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o -Nitrobenzyl Oxime Ethers Enable Photoinduced Cyclization Reaction to Provide Phenanthridines under Aqueous Conditions.

Hidenori OkamuraMomoka IidaYui KaneyamaFumi Nagatsugi
Published in: Organic letters (2023)
In this paper, we describe a novel N-O photolysis of o -nitrobenzyl oxime ethers that enables the synthesis of phenanthridines via intramolecular cyclization reactions. Without the use of additional photocatalysts or photosensitizers, the process proceeds with an efficiency of ≤96% upon exposure of the sample to near-visible light (405 nm) under aqueous conditions. Through the photoinduced production of a fluorescent phenanthridine derivative in HeLa cells, the progress of the reaction under biological conditions was demonstrated. This photoinduced cyclization reaction could be used as a different photochemical instrument to control biological processes by inducing the production of bioactive molecules.
Keyphrases
  • electron transfer
  • visible light
  • photodynamic therapy
  • cell cycle arrest
  • induced apoptosis
  • ionic liquid
  • cell death
  • oxidative stress
  • living cells
  • endoplasmic reticulum stress