Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents

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.

Chromene-Containing Aromatic Sulfonamides with Carbonic Anhydrase Inhibitory Properties

“…The classical CA inhibitors (CAIs) are the primary sulfonamides, which coordinate the zinc ion with their terminal deprotonated nitrogen atom and have been in clinical use for more than 70 years as diuretics and systemically acting antiglaucoma drugs [ 10 ]. Chromenes have attracted the interest of the scientific community due to their wide range of biological activities, such as antimicrobial [ 11 , 12 ], anticancer [ 13 , 14 ], anti-inflammatory [ 15 , 16 ], and CA inhibitors [ 17 , 18 , 19 , 20 , 21 ], nematicidal [ 22 ], antiallergic [ 23 ] Some sulfonamides also show antimicrobial [ 24 , 25 ], anticancer [ 26 , 27 ], antidiabetic [ 28 ], anti-inflammatory [ 15 , 29 ], and antitubercular [ 30 ] activities. Taking into account all of the above-mentioned, here we report the synthesis of (4-sulfamoylphenyl)-4 H -chromene-2-carboxamide derivatives for its incorporation into one scaffold chromene and sulfonamide moieties.…”

The Effect of Herniarin on Spatial Working Memory, Pain Threshold, and Oxidative Stress in Ischemic Hypoperfusion Model in Rats

“…A study by Vakili et al (2012) reported that saffron or its active ingredients could significantly decrease oxidative damage in ischemic tissues such as the brain [37]. Coumarin-dependent compounds have antimicrobial and anti-inflammatory activities [38], and such compounds have different biological properties, including antioxidant activity in laboratory conditions [16], and inhibition of cell proliferation [39].…”

Anti-Inflammatory and Antioxidant Effects of Soroseris hirsuta Extract by Regulating iNOS/NF-κB and NRF2/HO-1 Pathways in Murine Macrophage RAW 264.7 Cells

“…Therefore, extensive work has previously focused on the development of efficient and novel antioxidants and anti-inflammatory molecules. Various natural antioxidants have been characterized, and several anti-inflammatory agents, such as aspirin, are widely used [32]. However, the development of effective anti-inflammatory agents is still necessary.…”