Benzofuran-derived benzylpyridinium bromides as potent acetylcholinesterase inhibitors

A Simple and Efficient Process for the Synthesis of Novel Heterocycles Containing Benzofuran Moiety Using Thiocarbohydrazide as a Precursor

“…The chemistry of benzofurans has attracted the attention of researchers in both academia and industry due to their wide range of biological activities and their presence in many natural products . Various benzofurans showed antibacterial , antioxidant , anti‐inflammatory , cholinesterase inhibition , antidepressant , anticonvulsant , and anticancer activities . Various synthetic methods are reported for the production of benzofurans .…”

Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors

“…[13][14][15][16] According to the docking studies of these compounds, it was found that both terminal rings attached to the pyridinium were able to bind simultaneously to both CAS and PAS of the enzyme resulting in higher AChE inhibitory activity. [13][14][15][16] Among the reported studies, pyridinium derivatives having benzofuran ring were shown to have a significant AChE inhibitory activity and it was observed that benzofuran and phenyl moieties as terminal rings were interacted with both PAS and CAS of AChE. 15,16) On the other hand, many of compounds bearing hydrazonehydrazide functional group have been reported to possess ChE inhibitory activity.…”

“…[13][14][15][16] Among the reported studies, pyridinium derivatives having benzofuran ring were shown to have a significant AChE inhibitory activity and it was observed that benzofuran and phenyl moieties as terminal rings were interacted with both PAS and CAS of AChE. 15,16) On the other hand, many of compounds bearing hydrazonehydrazide functional group have been reported to possess ChE inhibitory activity. 17,18) The hydrazones have hydrogen donor and acceptor nitrogen atoms and ability to make hydrogen bound with amino acids in the gorge of the enzyme.…”

“…[9][10][11][12] Many reports indicated that compounds bearing aromatic/ heteroaromatic rings on lateral parts of pyridinium displayed high AChE inhibitory activity and act as dual binding inhibitors. [13][14][15][16] According to the docking studies of these compounds, it was found that both terminal rings attached to the pyridinium were able to bind simultaneously to both CAS and PAS of the enzyme resulting in higher AChE inhibitory activity. [13][14][15][16] Among the reported studies, pyridinium derivatives having benzofuran ring were shown to have a significant AChE inhibitory activity and it was observed that benzofuran and phenyl moieties as terminal rings were interacted with both PAS and CAS of AChE.…”

Design, synthesis, biological evaluation and docking study of 4-isochromanone hybrids bearing N-benzyl pyridinium moiety as dual binding site acetylcholinesterase inhibitors

“…Recently, some compounds with potent AChE inhibition activities were reported, in which, N-benzyl pyridinium moiety was introduced into a series of aromatic scaffolds and emerged as an essential structure for inhibition of AChE ( Figure 1). [22][23][24][25][26] Meanwhile, docking studies have revealed that the presence of N-benzyl pyridinium moiety contributed to inhibitor activity by interacting with CAS, and the aromatic part of the hetero rings might engage to favorable stacking interactions with PAS of AChE. These findings led us to propose a series of novel 4-isochromanone compounds through hybridization approach ( Figure 1).…”