Thioether-substituted Benzimidazolium Salts: Synthesis, Characterization, Crystal Structure, and Their Inhibitory Properties Against Acetylcholinesterase and Xanthine Oxidase

Yavuz, Kemal; Noma, Samir Abbas Ali; Şen, Betül; Tok, Tuğba Taşkın; Aktaş, Aydın; Ateş, Burhan; Osman, Bilgen; Aygün, Muhıttın; Gök, Yetkın

doi:10.1016/j.molstruc.2023.135640

Cited by 2 publications

(3 citation statements)

References 68 publications

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“…presence of 4-methylbenzyl group posses greater interaction with XO enzyme and showed more inhibitory activity. Further the molecular docking revealed that compound 66 showed various interaction as electrostatic interactions, hydrophobic interactions with Glu879, Arg880, Phe1009, His875, Ser876, Ala1078, Ala1079, Leu648, Phe914, and Leu648 residue 76 (Fig.…”

Section: Rsc Medicinal Chemistry Reviewmentioning

confidence: 99%

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Singh,

Debnath,

Chawla

et al. 2024

RSC Med. Chem.

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Section: Rsc Medicinal Chemistry Reviewmentioning

confidence: 99%

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Singh,

Debnath,

Chawla

et al. 2024

RSC Med. Chem.

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“…[22][23][24][25][26][27][28] Benzimidazolium salts are derivatives of 1,3-disubstituted benzimidazole and possess acidic hydrogen in the 2-position. Benzimidazolium salts are gaining attention for their significant pharmacological applications, including anticancer, antibiofilm, antibacterial, antifungal, and enzyme inhibition [29][30][31][32][33][34] Carbonic anhydrase (EC 4.2.1.1, CA) is a ubiquitous class of zinc-containing metalloenzymes found in both prokaryotes and eukaryotes. [35,36] These metalloenzymes efficiently catalyze the reversible essential hydration of carbon dioxide.…”

Section: Introductionmentioning

confidence: 99%

“…Benzimidazolium salts are derivatives of 1,3‐disubstituted benzimidazole and possess acidic hydrogen in the 2‐position. Benzimidazolium salts are gaining attention for their significant pharmacological applications, including anticancer, antibiofilm, antibacterial, antifungal, and enzyme inhibition [29–34] …”

Section: Introductionmentioning

confidence: 99%

Benzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesterase

Öner,

Gök,

Demir

et al. 2023

Chemistry & Biodiversity

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This report presents the synthesis and characterization of a range of benzimidazolium salts featuring 3‐cyanopropyl groups on the 1st nitrogen atom and varied alkyl groups on the 3rd 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 (Ki 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 (Ki) values of the related compounds in this study. Potential compounds were also evaluated by their pharmacokinetic properties were predicted.

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Thioether-substituted Benzimidazolium Salts: Synthesis, Characterization, Crystal Structure, and Their Inhibitory Properties Against Acetylcholinesterase and Xanthine Oxidase

Cited by 2 publications

References 68 publications

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Benzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesterase

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