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Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2016). Articles in this Issue were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence. Articles are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
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Sci. Pharm. 2012, 80(4), 825-836; https://doi.org/10.3797/scipharm.1206-04 (registering DOI)

Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation

1
Université de Rennes 1, Institut des Sciences Chimiques de Rennes (ISCR), UMR CNRS 6226, groupe Ingénièrie Chimique et Molécules pour le Vivant (ICMV), Bât. 10A, campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France
2
Université d'Abobo-Adjamé, Laboratoire de Chimie Bioorganique et de Subtances Naturelles (LCBSN), BP 802, Abidjan 02, République de la Côte d'Ivoire
3
Protein Phosphorylation and Human Disease Group, Station Biologique CNRS, Place G. Tessier, BP 74, 29682 Roscoff, France
4
ManRos Therapeutics (From Sea to Pharmacy), Hôtel de Recherche, Centre de Perharidy, 29680 Roscoff, France
5
Université de Rennes 1, ImPACcell Platform, IFR 140, Bât. 8, 2 Avenue du Prof. Léon Bernard, CS 34317, 35043 Rennes Cedex, France
*
Author to whom correspondence should be addressed.
Received: 4 June 2012 / Accepted: 16 September 2012 / Published: 16 September 2012
PDF [187 KB, uploaded 30 September 2016]

Abstract

New N,N'-bis(5-arylidene-4-oxo-4,5-dihydrothiazoline-2-yl)diamine derivatives 5 were prepared in two steps from rhodanine and piperazine, or 1,4-bis(3-amino-propyl)piperazine, under microwave reaction conditions with retention of configuration. Some of these compounds were tested for in vitro antiproliferative activities and for their kinase inhibitory potencies towards six kinases (CDK5/p25, GSK3α/β, DYRK1A, DYRK2, CLK1, and CLK2). The compound 5d showed nanomolar activity towards DYRK1A kinase (IC50 = 0.041 μM).
Keywords: 5-Arylidene rhodanine; 2,2'-(Piperazine-1,4-diyl)bis(5-benzylidene-1,3-thiazol-4(5H)-one); Microwave irradiation; Cytotoxity; Protein kinase; Diamines 5-Arylidene rhodanine; 2,2'-(Piperazine-1,4-diyl)bis(5-benzylidene-1,3-thiazol-4(5H)-one); Microwave irradiation; Cytotoxity; Protein kinase; Diamines
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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MDPI and ACS Style

COULIBALY, W.K.; PAQUIN, L.; BÉNIÉ, A.; BEKRO, Y.-A.; DURIEUX, E.; MEIJER, L.; LE GUÉVEL, R.; CORLU, A.; BAZUREAU, J.-P. Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation. Sci. Pharm. 2012, 80, 825-836.

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