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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Identification of a new bis-amino acid glycoside selectively toxic to multiple myeloma cells.
TL;DR: A Western blot analysis suggested that this compound could potentiate the cleavage of poly ADP-ribose polymerase in MM cells, leading to apoptosis, and was determined to be selectively toxic for multiple myeloma among a series of cancer cell lines with no toxicity to a control line.
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Synthesis of 1,4,5-trisubstituted triazoles by [3+2] cycloaddition of a ruthenium azido complex with ynoate esters
Chao-Wan Chang,Gene-Hsiang Lee +1 more
TL;DR: The [3 + 2] cycloaddition reactions of a series of ynoate esters with a ruthenium azido complex [Ru]−N 3, N 3, 4, 5 and N 3 - 7a were investigated by single-crystal X-ray diffraction analysis.
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Ciprofloxacin-Tethered 1,2,3-Triazole Conjugates: New Quinolone Family Compounds to Upgrade Our Antiquated Approach against Bacterial Infections
TL;DR: Interestingly, some of the conjugates showed superior antimicrobial activity as compared to the control drug ciprofloxacin, and the three compounds 4i, 4j, and 4n showed strong activity with minimum inhibitory concentration (MIC) 0.78 μM, while the compound 4g showed MIC 1.56 μM.
Journal ArticleDOI
Green Synthesis and Anticancer Potential of 1,4-Dihydropyridines-Based Triazole Derivatives: In Silico and In Vitro Study
Sabera Bijani,Danish Iqbal,Sheefa Mirza,Vicky Jain,Sadaf Jahan,Mohammed Abdullah I Alsaweed,Yahya Madkhali,Suliman A. Alsagaby,Saeed Banawas,Abdulrahman Algarni,Faris Alrumaihi,Rakesh Rawal,Wael Alturaiki,Anamik Shah +13 more
TL;DR: The present data indicate that dihydropyridine-linked 1,2,3-triazole conjugates can be generated as potent anticancer agents.
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.