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Molbank 2016, 2016(2), M894;


Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, Brazil
Faculdade de Farmácia, Centro Universitário Ritter dos Reis, Rua Orfanotrófio 55, 91849-440 Porto Alegre-RS, Brazil
Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, Rua Sérgio Buarque de Holanda 250, 13083-859 Campinas-SP, Brazil
Departamento de Química Orgânica, Instituto de Química, Universidade Estadual de Campinas, Rua Josué de Castro s/n, 13083-970 Campinas-SP, Brazil
Author to whom correspondence should be addressed.
Academic Editor: Norbert Haider
Received: 8 February 2016 / Revised: 22 March 2016 / Accepted: 31 March 2016 / Published: 11 April 2016
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Nature often produces compounds with a high degree of symmetry to reduce structural information and complexity. Synthesis of identical twin drugs, through the linkage of two identical pharmacophoric entities, is a classical strategy to produce more potent and/or selective drugs. Herein, two units of the privileged core of the coumarin hymecromone were linked together using “click chemistry”. Synthesis of 1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole was achieved by coupling of two identical units of an azido coumarin with a symmetrical alkine using copper(I)-catalyzed alkyne-azide cycloaddition reaction, in good yields and with complete regioselectivity. View Full-Text
Keywords: coumarins; twin drugs; click chemistry; pechmann condensation coumarins; twin drugs; click chemistry; pechmann condensation

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Torres, F.C.; de Azambuja, G.O.; Gonçalves, I.L.; Gonçalves, G.A.; von Poser, G.L.; Kawano, D.F.; Eifler-Lima, V.L. 1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole. Molbank 2016, 2016, M894.

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