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N-Alkylation of 2-Methoxy-10H-Phenothiazine Revisited. A Facile Entry to Diversely N-substituted Phenothiazine-Coumarin Hybrid Dyes

preprint
submitted on 21.08.2020 and posted on 24.08.2020 by Valentin Quesneau, Kevin Renault, Myriam Laly, Sébastien Jenni, Flavien Ponsot, Anthony ROMIEU

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.

Funding

Butyrylcholinesterase-based fluorescent and/or colorimetric detection of organophosphorus nerve agents – DetectOP_BChE

Agence Nationale de la Recherche

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A luminogenic real-time detection system for monitoring enzymatic manufacturing of oligonucleotides – LuminoManufacOligo

Agence Nationale de la Recherche

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Projet ISITE BFC BacterioBioSens (ANR-15-IDEX-0003)

PO FEDER-FSE Bourgogne 2014/2020

History

Email Address of Submitting Author

anthony.romieu@u-bourgogne.fr

Institution

Univ. Bourgogne Franche-Comté

Country

France

ORCID For Submitting Author

0000-0002-2300-4499

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1 08-21-2020

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