Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase

Behcet, Ayten; Caglilar, Tuba; Celepci, Duygu Barut; AKTAŞ, AYDIN; Taslimi, Parham; GÖK, YETKİN; Aygun, Muhittin; Kaya, Ruya; Gülçin, İlhami

doi:10.1016/j.molstruc.2018.05.077

Makale Tam Makale Uluslararası 2018

Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase

Ayten Behcet, Tuba Caglilar, Duygu Barut Celepci, AYDIN AKTAŞ, Parham Taslimi, YETKİN GÖK, Muhittin Aygun, Ruya Kaya, İlhami Gülçin

Journal of Molecular Structure Cilt 1170 · ss. 160–169 · 15.10.2018

DOI ile aç

Özet

This paper reports the synthesis of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl substituted benzimidazolium salts. The benzimidazolium salts were synthesized by N-substituted benzimidazolium and aryl halides. The 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl substituted benzimidazolium salts were characterized by using H-1 NMR, C-13 NMR, FT-IR spectroscopy and elemental analysis techniques. Molecular and crystal structure of the complex 2d and 3d were obtained by single-crystal X-ray diffraction method. Additionally, The enzyme inhibition activities of the benzimidazolium salts were investigated. These 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl substituted benzimidazolium salts (1, 2a-g, and 3a-f) showed good inhibitory action against acetylcholinesterase (AChE), and human (h) carbonic anhydrase (CA) isoforms I, and II. Ki values for AChE were in range of 5.97 +/- 0.56 -23.15 +/- 3.98 nM. On the other hand, the hCA I, and II isoenzymes were effectively inhibited by these compounds, with K-i values in the range of 17.33 +/- 4.55-99.23 +/- 44.91 nM for hCA I, and 33.98 +/- 3.43 -113.23 +/- 39.31 nM for hCA II, respectively. (C) 2018 Elsevier B.V. All rights reserved.

Anahtar kelimeler

carbonic anhydrase antioxidant DERIVATIVES Acetylcholinesterase Butyrylcholinesterase enzyme inhibition Benzimidazole BROMOPHENOLS Catalytic activity COMPLEXES SYNTHESIS ISOENZYMES HCA I N-heterocyclic carbenes ESTERASE NHC PRECURSORS N-heterocyclic carbenes precursors Single-crystal X-ray diffraction

Atıf için künye

Behcet, A., Caglilar, T., Celepci, D. B., AKTAŞ, A., Taslimi, P., GÖK, Y., Aygun, M., Kaya, R., & Gülçin, İ. (2018). Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase. Journal of Molecular Structure, 1170, 160–169. https://doi.org/10.1016/j.molstruc.2018.05.077

BibTeX

@article{behcet2018-67790,
  author = {Behcet, Ayten and Caglilar, Tuba and Celepci, Duygu Barut and AKTAŞ, AYDIN and Taslimi, Parham and GÖK, YETKİN and Aygun, Muhittin and Kaya, Ruya and Gülçin, İlhami},
  title = {Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase},
  journal = {Journal of Molecular Structure},
  year = {2018},
  volume = {1170},
  pages = {160--169},
  issn = {0022-2860},
  doi = {10.1016/j.molstruc.2018.05.077},
  url = {https://akademik.atauni.edu.tr/yayinlar/67790-synthesis-characterization-and-crystal-structure-of-2-4-hydroxyphenylethyl-and-2}
}