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

Wacothon Karime COULIBALY; Ludovic PAQUIN; Anoubilé BÉNIÉ; Yves-Alain BEKRO; Emilie DURIEUX; Laurent MEIJER; Rémy LE GUÉVEL; Anne CORLU; Jean-Pierre BAZUREAU

doi:10.3797/scipharm.1206-04

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Article

16 September 2012

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

and

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

Université d'Abobo-Adjamé, Laboratoire de Chimie Bioorganique et de Subtances Naturelles (LCBSN), BP 802, Abidjan 02, République de la Côte d'Ivoire

Protein Phosphorylation and Human Disease Group, Station Biologique CNRS, Place G. Tessier, BP 74, 29682 Roscoff, France

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ManRos Therapeutics (From Sea to Pharmacy), Hôtel de Recherche, Centre de Perharidy, 29680 Roscoff, France

Sci. Pharm.2012, 80(4), 825-836;https://doi.org/10.3797/scipharm.1206-04

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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

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