N-Alkylation of 2-methoxy-10H-phenothiazine revisited. A facile entry to diversely N-substituted phenothiazine-coumarin hybrid dyes
2020
Quesneau, Valentin | Renault, Kévin | Laly, Myriam | Jenni, Sébastien | Ponsot, Flavien | Romieu, Anthony
N-Alkylation of 2-methoxy-10H-phenothiazine, a valuable building block for the synthesis of bioactive compounds and reaction-based fluorescent probes, has been revisited aimed at introducing a substituent easily convertible into cationic or zwitterionic side chains. We focused our attention on the 3-dimethylaminopropyl group since its derivatization through reactions with various alkyl halides or sultones is a well-established and effective way to enhance polarity of diverse hydrophobic molecular scaffolds. This two-step functionalization approach was applied to the synthesis of novel phenothiazine-coumarin hybrid dyes whose spectral features, especially their NIR-I emission, have been determined in aqueous media with the ultimate goal of identifying novel fluorescent markers for bioanalytical applications, including fluorogenic detection of reactive oxygen species (ROS) through selective S-oxidation reaction of phenothiazine scaffold.
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