Issue 22, 2014

Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates

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.

Graphical abstract: Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2013
Accepted
18 Mar 2014
First published
18 Mar 2014

Org. Biomol. Chem., 2014,12, 3671-3678

Author version available

Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates

H. Steenackers, D. Ermolat'ev, T. T. T. Trang, B. Savalia, U. K. Sharma, A. De Weerdt, A. Shah, J. Vanderleyden and E. V. Van der Eycken, Org. Biomol. Chem., 2014, 12, 3671 DOI: 10.1039/C3OB42282H

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