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, characterization and antimicrobial activity of some substituted 1,2,3-triazoles.
Bantwal Shivarama Holla,Manjathuru Mahalinga,Mari Sithambaram Karthikeyan,Boja Poojary,P. M. Akberali,Nalilu Suchetha Kumari +5 more
TL;DR: Two substituted 1,2, 3-triazoles 4 and 6 have been synthesized by the 1,3-dipolar cycloaddition reaction of 4-azido-8-(trifluoromethyl)quinoline 2 with ethyl acetoacetate and acetylacetone, respectively and screened for their antimicrobial activity.
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Azide–Alkyne Coupling: A Powerful Reaction for Bioconjugate Chemistry
Rolf Breinbauer,Maja Köhn +1 more
TL;DR: The groups of Sharpless and Finn applied the azide ± alkyne coupling in the parallel synthesis of a highly active Azide ±Alkyne Coupling: A Powerful Reaction for Bioconjugate Chemistry.
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Clubbed [1,2,3] triazoles by fluorine benzimidazole: a novel approach to H37Rv inhibitors as a potential treatment for tuberculosis.
Charansingh H. Gill,Ganesh R. Jadhav,Mohammad U. Shaikh,Rajesh P. Kale,Anant R. Ghawalkar,Deepak R. Nagargoje,Mahendra Ramesh Shiradkar +6 more
TL;DR: A Novel Clubbed [1,2,3] triazoles with fluorine benzimidazole series of H37Rv strain inhibitors, potentially useful for the treatment of tuberculosis is disclosed on the basis of promising results of preliminary antimicrobial study.
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Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives.
Marilia S. Costa,Nubia Boechat,Érica A. Rangel,Fernando de C. da Silva,Alessandra Mendonça Teles de Souza,Carlos Rangel Rodrigues,Helena Carla Castro,Ivan Neves Junior,Maria C.S. Lourenço,Solange M. S. V. Wardell,Vitor F. Ferreira +10 more
TL;DR: The SAR study indicated the importance of the hydrogen bond acceptor subunit (3a-l), the position in the aromatic ring, the planarity of triazole and phenyl rings in these compounds, and a correlation between the uniform HOMO coefficient distribution and the anti-tubercular activity.
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Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization.
Matthew Whiting,Jonathan C. Tripp,Ying-Chuan Lin,William Lindstrom,Arthur J. Olson,John H. Elder,K. Barry Sharpless,Valery V. Fokin +7 more
TL;DR: The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), which provides ready access to 1,4-disubstituted-1,2,3-triazoles, was used to unite a focused library of azide -containing fragments with a diverse array of functionalized alkyne-containing building blocks, which led to the rapid identification of a lead structure and readily enabled optimization of both azide and alkynes fragments.