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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Journal ArticleDOI
1,4-Substituted Triazoles as Nonsteroidal Anti-Androgens for Prostate Cancer Treatment
Claudia Ferroni,Antonella Pepe,Yeong Sang Kim,Sunmin Lee,Andrea Guerrini,Marco Daniele Parenti,Anna Tesei,Alice Zamagni,Michela Cortesi,Nadia Zaffaroni,Michelandrea De Cesare,Giovanni Luca Beretta,Jane B. Trepel,Sanjay V. Malhotra,Greta Varchi +14 more
TL;DR: Biological and theoretical evaluation demonstrated that the introduction of the triazole core in the scaffold of nonsteroidal antiandrogens allowed the development of small molecules with improved overall AR-antagonist activity, and compound 14d displayed promising in vitro antitumor activity.
Journal ArticleDOI
Synthesis of 1,2,4-triazole-linked urea/thiourea conjugates as cytotoxic and apoptosis inducing agents.
Ramya Tokala,Swarna Bale,Ingle Pavan Janrao,Aluri Vennela,Niggula Praveen Kumar,Kishna Ram Senwar,Chandraiah Godugu,Nagula Shankaraiah +7 more
TL;DR: A new series of 1,2,4-triazole-linked urea and thiourea conjugates synthesized and evaluated for their in vitro cytotoxicity against selected human cancer cell lines were found to be safer with low cytot toxicity profile.
Journal ArticleDOI
Application of triazoles as bioisosteres and linkers in the development of microtubule targeting agents
M. Shaheer Malik,Saleh A. Ahmed,Saleh A. Ahmed,Ismail Althagafi,Mohammed Azam Ansari,Ahmed Kamal +5 more
TL;DR: The present review highlights the advances in this promising area of drug discovery and development in the use of triazoles as bioisosteres and linkers in the development of microtubule targeting agents.
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Multicomponent click synthesis of new 1,2,3-triazole derivatives of pyrimidine nucleobases: promising acidic corrosion inhibitors for steel.
Rodrigo González-Olvera,Araceli Espinoza-Vázquez,Guillermo E. Negrón-Silva,Manuel Palomar-Pardavé,Mario Romero-Romo,Rosa Santillan +5 more
TL;DR: These heterocyclic compounds synthesized by one-pot copper(I)-catalyzed 1,3-dipolar cycloaddition reactions between N-1-propargyluracil and thymine, sodium azide and several benzyl halides are promising acidic corrosion inhibitors for steel.
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Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: a strategy for highly efficient Wolff 1,2,3-triazole synthesis.
TL;DR: A catalytic and highly efficient Wolff's cyclocondensation of α-diazoketones with aromatic and aliphatic amines has been realized for the first time by utilizing the strategy of an intramolecular hydrogen bonding-activating carbonyl group.
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.
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.