A convenient approach to synthesize substituted 5-Arylidene-3-m-tolyl thiazolidine-2, 4-diones by using morpholine as a catalyst and its theoretical study

PLoS One. 2021 Mar 4;16(3):e0247619. doi: 10.1371/journal.pone.0247619. eCollection 2021.

Abstract

Thiazolidinediones are very important and used as a drug for the treatment of type 2 diabetes. Here, we report a convenient approach to synthesis 3-m-tolyl-5-arylidene-2,4-thiazolidinediones (TZDs) derivatives 7a-e in two steps with moderate to good yield using morpholine as a catalyst. All the structures were confirmed by their spectral IR, 1H NMR and 13C NMR data. The anti-diabatic activity of all synthesized molecules is evaluated by docking with peroxisome proliferator-activated receptor-γ (PPARγ). Preliminary flexible docking studies reveals that our compounds 7a, 7d and 7e showed better binding affinity with the protein and could be a potential candidate for the treatment of type 2 diabetes in near future.

MeSH terms

  • Carbon-13 Magnetic Resonance Spectroscopy / methods
  • Catalysis
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry*
  • Hypoglycemic Agents / metabolism
  • Models, Chemical
  • Molecular Docking Simulation
  • Molecular Structure
  • Morpholines / chemistry*
  • PPAR gamma / chemistry
  • PPAR gamma / metabolism
  • Protein Binding
  • Proton Magnetic Resonance Spectroscopy / methods
  • Spectrophotometry, Infrared / methods
  • Structure-Activity Relationship
  • Thiazolidinediones / chemical synthesis
  • Thiazolidinediones / chemistry*
  • Thiazolidinediones / metabolism
  • Thiazolidines / chemistry*

Substances

  • Hypoglycemic Agents
  • Morpholines
  • PPAR gamma
  • Thiazolidinediones
  • Thiazolidines
  • morpholine

Grants and funding

The author(s) received no specific funding for this work.