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Benzimidazole-based pyrrole/piperidine analogs (<b>1</b>–<b>26</b>) were synthesized and then screened for their acetylcholinesterase and butyrylcholinesterase activities. All the analogs showed good to moderate cholinesterase activities. Synthesized compounds (<b>1</b>–<b>13</b>) were screened in cholinesterase enzyme inhibition assays and showed AChE activities in the range of IC₅₀ = 19.44 ± 0.60 µM to 36.05 ± 0.4 µM against allanzanthane (IC₅₀ = 16.11 ± 0.33 µM) and galantamine (IC₅₀ = 19.34 ± 0.62 µM) and varied BuChE inhibitory activities, with IC₅₀ values in the range of 21.57 ± 0.61 µM to 39.55 ± 0.03 µM as compared with standard allanzanthane (IC₅₀ = 18.14 ± 0.05 µM) and galantamine (IC₅₀ = 21.45 ± 0.21 µM). Similarly, synthesized compounds (<b>14</b>–<b>26</b>) were also subjected to tests to determine their in vitro AChE inhibitory activities, and the results obtained corroborated that all the compounds showed varied activities in the range of IC₅₀ = 22.07 ± 0.13 to 42.01 ± 0.02 µM as compared to allanzanthane (IC₅₀ = 20.01 ± 0.12 µM) and galantamine (IC₅₀ = 18.05 ± 0.31 µM) and varied BuChE inhibitory activities, with IC₅₀ values in the range of 26.32 ± 0.13 to 47.03 ± 0.15 µM as compared to standard allanzanthane (IC₅₀ = 18.14 ± 0.05 µM) and galantamine (IC₅₀ = 21.45 ± 0.21 µM). Binding interactions of the most potent analogs were confirmed through molecular docking studies. The active analogs <b>2</b>, <b>4</b>, <b>10</b> and <b>13</b> established numerous interactions with the active sites of targeted enzymes, with docking scores of −10.50, −9.3, −7.73 and −7.8 for AChE and −8.97, −8.2, −8.20 and −7.6 for BuChE, respectively.