5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases

Rosanna Maccari, Paolo Paoli, Rosaria Ottanà, Michela Jacomelli, Rosella Ciurleo, Giampaolo Manao, Theodora Steindl, Thierry Langer, Maria Gabriella Vigorita, Guido Camici

Research output: Contribution to journalArticlepeer-review


4-(5-Arylidene-2,4-dioxothiazolidin-3-yl)methylbenzoic acids (2) were synthesized and evaluated in vitro as inhibitors of PTP1B and LMW-PTP, two protein tyrosine phosphatases (PTPs) which act as negative regulators of the metabolic and mitotic signalling of insulin. The synthesis of compounds 2 represents an example of utilizing phosphotyrosine-mimetics to identify effective low molecular weight nonphosphorus inhibitors of PTPs. Several thiazolidinediones 2 exhibited PTP1B inhibitory activity in the low micromolar range with moderate selectivity for human PTP1B and IF1 isoform of human LMW-PTP compared with other related PTPs.

Original languageEnglish
Pages (from-to)5137-5149
Number of pages13
JournalBioorganic and Medicinal Chemistry
Issue number15
Publication statusPublished - Aug 1 2007


  • Diabetes mellitus
  • Molecular modelling
  • Protein tyrosine phosphatases
  • PTP1B and LMW-PTP inhibitors

ASJC Scopus subject areas

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


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