0000000001304701
AUTHOR
Pierre Koch
showing 32 related works from this author
(2S,3′S,3a'R,5′R,7a'R)-5′-[(E)-5-(Furan-3-yl)-2-methylpent-1-en-1-yl]-3-hydroxy-3′,4,7′-trimethyl-1′,2′,3′,3a',5′,7a'-hexahydro-5H-spiro[furan-2,4′-i…
2020
The title compound, ircinianin, C25H32O4, belongs to the sesterterpene tetronic acid compound family and was isolated from the marine sponge Ircinia wistarii. These chemical scaffolds are pharmacologically relevant, since they represent a new class of glycine receptor modulators. The furan ring makes a dihedral angle of 35.14 (12)° to the 4-hydroxy-3-methylfuran-2(5H)-one ring. The crystal packing is characterized by intermolecular O—H...O hydrogen bonds, which generate [010] chains.
1-[2-(Benzylamino)-4-pyridyl]-2-(4-fluorophenyl)ethane-1,2-dione
2009
The crystal structure of the title compound, C20H15FN2O2, contains two crystallographically independent molecules, which are related by a pseudo-inversion center and linked into dimersviaintermolecular N—H...N hydrogen bonds. The 4-fluorophenyl ring of moleculeAmakes dihedral angles of 17.17 (16) and 62.25 (15)°, respectively, with the phenyl and pyridine rings. The 4-fluorophenyl ring of moleculeBmakes dihedral angles of 8.50 (16) and 64.59 (15)°, respectively, with the phenyl and pyridine rings. The dihedral angle between the pyridine ring and the phenyl ring of moleculeA[60.97 (15)°] is bigger than in moleculeB[59.49 (15)°]. The dihedral angle between the two pyridine rings is 1.37 (14)°…
Selective mono-de-O-acetylation of the per-O-acetylated brasilicardin carbohydrate side chain
2021
Abstract Methanol dried over powdered 4 A molecular sieves can be used for a selective mono-de-O-acetylation of the phenolic acetyl group of the per-O-acetyl protected brasilicardin A carbohydrate side chain. This reaction opens a practical procedure for a synthetic access to derivates of the immunosuppressive and cytotoxic natural product brasilicardin A.
4-(4-Fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amine
2012
In the title compound, C20H12Cl3FN4, the pyrazole ring forms dihedral angles of 47.51 (9), 47.37 (9) and 74.37 (9)° with the directly attached 4-fluorophenyl, pyridine and 2,4,6-trichlorophenyl rings, respectively. Only one of the two amino H atoms is involved in hydrogen bonding. The crystal packing is characterized by N—H...N hydrogen bonds, which result in infinite chains parallel to the c axis.
N-{4-[3-(4-Fluorophenyl)pyrido[2,3-b]pyrazin-2-yl]-2-pyridyl}isopropylamine
2009
In the crystal structure of the title compound, C21H18FN5, the pyridopyrazine ring system forms dihedral angles of 33.27 (7) and 48.69 (9)° with the 4-fluorophenyl and pyridine ring, respectively. The dihedral angle of the 4-fluorophenyl and pyridine rings is 57.45 (8)°. The crystal packing is characterized by an intermolecular N—H...N hydrogen bond.
tert-Butyl N-benzyl-N-(4-methyl-2-pyridyl)carbamate
2008
In the crystal structure of the title compound, C18H22N2O2, the pyridine ring makes dihedral angles of 83.71 (6) and 9.2 (1)° with the phenyl ring and the carbamate plane, respectively. The phenyl ring and the carbamate plane are nearly perpendicular to one another, with a dihedral angle of 87.17 (7)°.
5-(4-Fluoro-phen-yl)-4-(4-pyrid-yl)-1,3-oxazol-2-amine.
