Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases

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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.
Publisher
AMER CHEMICAL SOC
Issue Date
2015-06
Language
English
Article Type
Article
Keywords

C-H BOND; CARBON-CARBON BONDS; RUTHENIUM(II) CARBOXYLATE; DIRECTING GROUPS; ACTIVATION; FUNCTIONALIZATION; OXYGENATION; PALLADIUM; ARENES; ARYLATIONS

Citation

ORGANIC LETTERS, v.17, no.10, pp.2550 - 2553

ISSN
1523-7060
DOI
10.1021/acs.orglett.5b01138
URI
http://hdl.handle.net/10203/199128
Appears in Collection
CH-Journal Papers(저널논문)
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