Microwave-assisted synthesis of 1-substituted-1H-benzimidazolium salts: Non-competitive inhibition of human carbonic anhydrase I and II

Karlik O., GENÇER N., KARATAŞ M. O., ERGÜN A., Cikrikci K., ARSLAN O., ...More

ARCHIV DER PHARMAZIE, vol.352, no.4, 2019 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 352 Issue: 4
  • Publication Date: 2019
  • Doi Number: 10.1002/ardp.201800325
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Keywords: benzimidazole, benzimidazolium salt, carbonic anhydrase, inhibitors, microwave chemistry, BENZIMIDAZOLIUM SALTS, SELECTIVE INHIBITORS, ESTERASE-ACTIVITIES, ISOFORMS, COUMARIN, IMIDAZOLIUM, COMPLEXES, SCAFFOLDS, POTENT
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

A series of 1-substituted-1H-benzimidazolium p-toluenesulfonate salts were synthesized in good yields by the reaction of 1-substituted benzimidazole derivatives and p-toluenesulfonic acid under microwave irradiation. Two iodide salts were synthesized by the anion exchange reaction of the corresponding p-toluenesulfonate salt and NaI. All compounds were characterized by H-1 NMR, C-13 NMR, IR, LC-MS spectroscopic methods, and elemental analyses. The crystal structure of 1-methoxyethyl-1H-benzimidazolium p-toluenesulfonate 2d showed that cation and anion are interconnected by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. All compounds were examined as inhibitor of human carbonic anhydrase (hCA) I and II, and all of them inhibited hCA I and hCA II. Kinetic investigation results revealed that these compounds inhibit hCA I and hCA II in a non-competitive manner. The iodide salts had higher inhibitory activity than their corresponding p-toluenesulfonate salts.