2010
In the crystal structure of the title compound, C14H10FN3O, the plane of the isoxazole ring makes dihedral angles of 35.72 (9) and 30.00 (9)°, respectively, with those of the 4-fluorophenyl and pyridine rings. The plane of the 4-fluorophenyl ring makes a dihedral angle of 45.85 (8)° with that of the pyridine ring. The crystal structure is stabilized by intermolecular N—H...N hydrogen bonding. The two types of hydrogen bonds result in two chains, extending along the a axis, which are related by centres of symmetry.
Structural Optimization of a Pyridinylimidazole Scaffold: Shifting the Selectivity from p38α Mitogen-Activated Protein Kinase to c-Jun N-Terminal Kin…
2018
Starting from known p38α mitogen-activated protein kinase (MAPK) inhibitors, a series of inhibitors of the c-Jun N-terminal kinase (JNK) 3 was obtained. Altering the substitution pattern of the pyridinylimidazole scaffold proved to be effective in shifting the inhibitory activity from the original target p38α MAPK to the closely related JNK3. In particular, a significant improvement for JNK3 selectivity could be achieved by addressing the hydrophobic region I with a small methyl group. Furthermore, additional structural modifications permitted to explore structure–activity relationships. The most potent inhibitor 4-(4-methyl-2-(methylthio)-1H-imidazol-5-yl)-N-(4-morpholinophenyl)pyridin-2-a…
(2S,3S)-2-Azaniumyl-4-[(1S,4aS,4bS,6S,7S,8aS,10aS)-6,7-dihydroxy-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]-…
2018
The title compound, which crystallized as a methanol and water solvate, C24H41NO5·CH4O·H2O, was obtained by heterologous expression of the brasilicardin gene cluster in the bacterium Amycolatopsis japonicum. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.
tert-Butyl N-benzyl-N-[4-(4-fluorobenzoylmethyl)-2-pyridyl]carbamate
2008
In the crystal structure of the title compound, C25H25FN2O3, the pyridine ring makes dihedral angles of 75.1 (3), 39.4 (3) and 74.6 (3)° with the phenyl ring, the carbamate plane and the 4-fluorophenyl ring, respectively. The phenyl ring makes dihedral angles of 77.2 (3) and 23.6 (3)° with the carbamate plane and the 4-fluorophenyl ring, respectively. The 4-fluorophenyl ring is perpendicular to the carbamate plane, the dihedral angle between them being 89.5 (3)°.
4-[3-(4-Fluorophenyl)quinoxalin-2-yl]-N-isopropylpyridin-2-amine
2009
In the crystal structure of the title compound, C22H19FN4, the quinoxaline system makes dihedral angles of 32.07 (13) and 69.64 (13)° with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 71.77 (16)° with the pyridine ring. The crystal structure is stabilized by intermolecular N—H...N hydrogen bonding.
2-(4-Fluorophenyl)-3-(4-pyridyl)pyrido[2,3-b]pyrazine
2009
In the crystal structure of the title compound, C18H11FN4, the pyridopyrazine system makes dihedral angles of 45.51 (7) and 44.75 (7)° with the attached 4-fluorophenyl ring and the pyridine ring, respectively. The 4-fluorophenyl ring makes a dihedral angle of 54.54 (8)° with the pyridine ring. The pyridine ring part of the pyridopyrazine ring and the pyrazine ring of two c-glide-plane-related molecules form π–π interactions. The angle between the planes is 2.09 (7)° and the distance between the centroids is 3.557 (1)Å.
tert-ButylN-(4-methyl-2-pyridyl)carbamate
2008
The crystal structure of the title compound, C11H16N2O2, contains two crystallographically independent molecules forming dimers by pairs of intermolecular N—H...N hydrogen bonds. The two molecules are related by a pseudo-twofold axis. The dihedral angle between the pyridine ring and the carbamate plane differs in the two molecules [12.1 (3) and 3.5 (3)°].
(2S,3S)-2-Azaniumyl-4-[(1S,4aS,4bS,6S,7S,8aS,10aS)-6,7-dihydroxy-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]-…
2018
The title compound, which crystallized as a methanol and water solvate, C24H41NO5·CH4O·H2O, was obtained by heterologous expression of the brasilicardin gene cluster in the bacterium Amycolatopsis japonicum. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.
