Applications of triphenylpyrylium salt-sensitized electron-transfer photo-oxygenation reactions to the synthesis of benzo-fused 1,4-diaryl-2,3- dioxabicyclo[2.2.2]octanes as new antimalarial cyclic peroxides

Masaki Kamata, Jun Ichi Hagiwara, Tomoko Hokari, Chiharu Suzuki, Ryohta Fujino, Sayaka Kobayashi, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Benzo-fused 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes 4a-d (4a: Ar = C 6H5, 4b: Ar = p-FC6H4, 4c: Ar = p-MeC6H4, 4d: Ar = p-MeOC6H4) were synthesized by 2,4,6-triphenylpyrylium tetrafluoroborate (TPPBF 4)-sensitized photoinduced electron-transfer (PET)-promoted oxygenation reactions, and their in-vitro antimalarial activity was evaluated. The results showed that these substances have sufficiently high activity to enable them to serve as antimalarial lead compounds. In addition, TPPBF 4-biphenyl-cosensitized PET oxygenation was shown to be an efficient method for introduction of an O-O moiety in the construction of antimalarial cyclic peroxides. Graphical Abstract: New antimalarial bicyclic peroxides 4 were synthesized by TPPBF4-sensitized photoinduced electron-transfer oxygenation reactions.[Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)127-137
Number of pages11
JournalResearch on Chemical Intermediates
Volume39
Issue number1
DOIs
Publication statusPublished - Jan 2013

Keywords

  • Antimalarial activity
  • Cyclic peroxide
  • Photo-oxygenation
  • Photoinduced electron transfer
  • Single electron transfer
  • Triphenylpyrylium salt

ASJC Scopus subject areas

  • Chemistry(all)

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