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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

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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
 
  • 10 Gopalan B, Balasubramanian KK, In: Click Reactions in Organic Synthesis Chandrasekaran S. Wiley-VCH Weinheim, Germany 2016; 25-76
    Crossref
  • 15 Röper S, Kolb HC, In: Fragment-Based Approaches in Drug Discovery Jahnke W, Erlanson DA. Wiley-VCH Weinheim, Germany 2006; 311-339
    Crossref
  • 29 de Carvalho da Silva F, do Carmo Cardoso MF, Ferreira PG, Ferreira VF, In: Chemistry of 1,2,3-Triazoles Dehaen W, Bakulev VA. Springer Cham, Switzerland 2015; 117-165
  • 30 Ma N, Wang Y, Zhao B.-X, Ye W.-C, Sheng J. Drug Des., Dev. Ther. 2015; 1585
  • 41 Reddy NB, Narayan GKASS, Hunnur RK, Kaushik VK, Badarinath G, Mamatha B, Aminul I. Pharm. Lett. 2012; 4: 674 and references cited therein
    Search in Google Scholar
  • 45 Zhou J, Bhattacharjee A, Chen S, Chen Y, Duffy E, Farmer J, Goldberg J, Hanselmann R, Ippolito JA, Lou R, Orbin A, Oyelere A, Salvino J, Springer D, Tran J, Wang D, Wu Y, Johnson G. Bioorg. Med. Chem. Lett. 2008; 18: 6175
    CrossrefPubMedSearch in Google Scholar
  • 53 Beck H, Jeske M, Thede K, Stoll F, Flamme I, Akbaba M, Ergüden JK, Karig G, Keldenich J, Oehme F, Militzer HC, Hartung IV, Thuss U. ChemMedChem 2018; 13: 988
    CrossrefPubMedSearch in Google Scholar
  • 57 Si X, Wang J, Cheng Y, Shi J, Cui L, Zhang H, Huang Y, Liu W, Chen L, Zhu J, Zhang S, Li W, Sun Y, Wang H, Zhang X, Wang M, Yang L, Zhang L. Ther. Adv. Med. Oncol. 2020; 12: 1
    CrossrefPubMedSearch in Google Scholar
  • 58 Bonnefond ML, Florent R, Lenoir S, Lambert B, Abeilard E, Giffard F, Louis MH, Elie N, Briand M, Vivien D, Poulain L, Gauduchon P, NʼDiaye M. Oncotarget 2018; 9: 33896
    CrossrefPubMedSearch in Google Scholar
  • 69 Oueis E, Santoni G, Ronco C, Syzgantseva O, Tognetti V, Joubert L, Romieu A, Weik M, Jean L, Sabot C, Nachone F, Renard P.-Y. Org. Biomol. Chem. 2014; 12: 156
    CrossrefPubMedSearch in Google Scholar
  • 70 Mocharla VP, Colasson B, Lee LV, Röper S, Sharpless KB, Wong C.-H, Kolb HC. Angew. Chem. Int. Ed. 2005; 44: 116
    Search in Google Scholar
  • 72 Hirose T, Maita N, Gouda H, Koseki J, Yamamoto T, Sugawara A, Nakano H, Hirono S, Shiomi K, Watanabe T, Taniguchi H, Sharpless KB, Ōmura S, Sunazuka T. Proc. Natl. Acad. Sci. U. S. A. 2013; 110: 15892
    CrossrefPubMedSearch in Google Scholar
  • 76 Whiting M, Muldoon J, Lin Y.-C, Silverman SM, Lindstrom W, Olson AJ, Kolb HC, Finn MG, Sharpless KB, Elder JH, Fokin VV. Angew. Chem. Int. Ed. 2006; 45: 1435
    CrossrefPubMedSearch in Google Scholar
