Isatin based Schiff bases as inhibitors of α-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies

Rahim F 1 , Malik F 2 , Ullah H 2 , Wadood A 3 , Khan F 2 , Javid MT 2 Show all authors , Taha M 4 , Rehman W 2 , Ur Rehman A 3 , Khan KM 5

Affiliations 

  • 1 Department of Chemistry, Hazara University, Mansehra 21120, Pakistan. Electronic address: [email protected]
  • 2 Department of Chemistry, Hazara University, Mansehra 21120, Pakistan
  • 3 Department of Biochemistry, Abdul Wali Khan University Mardan, Mardan 23200, Pakistan
  • 4 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, Malaysia; Faculty of Applied Science UiTM, 40450 Shah Alam, Selangor, Malaysia
  • 5 H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Bioorg Chem, 2015 Jun;60:42-8.
PMID: 25955493 DOI: 10.1016/j.bioorg.2015.03.005

Abstract

Isatin base Schiff bases (1-20) were synthesized, characterized by (1)H NMR and EI/MS and evaluated for α-glucosidase inhibitory potential. Out of these twenty (20) compounds only six analogs showed potent α-glucosidase inhibitory potential with IC50 value ranging in between 2.2±0.25 and 83.5±1.0μM when compared with the standard acarbose (IC50=840±1.73μM). Among the series compound 2 having IC50 value (18.3±0.56μM), 9 (83.5±1.0μM), 11 (3.3±0.25μM), 12 (2.2±0.25μM), 14 (11.8±0.15μM), and 20 (3.0±0.15μM) showed excellent inhibitory potential many fold better than the standard acarbose. The binding interactions of these active analogs were confirmed through molecular docking.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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