engleski

Novel iminocoumarin derived imidazo[4,5-b]pyridines as potential pH sensors

Benzazoles and coumarins are among the most privileged heterocyclic subunits in the medicinal chemistry due to their wide range of bioactivity. Iminocoumarine derivatives are known for their interesting spectroscopic properties as well as their application as fluorescent sensors. Monitoring pH range is crucial for studying many biological processes in live cell organelles. Conjugates of benzazoles and iminocoumarins are already being explored for pH sensing applications due to excellent spectroscopic response in correlation with pH value. This work presents the synthesis and spectroscopic characterization of novel iminocoumarine derived imidazo[4, 5- b]pyridines. Main percursor, 2- cyanomethylimidazo[4, 5-b]pyridine, was prepared in the cyclocondensation reaction with 2- cyanoacetamide, while targeted iminocoumarine derivatives were prepared in condensation with chosen 5-substituted salycil benzaldehydes. Nitro- substituted iminocoumarin was further condensed with 5-nitrosalycilbenzaldehid in order to explore additional conjugation on spectroscopic and pH sensing properties. The structures of newly prepared compounds were confirmed by means of 1H and 13C NMR spectroscopy as well as MS spectrometry. pH spectroscopic titrations will be performed in order to determine possible application as pH sensors in solutions followed by determination of pKa values experimentally as well as by computational approaches.

imidazo[4, 5-b]pyridines ; iminocoumarines ; pH sensors, spectroscopic characterization ; computational chemistry

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