Synthesis, alpha-glucosidase inhibition and in silico studies of some 4-(5-fluoro-2-substituted-1H-benzimidazol-6-yl)morpholine derivatives


Menteşe E., Baltaş N., Emirik M.

BIOORGANIC CHEMISTRY, cilt.101, 2020 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 101
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.bioorg.2020.104002
  • Dergi Adı: BIOORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chimica, EMBASE, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: Benzimidazole, Morpholine, Docking study, alpha-glucosidase inhibition, MICROWAVE-ASSISTED SYNTHESIS, BENZIMIDAZOLE DERIVATIVES, MOLECULAR DOCKING, EFFICIENT SYNTHESIS, FLUORINE, TRIAZOLE, POTENT, DRUGS, THIADIAZOLE, SKELETON
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

In this study, a new series of 4-(5-fluoro-2-substituted-1H-benzimidazol-6-yl)morpholine derivatives has been synthesized and screened for their alpha-glucosidase inhibitory potential. All molecules showed a considerable alpha-glucosidase inhibitory potential with IC50 values ranging from 20.46 +/- 0.21 to 0.18 +/- 0.01 mu g/mL when compared with the acarbose (IC50 = 8.16 +/- 0.12 mu g/mL) as the standard. Compound 4 k having methoxy group on phenyl ring had the highest inhibitory effect with IC50 = 0.18 +/- 0.01 mu g/mL value among the examined compounds. Electron-donating groups such as methyl and methoxy on the phenyl ring played an important role in the inhibition. Also, the Lineweaver-Burk plots analysis displayed that the inhibition type of 4k was the competitive mode like acarbose as standard. In silico studies were also performed to explore the binding interaction of the most active compound.