Development of Novel Imaging Fluorescent Agents Bearing Anti-Inflammatory Drugs: Synthesis, Structural Characterization and Evaluation of Biological Activity

A new series of 5,6-benzocoumarin derivatives carrying anti-inflammatory drugs were synthesized via alkylamide spacers, the target to develop novel imaging fluorescent agents as useful technique to cancer early discovery. Experimentally, treatment ofN-Boc-1,3-propanediamine with ethyl 5,6-benzocoumarin-3-carboxlate (III) under reflux conditions followed by hydrolyzed with CF3COOH to the corresponding primary amine (V), then treatment of derivative (V) with anti-inflammatory drugs have carboxylic group in presence of DCC (N,N'-dicyclohexylcarbodiimide) as catalyst and MeCN as solvent. The structure of the synthesized compounds was confirmed by FT-IR, NMR (H-1,C-13) spectral data as well as elemental analysis. The fluorescence properties study was investigated spectrophotometrically in methanol and maximum emission (lambda(em)) exhibited within range 411-436 nm, meanwhile, the quantum yields were calculated comparison to Rhodamine 6G as reference. Interestingly, the compound (III) gave a higher quantum yield (phi(F)= 0.96), meanwhile, compounds (VII,VIII,IXandXI) gave reasonable quantum yields (phi(F)) 0.60, 0.65, 0.78 and 0.84, respectively. All synthesized compounds were screened for their anti-AChE and antimicrobial activity. Based on the results, some of the compounds showed good activity in compared to the standard drugs.