  • 78 Tieu W, Soares da Costa TP, Yap MY, Keeling KL, Wilce MCJ, Wallace JC, Booker GW, Polyak SW, Abell AD. Chem. Sci. 2013; 4: 3533
    CrossrefSearch in Google Scholar
  • 79 Deprez-Poulain R, Hennuyer N, Bosc D, Liang WG, Enée E, Marechal X, Charton J, Totobenazara J, Berte G, Jahklal J, Verdelet T, Dumont J, Dassonneville S, Woitrain E, Gauriot M, Paquet C, Duplan I, Hermant P, Cantrelle F.-X, Sevin E, Culot M, Landry V, Herledan A, Piveteau C, Lippens G, Leroux F, Tang W.-J, van Endert P, Staels B, Deprez B. Nat. Commun. 2015; 6: 8250
    CrossrefPubMedSearch in Google Scholar
  • 81 Grimster NP, Stump B, Fotsing JR, Weide T, Talley TT, Yamauchi JG, Nemecz Á, Kim C, Ho K.-Y, Sharpless KB, Taylor P, Fokin VV. J. Am. Chem. Soc. 2012; 134: 6732
    CrossrefPubMedSearch in Google Scholar
  • 82 Soares da Costa TP, Tieu W, Yap MY, Pendini NR, Polyak SW, Pedersen DS, Morona R, Turnidge JD, Wallace JC, Wilce MCJ, Booker GW, Abell AD. J. Biol. Chem. 2012; 287: 17823
    CrossrefPubMedSearch in Google Scholar
  • 94 Millward SW, Henning RK, Kwong GA, Pitram S, Agnew HD, Deyle KM, Nag A, Hein J, Lee SS, Lim J, Pfeilsticker JA, Sharpless KB, Heath JR. J. Am. Chem. Soc. 2011; 133: 18280
    CrossrefPubMedSearch in Google Scholar
  • 95 Agnew HD, Rohde RD, Millward SW, Nag A, Yeo W.-S, Hein JE, Pitram SM, Tariq AA, Burns VM, Krom RJ, Fokin VV, Sharpless KB, Heath JR. Angew. Chem. Int. Ed. 2009; 48: 4944
    CrossrefPubMedSearch in Google Scholar
  • 102 Kidd SL, Osberger TJ, Mateu N, Sore HF, Spring DR. Front. Chem. (Lausanne, Switz.) 2018; 6: 460
    Search in Google Scholar
  • 103 Mondal M, Unver MY, Pal A, Bakker M, Berrier SP, Hirsch AKH. Chem.–Eur. J. 2016; 22: 14826
    Search in Google Scholar
  • 121 Hou J, Li Z, Fang Q, Feng C, Zhang H, Guo W, Wang H, Gu G, Tian Y, Liu P, Liu R, Lin J, Shi Y.-k, Yin Z, Shen J, Wang PG. J. Med. Chem. 2012; 55: 3066
    CrossrefPubMedSearch in Google Scholar
  • 122 Suzuki T, Ota Y, Ri M, Bando M, Gotoh A, Itoh Y, Tsumoto H, Tatum PR, Mizukami T, Nakagawa H, Iida S, Ueda R, Shirahige K, Miyata N. J. Med. Chem. 2012; 55: 9562
    CrossrefPubMedSearch in Google Scholar
  • 126 Zhou B, He Y, Zhang X, Xu J, Luo Y, Wang Y, Franzblau SG, Yang Z, Chan RJ, Liu Y, Zheng J, Zhang Z.-Y. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: 4573
    CrossrefPubMedSearch in Google Scholar
  • 145 Christodoulou MS, Mori M, Pantano R, Alfonsi R, Infante P, Botta M, Damia G, Ricci F, Sotiropoulou PA, Liekens S, Botta B, Passarella D. ChemPlusChem 2015; 80: 938
    CrossrefPubMedSearch in Google Scholar
  • 146 Keck TM, Banala AK, Slack RD, Burzynski C, Bonifazi A, Okunola-Bakare OM, Moore M, Deschamps JR, Rais R, Slusher BS, Newman AH. Bioorg. Med. Chem. 2015; 23: 4000
    CrossrefPubMedSearch in Google Scholar
