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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CuFeO2/tetrabutylammonium bromide catalyzes selective synthesis of 1,4‐disubstituted 1,2,3‐triazoles in neat water at room temperature
TL;DR: In this paper, a completely green medium including water as a solvent and antiviral CuFeO2 as a catalyst was described for the synthesis of 1,4-disubstituted 1,2,3-triazoles.
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Ramachary-Bressy-Wang [3+2]cycloaddition reaction: Synthesis of fully decorated 1,2,3-triazoles as potent anticancer and EGFR inhibitors
M. N,Satheesh Kumar Nukala,Narasimha Swamy Thirukovela,Rakesh Sreerama,Richard E,Pavan-Kumar Kamarajugadda,Sirassu Narsimha +6 more
TL;DR: In this paper , a general strategy was developed for the synthesis of new fully decorated 1,2,3-triazoles (5a-m & 6a-e) containing coumarine and sulfonyl-benzimidazole from 3-(2-((1-methyl-1H-benzo[d]imidaxol]-2-yl)sulfonyl)acetyl)-2H-chromen-2-one and several azides using Ramachary-Bressy-Wang organocatalytic cycloaddition method.
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Functionalization of bioactive substrates with a F5SCH = CH moiety
Valery K. Brel,Oleg I. Artyushin,Aleksandra A. Moiseeva,Elena V. Sharova,A. G. Buyanovskaya,Yulia V. Nelyubina +5 more
TL;DR: In this paper, a convenient approach to modify bioactive substrates such as daunorubicin, cytisine, and camphecene with a pentafluorosulfanylvinyl moiety has been suggested.
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Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity.
Thayane Melo de Queiroz,Erika V. M. Orozco,Valdenizia R. Silva,Luciano de S. Santos,Milena Botelho Pereira Soares,Daniel P. Bezerra,André Luiz Meleiro Porto +6 more
TL;DR: The copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction for the synthesis of β-keto-1,2,3-triazole derivatives 3a-f from ethinylestradiol and their application in the inhibition of two human cancer cells lines are reported.
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Synthesis of ruthenium triazolato complexes by the [3 + 2] cycloaddition of a ruthenium azido complex with acetylacetylenes
Chao-Wan Chang,Gene-Hsiang Lee +1 more
TL;DR: In this paper, a cycloaddition of two acetylacetylenes with ruthenium azido complex [Ru]-−N3 (1, [Ru] =η5-C5H5)(dppe)Ru, dppe=Ph2PCH2CH2PPh2) is reported and the metal-bound heterocyclic complexes produced are triazolato complexes.
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.