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5 results on '"pyridinylimidazole"'

1. N1-{4-[2-(Methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine

Author

Ahmed El-Gokha, Francesco Ansideri, Stanislav Andreev, Dieter Schollmeyer, Stefan Laufer, and Pierre Koch

Subjects
pyridinylimidazole, kinase inhibitor, c-Jun N-terminal kinase 3, JNK3, heterocycle, single crystal diffraction, Inorganic chemistry, QD146-197
Abstract

The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, IR and UV-VIS. Additionally, the structure of 2 was confirmed by single crystal X-ray diffraction. Pyridinylimidazole 2 displays moderate affinity towards the c-Jun N-terminal kinase 3 and shows selectivity versus the closely related p38α mitogen-activated protein kinase.

Published
2019
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2. 1-(3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-5-yl)-3-[4-({4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}amino)phenyl]thiourea methanol monosolvate

Author

Francesco Ansideri, Dieter Schollmeyer, and Pierre Koch

Subjects
crystal structure, fluorescein, thiourea, pyridinylimidazole, Crystallography, QD901-999
Abstract

The title compound, which crystallized as a methanol monosolvate, C41H27FN6O5S·CH3OH, was synthesized as a probe for a fluorescence polarization-based competition binding assay. The isobenzofuran fused-ring system is close to planar and orientated almost perpendicular to the central ring of the xanthene system. The dihedral angle between the benzene rings of the xanthene system is 10.0 (2)°, indicating a butterfly-like orientation. A short intramolecular C—F...π contact [F...π = 3.100 (4) Å and C—F...π = 139.9 (3)°] to the six-membered ring of the isobenzofuran system may influence the molecular conformation. The methanol solvent molecule is disordered over two orientations in a 0.6:0.4 ratio. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.

Published
2016
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3. Pyridinylimidazoles as GSK3β Inhibitors: The Impact of Tautomerism on Compound Activity via Water Networks

Author

Mark Kudolo, Stefan Laufer, Francesco Ansideri, Taiane Schneider, Fabian Heider, Letizia Pruccoli, Pierre Koch, Andrea Tarozzi, Angela De Simone, Márcia Inês Goettert, Vincenza Andrisano, Tatu Pantsar, Heider F., Pantsar T., Kudolo M., Ansideri F., De Simone A., Pruccoli L., Schneider T., Goettert M.I., Tarozzi A., Andrisano V., Laufer S.A., and Koch P.

Subjects
Stereochemistry, Drug target, Protein kinase inhibitors, quantum mechanic, glycogen synthase kinase-3β, molecular dynamics simulation, pyridinylimidazoles, quantum mechanics, tautomerism, 01 natural sciences, Biochemistry, Drug Discovery, Ic50 values, Protein kinase A, Glycogen synthase, biology, 010405 organic chemistry, Kinase, Chemistry, Organic Chemistry, Dual inhibitor, Tautomer, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, pyridinylimidazole, Protein kinase inhibitor, biology.protein, Selectivity
Abstract

[Image: see text] Glycogen synthase kinase-3β (GSK3β) is involved in many pathological conditions and represents an attractive drug target. We previously reported dual GSK3β/p38α mitogen-activated protein kinase inhibitors and identified N-(4-(4-(4-fluorophenyl)-2-methyl-1H-imidazol-5-yl)pyridin-2-yl)cyclopropanecarboxamide (1) as a potent dual inhibitor of both target kinases. In this study, we aimed to design selective GSK3β inhibitors based on our pyridinylimidazole scaffold. Our efforts resulted in several novel and potent GSK3β inhibitors with IC(50) values in the low nanomolar range. 5-(2-(Cyclopropanecarboxamido)pyridin-4-yl)-4-cyclopropyl-1H-imidazole-2-carboxamide (6g) displayed very good kinase selectivity as well as metabolical stability and inhibited GSK3β activity in neuronal SH-SY5Y cells. Interestingly, we observed the importance of the 2-methylimidazole’s tautomeric state for the compound activity. Finally, we reveal how this crucial tautomerism effect is surmounted by imidazole-2-carboxamides, which are able to stabilize the binding via enhanced water network interactions, regardless of their tautomeric state.

Published
2019
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4. N1-{4-[2-(Methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine

Author

Stanislav Andreev, Francesco Ansideri, Pierre Koch, Dieter Schollmeyer, Ahmed El-Gokha, and Stefan Laufer

Subjects
kinase inhibitor, 010402 general chemistry, 01 natural sciences, Biochemistry, Medicinal chemistry, High-performance liquid chromatography, chemistry.chemical_compound, Nucleophilic aromatic substitution, Diamine, Pyridine, lcsh:Inorganic chemistry, Physical and Theoretical Chemistry, Protein kinase A, Benzene, single crystal diffraction, JNK3, c-Jun N-terminal kinase 3, 010405 organic chemistry, Organic Chemistry, lcsh:QD146-197, 0104 chemical sciences, chemistry, pyridinylimidazole, Selectivity, Single crystal, heterocycle
Abstract

The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, IR and UV-VIS. Additionally, the structure of 2 was confirmed by single crystal X-ray diffraction. Pyridinylimidazole 2 displays moderate affinity towards the c-Jun N-terminal kinase 3 and shows selectivity versus the closely related p38α mitogen-activated protein kinase.

Published
2019

5. N1-{4-[2-(Methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine.

Author

El-Gokha, Ahmed, Ansideri, Francesco, Andreev, Stanislav, Schollmeyer, Dieter, Laufer, Stefan, and Koch, Pierre

Subjects
*MITOGEN-activated protein kinases, *SINGLE crystals, *PHENYLENEDIAMINES, *X-ray diffraction
Abstract

The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, IR and UV-VIS. Additionally, the structure of 2 was confirmed by single crystal X-ray diffraction. Pyridinylimidazole 2 displays moderate affinity towards the c-Jun N-terminal kinase 3 and shows selectivity versus the closely related p38α mitogen-activated protein kinase. [ABSTRACT FROM AUTHOR]

Published
2019
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