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Acyloxybenzyl and alkoxyalkyl prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents

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Abstract
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.
Keywords
Fosmidomycin, prodrugs, nonmevalonate pathway, isoprenoid biosynthesis, malaria, tuberculosis, METHYLERYTHRITOL PHOSPHATE-PATHWAY, PLASMODIUM-FALCIPARUM MALARIA, 1-DEOXY-D-XYLULOSE-5-PHOSPHATE REDUCTOISOMERASE, ESCHERICHIA-COLI, MEP PATHWAY, RESISTANCE, ANALOGS, INHIBITION, FR900098, PHARMACOKINETICS

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Citation

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MLA
Courtens, Charlotte, Martijn Risseeuw, Guy Caljon, et al. “Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.” ACS MEDICINAL CHEMISTRY LETTERS 9.10 (2018): 986–989. Print.
APA
Courtens, Charlotte, Risseeuw, M., Caljon, G., Cos, P., & Van Calenbergh, S. (2018). Acyloxybenzyl and alkoxyalkyl prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents. ACS MEDICINAL CHEMISTRY LETTERS, 9(10), 986–989.
Chicago author-date
Courtens, Charlotte, Martijn Risseeuw, Guy Caljon, Paul Cos, and Serge Van Calenbergh. 2018. “Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.” Acs Medicinal Chemistry Letters 9 (10): 986–989.
Chicago author-date (all authors)
Courtens, Charlotte, Martijn Risseeuw, Guy Caljon, Paul Cos, and Serge Van Calenbergh. 2018. “Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.” Acs Medicinal Chemistry Letters 9 (10): 986–989.
Vancouver
1.
Courtens C, Risseeuw M, Caljon G, Cos P, Van Calenbergh S. Acyloxybenzyl and alkoxyalkyl prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents. ACS MEDICINAL CHEMISTRY LETTERS. 2018;9(10):986–9.
IEEE
[1]
C. Courtens, M. Risseeuw, G. Caljon, P. Cos, and S. Van Calenbergh, “Acyloxybenzyl and alkoxyalkyl prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents,” ACS MEDICINAL CHEMISTRY LETTERS, vol. 9, no. 10, pp. 986–989, 2018.
@article{8584575,
  abstract     = {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.},
  author       = {Courtens, Charlotte and Risseeuw, Martijn and Caljon, Guy and Cos, Paul and Van Calenbergh, Serge},
  issn         = {1948-5875},
  journal      = {ACS MEDICINAL CHEMISTRY LETTERS},
  keywords     = {Fosmidomycin,prodrugs,nonmevalonate pathway,isoprenoid biosynthesis,malaria,tuberculosis,METHYLERYTHRITOL PHOSPHATE-PATHWAY,PLASMODIUM-FALCIPARUM MALARIA,1-DEOXY-D-XYLULOSE-5-PHOSPHATE REDUCTOISOMERASE,ESCHERICHIA-COLI,MEP PATHWAY,RESISTANCE,ANALOGS,INHIBITION,FR900098,PHARMACOKINETICS},
  language     = {eng},
  number       = {10},
  pages        = {986--989},
  title        = {Acyloxybenzyl and alkoxyalkyl prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents},
  url          = {http://dx.doi.org/10.1021/acsmedchemlett.8b00223},
  volume       = {9},
  year         = {2018},
}

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