The comparative antimalarial properties of weak base and neutral synthetic ozonides

Yuanqing Tang, Sergio Wittlin, Susan A. Charman, Jacques Chollet, Francis C.K. Chiu, Julia Morizzi, Lisa M. Johnson, Josefina Santo Tomas, Christian Scheurer, Chistopher Snyder, Lin Zhou, Yuxiang Dong, William N. Charman, Hugues Matile, Heinrich Urwyler, Arnulf Dorn, Jonathan L. Vennerstrom

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Thirty-three N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in Plasmodium berghei-infected mice. A wide range of Log P/DpH 7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.

Original languageEnglish (US)
Pages (from-to)563-566
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number2
DOIs
StatePublished - Jan 15 2010

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Keywords

  • 1,2,4-Trioxolanes
  • Antimalarial
  • Artemisinin
  • Peroxides
  • Secondary ozonides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Tang, Y., Wittlin, S., Charman, S. A., Chollet, J., Chiu, F. C. K., Morizzi, J., Johnson, L. M., Tomas, J. S., Scheurer, C., Snyder, C., Zhou, L., Dong, Y., Charman, W. N., Matile, H., Urwyler, H., Dorn, A., & Vennerstrom, J. L. (2010). The comparative antimalarial properties of weak base and neutral synthetic ozonides. Bioorganic and Medicinal Chemistry Letters, 20(2), 563-566. https://doi.org/10.1016/j.bmcl.2009.11.088