TMEDA-derived biscationic amphiphiles: An economical preparation of potent antibacterial agents.

Autor: Black JW; Department of Chemistry, Villanova University, Villanova, PA 19085, United States., Jennings MC; Department of Chemistry, Temple University, Philadelphia, PA 19122, United States., Azarewicz J; Department of Chemistry, Temple University, Philadelphia, PA 19122, United States., Paniak TJ; Department of Chemistry, Villanova University, Villanova, PA 19085, United States., Grenier MC; Department of Chemistry, Villanova University, Villanova, PA 19085, United States., Wuest WM; Department of Chemistry, Temple University, Philadelphia, PA 19122, United States., Minbiole KP; Department of Chemistry, Villanova University, Villanova, PA 19085, United States. Electronic address: kevin.minbiole@villanova.edu.
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2014 Jan 01; Vol. 24 (1), pp. 99-102. Date of Electronic Publication: 2013 Dec 04.
DOI: 10.1016/j.bmcl.2013.11.070
Abstrakt: Bis-alkylated derivatives of N,N,N',N'-tetramethylethylenediamine (TMEDA) represent a well-known class of versatile biscationic amphiphiles, owing to their low cost and ease of preparation. Asymmetric TMEDA derivatives, however, have been studied significantly less, particularly in regards to their antimicrobial properties. We have thus prepared a series of 36 mono- and bis-alkylated TMEDA derivatives to evaluate their inhibition of bacterial growth. This series of compounds showed low micromolar activity against a panel of four bacteria. Optimal inhibition was observed when the biscationic amphiphiles possessed modest asymmetry and were composed of between 20 and 24 total carbon atoms in the side chains. These amphiphiles were prepared in a simple two-step procedure, utilizing inexpensive materials and atom-economical reactions, making them practical for further development.
(Copyright © 2013 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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