Benzoxaborole antimalarial agents. Part 2: Discovery of fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles

26 Jan 2012

Yong-Kang Zhang, Jacob J. Plattner, Yvonne R. Freund, Eric E. Easom, Yasheen Zhou, Long Ye, Huchen Zhou, David Waterson, Francisco-Javier Gamo, Laura M. Sanz, Min Ge, Zhiya Li, Lingchao Li, Hailong Wang, Han Cui

Bioorganic & Medicinal Chemistry Letters

DOI: 10.1016/j.bmcl.2011.12.096


A series of new boron-containing benzoxaborole compounds was designed and synthesized for a continuing structure–activity relationship (SAR) investigation to assess the antimalarial activity changes derived from side-chain structural variation, substituent modification on the benzene ring and removal of boron from five-membered oxaborole ring. This SAR study demonstrated that boron is required for the antimalarial activity, and discovered that three fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 14 and 20) have excellent potencies (IC50 0.026–0.209 μM) against Plasmodium falciparum.

The full article can be viewed on the Science Direct website