Synthesis, in vitro and computational studies of 1,4-disubstituted 1,2,3-triazoles as potential α-glucosidase inhibitors

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Abstract

1,4-Disubstituted-1,2,3-triazoles were synthesized by Cu(I) catalyzed click reaction, where the azides, with electron donating and electron withdrawing groups acted as 1,3-dipoles and 1-ethynyl-1-cyclohexanol served as the terminal alkyne. These synthesized triazoles were subjected to enzymatic assay which showed promising activity against α-glucosidase; 1-(2-cyano-4-nitrophenyl)-4-(1-hydroxycyclohexyl)-1H-1,2,3-triazole 3m being the most active members of the library. Molecular docking studies of these triazoles with the homology-modeled α-glucosidase protein were also performed to delineate ligand-protein interactions at molecular level which suggested that Phe157, Arg312 and His279 are the major interacting residues in the biding site of the protein and may have a significant role in the inhibition of enzyme's function.

Original languageEnglish (US)
Pages (from-to)1029-38
Number of pages10
JournalBioorganic and Medicinal Chemistry Letters
Volume26
Issue number3
DOIs
StatePublished - Feb 1 2016

Keywords

  • Amino Acid Sequence
  • Bacillus cereus
  • Binding Sites
  • Catalytic Domain
  • Click Chemistry
  • Glycoside Hydrolase Inhibitors
  • Hydrogen Bonding
  • Molecular Docking Simulation
  • Molecular Sequence Data
  • Saccharomyces cerevisiae
  • Sequence Alignment
  • Structure-Activity Relationship
  • Triazoles
  • alpha-Glucosidases
  • Journal Article
  • Research Support, Non-U.S. Gov't

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