Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors

Camille Déliko Dago; Wacothon Karime Coulibaly; Yves-Alain Bekro; Janat A. Mamyrbekova-Bekro; Beatrice Foll-Josselin; Audrey Defontaine; Claire Delehouze; Stéphane Bach; Sandrine Ruchaud; Rémy Le Guével; Anne Corlu; Philippe Jehan; Fabian Lambert; Nicolas Le Yondre; Jean-Pierre Bazureau; Christelle Ambeu

doi:10.1007/s00044-016-1719-3

Journal articles

Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors

Camille Déliko Dago ^{1, 2} Wacothon Karime Coulibaly ¹ Yves-Alain Bekro ² Janat A. Mamyrbekova-Bekro ² Beatrice Foll-Josselin ³ Audrey Defontaine ³ Claire Delehouze ³ Stéphane Bach ³ Sandrine Ruchaud ³ Rémy Le Guével ⁴ Anne Corlu ^{4, 5} Philippe Jehan Fabian Lambert Nicolas Le Yondre ⁶ Jean-Pierre Bazureau ¹ Christelle Ambeu ^{2, 1}

1 ISCR - Institut des Sciences Chimiques de Rennes

2 LCBOSN - Laboratoire de Chimie Bioorganique et des Substances Naturelles

3 P3H - Phophorylation de protéines et Pathologies Humaines

4 ImPACcell - Plate-forme ImPACcell

5 Foie, métabolismes et cancer

6 CRMPO - Centre Régional de Mesures Physiques de l'Ouest

Abstract : The synthesis of a series of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones hydrochlorides was reported. The key step of this synthetic approach involved a "one-pot two-step" protocol under microwave dielectric heating with good stereocontrol of the Knoevenagel condensation for all these new 5-arylidene rhodanines. The 18 new compounds were evaluated for their in vitro cell proliferation inhibition and also for their kinase inhibitory potencies against seven protein kinases. Two compounds (7f and 7r) were identified as potential protein kinase inhibitors. New (5Z) 3-(3-aminopropyl)-5-arylidene rhodanine derivatives 7a-r were synthesized in four steps with overall yields ranging from 7 to 68 % and tested against seven protein kinases (HsCDK5-p25, GSK3 alpha/beta, SsCK1 delta/epsilon, HsHaspin, HsRIPK3, HsPIM1 and Aurora B).

Keywords : phosphorylation rhodanine derivatives affinity-chromatography biological evaluation immobilized axin beta inhibitors leucettamine b cell lines discovery reductase

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Journal articles

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Chemical Sciences

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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01414293
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Submitted on : Monday, December 12, 2016 - 11:27:06 AM
Last modification on : Thursday, January 14, 2021 - 11:15:29 AM

Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors

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Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors

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