Antimalarial activity of aryl-substituted 2-ethoxyacetamides

CHED 1284

Joshua W. Major, gutterid@usna.edu1, Clare E. Gutteridge, gutterid@usna.edu1, and Apurba K. Bhattacharjee, apurba.bhattacharjee@na.amedd.army.mil2. (1) Department of Chemistry, United States Naval Academy, 572M Holloway Road, Mailstop 9B, Annapolis, MD 21402, (2) Experimental Therapeutics, Molecular Modeling, Walter Reed Army Institute of Research, 503 Robert Grant Road, Silver Spring, MD 20910
The chalcone class of compounds appears to possess antimalarial activity by a mechanism distinct from those employed by other antimalarial agents. We have developed a pharmacophore from the structure-activity relations of the chalcones, and with it determined that 2-ethoxy-2,N-diphenylacetamides should also mediate antimalarial effects by this novel mechanism. In contrast to the chalcones which we have shown to be susceptible to metabolic degradation, such acetamides are potentially metabolically stable. We will describe a four-step synthesis of a series of bisarylated 2-ethoxyacetamides, their in vitro efficacy against Plasmodium falciparum and the emerging in vitro structure-activity relations of these compounds.
 

Undergraduate Research Poster Session: Medicinal Chemistry
2:00 PM-4:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008