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Rutjes, F. P. J. T. : 2022 Science of Synthesis, 2021/4: Click Chemistry DOI: 10.1055/sos-SD-235-00082
Click Chemistry

2.5 CuAAC and Metal-Free 1,3-Dipolar Huisgen Cycloadditions in Drug Discovery

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Editor: Rutjes, F. P. J. T. 

Authors: Agrahari, A. K.; Alabugin, I. V. ; Beke-Somfai, T. ; Blanco-Ania, D. ; Bratlie, K. M. ; Carlson, J. C. T. ; Friscourt, F. ; Giel, M.-C. ; Harris, T. ; Houk, K. N. ; Janssen, L. J. N.; Kacprzak, K. M.; Kann, N. ; Kovalová, A.; Kuba, W. ; La Venia, A.; Liskamp, R. M. J. ; Meuleman, T. J.; Mikula, H. ; Mishra, A.; Moses, J. E. ; Ort, F. F.; Page, K. M.; Paterson, A. J. ; Rutjes, F. P. J. T. ; Rutkowski, J.; Singh, R.; Sinha, A. K.; Skiera, I.; Smedley, C. J. ; Svatunek, D. ; Tiwari, V. K. ; van Hest, J. C. M. ; Vrabel, M. ; Wilkovitsch, M. ; Xu, Z.; Zhang, C.

Title: Click Chemistry

Print ISBN: 9783132435568; Online ISBN: 9783132435575; Book DOI: 10.1055/b000000077

1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

Proclaimed by Sharpless in 2001, the manifesto of click chemistry philosophy shifted the focus from target-oriented to drug-like-oriented synthesis, and has enormously accelerated the drug-discovery process over the last two decades. Copper(I)-catalyzed and metal-free versions of the Huisgen 1,3-dipolar cycloaddition of azides and alkynes have become the reference click chemistry synthetic tools. These processes are adaptable to various drug-design modes such as kinetic target guided synthesis (in situ click chemistry assembling; KTGS), combinatorial chemistry/high-throughput-screening approaches, or structure-based rational projecting. Moreover, the facile click chemistry derivatization of natural or synthetic products, linking molecules or improving the stability of leads by installation of 1,2,3-triazoles, is another important stream of bioactivities. This review is intended to provide a general overview of click-chemistry-powered drug design, with dozens of successful examples resulting in the discovery of nanomolar-active 1,2,3-triazoles in every stage of drug development.

Key words

alkynes - azides - click chemistry - combinatorial chemistry - copper-catalyzed azide–alkyne cycloaddition (CuAAC) - dipolar cycloaddition - drug design - kinetic target guided synthesis (KTGS) - lead compounds - 1,2,3-triazoles
 
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