3]octreotide peptides via a combination of Cu(I)-catalyzed "click" cycloaddition and thio acid/sulfonyl azide "sulfo-click" amidation and their in vivo evaluation.
Cheng-Bin Yim,Ingrid Dijkgraaf,Remco Merkx,Cees Versluis,Annemarie Eek,Gwenn E. Mulder,Dirk T. S. Rijkers,Otto C. Boerman,Rob M. J. Liskamp +8 more
TL;DR: The design, synthesis, and biological evaluation of a series of DOTA-conjugated monomeric, dimeric, and tetrameric [Tyr(3)]octreotide-based analogues as a tool for tumor imaging and/or radionuclide therapy and can be exploited for therapeutic applications are described.