Microwave-assisted synthesis of 1-substituted-1H-benzimidazolium salts: Non-competitive inhibition of human carbonic anhydrase I and II
ARCHIV DER PHARMAZIE, cilt.352, sa.4, 2019 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 352 Sayı: 4
- Basım Tarihi: 2019
- Doi Numarası: 10.1002/ardp.201800325
- Dergi Adı: ARCHIV DER PHARMAZIE
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
- Anahtar Kelimeler: benzimidazole, benzimidazolium salt, carbonic anhydrase, inhibitors, microwave chemistry, BENZIMIDAZOLIUM SALTS, SELECTIVE INHIBITORS, ESTERASE-ACTIVITIES, ISOFORMS, COUMARIN, IMIDAZOLIUM, COMPLEXES, SCAFFOLDS, POTENT
- Ondokuz Mayıs Üniversitesi Adresli: Evet
Özet
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.