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

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.

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N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

Molbank ◽

10.3390/m1181 ◽

2021 ◽

Vol 2021 (1) ◽

pp. M1181

Author(s):

Valentin Wydra ◽

Stefan Gerstenecker ◽

Dieter Schollmeyer ◽

Stanislav Andreev ◽

Teodor Dimitrov ◽

...

Keyword(s):

Title Compound ◽

High Resolution Mass Spectrometry ◽

Nucleophilic Aromatic Substitution ◽

Resonance Spectroscopy ◽

Aromatic Substitution ◽

X Ray Diffraction ◽

Inhibitory Potency ◽

X Ray ◽

Step Procedure ◽

Resolution Mass

Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2).

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Nitroxide radicals appended to phthalonitriles: synthesis, structural characterization and photophysical properties

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229621001832 ◽

2021 ◽

Vol 77 (3) ◽

pp. 137-143

Author(s):

Ismail Fidan ◽

Emel Onal ◽

Catherine Hirel

Keyword(s):

Magnetic Measurements ◽

Photophysical Properties ◽

Nucleophilic Aromatic Substitution ◽

Structural Studies ◽

Aromatic Substitution ◽

Nitronyl Nitroxide ◽

X Ray Diffraction ◽

X Ray ◽

Microwave Assisted ◽

Ft Ir

The syntheses of 4-[4-(4,4,5,5-tetramethyl-2-imidazoline-3-oxide-1-oxyl-2-yl)phenoxy]phthalonitrile (3, C21H19N4O3) and 4-[4-(4,4,5,5-tetramethyl-2-imidazoline-1-oxyl-2-yl)phenoxy]phthalonitrile (4) were carried out by microwave-assisted nucleophilic aromatic substitution of 4-nitrophthalonitrile (2) by the pre-formed 2-(4-hydroxyphenyl)-4,4,5,5-tetramethyl-2-imidazoline-3-oxide-1-oxyl (1). Compounds 3 and 4 were characterized unambiguously by a rich array of analyses, such as melting point, FT–IR, MALDI–TOF MS, elemental analysis, UV–Vis, CV, EPR, magnetic measurements and single-crystal X-ray diffraction. Structural studies demonstrate that the C—H...X and C—X...π (X = O and N) interactions in the radical nitronyl nitroxide groups play an important role in the assembly of the crystal structures. Moreover, cyclic voltammetry analyses show that the phthalonitrile substituent retains the redox properties of the Ullman radicals.

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Synthesis, C-13 NMR, and X-ray crystal structure of N6,N9-octamethylenepurinecyclophane

Canadian Journal of Chemistry ◽

10.1139/v92-030 ◽

1992 ◽

Vol 70 (1) ◽

pp. 186-196 ◽

Cited By ~ 2

Author(s):

R. A. Bell ◽

R. Faggiani ◽

H. N. Hunter ◽

C. J. L. Lock

Keyword(s):

Crystal Structure ◽

Direct Methods ◽

Chloride Ion ◽

Nucleophilic Aromatic Substitution ◽

Nucleophilic Attack ◽

Aliphatic Chain ◽

Aromatic Substitution ◽

X Ray Diffraction ◽

X Ray ◽

Small Distortion

The synthesis and structure determination of N6,N9-octamethylenepurine cyclophane by single crystal X-ray diffraction is reported. The cyclophane was prepared from 6-chloropurine and 8-aminooctanoic acid as starting materials. The aminooctyl fragment was first attached to N9 of 6-chloropurine by means of the Mitsunobu reaction and cyclization to the cyclophane effected by nucleophilic attack of the amino group at the C6 position and displacement of chloride ion. Reversing the reaction strategy did not result in formation of the cyclophane. Crystals of the cyclophane were monoclinic, P2/n, a = 9.620(3), b = 12.266(3), c = 11.994(2), Å, β = 111.25(2)°, Z = 4. Intensities were measured with a Nicolet P3 diffractometer and MoKα radiation at room temperature. The structure was solved by direct methods and refined to R = 0.0683, Rw = 0.0493 based on 1730 reflections. The molecule shows some strain, but bond lengths and angles are normal. Attempts to relieve the strain are made by a small distortion of the purine rings and bending of the N6 and C8′ atoms out of the planes to which they are attached (0.314(4), 0.459(5) Å). Further, the N6,H6,Cl′ group is twisted by 30° from the pyrimidine plane and the torsion angles in the aliphatic chain are distorted from the idealized 60, 120, 180° (average, 13.6°; range 5.1–24.9°). These distortions result in some weakening of the π-bonding in the adenine moiety. Keywords: purinophane synthesis, nucleophilic aromatic substitution, conformational analysis, crystal structure.

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