Methyl 4-[5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-imidazol-2-ylsulfanyl]butanoate
2008
The title compound, C19H18FN3O2S, was synthesized in the course of studies on 2-alkylsufanylimidazoles as p38 mitogen-activated protein kinase inhibitors. The synthesis was achieved by nucleophilic substitution of 4-(4-fluorophenyl)-5-(pyridin-4-yl)-1,3-dihydroimidazole-2-thione with methyl 4-bromobutanoate. The five-membered heterocycle makes dihedral angles of 32.4 (2) and 18.3 (2)° with the fluorophenyl and pyridinyl rings, respectively, indicating a low degree of conjugation between these rings. Intramolecular C—H...N and intermolecular N—H...N hydrogen bonds as well as C—H...π interactions seem to be effective in stabilization of the crystal stru…
4-(4-Fluorophenyl)-1-(4-nitrophenyl)-3-(pyridin-4-yl)-1H-pyrazol-5-amine
2012
In the crystal structure of the title compound, C20H14FN5O2, the pyrazole ring forms dihedral angles of 59.3 (2), 25.6 (2) and 46.0 (2)° with the directly attached 4-fluorophenyl, pyridine and nitrophenyl rings, respectively. The crystal packing is characterized by intermolecular N—H...N and N—H...O hydrogen bonds.
4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine
2016
In the title compound, C17H21N3O, the pyridine rings make a dihedral angle of 84.44 (5)°. In the crystal, a C—H...N interaction forms a chain of molecules propagating along the twofold screw axis.
4-[5-Amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrazol-1-yl]benzonitrile
2012
In the crystal structure of the title compound, C21H14FN5, the pyrazole ring forms dihedral angles of 38.0 (1), 40.0 (1) and 28.5 (1)° with the directly attached 4-fluorophenyl, pyridine and benzonitrile rings, respectively. The crystal packing is characterized by N—H...N hydrogen bonds, which result in a two-dimensional network parallel to theac-plane.
3-(4-Fluorophenyl)-2-(4-pyridyl)pyrido[2,3-b]pyrazine
2009
In the crystal structure of the title compound, C18H11FN4, the pyridopyrazine ring makes dihedral angles of 34.67 (7) and 52.24 (7)° with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 59.56 (9)° with the pyridine ring.
(E)-1-(Pyridin-4-yl)propan-1-one O-tosyl oxime
2017
The title compound, C15H16N2O3S, was obtained by the reaction of (E)-1-(pyridin-4-yl)propan-1-one oxime andpara-toluenesulfonic acid. The pyridine ring makes a dihedral angle of 54.70 (10)° with the benzene ring. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming a chain along thec-axis direction.
4-(4-Fluorophenyl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine
2012
In the title compound, C20H15FN4, the pyrazole ring forms dihedral angles of 43.51 (6), 39.95 (6) and 32.23 (6)° with the directly attached 4-fluorophenyl, pyridine and phenyl rings, respectively. The crystal packing is stabilized by intermolecular N—H...N and N—H...F hydrogen bonds.
4-[2-(4-Fluorophenyl)furan-3-yl]pyridine
2009
In the crystal structure of the title compound, C(15)H(10)FNO, the furan ring makes dihedral angles of 40.04 (11) and 25.71 (11)° with the pyridine and 4-fluoro-phenyl rings, respectively. The pyridine ring makes a dihedral angle of 49.51 (10)° with the 4-fluoro-phenyl ring. Non-conventional C-H⋯F and C-H⋯N hydrogen bonds are effective in the stabilization of the crystal structure.
