Evaluation of in vitro aldose redutase inhibitory activity of 5-arylidene-2,4-thiazolidinediones

Rosanna Maccari, Rosaria Ottanà, Rosella Ciurleo, Maria Gabriella Vigorita, Dietmar Rakowitz, Theodora Steindl, Thierry Langer

Research output: Contribution to journalArticlepeer-review


A number of 5-arylidene-2,4-thiazolidinediones containing a hydroxy or a carboxymethoxy group in their 5-benzylidene moiety have been synthesised and evaluated as in vitro aldose reductase (ALR2) inhibitors. Most of them exhibited strong inhibitory activity, with IC50 values in the range between 0.20 and 0.70 μM. Molecular docking simulations into the ALR2 active site highlighted that the phenolic or carboxylic substituents of the 5-benzylidene moiety can favourably interact, in alternative poses, either with amino acid residues lining the lipophilic pocket of the enzyme, such as Leu300, or with the positively charged recognition region of the ALR2 active site.

Original languageEnglish
Pages (from-to)3886-3893
Number of pages8
JournalBioorganic and Medicinal Chemistry Letters
Issue number14
Publication statusPublished - Jul 15 2007


  • 2,4-Thiazolidinediones
  • Aldose reductase
  • Diabetes mellitus
  • Molecular docking

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science


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