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 journalArticle

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

Fingerprint Dive into the research topics of 'Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes'. Together they form a unique fingerprint.

  • Cite this

    Kim, H. S., Begum, K., Ogura, N., Wataya, Y., Nonami, Y., Ito, T., Masuyama, A., Nojima, M., & McCullough, K. J. (2003). Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes. Journal of medicinal chemistry, 46(10), 1957-1961. https://doi.org/10.1021/jm020387b