Synthesis and structure–activity relationships of novel benzoxaboroles as a new class of antimalarial agents

29 Mar 2011

Yong-Kang Zhang, Jacob J. Plattner, Yvonne R. Freund, Eric E. Easom, Yasheen Zhou, Jiri Gut, Philip J. Rosenthal, David Waterson, Francisco-Javier Gamo, Inigo Angulo-Barturen, Min Ge, Zhiya Li, Lingchao Li, Yong Jian, Han Cui, Hailong Wang, Jian Yang

Bioorganic & Medicinal Chemistry Letters

DOI: 10.1016/j.bmcl.2010.12.034


A series of boron-containing benzoxaborole compounds was designed and synthesized for a structure–activity relationship investigation surrounding 7-(HOOCCH2CH2)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1) with the goal of discovering a new antimalarial treatment. Compound 1 demonstrates the best potency (IC50 = 26 nM) against Plasmodium falciparum and has good drug-like properties, with low molecular weight (206.00), low ClogP (0.86) and high water solubility (750 μg/mL at pH 7).

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