Abstract
New pyranocoumarin and coumarin-sulfonamide derivatives were prepared and evaluated for their antioxidant, antimicrobial, and/or anti-inflammatory activities. Coumarin-sulfonamide compounds 8a–d demonstrated significant antioxidant activity, while 7c,d, 8c,d, and 9c,d exhibited antimicrobial activity equal to or higher than the standard antimicrobials against at least one tested microorganism. Regarding the anti-inflammatory testing, pyranocoumarins 2b, 3a,b and 5c and coumarin-sulfonamide compound 9a showed more potent antiproteinase activity than aspirin in vitro; however, five compounds were as potent as aspirin. The anti-inflammatory activity of the promising compounds was further assessed pharmacologically on formaldehyde-induced rat paw oedema and showed significant inhibition of oedema. For in vitro COX-inhibitory activity of coumarin derivatives, pyranocoumarin derivative 5a was the most selective (SI = 152) and coumarin-sulfonamide derivative 8d was most active toward COX-2 isozyme. The most active derivatives met the in silico criteria for orally active drugs; thus, they may serve as promising candidates to develop more potent and highly efficient antioxidant, antimicrobial, and/or anti-inflammatory agents.
Highlights
Many diseases result from oxidative stress caused by the overproduction of reactive oxygen species (ROS) [1], which play an essential role in the pathogenesis of cardiovascular and neurodegenerative diseases as well as in tumour growth, and age-related disorders
Facile and green chemistry methods were used for synthesising new coumarin derivatives via the routes illustrated in Schemes 1 and 2
All of these derivatives have a chiral centre at Position 4, which are confirmed by one and, in some cases, two dimensional NMR spectroscopy and supported by the
Summary
Many diseases result from oxidative stress caused by the overproduction of reactive oxygen species (ROS) [1], which play an essential role in the pathogenesis of cardiovascular and neurodegenerative diseases as well as in tumour growth, and age-related disorders. Inflammatory diseases can affect the quality of life of many patients; the current medicinal drugs are not always effective and may cause serious adverse effects [2]. Molecules 2020, 25, 3251 causes of death globally [3], and antimicrobial resistance has been commonly reported worldwide [3,4]. These obstacles necessitate the search for new therapies with potential antioxidant, anti-inflammatory, and antimicrobial activities. Coumarin derivatives have increasingly appealed to medicinal chemists because of their potential role in preventing and treating diseases [5,6]
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