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Paper | Special issue | Vol 80, No. 2, 2010, pp.977-988
Published online, 15th October, 2009
DOI: 10.3987/COM-09-S(S)69
Utilization of the Suzuki Coupling to Enhance the Antituberculosis Activity of Aryloxazoles

Garrett C. Moraski, Scott G. Franzblau, and Marvin J. Miller*

*Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46656, U.S.A.

Abstract

Potent antituberculosis aryl oxazoles can be made in an efficient three step process--formation of β-hydroxy amides with serine benzyl ester; cyclization to afford oxazolines; and then dehydration to give the corresponding oxazoles. Furthermore, incorporation of an appropriate aryl halide allows utilization of the Suzuki cross coupling reaction to access new chemical space and more elaborate analogs. The compounds prepared by this method were shown to possess improved activity against M. tuberculosis, extremely low toxicity toward VERO cells and, as a result, high therapeutic indexes.