title: Synthesis of novel 5-arylidenethiazolidinones with apoptotic properties via a three component reaction using piperidine as a bifunctional reagent.
abstract: 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.
authors.affiliation: Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Chithera, Dadri, GautamBudh Nagar, Uttar Pradesh 201308, India. subhabrata.sen@snu.edu.in.
authors.forename: Chandramohan
authors.initials: C
authors.lastname: Bathula
authors.forename: Sayantan
authors.initials: S
authors.lastname: Tripathi
authors.forename: Ramprasad
authors.initials: R
authors.lastname: Srinivasan
authors.forename: Kunal Kumar
authors.initials: KK
authors.lastname: Jha
authors.forename: Arnab
authors.initials: A
authors.lastname: Ganguli
authors.forename: G
authors.initials: G
authors.lastname: Chakrabarti
authors.forename: Shailja
authors.initials: S
authors.lastname: Singh
authors.forename: Parthapratim
authors.initials: P
authors.lastname: Munshi
authors.forename: Subhabrata
authors.initials: S
authors.lastname: Sen
mesh_terms: D017209:Apoptosis / Q000187:drug effects*; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D007202:Indicators and Reagents / Q000737:chemistry; D061986:MCF-7 Cells; D008958:Models, Molecular; D008968:Molecular Conformation; D010880:Piperidines / Q000737:chemistry*; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D007202:Indicators and Reagents; D010880:Piperidines; D053778:Thiazolidines; C032727:piperidine