A Synthetic Route to 3‐(Heteroaryl)‐7‐hydroxycoumarins Designed for Biosensing Applications

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Abstract
A straightforward method to synthesize 3‐(2‐benzimidazolyl)‐7‐hydroxycoumarins, based on the condensation reaction of 7‐acetoxy‐3‐formylcoumarin with various C‐ and/or N‐substituted ortho‐phenylenediamine derivatives is presented. This unusual approach proved particularly effective for introducing different hydrophilic groups (carboxylic or sulfonic acids or trimethylalkylammonium moieties) onto the heteroaryl scaffold, leading to cyan‐green emitting coumarins that were both water‐soluble and strongly fluorescent under physiological conditions. The further extension of this condensation reaction to bis(2‐aminophenyl)diselenide enabled the first synthesis of 3‐(2‐benzoselenazolyl)‐7‐hydroxycoumarin. The potential utility of these new 7‐hydroxycoumarins was demonstrated through the synthesis and spectroscopic and analyte‐responsive behavior of fluorogenic probes suitable for sensing biologically relevant thiols and urokinase, a protease that plays a key role in cancer invasion and metastasis.

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