Abstract
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.
Highlights
Nature-based small molecular weight ligands, such as stilbenes (1,3-diphenylpropenes) are important as anticancer agents, but are useful for the treatment of various human disorders including diabetes, neurological and cardiovascular diseases, as well as other chronic diseases [1,2]
NMR spectrum of 2 showed the presence of an intense singlet at δ = 2.31 ppm integrating for three protons, which corresponds to the methyl group and a set of intense doublets in the aromatic region each integrating for two protons for the para substituted phenyl ring of the incorporated p-toluenesulfonyl group
X-ray diffraction (XRD) method provided an unambiguous proof of the existence of thermodynamically favourable sixmembered intramolecular hydrogen bonding interaction between sulfonamide hydrogen and carbonyl oxygen in the solid state
Summary
Nature-based small molecular weight ligands, such as stilbenes (1,3-diphenylpropenes) are important as anticancer agents, but are useful for the treatment of various human disorders including diabetes, neurological and cardiovascular diseases, as well as other chronic diseases [1,2]. Pterostilbene (trans-3,5-dimethoxy-4-hydroxystilbene) (B) shown, for example, have been proven to be potent multiple molecular modulators for age-related diseases, including oxidative damage, inflammation, neurodegeneration, obesity, diabetes, and cardiovascular diseases [2,3]. Generally associated with their traditional use as antibacterial drugs, sulfonamide based compounds have been found to inhibit cancer related carbonic anhydrase, cysteine protease, HIV protease, cyclooxygenases (COXs), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities [6]. The sulfonamide group generally adopts tetrahedral geometry, which makes its oxygen atoms to form hydrogen drugs, sulfonamide based compounds have been found to inhibit cancer related carbonic anhydrase, cysteine protease, HIV protease, cyclooxygenases (COXs), acetylcholin of 19 esterase (AChE) and butyrylcholinesterase (BChE) activities [6]. This group is capable ofbonds forming relatively strong electrostatic and hydrogen bondingMoreover, interactions in higher dimensions than amide analogues, for example
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