title: Rh(III)-catalyzed direct C-H/C-H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors.
abstract: Rh-catalyzed direct C-H/C-H cross-coupling reaction of various (hetero)arenes with quinones is developed. This protocol is effective for a broad range of both quinone and arene substrates and a wide range of directing groups for this reaction, affording structurally diverse aryl-substituted quinones with high synthetic utility. Moreover, the present synthetic route allowed for the rapid construction of the carbazole quinone moiety that was identified as a new inhibitor scaffold for GSKβ.
authors.affiliation: Department of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon, 305-701, Korea.
authors.forename: Youngtaek
authors.initials: Y
authors.lastname: Moon
authors.forename: Yujeong
authors.initials: Y
authors.lastname: Jeong
authors.forename: Daehyuk
authors.initials: D
authors.lastname: Kook
authors.forename: Sungwoo
authors.initials: S
authors.lastname: Hong
mesh_terms: D000255:Adenosine Triphosphate / Q000378:metabolism; D002227:Carbazoles / Q000737:chemistry*; D002384:Catalysis; D055808:Drug Discovery; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D038362:Glycogen Synthase Kinase 3 / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D000071679:Glycogen Synthase Kinase 3 beta; D006801:Humans; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D062105:Molecular Docking Simulation; D011809:Quinones / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D002227:Carbazoles; D004791:Enzyme Inhibitors; D006841:Hydrocarbons, Aromatic; D011809:Quinones; C041514:carbazole; D000255:Adenosine Triphosphate; D012238:Rhodium; D000071679:Glycogen Synthase Kinase 3 beta; D038362:Glycogen Synthase Kinase 3