title: Metal-Free meta-Selective Alkyne Oxyarylation with Pyridine N-Oxides: Rapid Assembly of Metyrapone Analogues.
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.
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria.
authors.forename: Xiangyu
authors.initials: X
authors.lastname: Chen
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria.|Institute of Theoretical Chemistry, University of Vienna, Währinger Strasse 17, 1090, Vienna, Austria.
authors.forename: Stefan A
authors.initials: SA
authors.lastname: Ruider
authors.affiliation: Pharmaceutical and Medicinal Chemistry, Saarland University and Helmholtz Institute for Pharmaceutical Research, Campus E8.1, 66123, Saarbrücken, Germany.
authors.forename: Rolf W
authors.initials: RW
authors.lastname: Hartmann
authors.affiliation: Institute of Theoretical Chemistry, University of Vienna, Währinger Strasse 17, 1090, Vienna, Austria.
authors.forename: Leticia
authors.initials: L
authors.lastname: González
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria.
authors.forename: Nuno
authors.initials: N
authors.lastname: Maulide
keywords: 11β-hydroxylase (CYP11B1); alkynes; density functional calculations; oxyarylations; pyridine N-oxides