Synthesis and Molecular Docking Studies of (E)-4-(Substituted-benzylideneamino)-2H-Chromen-2-one Derivatives: Entry to New Carbonic Anhydrase Class Of Inhibitors

The present article illustrated the synthesis and characterization of a novel series of (E)- 4-(substituted- benzylideneamino)2H- chromen- 2- one derivatives 4a- 4j in good to excellent yields. The target compounds were synthesized by refluxing 4- aminocoumarin with aromatic aldehydes in ethanol. The structural confirmation was achieved by spectroscopic techniques such as (1H, 13C- NMR and FT- IR) and elemental analysis. The synthesized compounds were evaluated for carbonic anhydrase II (CA- II) inhibition and free radical scavenging activity. All the compounds showed CA- II inhibition in the micro molar range. The compound 4c exhibited higher potential in the series with IC50 = 0.0928 +/- 0.00545 mu M (standard Acetazolamide IC50 = 0.997 +/- 0.0586 mu M). Pharmacological investigations showed that the synthesized compounds 4a- 4j obey Lipinsk's rule. Compound 4c elicited drug likeness and showed drug score value of 0.05. Molecular docking analysis showed that compound 4c interacts with Asn66 and Gln91 amino acid residues.. Graphical Abstract. [GRAPHICS] .