INVESTIGATION ON THE SYNTHESIS OF NEW 3-[4-(ARYLALKOXY)PHENYLETHYL]-2-THIOXO-1,3-THIAZOLIDIN-4-ONES AND THEIR BIOLOGICAL EVALUATION AGAINST CANCER CELLS

Authors

  • Camille D. Dago Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Bât. 10A, Campus de Beaulieu, 263 Avenue du Général Leclerc, CS 74205, Rennes Cedex 35042
  • Christelle N'ta Ambeu Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Bât. 10A, Campus de Beaulieu, 263 Avenue du Général Leclerc, CS 74205, Rennes Cedex 35042
  • Wacothon K. Coulibaly UFR des Sciences Biologiques, Université Péléforo Gon Coulibaly, BP 1328, Korhogo
  • Janat A. Mamyrbekova-Bekro Laboratoire de Chimie Bioorganique et de Substances Naturelles, Université Nangui Abrogoua, BP 802, Abidjan 02
  • Rémy Le Guével Université de Rennes 1, ImPACcell Platform, SFR Biosit, Bât. 8, Campus Villejean, 2 Avenue du Prof. Léon Bernard, CS 34317, Rennes Cedex 35043
  • Anne Corlu Université de Rennes 1, ImPACcell Platform, SFR Biosit, Bât. 8, Campus Villejean, 2 Avenue du Prof. Léon Bernard, CS 34317, Rennes Cedex 35043
  • Jean-Pierre Bazureau Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Bât. 10A, Campus de Beaulieu, 263 Avenue du Général Leclerc, CS 74205, Rennes Cedex 35042

DOI:

https://doi.org/10.1007/3508

Keywords:

3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1, 3-thiazolidin-4-one, rhodanine, microwave irradiation, tumoral cell lines

Abstract

Herein, we report on the 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones without 5-arylidene fragments starting from tyramine The construction involved protection with Boc2O, regioselective O-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl)trithiocarbonate under microwave irradiation. The intermediates and the N-substituted rhodanine have been also evaluated for their in vitro inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line.

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Published

2017-04-18

Issue

Vol. 53 No. 3 (2017): Privileged heterocyclic scaffolds in chemical biology and drug discovery: synthesis and bioactivity

Section

Original Papers