Vinyl functionalized 5,6-dimethylbenzimidazolium salts: Synthesis and biological activities

KARACA E. Ö., Bingöl Z., GÜRBÜZ N., ÖZDEMİR İ., GÜLÇİN İ.

Journal of Biochemical and Molecular Toxicology, cilt.37, sa.2, 2023 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 37 Sayı: 2
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1002/jbt.23255
  • Dergi Adı: Journal of Biochemical and Molecular Toxicology
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Applied Science & Technology Source, BIOSIS, Biotechnology Research Abstracts, Chemical Abstracts Core, EMBASE, Environment Index, Food Science & Technology Abstracts, MEDLINE
  • Anahtar Kelimeler: 5,6-dimethylbenzimidazolium salts, acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase, enzyme inhibition, alpha-glycosidase, POTENT CARBONIC-ANHYDRASE, CROSS-COUPLING REACTIONS, CRYSTAL-STRUCTURE, INHIBITORY PROPERTIES, CATALYTIC-ACTIVITY, ALPHA-GLYCOSIDASE, ACETYLCHOLINE ESTERASE, HETEROCYCLIC CARBENES, ALKENE METATHESIS, ISOENZYMES I
  • Atatürk Üniversitesi Adresli: Evet

Özet

© 2022 Wiley Periodicals LLC.A series of vinyl functionalized 5,6-dimethylbenzimidazolium salts are synthesized. All compounds were fully characterized by elemental analyses, MS, 1H-NMR, 13C-NMR, and IR spectroscopy techniques. Enzyme inhibition is a very active area of research in drug design and development. In this study, the synthesized novel benzimidazolium salts were evaluated toward the human erythrocyte carbonic anhydrase I (hCA I), and II (hCA II) isoenzymes, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. They demonstrated highly potent inhibition ability against hCA I with Ki values of 484.8 ± 62.6–1389.7 ± 243.2 nM, hCA II with Ki values of 298.9 ± 55.7–926.1 ± 330.0 nM, α-glycosidase with Ki values of 170.3 ± 27–760.1 ± 269 μM, AChE with Ki values of 27.1 ± 3–77.6 ± 1.7 nM, and BChE with Ki values of 21.0 ± 5–61.3 ± 15 nM. As a result, novel vinyl functionalized 5,6-dimethylbenzimidazolium salts (1a–g) exhibited effective inhibition profiles toward studied metabolic enzymes. Therefore, we believe that these results may contribute to the development of new drugs particularly to treat some global disorders including glaucoma, Alzheimer's disease, and diabetes.