Synthesis and antiproliferative effect of novel 4-thiazolidinone-, pyridine- and piperazine-based conjugates on human leukemic cells

Eur J Med Chem. 2014 Jun 23:81:341-9. doi: 10.1016/j.ejmech.2014.05.009. Epub 2014 May 4.

Abstract

The present work reveals the synthesis and antiproliferative effect of a series of 2, 3 disubstituted 4-thiazolidinone analogues on human leukemic cells. The chemical structures of newly synthesized compounds were confirmed by IR, (1)H NMR, (13)C NMR and mass spectral analysis. Compound methyl 3-methoxy-4-(4-oxo-3-(5-(piperazin-1-yl)pyridin-2-yl)thiazolidin-2-yl)benzoate (5) displayed potent activity (IC509.71, 15.24 and 19.29 μM) against Nalm6, K562, Jurkat cells. Cell cycle analysis and mitochondrial membrane potential further confirmed that compound 5 is cytotoxic and able to induce cell death.

Keywords: Apoptosis; Chemotherapeutics; Cytotoxicity; Leukemia; Propylphosphonic anhydride (T(3)P(®)); Thiazolidinones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Cycle / drug effects
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Humans
  • K562 Cells
  • Leukemia / pathology*
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Structure
  • Piperazine
  • Piperazines / chemistry
  • Piperazines / pharmacology*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Structure-Activity Relationship
  • Thiazolidines / chemistry
  • Thiazolidines / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Piperazines
  • Pyridines
  • Thiazolidines
  • Piperazine
  • pyridine