Synthesis and in vitro antimalarial activity of sulfone endoperoxides

Mario D. Bachi, Edward E. Korshin, Poonsakdi Ploypradith, Jared N. Cumming, Suji Xie, Theresa A. Shapiro, Gary H. Posner

Research output: Contribution to journalArticlepeer-review

Abstract

A series of 4,8-dimethyl-4-phenylsulfonylmethyl-2,3- dioxabicyclo[3.3.l]nonanes, carrying a variety of substituents at position-8 (4) were prepared by a short and efficient method from R-(+)-limonene. Key reactions include thiol oxygen cooxidation, and alkylation and acylation of a sterically hindered tertiary alcohol compatible with the endoperoxy functionality. Some of compounds 4, which are structurally related to yingzhaosu A (2), were found to exhibit in vitro antimalarial activity comparable to that of artemisinin (1) and superior to that of arteflene (3).

Original languageEnglish (US)
Pages (from-to)903-908
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume8
Issue number8
DOIs
StatePublished - Apr 21 1998

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Synthesis and in vitro antimalarial activity of sulfone endoperoxides'. Together they form a unique fingerprint.

Cite this