  • 153 Díaz JL, Christmann U, Fernández A, Torrens A, Port A, Pascual R, Álvarez I, Burgueño J, Monroy X, Montero A, Balada A, Vela JM, Almansa C. J. Med. Chem. 2015; 58: 2441
    CrossrefPubMedSearch in Google Scholar
  • 156 Doiron JE, Le CA, Ody BK, Brace JB, Post SJ, Thacker NL, Hill HM, Breton GW, Mulder MJ, Chang S, Bridges TM, Tang L, Wang W, Rowe SM, Aller SG, Turlington M. Chem.–Eur. J. 2019; 25: 3662
    CrossrefPubMedSearch in Google Scholar
  • 157 Mugnaini C, Nocerino S, Pedani V, Pasquini S, Tafi A, De Chiaro M, Bellucci L, Valoti M, Guida F, Luongo L, Dragoni S, Ligresti A, Rosenberg A, Bolognini D, Cascio MG, Pertwee RG, Moaddel R, Maione S, Di Marzo V, Corelli F. ChemMedChem 2012; 7: 920
    CrossrefPubMedSearch in Google Scholar
  • 165 Chen J, Ma L, Zhang R, Tang J, Lai H, Wang J, Wang G, Xu Q, Chen T, Peng F, Qiu J, Liang X, Cao D, Ran Y, Peng A, Wei Y, Chen L. Arch. Pharm. (Weinheim, Ger.) 2012; 345: 945
    CrossrefPubMedSearch in Google Scholar
  • 170 Kacprzak KM, In: Natural Products: Phytochemistry, Botany and Metabolism of Alkaloids, Phenolics and Terpenes Ramawat KG, Mérillon J.-M. Springer Heidelberg 2013; 643
    Crossref
  • 180 Yu F, Peng Y, Wang Q, Shi Y, Si L, Wang H, Zheng Y, Lee E, Xiao S, Yu M, Li Y, Zhang C, Tang H, Wang C, Zhang L, Zhou D. Eur. J. Med. Chem. 2014; 77: 258
    CrossrefPubMedSearch in Google Scholar
  • 181 Yu F, Wang Q, Zhang Z, Peng Y, Qiu Y, Shi Y, Zheng Y, Xiao S, Wang H, Huang X, Zhu L, Chen K, Zhao C, Zhang C, Yu M, Sun D, Zhang L, Zhou D. J. Med. Chem. 2013; 56: 4300
    CrossrefPubMedSearch in Google Scholar
  • 185 Travelli C, Aprile S, Rahimian R, Grolla AA, Rogati F, Bertolotti M, Malagnino F, di Paola R, Impellizzeri D, Fusco R, Mercalli V, Massarotti A, Stortini G, Terrazzino S, Del Grosso E, Fakhfouri G, Troiani MP, Alisi MA, Grosa G, Sorba G, Canonico PL, Orsomando G, Cuzzocrea S, Genazzani AA, Galli U, Tron GC. J. Med. Chem. 2017; 60: 1768
    CrossrefPubMedSearch in Google Scholar
  • 186 Travelli C, Aprile S, Mattoteia D, Colombo G, Clemente N, Scanziani E, Terrazzino S, Alisi MA, Polenzani L, Grosa G, Genazzani AA, Tron GC, Galli U. Eur. J. Med. Chem. 2019; 181: 111576
    CrossrefPubMedSearch in Google Scholar
  • 187 Theeramunkong S, Galli U, Grolla AA, Caldarelli A, Travelli C, Massarotti A, Troiani MP, Alisi MA, Orsomando G, Genazzani AA, Tron GC. MedChemComm 2015; 6: 1891
    CrossrefSearch in Google Scholar
  • 190 Taddei M, Ferrini S, Giannotti L, Corsi M, Manetti F, Giannini G, Vesci L, Milazzo FM, Alloatti D, Guglielmi MB, Castorina M, Cervoni ML, Barbarino M, Foderà R, Carollo V, Pisano C, Armaroli S, Cabri W. J. Med. Chem. 2014; 57: 2258
    CrossrefPubMedSearch in Google Scholar