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Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells

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Chemistry of Heterocyclic Compounds Aims and scope

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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Two of us (C.D.D. and C.N.A.) wish to thank the Benianh International Foundation, ElecBTP and the Ministère de l'Enseignement Supérieur et de la Recherche de la Côte d'Ivoire for their respective grants. Financial support of this program carried out under the French National Cancer Institute “Cancéropôle Grand Ouest” by contract “Ion Channel- Network CGO 2012”, is gratefully acknowledged.

The authors are grateful to the assistance of the staff of the CRMPO analytical chemistry core facility for HRMS analysis (CRMPO platform SFS ScanMAT, Université de Rennes 1, Bât. 11A, Campus de Beaulieu, Rennes, France).

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Authors and Affiliations

  1. 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, France

    Camille Déliko Dago, Christelle N’ta Ambeu & Jean-Pierre Bazureau

  2. Laboratoire de Chimie Bioorganique et de Substances Naturelles, Université Nangui Abrogoua, BP 802, Abidjan 02, Côte d’Ivoire

    Camille Déliko Dago, Christelle N’ta Ambeu, Yves-Alain Békro & Janat A. Mamyrbekova-Bekro

  3. UFR des Sciences Biologiques, Université Péléforo Gon Coulibaly, BP 1328, Korhogo, Côte d’Ivoire

    Wacothon Karime Coulibaly

  4. Université de Rennes 1, ImPACcell Platform, SFR Biosit, Bât. 8, Campus Villejean, 2 Avenue du Prof. Léon Bernard, CS 34317, Rennes Cedex, 35043, France

    Rémy Le Guével & Anne Corlu

  5. S2Wave Platform, SFS ScanMAT, Université de Rennes 1, Bât. 10A, Campus de Beaulieu, 263 Avenue du Général Leclerc, CS 74205, Rennes Cedex, 35042, France

    Jean-Pierre Bazureau

Authors
  1. Camille Déliko Dago
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  2. Christelle N’ta Ambeu
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  3. Wacothon Karime Coulibaly
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  4. Yves-Alain Békro
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  5. Janat A. Mamyrbekova-Bekro
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  6. Rémy Le Guével
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  7. Anne Corlu
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  8. Jean-Pierre Bazureau
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Corresponding author

Correspondence to Jean-Pierre Bazureau.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(3), 341–349

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Dago, C.D., Ambeu, C.N., Coulibaly, W.K. et al. Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells. Chem Heterocycl Comp 53, 341–349 (2017). https://doi.org/10.1007/s10593-017-2056-2

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  • DOI: https://doi.org/10.1007/s10593-017-2056-2

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