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 A., Caglilar T., CELEPCİ D. B., AKTAŞ A., Taslimi P., GÖK Y., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1170, pp.160-169, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1170
  • Publication Date: 2018
  • Doi Number: 10.1016/j.molstruc.2018.05.077
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.160-169
  • Keywords: N-heterocyclic carbenes precursors, Benzimidazole, Single-crystal X-ray diffraction, Carbonic anhydrase, Acetylcholinesterase, Enzyme inhibition, N-HETEROCYCLIC CARBENES, ISOENZYMES HCA I, COMPLEXES SYNTHESIS, CATALYTIC-ACTIVITY, NHC PRECURSORS, BUTYRYLCHOLINESTERASE, DERIVATIVES, ANTIOXIDANT, ESTERASE, BROMOPHENOLS
  • Inonu University Affiliated: Yes

Abstract

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.