Abstract
A series of 16 novel benzenesulfonamides incorporating 1,3,5-triazine moieties substituted with aromatic amines, dimethylamine, morpholine and piperidine were investigated. These compounds were assayed for antioxidant properties by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, 2,2`-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical decolarisation assay and metal chelating methods. They were also investigated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase, which are associated with several diseases such as Alzheimer, Parkinson and pigmentation disorders. These benzenesulfonamides showed moderate DPPH radical scavenging and metal chelating activity, and low ABTS cation radical scavenging activity. Compounds 2 b, 3d and 3 h showed inhibitory potency against AChE with % inhibition values of >90. BChE was also effectively inhibited by most of the synthesised compounds with >90% inhibition potency. Tyrosinase was less inhibited by these compounds.
Highlights
The 1,3,5-triazine scaffold, known as s-triazine, and its derivatives have a wide range of applications due to broad biological activities including antiviral, antibacterial, anti-inflammatory, antiHIV and more recently anti-cancer activity[1,2,3,4]
The rationale for designing this novel benzenesulfonamides incorporating 1,3,5-triazine structural motifs presented in this work are based on our previous work which showed efficient carbonic anhydrase IX inhibition potency associated with such derivatives[5,6,7,8,9,10,11,12]
The results revealed that benzenesulfonamides incorporating 1,3,5-triazine moieties 2(a-d) and 3(a-l) shows, in general, moderate DPPH radical scavenging and metal chelating activity, and low ABTS cation radical scavenging activity
Summary
The 1,3,5-triazine scaffold, known as s-triazine, and its derivatives have a wide range of applications due to broad biological activities including antiviral, antibacterial, anti-inflammatory, antiHIV and more recently anti-cancer activity[1,2,3,4]. Sulphonamides incorporating 1,3,5-triazine moieties were extensively studied as a potent and selective carbonic anhydrase inhibitors[5,6,7,8,9,10]. Alzheimer’s disease (AD), a progressive neurodegenerative disorder of the brain, is characterised by cognitive dysfunction, memory decrease, speech impairment and dementia, which is the leading cause of disability in elderly people in the world[13,14,15]. It affects about 50 million people worldwide and this number might triplicate to 152 million by 2050 (World Alzheimer report)[16], as life expectancy is increasing worldwide. Butyrylcholinesterase (BChE) is a non-specific cholinesterase enzyme that hydrolyses many different choline-based esters[19,20]
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