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Synthesis of novel 5-arylidenethiazolidinones with apoptotic properties: Via a three component reaction using piperidine as a bifunctional reagent
Published in Royal Society of Chemistry
PMID: 27396309
Volume: 14
Issue: 34
Pages: 8053 - 8063
The synthesis of a new library of 5-arylidenethiazolidinone compounds using an efficient three component reaction with thiazolidine-2,4-dione, piperidine and appropriate aldehydes is reported. This reaction is excellently high yielding, tolerant towards a variety of aldehydes and provides access to these compounds in a single step (in comparison to low yielding multistep syntheses reported in the literature). Once the reaction is complete, the desired product precipitates out of the reaction mixture and is isolated by filtration and purified by washing and recrystallization. These compounds revealed anti-proliferative activities against human breast cancer cells (MCF7 and MDA). Phenotypic profiling established the most active compound 17i (EC50 = 4.52 μM) as an apoptotic agent. A novel chemical proteomics approach identified β-actin-like protein 2, γ-enolase and macrophage migration inhibitory factor (MMIF) as putative cellular binding partners of 17i. © 2016 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetOrganic and Biomolecular Chemistry
PublisherData powered by TypesetRoyal Society of Chemistry
Open AccessNo