title: Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases.
abstract: An efficient protocol for Ru(II)-catalyzed direct C-H oxygenation of a broad range of flavone and chromone substrates was developed. This convenient and powerful synthetic tool allows for the rapid installation of the hydroxyl group into the flavone, chromone, and other related scaffolds and opens the way for analog synthesis of highly potent Aurora kinase inhibitors. The molecular docking simulations indicate that the formation of bidentate H-bonding patterns in the hinge regions between the 5-hydroxyflavonoids and Ala213 was the significant binding force, which is consistent with experimental and computational findings.
authors.affiliation: †Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Korea.|‡Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Korea.
authors.forename: Kiho
authors.initials: K
authors.lastname: Kim
authors.affiliation: †Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Korea.|‡Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Korea.
authors.forename: Hyeonjeong
authors.initials: H
authors.lastname: Choe
authors.affiliation: †Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Korea.|‡Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Korea.
authors.forename: Yujeong
authors.initials: Y
authors.lastname: Jeong
authors.affiliation: ‡Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Korea.
authors.forename: Jun Hee
authors.initials: JH
authors.lastname: Lee
authors.affiliation: †Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Korea.|‡Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Korea.
authors.forename: Sungwoo
authors.initials: S
authors.lastname: Hong
mesh_terms: D064127:Aurora Kinases / Q000037:antagonists & inhibitors*; D002867:Chromones / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D047309:Flavones / Q000737:chemistry*; D017665:Hydroxyl Radical; D006900:Hydroxylation; D015394:Molecular Structure; D047428:Protein Kinase Inhibitors / Q000737:chemistry; D017434:Protein Structure, Tertiary; D012428:Ruthenium / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D002867:Chromones; D047309:Flavones; D047428:Protein Kinase Inhibitors; D017665:Hydroxyl Radical; D012428:Ruthenium; D064127:Aurora Kinases; C043562:flavone