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
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-04-01
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| Series: | Molbank |
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| Online Access: | http://www.mdpi.com/1422-8599/2016/2/M894 |
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| author | Fernando Cidade Torres Gabriel Oliveira de Azambuja Itamar Luís Gonçalves Guilherme Arraché Gonçalves Gilsane Lino von Poser Daniel Fábio Kawano Vera Lucia Eifler-Lima |
| author_facet | Fernando Cidade Torres Gabriel Oliveira de Azambuja Itamar Luís Gonçalves Guilherme Arraché Gonçalves Gilsane Lino von Poser Daniel Fábio Kawano Vera Lucia Eifler-Lima |
| author_sort | Fernando Cidade Torres |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T21:19:03Z |
| format | Article |
| id | doaj.art-646b4b0d65fb4febadf1164eb52ab8ab |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-04-12T21:19:03Z |
| publishDate | 2016-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-646b4b0d65fb4febadf1164eb52ab8ab2022-12-22T03:16:21ZengMDPI AGMolbank1422-85992016-04-0120162M89410.3390/M894M8941-[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-triazoleFernando Cidade Torres0Gabriel Oliveira de Azambuja1Itamar Luís Gonçalves2Guilherme Arraché Gonçalves3Gilsane Lino von Poser4Daniel Fábio Kawano5Vera Lucia Eifler-Lima6Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, BrazilFaculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, BrazilFaculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, BrazilFaculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, BrazilFaculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, BrazilFaculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, Rua Sérgio Buarque de Holanda 250, 13083-859 Campinas-SP, BrazilFaculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre-RS, BrazilNature 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.http://www.mdpi.com/1422-8599/2016/2/M894coumarinstwin drugsclick chemistrypechmann condensation |
| spellingShingle | Fernando Cidade Torres Gabriel Oliveira de Azambuja Itamar Luís Gonçalves Guilherme Arraché Gonçalves Gilsane Lino von Poser Daniel Fábio Kawano Vera Lucia Eifler-Lima 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 coumarins twin drugs click chemistry pechmann condensation |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | coumarins twin drugs click chemistry pechmann condensation |
| url | http://www.mdpi.com/1422-8599/2016/2/M894 |
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