Development of Novel Imaging Fluorescent Agents Bearing Anti-Inflammatory Drugs: Synthesis, Structural Characterization
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evelopment of Novel Imaging Fluorescent Agents Bearing Anti-Inflammatory Drugs: Synthesis, Structural Characterization and Evaluation of Biological Activity Nabeel A. Abdul-Ridaa, Shaimaa Adnanb, and Qassim A. H. Jaberb, 1 aDepartment
b
of Chemistry, College of Science, University of Qadisiyah, Diwanyiah, Iraq Department of Chemistry, College of Education, University of Al-Qadisiyah, Diwanyiah, Iraq Received January 18, 2020; revised January 27, 2020; accepted January 29, 2020
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-3carboxlate (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 (1H,13C) spectral data as well as elemental analysis. The fluorescence properties study was investigated spectrophotometrically in methanol and maximum emission (λem) 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 (ΦF = 0.96), meanwhile, compounds (VII, VIII, IX and XI) gave reasonable quantum yields (ΦF) 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. Keywords: benzocoumarin, fluorescence, anti-inflammatory drugs (NSAIDs), acetylcholinesterase DOI: 10.1134/S1068162020040032
INTRODUCTION Many natural and synthetic compounds containing coumarin nucleus, exhibit various biological and pharmacological activities, which led recently to appear an increasing interest in their synthesis [1–3]. Further, benzocoumarins and its derivatives were exhibited diverse biological activities such as antiinflammatory [4], antimicrobial [5], antioxidant [6], antithrombotic [7], anti HIV [8], anti-tubercular [9], as well as lipid lowering properties [10]. Newly, benzocoumarin derivatives were showed significant antitumor activities against some cancer cell lines [11]. Fluorescence imaging (FI) is one of the importance techniques in biomedical field for monitoring the cells and tissues both in vitro and in vivo [12]. Due to the conjugated aromatic rings, coumarin and benzocomarin derivatives were showed good photophysical properties [13]. Al-Masoudi et al. [9] have synthesized several coumarin and benzocomarin analogs as well as their fluorescence properties study, they are found that the methyl 5,6-benzocoumarin-3-carboxylate have a higher quantum yield (ΦF = 0.98) in com1 Corresponding
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