Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes

Hye Sook Kim, Khurshida Begum, Naoki Ogura, Yusuke Wataya, Yuji Nonami, Toyonari Ito, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide afforded 1,2-bishydroperoxide 3, which could be cycloalkylated on treatment with silver oxide and a 1,ω-diiodoalkane to provide the tricyclic peroxides 12. Trimethylsilylation of 3 followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 14 containing a 1,2,4,5-tetroxepane structure. Photooxygenation of 1 in the presence of either unsaturated hydroperoxides or unsaturated alcohols followed by bis(collidine)-iodine hexafluorophosphate promoted cyclization gave the corresponding cyclic peroxides 15-17. Several of these cyclic peroxides showed substantial antimalarial activity particularly in vitro.

Original languageEnglish
Pages (from-to)1957-1961
Number of pages5
JournalJournal of medicinal chemistry
Volume46
Issue number10
DOIs
Publication statusPublished - May 8 2003

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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