Abstract
This manuscript reports the synthesis of a series of N-substituted derivatives of 2-phenitidine. First, the reaction of 2-phenitidine (1) with benzene sulfonyl chloride (2) yielded N-(2-ethoxyphenyl) benzenesulfonamide (3), which further on treatment with sodium hydride and alkyl halides (4a-g) furnished into new sulfonamides (5a-g). Second, the phenitidine reacted with benzoyl chloride (6) and acetyl chloride (8) to yield the reported N-benzoyl phenitidine (7) and N-acetyl phenitidine (9), respectively. These derivatives were characterized by infrared spectroscopy, ¹H-NMR, and EI-MS, and then screened against acetylcholinesterase, butylcholinesterase, and lipoxygenase enzyme, and were found to be potent inhibitors of butyrylcholinesterase alone.
Highlights
Compounds bearing the -SO2-NH- group have long been known to be potent inhibitors of carbonic anhydrase (CA) (Remko et al, 2010; Supuran et al, 2003), and are widely used as antibacterial agents
Synthesis of sulfonamides involves the nucleophilic attack of ammonia or amine on a sulfonyl halide (Chan et al, 2002; Shaabani et al, 2007)
Arylsulfonyl azides can be reduced to convert into arylsulfonamides (Boruah et al, 1997)
Summary
Compounds bearing the -SO2-NH- group (the sulfonamide group) have long been known to be potent inhibitors of carbonic anhydrase (CA) (Remko et al, 2010; Supuran et al, 2003), and are widely used as antibacterial agents. The major functions of AChE and BChE are to catalyze the hydrolysis of the neurotransmitter acetylcholine, and to terminate the nerve impulse at the cholinergic synapses (Cygler et al, 1993; Tougu et al, 2001). It has been found that BChE (E.C 3.1.1.8) inhibition is an effective tool for the treatment of Alzheimer’s disease and related dementias. A survey of the literature revealed that slight modifications in the structure can result in qualitative as well as quantitative changes in activity, which prompted us to undertake the synthesis of various 2-phenitidine derivatives and to study their structure-activity relationship by screening them against DPPH, AChE, BChE, and lipoxygenase (LOX), and these were found to be active against BChE, and were possible entrants for the treatment of Alzheimer’s disease
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