0000000000204871
AUTHOR
Katrin Kinkel
showing 4 related works from this author
4-[5-(4-Fluorophenyl)-3-isopropylisoxazol-4-yl]pyridin-2(1H)-one
2007
The crystal structure of the title compound, C17H15FN2O2, was determined as part of a study of the biological activity of pyridine-substituted isoxazole derivatives as mitogen-activated protein kinase (MAPK) inhibitors. In the crystal structure of the title compound, the compound exists in the lactam and not in the tautomeric pyridin-2-ol form. As the aromatic pyridine nitrogen is considered to be important for accepting a hydrogen bond from p38MAPK, the structure of the lactam unit is correlated with the loss of biological activity of the title compound in the p38MAPK assay. In the crystal structure, the lactam is involved in hydrogen bonds, forming chains along the b axis.
From Five- to Six-Membered Rings: 3,4-Diarylquinolinone as Lead for Novel p38MAP Kinase Inhibitors
2007
In this study we describe the design, synthesis, and biological evaluation of 3-(4-fluorophenyl)-4-pyridin-4-ylquinoline-2(1H)-one (5) as a new inhibitor of MAPK with a p38alphaMAPK IC50 of 1.8 muM. By keeping the common vicinal pyridine/4-F-phenyl pharmacophore, such as in prototypical imidazole 20 or isoxazole 13 but in 5 connected to the six-membered quinoline core, we were particularly interested in comparing biological activity, details of molecular geometry, and different binding modes of these compounds. Compounds 20 and 13 were active both in the p38alpha- and JNK3-assay, whereas 5 was selective for p38alpha, with no JNK3 inhibition. By comparing the X-ray structures of the compound…
2,2-Dimethyl-N-[3-(3,4,5-trimethoxybenzoyl)pyridin-4-yl]propanamide
2007
The title compound, C20H24N2O5, was found to have an intramolecular N—H⋯O bond with an N⋯O distance of 2.646 (2) A. In the crystal structure, molecules form dimers along the c axis by aromatic stacking interactions. The X-ray crystallographic analysis was carried out to correlate the solid-state geometry with virtual structural information obtained by modelling.
3-(4-Fluorophenyl)-1-methyl-4-(4-pyridyl)quinolin-2(1H)-one
2007
The title compound, C21H15FN2O, was synthesized in the course of our studies of p38 mitogen-activated protein kinase inhibitors. It has been investigated by 1H and 13C NMR spectroscopy and was proven by X-ray crystallographic analysis to be the N-methyl rather than the O-methyl isomer. In the crystal structure, a three-dimensional network is formed consisting of quinolinone aromatic stacking interactions and weak C—H⋯O and C—H⋯N hydrogen bonds.