Synthesis and Characterization of 7-Hydroxy-4-Methylcoumarin-3-Ethyl Acetate and Its Derivatives
Abstract
Coumarin is a class of compound found abundantly in plants, bacteria and fungi. It is well known for its vast biological activities such as antibacterial, cyclooxygenase inhibition, antimutagenic, scavenging of reactive oxygen species (ROS), anti-inflammatory, anticoagulant, lipoxygenase, CNS stimulants, antithrombotic, vasodilatory, and anticancer activity. In this study, 7-hydroxy-4-methylcoumarin-3-ethyl acetate 1 and its derivatives 2-4 were synthesized. 7-hydroxy-4-methylcoumarin-3-ethyl acetate 1 was synthesized via Pechmann reaction from resorcinol and diethyl acetyl succinate as precursors. Then, several steps of reaction carried out for structural modification of the coumarin were performed. The first reaction is hydrazinolysis of ester group present in coumarin to form 7-hydroxy-4-methylcoumarin-3-acetohydrazide 2. Further reactions were carried out using Williamson etherification in the presence of potassium carbonate as mild base. The Williamson etherification was carried out by using isobutyl chloride to yield 7-isobutyloxy-4-methylcoumarin-3-ethyl acetate 3. Similar to the Williamson esterification reaction, 1-chloroacetone was reacted with 7-hydroxy-4-methylcoumarin-3-ethyl acetate 1 to yield O-alkylated product 7-(2-oxopropoxy)-4-methylcoumarin-3-ethyl acetate 4. The synthesized compounds were characterized using spectroscopic techniques including attenuated total reflection - infrared spectroscopy (ATR-IR) and nuclear magnetic resonance (NMR).
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