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

Fingerprint

Octanes
Oxygenation
Peroxides
Antimalarials
Salts
Electrons
Lead compounds

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

In: Research on Chemical Intermediates, Vol. 39, No. 1, 01.2013, p. 127-137.

Research output: Contribution to journalArticle

@article{0c42c80598b241e1b06099e7fbea79cd,
title = "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",
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.]",
keywords = "Antimalarial activity, Cyclic peroxide, Photo-oxygenation, Photoinduced electron transfer, Single electron transfer, Triphenylpyrylium salt",
author = "Masaki Kamata and Hagiwara, {Jun Ichi} and Tomoko Hokari and Chiharu Suzuki and Ryohta Fujino and Sayaka Kobayashi and Hye-Sook Kim and Yusuke Wataya",
year = "2013",
month = "1",
doi = "10.1007/s11164-012-0637-3",
language = "English",
volume = "39",
pages = "127--137",
journal = "Research on Chemical Intermediates",
issn = "0922-6168",
publisher = "Springer Netherlands",
number = "1",

}

TY - JOUR

T1 - 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

AU - Kamata, Masaki

AU - Hagiwara, Jun Ichi

AU - Hokari, Tomoko

AU - Suzuki, Chiharu

AU - Fujino, Ryohta

AU - Kobayashi, Sayaka

AU - Kim, Hye-Sook

AU - Wataya, Yusuke

PY - 2013/1

Y1 - 2013/1

N2 - 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.]

AB - 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.]

KW - Antimalarial activity

KW - Cyclic peroxide

KW - Photo-oxygenation

KW - Photoinduced electron transfer

KW - Single electron transfer

KW - Triphenylpyrylium salt

UR - http://www.scopus.com/inward/record.url?scp=84871814918&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84871814918&partnerID=8YFLogxK

U2 - 10.1007/s11164-012-0637-3

DO - 10.1007/s11164-012-0637-3

M3 - Article

VL - 39

SP - 127

EP - 137

JO - Research on Chemical Intermediates

JF - Research on Chemical Intermediates

SN - 0922-6168

IS - 1

ER -