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Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.

Two classes of prodrugs of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. To this end, a novel efficient synthesis route was developed involving a cross metathesis reaction as a key step. Alkoxyalkyl prodrugs show decent antimalarial activities, but acyloxybenzyl prodrugs proved to be the most interesting and show enhanced antimalarial and antitubercular activity. The most active antimalarial analogues show low nanomolar IC50 values.