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Antimicrobial Agents and Chemotherapy, February 1998, p. 339-343, Vol. 42, No. 2
0066-4804/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.

Synthesis and Evaluation of Dinitroanilines for Treatment of Cryptosporidiosis

John W. Benbow,1,* Erin L. Bernberg,1 Anna Korda,1 and Jan R. Mead2,3

Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 180151; and Department of Pediatrics, Emory University, Atlanta, Georgia 300222; and Veterans Affairs Medical Center, Decatur, Georgia 300333

Received 2 May 1997/Returned for modification 8 September 1997/Accepted 18 November 1997

The efficacy of a series of dinitroaniline herbicide derivatives for the treatment of Cryptosporidium parvum infections has been studied. The lead compounds oryzalin (compound 1) and trifluralin (compound 2) have low water solubility (<3 ppm) which was alleged to be a major contributor to their poor pharmacokinetic availability. Derivatives of compounds 1 and 2 were synthesized. In these derivatives the functionality at the C-1 amine position or the C-4 position was substituted with groups with various hydrophilicities to determine if a direct relation existed between water solubility and overall activity. The chlorinated precursors of these derivatives were also examined and were found to be less active in the C. parvum assays, a result in direct contrast to earlier work with Leishmania. Enhanced water solubility alone did not overcome the drug availability problem; however, several candidates with similar activities but with toxicities lower than those of the lead compounds were produced.

* Corresponding author. Mailing address: Department of Chemistry, Lehigh University, 6 E. Packer Ave., Bethlehem, PA 18015. Phone: (610) 758-3469. Fax: (610) 758-6536. E-mail: jwb4{at}lehigh.edu.

Antimicrobial Agents and Chemotherapy, February 1998, p. 339-343, Vol. 42, No. 2
0066-4804/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.


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