The structure and antimalarial activity of dispiro-1,2,4,5-tetraoxanes derived from (+)-dihydrocarvone

Yuxiang Dong, Kevin J. McCullough, Sergio Wittlin, Jacques Chollet, Jonathan L Vennerstrom

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

An unsaturated dispiro 1,2,4,5-tetraoxane formed by peroxidation of (+)-dihydrocarvone was converted into four structurally diverse derivatives. X-ray crystallographic analysis shows that the structures possess central tetraoxane rings with spiro-2,5-disubstituted cyclohexylidene substituents and 6-membered rings in classical chair conformations. As polarity in the tetraoxane series increased, in vitro potency against Plasmodium falciparum decreased.

Original languageEnglish (US)
Pages (from-to)6359-6361
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number22
DOIs
StatePublished - Nov 15 2010

Fingerprint

Tetraoxanes
Antimalarials
Plasmodium falciparum
Conformations
X-Rays
Derivatives
X rays
dihydrocarvone

Keywords

  • 1,2,4,5-Tetraoxane
  • Antimalarial
  • Artemisinin
  • Peroxide

ASJC Scopus subject areas

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

Cite this

The structure and antimalarial activity of dispiro-1,2,4,5-tetraoxanes derived from (+)-dihydrocarvone. / Dong, Yuxiang; McCullough, Kevin J.; Wittlin, Sergio; Chollet, Jacques; Vennerstrom, Jonathan L.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 20, No. 22, 15.11.2010, p. 6359-6361.

Research output: Contribution to journalArticle

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