A series of 3,3-arylidene bis (4-hydroxycoumarins) 2 were synthesized by the reaction of aromatic aldehydes with
4-hydroxycoumarin
using dodecylbenzenesulfonic acid as Brønsted acid-surfactant
catalyst in aqueous media and under microwave irradiation. The present
method is operationally simple and the use of water as the reaction
medium makes the process environmentally benign. The epoxydicoumarins 5 were then obtained with a good yield by heating 3,3′-arylidenebis-4-hydroxycoumarins 2 in acetic anhydride. Techniques such as elemental analysis, 1H, 13C–1H NMR, and infrared spectroscopy
were employed to characterize these compounds. The synthesized compounds
displayed good antibacterial potential against Escherichia
coli (ATCC 25988), Pseudomonas aeruginosa (ATCC 27853), Klebsilla pneumonia (ATCC 700603), Staphylococcus aureus (ATCC 29213), methicillin-resistant Staphylococcus
aureus (ATCC 43300) and Candida albicans (ATCC 14053). The MIC values of 23 mg/mL for compound 5e against Escherichia coli (ATCC 25988)
and 17 mg/mL for 2a were observed. Furthemore, a molecular
docking simulation has been performed to evaluate the antibacterial
activities and the probable binding modes of the studied compounds 2a–f and 5a–g toward the active
sites of a series of well known antibacterial targets. Among the investigated
compounds, the binding modes and docking scores demonstrate that 2a has the most antibacterial and antifungal activities. Additionally,
DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS has been tested for
their ability to scavenge hydrogen peroxide and free radicals. According
to our results, these compounds exhibit excellent radical scavenging
properties. Furthermore, compounds 2–5 were evaluated
for anti-inflammatory activity by indirect haemolytic and lipoxygenase
inhibition assays and revealed good activity.