Photochemical cleavage reaction of 8-quinolinyl sulfonates that are halogenated and nitrated at the 7-position

Shinya Ariyasu, Kengo Hanaya, Megumi Tsunoda, Masanori Kitamura, Masanori Hayase, Ryo Abe, Shin Aoki

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Photochemical bond-cleavage reactions are potentially useful in chemistry, bioorganic chemistry and medicinal chemistry. We previously reported on a photochemical cleavage reaction of 8-quinolinyl sulfonate (8-QS) derivatives in aqueous solution at neutral pH, which we proposed to proceed via an excited triplet state. In this report, we report on the synthesis of some new photocleavable 8-QS derivatives, in which halogen atoms or a nitro group was introduced at the 7-position, in an attempt to improve photoreactive properties and to produce a red-shift in the irradiation wavelength. The introduction of bromine and iodine resulted in an acceleration in the photoreaction by about 1.5 times, possibly due to a heavy atom effect. It was also found that 7-nitro-8-QS absorbs at >360 nm, and, as a result, the S-O bond of this compound can be cleaved by photoirradiation with a fluorescent lamp in aqueous solution and on silicon surface.

Original languageEnglish
Pages (from-to)1355-1362
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume59
Issue number11
DOIs
Publication statusPublished - 2011 Nov
Externally publishedYes

Fingerprint

Photochemical reactions
Derivatives
Bromine
Atoms
Fluorescent lamps
Halogens
Pharmaceutical Chemistry
Silicon
Excited states
Iodine
Irradiation
Wavelength

Keywords

  • 8-Quinolinol
  • Halogenation
  • Nitration
  • Photolysis
  • Sulfonate

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Photochemical cleavage reaction of 8-quinolinyl sulfonates that are halogenated and nitrated at the 7-position. / Ariyasu, Shinya; Hanaya, Kengo; Tsunoda, Megumi; Kitamura, Masanori; Hayase, Masanori; Abe, Ryo; Aoki, Shin.

In: Chemical and Pharmaceutical Bulletin, Vol. 59, No. 11, 11.2011, p. 1355-1362.

Research output: Contribution to journalArticle

Ariyasu, Shinya ; Hanaya, Kengo ; Tsunoda, Megumi ; Kitamura, Masanori ; Hayase, Masanori ; Abe, Ryo ; Aoki, Shin. / Photochemical cleavage reaction of 8-quinolinyl sulfonates that are halogenated and nitrated at the 7-position. In: Chemical and Pharmaceutical Bulletin. 2011 ; Vol. 59, No. 11. pp. 1355-1362.
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