Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors - Archive ouverte HAL Access content directly
Journal Articles Medicinal Chemistry Research Year : 2016

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

Rémy Le Guével
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Philippe Jehan
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Fabian Lambert
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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).
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Dates and versions

hal-01414293 , version 1 (12-12-2016)

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Camille Déliko Dago, Wacothon Karime Coulibaly, Yves-Alain Bekro, Janat A. Mamyrbekova-Bekro, Beatrice Foll-Josselin, et al.. Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene-2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors. Medicinal Chemistry Research, 2016, 25 (12), pp.2940--2958. ⟨10.1007/s00044-016-1719-3⟩. ⟨hal-01414293⟩
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