Synthesis and structure–activity relationships of novel benzoxaboroles as a new class of antimalarial agents
- Department for International Development
- 1 January 2011
- Document Type:
- Journal Article
- Rosenthal, P.J., Wang, H.L., Angulo-Barturen, I., Plattner, J.J., Waterson, D. Easom, E.E., Ge, M., Jian, Y., Li, L.C., Li, Z.Y., Zhang, Y.K., Cui, H., Freund, Y.R., Gamo, F.J., Gut, J., Yan, J., and Zhou, Y.
A series of boron-containing benzoxaborole compounds was designed and synthesized for a structure–activity relationship investigation surrounding 7-(HOOCCH<sub>2</sub>CH<sub>2</sub>)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1) with the goal of discovering a new antimalarial treatment. Compound 1 demonstrates the best potency (IC<sub>50</sub> = 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).
Angulo-Barturen, I.; Cui, H.; Easom, E.E.; Freund, Y.R.; Gamo, F.J.; Ge, M.; Gut, J.; Jian, Y.; Li, L.C.; Li, Z.Y.; Plattner, J.J.; Rosenthal, P.J.; Wang, H.L.; Waterson, D.; Yan, J.; Zhang, Y.K.; Zhou, Y. Synthesis and structure&#8211;activity relationships of novel benzoxaboroles as a new class of antimalarial agents. Bioorganic and Medicinal Chemistry Letters (2011) 21 (2) 644-651. [DOI: 10.1016/j.bmcl.2010.12.034]
Published: 1 January 2011