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- Title
Metal-Free meta-Selective Alkyne Oxyarylation with Pyridine N-Oxides: Rapid Assembly of Metyrapone Analogues.
- Authors
Chen, Xiangyu; Ruider, Stefan A.; Hartmann, Rolf W.; González, Leticia; Maulide, Nuno
- Abstract
An efficient metal-free oxyarylation of electron-poor alkynes with pyridine N-oxides has been developed. This transformation affords meta-substituted pyridines analogous to the drug metyrapone in high regioselectivities. Density functional theory (DFT) calculations provided important insight into the mechanism. Evaluation of the inhibitory properties revealed the most active CYP11B1 inhibitor of these derivatives, with two-digit nanomolar inhibitory activity akin to that of metyrapone.
- Subjects
METOPIRONE; NITROGEN oxides; ENZYME inhibitors; PYRIDINE synthesis; DENSITY functional theory
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 49, p15424
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201607988