| Summary: | <i>N</i>-(2-Acetyl-4-bromophenyl)-4-methylbenzenesulfonamide (<b>2</b>) was transformed into 5-(4-methoxymethylstyryl)-2-(<i>p</i>-tolylsulfonamido)acetophenone (<b>3a</b>) and 5-(4- trifluoromethylstyryl)-2-(<i>p</i>-tolylsulfonamido)acetophenone (<b>3b</b>). Their structures were determined using a combination of NMR (<sup>1</sup>H & <sup>13</sup>C) and mass spectroscopic as well as single crystal X-ray diffraction techniques. These compounds and the corresponding precursor, 2-amino-5-bromoacetophenone (<b>1</b>), were evaluated through enzymatic assays in vitro for inhibitory effect against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities as well as antioxidant effect through the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide (NO) free radical scavenging assays. Molecular docking was performed on <b>3a</b> to determine plausible protein–ligand interactions on a molecular level. Their drug likeness properties (absorption, distribution, metabolism, and excretion) and ability to cross the blood–brain barrier (BBB) have also been predicted at theoretical level.
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