This report presents the synthesis and characterization of a range of benzimidazolium salts featuring 3-cyanopropyl groups on the 1^st nitrogen atom and varied alkyl groups on the 3^rd nitrogen atom within the benzimidazole structure. Benzimidazolium salts were synthesized by N-alkylation of 1-alkyl benzimidazole with 3-cyanopropyl-bromide. The new salts were characterized by ¹H and ¹³C-NMR, FT-IR spectroscopic and elemental analysis techniques. In this study, the enzyme inhibition abilities of seven nitrile substituted benzimidazolium salts were investigated against acetylcholinesterase (AChE) and carbonic anhydrase isoenzymes I and II (hCA I and hCA II). They showed a highly potent inhibition effect on AChE, hCA I and hCA II (K_i values are in the range of 26.71–119.09 nM for AChE, 19.77 to 133.68 nM for hCA I and 13.09 to 266.38 nM for hCA II). Reflecting the binding mode of the synthesized cyanopropyl series, the importance of the 2,3,5,6-tetramethylbenzyl, 3-methylbenzyl and 3-benzyl groups for optimal interactions with target proteins, evaluated by molecular docking studies. At the same time, the docking findings support the inhibition constants (K_i) values of the related compounds in this study. Potential compounds were also evaluated by their pharmacokinetic properties were predicted.

中文翻译：

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带有腈部分的苯并咪唑鎓盐：碳酸酐酶和乙酰胆碱酯酶的合成、酶抑制分析和分子对接分析

本报告介绍了一系列苯并咪唑鎓盐的合成和表征，这些苯并咪唑盐在苯并咪唑结构中的第^{一个氮原子上具有 3-氰基丙基，在第三个}氮原子上具有不同的烷基。苯并咪唑鎓盐是通过 1-烷基苯并咪唑与 3-氰基丙基溴的 N-烷基化合成的。新盐通过¹ H 和¹³ C-NMR、FT-IR 光谱和元素分析技术进行了表征。在本研究中，研究了七种腈取代的苯并咪唑鎓盐对乙酰胆碱酯酶（AChE）和碳酸酐酶同工酶 I 和 II（hCA I 和 hCA II）的酶抑制能力。它们对 AChE、hCA I 和 hCA II 表现出高效的抑制作用（AChE 的 K _i值范围为 26.71–119.09 nM，hCA I 的 K i 值范围为 19.77 至 133.68 nM，hCA II 的 K i 值范围为 13.09 至 266.38 nM）。通过分子对接研究评估了 2,3,5,6-四甲基苯甲基、3-甲基苯甲基和 3-苯甲基对于与靶蛋白最佳相互作用的重要性，反映了合成的氰丙基系列的结合模式。同时，对接结果支持了本研究中相关化合物的抑制常数（K _{i ）值。}还通过预测潜在的化合物的药代动力学特性来评估它们。