Double prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents.

Courtens, Charlotte;Risseeuw, Martijn;Caljon, Guy;Maes, Louis;Van Calenbergh, Serge;et.al.
(2019) Bioorganic & Medicinal Chemistry Letters : the tetrahedron journal for research at the interface of chemistry and biology — Vol. 29, n° 10, p. 1232-1235 (2019)

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Authors
  • Courtens, Charlotte
    Author
  • Risseeuw, Martijn
    Author
  • Caljon, Guy
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  • Maes, Louis
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  • Martin, AnandiUCLouvain
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  • Van Calenbergh, Serge
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Abstract
A series of eleven double prodrug derivatives of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. A pivaloyloxymethyl (POM) phosphonate prodrug modification was combined with various prodrug derivatisations of the hydroxamate moiety. The majority of compounds showed activity comparable with or inferior to fosmidomycin against P. falciparum. N-benzyl substituted carbamate prodrug 6f was the most active antimalarial analog with an IC value of 0.64 µM. Contrary to fosmidomycin and parent POM-prodrug 5, 2-nitrofuran and 2-nitrothiophene prodrugs 6i and 6j displayed promising antitubercular activities.
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Courtens, C., Risseeuw, M., Caljon, G., Maes, L., Cos, P., Martin, A., & Van Calenbergh, S. (2019). Double prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents. Bioorganic & Medicinal Chemistry Letters : the tetrahedron journal for research at the interface of chemistry and biology, 29(10), 1232-1235. https://doi.org/10.1016/j.bmcl.2019.03.009 (Original work published 2019)