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

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

  • Bioorg Chem. 2020 Aug;101:104002. doi: 10.1016/j.bioorg.2020.104002.
Emre Menteşe 1 Nimet Baltaş 2 Mustafa Emirik 3
Affiliations

Affiliations

  • 1 Department of Chemistry, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, Rize, Turkey. Electronic address: emre.mentese@erdogan.edu.tr.
  • 2 Department of Chemistry, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, Rize, Turkey. Electronic address: nimet.baltas@erdogan.edu.tr.
  • 3 Department of Chemistry, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, Rize, Turkey. Electronic address: mustafa.emirik@erdogan.edu.tr.
Abstract

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 α-glucosidase inhibitory potential. All molecules showed a considerable α-glucosidase inhibitory potential with IC50 values ranging from 20.46 ± 0.21 to 0.18 ± 0.01 µg/mL when compared with the acarbose (IC50 = 8.16 ± 0.12 µg/mL) as the standard. Compound 4 k having methoxy group on phenyl ring had the highest inhibitory effect with IC50 = 0.18 ± 0.01 µg/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.

Keywords

Benzimidazole; Docking study; Morpholine; α-glucosidase inhibition.

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