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A Synthetic Route to 3‐(Heteroaryl)‐7‐hydroxycoumarins Designed for Biosensing Applications
Author(s) -
Roubinet Benoît,
Chevalier Arnaud,
Renard PierreYves,
Romieu Anthony
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403215
Subject(s) - chemistry , combinatorial chemistry , cyan , condensation reaction , knoevenagel condensation , fluorescence , analyte , organic chemistry , catalysis , chromatography , physics , quantum mechanics , art , visual arts
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.