Synthesis of 7‐{[2‐(4‐ substituted phenyl)‐2‐oxoethyl] amino}‐4‐methyl‐2H‐1‐benzopyran‐2‐one derivatives and evaluation of their pharmacological activities

Abstract

In this study, a novel series of 7‐[2‐(4‐substituted)‐2‐oxoethyl]amino‐4‐methyl‐2H‐1‐benzopyran‐2‐one derivatives (3 a‐f) were synthesized using 7‐amino‐4‐methyl coumarin and p‐substituted phenacyl bromides, and their pharmacological effects were examined. This reaction was carried out with potassium carbonate as a catalyst in dimethylformamide for 24 h at ambient temperature. The structures of synthesized compounds have been characterized by analysis using FTIR, NMR (1H and 13C) and Mass spectroscopic techniques, and their antibacterial, antidiabetic, and anti‐inflammatory properties have been explored. All synthesized compounds have exhibited good antibacterial activity against S. aureus, B. substilis, E. coli, and S. typhi.Compound 3 f shows maximum activity (zone of inhibition) at a 12 g/mL concentration compared to others. Compounds 3 c and 3 f showed excellent α‐amylase activity and had the lowest IC50 values for α‐glucosidase enzyme activities. The least IC50 value (12.42±0.27 g/mL) was demonstrated by the 3 e compound, which exhibited potent anti‐inflammatory activities. in silico Molecular docking studies suggested that compounds 3 f and 3 a interacted effectively with 4DO3: FAAH and 5DI1: MAP4 K4 proteins with good binding energies of −10.3 and −9.5 Kcal/mol, respectively.