Ethyl 5-amino-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazole-4-carboxylate dimethyl sulfoxide hemisolvate
2012
The asymmetric unit of the title compound, C17H13Cl3N4O2·0.5C2H6OS, contains two almost identical molecules and one dimethyl sulfoxide (DMSO-d6) solvent molecule. The pyrazole ring forms dihedral angles of 54.6 (4) and 80.0 (4)° in one molecule, and dihedral angles of 54.2 (4) and 81.2 (4)° in the other molecule, with the directly attached pyridine and trichlorophenyl rings, respectively. The dihedral angles of the pyridine and trichlorophenyl rings are 51.2 (4) and 52.0 (4)°, respectively. The crystal packing is characterized by intra- and intermolecular hydrogen bonds. The crystal is a nonmeroh…
(E)-1-(Pyridin-4-yl)propan-1-one oxime
2016
The asymmetric unit of the title compound, C8H10N2O, contains two crystallographically independent molecules of slightly different conformation, which are linkedviaan intermolecular O—H...N hydrogen bond. The dihedral angle between the pyridine ring and the oxime plane of moleculeA[2.09 (19)°] is smaller than in moleculeB[16.50 (18)°].
3-(4-Fluorophenyl)-6-methoxy-2-(4-pyridyl)quinoxaline
2009
In the title compound, C20H14FN3O, the quinoxaline system makes dihedral angles of 32.38 (7) and 48.04 (7)° with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 57.77 (9)° with the pyridine ring. In the crystal, the molecules form dimeric C—H...N hydrogen-bonded R22(20) ring motifs lying about crystallographic inversion centers. The dimeric units stack via π–π interactions between methoxyphenyl rings and pyridine–fluorophenyl rings with centroid–centroid distances of 3.720 (1) and 3.823 (1) Å, …
4-[5-(4-Fluorophenyl)-1H-imidazol-4-yl]pyridine
2009
In the title compound, C(14)H(10)FN(3), the imidazole ring makes dihedral angles of 28.2 (1) and 36.60 (9)° with the pyridine ring and the 4-fluoro-phenyl ring, respectively. The pyridine ring forms a dihedral angle of 44.68 (9)° with the 4-fluoro-phenyl ring. Inter-molecular N-H⋯N hydrogen bonds are observed in the crystal structure.
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 …
2016
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 rat…
1-{3-[(7-Fluoro-9H-pyrimido[4,5-b]indol-4-yl)(methyl)amino]piperidin-1-yl}propan-1-one
2021
The title compound, C19H22FN5O, has been synthesized as an inhibitor of glycogen synthase kinase-3β. Two molecules interact via two N—H...N hydrogen bonds, forming centrosymmetric dimers.
4-[2-(4-Fluorophenyl)-1H-pyrrol-3-yl]pyridine
2009
In the crystal structure of the title compound, C(15)H(11)FN(2), the pyrrole ring makes dihedral angles of 33.19 (9) and 36.33 (10)° with the pyridine and 4-fluoro-phenyl rings, respectively. The pyridine ring makes a dihedral angle of 46.59 (9)° with the 4-fluoro-phenyl ring. In the crystal structure, an N-H⋯N hydrogen bond joins the mol-ecules into chains.
CCDC 2058115: Experimental Crystal Structure Determination
2021
Related Article: Michael Eitel, Dhafer S. Zinad, Dieter Schollmeyer, Harald Gross, Pierre Koch|2021|Carbohydr.Res.|504|108312|doi:10.1016/j.carres.2021.108312
CCDC 1824231: Experimental Crystal Structure Determination
2018
Related Article: Francesco Ansideri, Joana T. Macedo, Michael Eitel, Ahmed El-Gokha, Dhafer S. Zinad, Camilla Scarpellini, Mark Kudolo, Dieter Schollmeyer, Frank M. Boeckler, Bärbel S. Blaum, Stefan A. Laufer, and Pierre Koch|2018|ACS Omega|3|7809|doi:10.1021/acsomega.8b00668
CCDC 1917242: Experimental Crystal Structure Determination
2019
Related Article: Stanislav Andreev, Tatu Pantsar, Francesco Ansideri, Mark Kudolo, Michael Forster, Dieter Schollmeyer, Stefan A. Laufer, Pierre Koch|2019|Molecules|24|2331|doi:10.3390/molecules24122331