Synthesis and evaluation of amphiphilic quaternary ammonium antimicrobials

ORGN 129

James H. Wynne, jwynne@ccs.nrl.navy.mil1, William L. Straube2, Arthur W. Snow1, and Joanne M. Jones-Meehan1. (1) Chemistry Division, Naval Research Laboratory, 4555 Overlook AVE, SW, Washington, DC 20375, (2) Howard County Community College, 10901 Little Patuxent Parkway, Columbia, MD 21044
A homologous series of amphiphilic quaternary ammonium salts (3, R1=H, CH3; n=1-4; R2=nC6H13 - nC16H33; X=Br, Cl) were synthesized from the halogen terminated monodisperse oxyethylene and tertiary amine precursors. This one-pot process resulted in easily isolatable products and high yields. The number of oxyethylene units regulate the hydrophilic-hydrophobic balance and subsequent miscibility, as well as, correlate with the minimum inhibitory concentration for both Gram-positive and Gram–negative bacteria. Synthesis, trends in antimicrobial performance, as well as structural-activity correlations are reported.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006