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Benzoxaborole antimalarial agents. Part 4. Discovery of potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles. 2015
Yong-Kang Zhang, and
Jacob J Plattner, and
Eric E Easom, and
Robert T Jacobs, and
Denghui Guo, and
Virginia Sanders, and
Yvonne R Freund, and
Brice Campo, and
Philip J Rosenthal, and
Wei Bu, and
Francisco-Javier Gamo, and
Laura M Sanz, and
Min Ge, and
Liang Li, and
Jie Ding, and
Yin Yang
†Anacor Pharmaceuticals, Inc., 1020 East Meadow Circle, Palo Alto, California 94303, United States.
A series of 6-hetaryloxy benzoxaborole compounds was designed and synthesized for a structure-activity relationship (SAR) investigation to assess the changes in antimalarial activity which result from 6-aryloxy structural variation, substituent modification on the pyrazine ring, and optimization of the side chain ester group. This SAR study discovered highly potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 27-34) with IC50s = 0.2-22 nM against cultured Plasmodium falciparum W2 and 3D7 strains. Compound 9 also demonstrated excellent in vivo efficacy against P. berghei in infected mice (ED90 = 7.0 mg/kg).
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