Boosting 3 H -Benzo[ f ]chromen-3-one Chalcone with Anti-inflammatory Drugs: Synthesis, Characterization, and Evaluation
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oosting 3H-Benzo[f]chromen-3-one Chalcone with Anti-inflammatory Drugs: Synthesis, Characterization, and Evaluation of Cytotoxicity and Antimicrobial Activity Q. A. H. Jabera,*, N. A. Abdul-Ridab, and Sh. Adnana a
Department of Chemistry, College of Education, University of Al-Qadisiyah, Diwaniyah, 58001 Iraq b
Department of Chemistry, College of Science, University of Qadisiyah, Diwaniyah, 58001 Iraq *e-mail: [email protected] Received March 18, 2020; revised March 26, 2020; accepted March 29, 2020
Abstract—A series of novel 3H-benzo[f]chromen-3-one derivatives bearing non-steroidal anti-inflammatory drug moieties were synthesized with good yields. Benzo[f]coumarin chalcone was prepared via Claisen– Schmidt condensation between 2-acetyl-3H-benzo[f]chromen-3-one and 4-hydroxybenzaldehyde in basic medium and was then esterified with carboxylic acids (drugs) in the presence of phosphoryl chloride and anhydrous zinc(II) chloride. The newly synthesized compounds were characterized by FT-IR and 1H and 13C NMR spectra and elemental analyses and were screened in vitro for their anticancer and antimicrobial activity. Some of the tested compounds showed a good activity in comparison to standard drugs. Keywords: benzo[f]chromen-3-one, chalcone, anti-inflammatory drugs, esterification
DOI: 10.1134/S1070428020090195 INTRODUCTION
RESULTS AND DISCUSSION
Fused chromenes play a very significant role in medicinal chemistry and are used as valuable basic core for the design and synthesis of pharmacologically active compounds [1, 2]. Coumarin and its derivatives possess a wide range of biological activities such as antimicrobial [3], anticancer [4–7], anticoagulant [8], analgesic [9], ulcerogenic [10], antiviral [11], antimalarial [12], anti-inflammatory [13, 14], antidepressant [15], and antioxidant [16, 17] and inhibit HIV protease [18], acetylcholinesterase [19], monoamine oxidase B (MAO-B) [20], and steroid 5α-reductase [21]. In addition, compounds with a chalcone backbone are known to possess a wide range of biological activities [22, 23]. Many coumarin derivatives were designed and found to be promising as organic fluorescent materials for potential applications in biochemical and biological imaging due to their light emission properties [24]. In this work, we report the synthesis of a new series of benzocoumarin derivatives conjugated with anti-inflammatory drugs and their biological evaluation.
Initially, we prepared 3-acetyl-5,6-benzocoumarin 3 by treatment of 2-hydroxynaphthaldehyde 1 with ethyl acetoacetate 2 in the presence of piperidine. The condensation of 3 with 4-hyroxybenzaldehyde gave benzocoumarin chalcone 4, and the latter was coupled with anti-inflammatory drugs, namely clonixin, sulindac, mefenamic acid, flurbiprofen, indomethacin, ketoprofen, and oxaprozin) via esterification in the presence of phosphoryl chloride and anhydrous zinc chloride (Scheme 1). The structures of 5–11 were determined by spectroscopic methods (FT-IR, 1H and 13C NMR) and elemental analyses. The FT-IR spectra of 5–11 showed char
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