title: Synthesis of N,N'-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines bearing various linkers and biological evaluation as potential inhibitors of kinases.
abstract: The synthesis in 4 steps of new N,N'-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines issued from various symmetric primary diamines as linkers was reported. The key step of our strategy has been the sulphur/nitrogen displacement of (5Z)-5-arylidene-2-ethylsulfanyl-3,5-dihydro-4H-imidazol-4-ones 6 with respectively ethylenediamine 7a, piperazine 7b and N,N'-bis(3-aminopropyl)piperazine 7c using solvent-free reaction conditions under microwave irradiation with retention of configuration. These compounds were tested for their kinase inhibitory potencies toward four kinases (GSK-3α/β, DYRK1A, CLK1 and CLK3).
authors.affiliation: Université de Rennes 1, Institut des Sciences Chimiques de Rennes, UMR CNRS 6226, groupe Ingénierie Chimique et Molécules pour Vivant, Bât. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France.
authors.forename: Wacothon Karime
authors.initials: WK
authors.lastname: Coulibaly
authors.forename: Ludovic
authors.initials: L
authors.lastname: Paquin
authors.forename: Anoubilé
authors.initials: A
authors.lastname: Bénie
authors.forename: Yves-Alain
authors.initials: YA
authors.lastname: Bekro
authors.forename: Emilie
authors.initials: E
authors.lastname: Durieu
authors.forename: Laurent
authors.initials: L
authors.lastname: Meijer
authors.forename: Jean Pierre
authors.initials: JP
authors.lastname: Bazureau
mesh_terms: D000818:Animals; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D038362:Glycogen Synthase Kinase 3 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000071679:Glycogen Synthase Kinase 3 beta; D051379:Mice; D008872:Microwaves; D015394:Molecular Structure; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017346:Protein Serine-Threonine Kinases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D051381:Rats; D013329:Structure-Activity Relationship; D013552:Swine; D000097603:Dyrk Kinases
chemical_list: D003959:Diamines; D038362:Glycogen Synthase Kinase 3; D000071679:Glycogen Synthase Kinase 3 beta; D047428:Protein Kinase Inhibitors; D017346:Protein Serine-Threonine Kinases; D011505:Protein-Tyrosine Kinases; D000097603:Dyrk Kinases; C066780:Clk dual-specificity kinases; C448021:glycogen synthase kinase 3 alpha