Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 22, Pages 3671-3678Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob42282h
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Funding
- Research Fund of the KU Leuven [BOF-IDO/11/008]
- Institute for the Promotion of Innovation through Science and Technology in Flanders [IWT-SBO 120050]
- Fund for Scientific Research (FWO) - Flanders (Belgium)
- Erasmus Mundus External Cooperation Window Lot 15 India [EMECW15]
- 322-program of Vietnamese Government
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A microwave-assisted protocol was developed for the construction of 2-amino-1H-imidazole/triazole conjugates starting from the previously described 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts. The process involves a one-pot hydrazinolysis/Dimroth-rearrangement of these salts followed by a ligand-free copper nanoparticle-catalyzed azide-alkyne Huisgen cycloaddition. The 2-amino-1H-imidazole/triazole conjugates showed moderate to high preventive activity against biofilms of S. Typhimurium, E. coli, P. aeruginosa and S. aureus. The most active compounds had BIC50 values between 1.3 and 8 mu M. A remarkable finding was that introduction of the triazole moiety into the side chain of 2-aminoimidazoles with a long (C-8-C-13) 2N-alkyl chain did drastically improve their activity. Conclusively, the 2-amino-1H-imidazole/triazole scaffold provides a lead structure for further design and development of novel biofilm inhibitors.
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