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
More filters
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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
More filters
Journal ArticleDOI
Model Studies Toward the Synthesis of Thymidine Oligonucleotides with Triazole Internucleosidic LinkagesVia Iterative Cu(I)-Promoted Azide–Alkyne Ligation Chemistry
TL;DR: A new approach has been explored to oligothymidines in which triazole internucleosidic linkages replace the native phosphodiester groups, based on the repetition of the copper(I)-catalyzed azide–alkyne cycloaddition as a key ligation process of suitably functionalized thymidine building blocks.
Journal ArticleDOI
Click Chemistry Approach to New N-Substituted Aminocyclitols as Potential Pharmacological Chaperones for Gaucher Disease†
TL;DR: New N-alkylaminocyclitols bearing a 1,2,3-triazole system at different positions of the alkyl chain have been prepared as potential GCase pharmacological chaperones using click chemistry approaches, revealing a determinant effect of the location of the triazole ring on the activity.
Journal ArticleDOI
Exploration of click reaction for the synthesis of modified nucleosides as chitin synthase inhibitors.
Preeti M. Chaudhary,Sayalee R. Chavan,Fazal Shirazi,Meenakshi Razdan,Prachi Nimkar,Shailaja P. Maybhate,Anjali P. Likhite,Rajesh G. Gonnade,Braja G. Hazara,Mukund V. Deshpande,Sunita Ranjan Deshpande +10 more
TL;DR: Click reaction approach toward the synthesis of two sets of novel 1,2,3-triazolyl linked uridine derivatives 19a-19g and 21a-21g was achieved by Cu(I))-catalyzed 1, 3-dipolar cycloaddition of 5'-azido-5'-deoxy-2',3'-O-(1-methylethylidene)uridine).
Book ChapterDOI
Azide–Alkyne 1,3-Dipolar Cycloadditions: a Valuable Tool in Carbohydrate Chemistry
TL;DR: The efficient catalyzed version of the 1,3-dipolar cycloaddition reaction of azides and alkynes in carbohydrate chemistry has joined in a short period of time a select group of the most efficient and useful organic reactions.
Journal ArticleDOI
Synthesis and structure-affinity relationship investigations of 5-heteroaryl-substituted analogues of the antipsychotic sertindole. A new class of highly selective alpha(1) adrenoceptor antagonists.
Thomas Balle,Jens Kristian Perregaard,Martha Teresa Ramirez,Anna Kirstine Larsen,Karina Krøjer Søby,Tommy Liljefors,Kim Andersen +6 more
TL;DR: A new basic Pharmacophore for alpha 1-adrenoceptor antagonists based on a previously reported pharmacophore model for dopamine D2 antagonist is suggested.