Weak base dispiro-1,2,4-trioxolanes: Potent antimalarial ozonides

Yuanqing Tang, Yuxiang Dong, Sergio Wittlin, Susan A. Charman, Jacques Chollet, Francis C.K. Chiu, William N. Charman, Hugues Matile, Heinrich Urwyler, Arnulf Dorn, Saroj Bajpai, Xiaofang Wang, Maniyan Padmanilayam, Jean M. Karle, Reto Brun, Jonathan L. Vennerstrom

Research output: Contribution to journalArticle

53 Scopus citations

Abstract

Thirty weak base 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. Amino amide trioxolanes had the best combination of antimalarial and biopharmaceutical properties. Guanidine, aminoxy, and amino acid trioxolanes had poor antimalarial activity. Lipophilic trioxolanes were less stable metabolically than their more polar counterparts.

Original languageEnglish (US)
Pages (from-to)1260-1265
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number5
DOIs
StatePublished - Mar 1 2007

Keywords

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

ASJC Scopus subject areas

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

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    Tang, Y., Dong, Y., Wittlin, S., Charman, S. A., Chollet, J., Chiu, F. C. K., Charman, W. N., Matile, H., Urwyler, H., Dorn, A., Bajpai, S., Wang, X., Padmanilayam, M., Karle, J. M., Brun, R., & Vennerstrom, J. L. (2007). Weak base dispiro-1,2,4-trioxolanes: Potent antimalarial ozonides. Bioorganic and Medicinal Chemistry Letters, 17(5), 1260-1265. https://doi.org/10.1016/j.bmcl.2006.12.007