Title: Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates
Authors: Steenackers, Hans ×
Ermolatev, Denis
Trang, Tran Thi Thu
Savalia, Bharat
Sharma, Upendra Kumar
De Weerdt, Ami
Shah, Anamik
Vanderleyden, Jos
Van der Eycken, Erik #
Issue Date: Jun-2014
Publisher: Royal Society of Chemistry
Series Title: Organic & Biomolecular Chemistry vol:12 issue:22 pages:3671-3678
Article number: 10.1039/c3ob42282h
Abstract: 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 μM. A remarkable finding was that introduction of the triazole moiety into the side chain of 2-aminoimidazoles with a long (C8-C13) 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.
ISSN: 1477-0520
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Centre of Microbial and Plant Genetics
Molecular Design and Synthesis
Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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