Bis-alkylated derivatives of N,N,N',N'-tetramethylethylenediamine (TMEDA) represent a well-known class of biscationic amphiphiles, owing to their low cost and ease of preparation. We have prepared a series of 36 mono- and bis-alkylated TMEDA derivatives, including asymmetric variants, 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 bis-cationic amphiphiles possessed modest asymmetry and were composed of between 20-24 total carbon atoms in the side chains. This method has been extended to related structures with three amine groups.  These amphiphiles were prepared in simple one- and two-step procedures, utilizing inexpensive materials and atom-economical reactions.

Polyamine-derived amphiphiles: Straightforward preparations of potent antibacterial agents

248th National Meeting (2014)

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