N. A. Abdul-Rida, S. Adnan, Q. A. Jaber
Jul 1, 2020
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Journal
Russian Journal of Bioorganic Chemistry
Abstract
Abstract 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 of N -Boc-1,3-propanediamine with ethyl 5,6-benzocoumarin-3-carboxlate ( III ) under reflux conditions followed by hydrolyzed with CF 3 COOH 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 ( 1 H, 13 C) spectral data as well as elemental analysis. The fluorescence properties study was investigated spectrophotometrically in methanol and maximum emission (λ 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 (Φ F = 0.96), meanwhile, compounds ( VII , VIII , IX and XI ) gave reasonable quantum yields (Φ 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.