Optimization of imidazole-4,5-dicarboxylic acid libraries from anilines and alkanamines

CHED 1311

Kelly Lawson, kelly-lawson@utulsa.edu1, John C. DiCesare, john-dicesare@utulsa.edu2, and Paul W. Baures, paul-baures@utulsa.edu2. (1) Department of Chemistry and Biochemistry, The University of Tulsa, Keplinger Hall, 800 South Tucker Drive, Tulsa, OK 74104, (2) Department of Chemistry and Biochemistry, University of Tulsa, Keplinger Hall, 800 South Tucker Drive, Tulsa, OK 74104
This research utilizes imidazole-4,5-dicarboxylic acid (145DA) as a scaffold for the synthesis of a molecular libraries, the purpose of which is to discover biologically active small molecules to study the cell. For example, derivatives of I45DA bearing anilines and alkanamines are known in the literature to have anti-proliferative activity in HL-60 cells [J. Med. Chem. 2005, 48, 5955-5965]. Our objective in this project was to optimize the synthesis and purification of these I45DA derivatives in order to simplify the production of molecular libraries. The reaction was varied with respect to solvent, temperature, time, and stoichiometry of reagents. These derivatives also require an intermediate whose purification method was varied. We characterized the products or reaction mixtures by using 1H-NMR spectroscopy or LC-MS or both. The results of these efforts will be applied to the synthesis of molecular libraries for subsequent testing as part of the NIH Roadmap.
 

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