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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ADP-ribosyl-N₃: A Versatile Precursor for Divergent Syntheses of ADP-ribosylated Compounds.
Lingjun Li,Li Qianqian,Shengqiang Ding,Pengyang Xin,Yuqin Zhang,Shenlong Huang,Guisheng Zhang +6 more
TL;DR: In this paper, ADP-ribosyl-N3 was designed and synthesized for the first time and a divergent post-modification strategy was developed to prepare structurally diverse ADp- ribosylated compounds including novel nucleotides and peptides bearing ADP.
Journal ArticleDOI
A novel synthetic acanthoic acid analogues and their cytotoxic activity in cholangiocarcinoma cells.
Teerapich Kasemsuk,Natthiya Saehlim,Patcharee Arsakhant,Gunya Sittithumcharee,Seiji Okada,Rungnapha Saeeng +5 more
TL;DR: Evaluation of their biological activities against four cell lines of cholangiocarcinoma cells showed that 3d exhibited the strongest activity with an IC50 value of 18 µM against KKU-213 cell line, which was 8 fold more potent than acanthoic acid.
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A novel ent-kaurane diterpenoid analog, DN3, selectively kills human gastric cancer cells via acting directly on mitochondria
TL;DR: The findings indicate that DN3 is a potential agent for the treatment of gastric cancer through acting directly on mitochondria, and would be useful for us to design more and better anti‐cancer compounds.
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Synthesis of medicinally important quinazolines decorated with 1,4-disubstituted-1,2,3-triazoles using CuSO4·5H2O–Et3N catalytic system
TL;DR: In this paper, the additive effect of triethylamine in the presence of Cu(II) sulfate pentahydrate was studied and it was shown that triethylimine is essential for the activation of the copper catalyst and is responsible for the reaction between aliphatic/aromatic heterocyclic alkyne(s) and azide(s), which otherwise did not react under the standard reaction conditions that are often used in click chemistry.
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.