Article 2023 · 8 atıf

Acetylphenyl-substituted imidazolium salts: synthesis, characterization, in silico studies and inhibitory properties against some metabolic enzymes

Demirci, Ozlem, Tezcan, Burcu, Demir, Yeliz, Taskin-Tok, Tugba, Gok, Yetkin, Aktas, Aydin, Guzel, Bilgehan, Gulcin, Ilhami

Özet

Herein, we present how to synthesize thirteen new 1-(4-acetylphenyl)-3-alkylimidazolium salts by reacting 4-(1-H-imidazol-1-yl)acetophenone with a variety of benzyl halides that contain either electron-donating or electron-withdrawing groups. The structures of the new imidazolium salts were conformed using different spectroscopic methods (H-1 NMR, C-13 NMR, F-19 NMR, and FTIR) and elemental analysis techniques. Furthermore, these compounds' the carbonic anhydrase (hCAs) and acetylcholinesterase (AChE) enzyme inhibition activities were investigated. They showed a highly potent inhibition effect toward AChE and hCAs with K-i values in the range of 8.30 & PLUSMN; 1.71 to 120.77 & PLUSMN; 8.61 nM for AChE, 16.97 & PLUSMN; 2.04 to 84.45 & PLUSMN; 13.78 nM for hCA I, and 14.09 & PLUSMN; 2.99 to 69.33 & PLUSMN; 17.35 nM for hCA II, respectively. Most of the synthesized imidazolium salts appeared to be more potent than the standard inhibitor of tacrine (TAC) against AChE and Acetazolamide (AZA) against CA. In the meantime, to prospect for potential synthesized imidazolium salt inhibitor(s) against AChE and hCAs, molecular docking and an ADMET-based approach were exerted.

Anahtar Kelimeler

Acetylcholinesterase Acetyl group ADMET Carbonic anhydrase Imidazolium salt Molecular docking N-HETEROCYCLIC CARBENES CARBONIC-ANHYDRASE I BIOLOGICAL EVALUATION ACETYLCHOLINE ESTERASE BENZIMIDAZOLIUM SALTS CRYSTAL-STRUCTURE HCA I DERIVATIVES BUTYRYLCHOLINESTERASE ANTIOXIDANT

WoS Kategorileri

Biochemistry & Molecular Biology Chemistry, Applied Chemistry, Medicinal Chemistry, Multidisciplinary

Sürdürülebilir Kalkınma Amaçları

Sağlık ve Kaliteli Yaşam

Künye

Dergi: MOLECULAR DIVERSITY
Yıl: 2023
Cilt: 27
Sayı: 6
Sayfa: 2767-2787
ISSN: 1381-1991
eISSN: 1573-501X
DOI: 10.1007/s11030-022-10578-3
WoS UID: WOS:000898457600001

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