4-(3-Fluoroanilino)thieno[2,3-b]pyridine-6-carboxylic acid
نویسندگان
چکیده
In the title compound, C(14)H(9)FN(2)O(2)S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194 Å), with the carb-oxy-lic acid group [dihedral angle = 11.9 (3)°] and the benzene ring [71.1 (4)°] being twisted out of this plane to different extents. An intra-molecular N-H⋯O(carbon-yl) hydrogen bond closes an S(6) ring. Supra-molecular chains along [01-1] mediated by O-H⋯N(pyridine) hydrogen bonds feature in the crystal. A three-dimensional architecture is completed by π-π inter-actions occurring between the benzene ring and the two rings of the thieno[2,3-b]pyridine residue [centroid-centroid distances = 3.6963 (13) and 3.3812 (13) Å]. The F atom is disordered over the two meta sites in a near statistical ratio [0.545 (5):0.455 (5)].
منابع مشابه
Synthesis of some new Thieno[2,3-b]pyridines, Pyrimidino[4',5':4,5]thieno[2,3-b]pyridine and Pyridines Incorporating 5-Bromobenzofuran-2-yl Moiety.
2-Sulfanyl-6-(2-thienyl)pyridine-3-carbonitrile, 1-Amino-6-(5-bromo-benzofuran-2-yl)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile, thieno[2,3-b]pyridins, pyrimidino[4',5':4,5] thieno[2,3-b]pyridine, quinazoline and carbamate derivatives were synthesized from sodium 3-(5-bromobenzofuran-2-yl)-3-oxoprop-1-en-1-olate with. The newly synthesized compounds were elucidated by elemental analysis, spectra...
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In the title compound, C(35)H(26)Cl(3)N(3)O(5)S(3), the dihedral angle between the mean plane through the thieno[2,3-b]pyridine ring system and the attached benzene ring is 3.89 (6)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, forming chains parallel to [100].
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In the title compound, C(21)H(16)FN(3)OS, the thieno[2,3-b]pyridine system forms dihedral angles of 10.57 (12) and 83.87 (5)° with the fluoro-phenyl ring at the 6-position and the phenyl ring of the benzyl group, respectively. In the crystal, mol-ecules are linked by weak N-H⋯N anf N-H⋯O hydrogen bonds and π-π stacking inter-actions involving fluoro-phenyl rings of adjacent mol-ecules, with a c...
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The title compounds were prepared by reaction of 1,1'-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)diethanone (1) with different aromatic aldehydes 2a-c, namely Furfural (2a), 4-chlorobenzaldehyde (2b) and 4-methoxybenzaldhyde (2c) to yield the corresponding α,β-unsaturated ketones 3a-c. Compound 3 was reacted with malononitrile, 2-cyanoacetamide or 2-cyanothioacetamide yielded the corresponding ...
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It is now established that the thieno[2,3-b]pyridines are a potent class of antiproliferatives. One of the main issues encountered for their clinical application is their low water solubility. In order to improve this, two strategies were pursued. First, a morpholine moiety was tethered to the molecular scaffold by substituting the sulphur atom with nitrogen, resulting in a 1H-pyrrolo[2,3-b]pyr...
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