title: Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that Inhibit ALK5 Kinase.
abstract: C-H activation of position 3 of a substituted pyrazole ring catalyzed by palladium(II) was straightforward and convenient for arylated or heteroarylated 5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles. Moreover, we introduced simple protection of the nitrogen in the pyridin-2-yl directing group, which otherwise does not allow a cross-coupling reaction, by transformation to the N-oxide. Selected final products were reasonably selective ALK5 kinase inhibitors.
authors.affiliation: Department of Chemistry, Faculty of Science, Masaryk University , Kotlářská 2, 611 37 Brno, Czech Republic.
authors.forename: Lukáš
authors.initials: L
authors.lastname: Tenora
authors.affiliation: Department of Chemistry, Faculty of Science, Masaryk University , Kotlářská 2, 611 37 Brno, Czech Republic.
authors.forename: Juraj
authors.initials: J
authors.lastname: Galeta
authors.affiliation: Laboratory of Growth Regulators, Faculty of Science, Palacký University & Institute of Experimental Botany ASCR , Šlechtitelů 27, 783 71 Olomouc, Czech Republic.
authors.forename: Eva
authors.initials: E
authors.lastname: Řezníčková
authors.affiliation: Laboratory of Growth Regulators, Faculty of Science, Palacký University & Institute of Experimental Botany ASCR , Šlechtitelů 27, 783 71 Olomouc, Czech Republic.
authors.forename: Vladimír
authors.initials: V
authors.lastname: Kryštof
authors.affiliation: Department of Chemistry, Faculty of Science, Masaryk University , Kotlářská 2, 611 37 Brno, Czech Republic.
authors.forename: Milan
authors.initials: M
authors.lastname: Potáček
mesh_terms: D002384:Catalysis; D010165:Palladium / Q000737:chemistry*; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017346:Protein Serine-Threonine Kinases / Q000037:antagonists & inhibitors*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000077293:Receptor, Transforming Growth Factor-beta Type I; D018125:Receptors, Transforming Growth Factor beta / Q000037:antagonists & inhibitors*; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D047428:Protein Kinase Inhibitors; D011720:Pyrazoles; D018125:Receptors, Transforming Growth Factor beta; D010165:Palladium; D017346:Protein Serine-Threonine Kinases; D000077293:Receptor, Transforming Growth Factor-beta Type I