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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

1
Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, Brazil
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Faculdade de Farmácia, Centro Universitário Ritter dos Reis, Rua Orfanotrófio 55, 91849-440 Porto Alegre-RS, Brazil
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Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, Rua Sérgio Buarque de Holanda 250, 13083-859 Campinas-SP, Brazil
4
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
Molbank 2016, 2016(2), M894; https://doi.org/10.3390/M894
Received: 8 February 2016 / Revised: 22 March 2016 / Accepted: 31 March 2016 / Published: 11 April 2016
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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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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