Abstract
New 4-methyl-7-ethylcoumarin derivatives bearing the azo group were synthesized through series of sequential reactions and tested for their biological activity. Starting from 4-methyl-7-ethylcoumarin prepared from a reaction of m-ethyl phenol and ethyl acetoacetate by pechmann condensation reaction, nitration of 4 -methyl-7-ethyl coumarin using nitric acid was carried out in the presence of sulfuric acid to produce one isomer from 4-methyl-7-ethyl-8-nitrocoumarin under the cold condition at (2-5Cº). Then reducing nitro group used iron metal in an acidic medium to form corresponding amino coumarin, which was converted to azo dyes by reacting its diazonium salt with different phenol derivatives. Mass, FT-IR, 1H-NMR, 13C-NMR, UV spectra, and TLC chromatography signposted the preparation compounds. The synthetic compounds' biological activities were evaluated against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli) at 1×10-3M. It was found that compounds 4 and 6 have a broad spectrum against different types of bacteria, Staphylococcus aureus, and Escherichia coli, compared to the standard drug vancomycin. In contrast, all compounds showed moderate activity against fungi compared with nystatin. The newly synthesized compounds also showed powerful antioxidants compared with ascorbic acid as a standard, especially compound 7 , which showed high effectiveness as an antioxidant compared to the same reference Ascorbic Acid.
Keywords
Amino coumarin, Anti-microbial activity, Azo dyes, coumarin, Diazonium salt
Article Type
Article
How to Cite this Article
Kazem, Muntather Hossam and Ahamed, Luma S.
(2024)
"Synthesis and Biological Studies of 4‐Methyl-7‐Ethylcoumarin Derivatives Containing Azo Group,"
Baghdad Science Journal: Vol. 21:
Iss.
7, Article 23.
DOI: https://doi.org/10.21123/bsj.2023.9143
