N-Substituted pyrimidinethione and acetophenone derivatives as a new therapeutic approach in diabetes

Arch Pharm (Weinheim). 2020 Sep;353(9):e2000075. doi: 10.1002/ardp.202000075. Epub 2020 Jun 14.

Abstract

In this study, compounds with 4-hydroxybutyl, 4-phenyl, 5-carboxylate, and pyrimidine moieties were determined as α-glycosidase inhibitors. N-Substituted pyrimidinethione and acetophenone derivatives (A1-A5, B1-B11, and C1-C11) were good inhibitors of the α-glycosidase enzyme, with Ki values in the range of 104.27 ± 15.75 to 1,004.25 ± 100.43 nM. Among them, compound B7 was recorded as the best inhibitor, with a Ki of 104.27 ± 15.75 nM against α-glycosidase. In silico studies were carried out to clarify the binding affinity and interaction mode of the compounds with the best inhibition score against α-glycosidase from Saccharomyces cerevisiae. Compounds B7 (S) and B11 (R) exhibited a good binding affinity with docking scores of -8.608 and 8.582 kcal/mol, respectively. The docking results also showed that the 4-hydroxybutyl and pyrimidinethione moieties play a key role in S. cerevisiae and human α-glycosidase inhibition.

Keywords: N-substituted pyrimidinethione; acetophenone; diabetes mellitus; molecular docking; α-glycosidase.

MeSH terms

  • Acetophenones / chemical synthesis
  • Acetophenones / chemistry
  • Acetophenones / pharmacology*
  • Diabetes Mellitus / drug therapy
  • Glycoside Hydrolase Inhibitors / chemical synthesis
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Humans
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology*
  • Molecular Docking Simulation
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Saccharomyces cerevisiae / enzymology
  • Structure-Activity Relationship
  • Thiones / chemical synthesis
  • Thiones / chemistry
  • Thiones / pharmacology

Substances

  • Acetophenones
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • Pyrimidines
  • Thiones