Synthesis, Structure and Evaluation of the N-(2-Acetyl-4-(styryl)phenyl)-4-benzenesulfonamide Derivatives for Anticholinesterase and Antioxidant Activities

N-(2-Acetyl-4-bromophenyl)-4-methylbenzenesulfonamide (2) was transformed into 5-(4-methoxymethylstyryl)-2-(p-tolylsulfonamido)acetophenone (3a) and 5-(4- trifluoromethylstyryl)-2-(p-tolylsulfonamido)acetophenone (3b). Their structures were determined using a combination of NMR (1H & 13C) and ma...

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Bibliographic Details
Published in:Crystals (Basel) 2021-04, Vol.11 (4), p.341
Main Authors: Mphahlele, Malose, Gildenhuys, Samantha, Zamisa, Sizwe
Format: Article
Language:English
Subjects:
Acetophenone
Alzheimer's disease
antioxidant effect
Antioxidants
Binding sites
Blood-brain barrier
cholinesterases
Chromatography
Diabetes
Drugs
Free radicals
Hydrogen
hydrogen bonding
Molecular docking
N-(2-Acetyl-4-bromophenyl)-4-methylbenzenesulfonamide
Nitric oxide
NMR
Nuclear magnetic resonance
Scavenging
Single crystals
Suzuki-Miyaura cross-coupling
X-ray
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Summary:N-(2-Acetyl-4-bromophenyl)-4-methylbenzenesulfonamide (2) was transformed into 5-(4-methoxymethylstyryl)-2-(p-tolylsulfonamido)acetophenone (3a) and 5-(4- trifluoromethylstyryl)-2-(p-tolylsulfonamido)acetophenone (3b). Their structures were determined using a combination of NMR (1H & 13C) and mass spectroscopic as well as single crystal X-ray diffraction techniques. These compounds and the corresponding precursor, 2-amino-5-bromoacetophenone (1), 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 3a 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.
ISSN:2073-4352
2073-4352
DOI:10.3390/cryst11040341