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3-Amino-4,6-dimethyl-thieno[2,3-b]pyridine-2-carbonitrile.

ABSTRACT: The mol-ecule of the title compound, C(10)H(9)N(3)S, is almost planar, with a dihedral angle of 1.38 (4)° between the thio-phene and pyridine rings. In the crystal packing, mol-ecules are linked into layers parallel to the ab plane by inter-molecular N-H⋯N hydrogen bonds and by π⋯π stacking inter-actions involving adjacent pyridine and thio-phene rings with a centroid-centroid distance of 3.537 (3) Å.

SUBMITTER: Zeng XX

PROVIDER: S-EPMC2971991 | biostudies-literature |

REPOSITORIES: biostudies-literature

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6-Benzyl-2-[(triphenyl-?-phosphanyl-idene)amino]-4,5,6,7-tetra-hydro-thieno[2,3-c]pyridine-3-carbonitrile.

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Project description:The mol-ecule of the title compound, C(8)H(8)Br(2)O, is approximately planar with a maximum deviation of 0.063 (1) Å for one of the Br atoms. In the crystal, adjacent mol-ecules are joined inter-molecular O-H⋯O hydrogen bonds, forming chains parallel to [010]. The structure also features a short Br⋯Br inter-action of 3.362 (1) Å.

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Ethyl 3-amino-4H-thieno[2,3-b]pyridine-2-carboxyl-ate.

Project description:The mol-ecule of the title compound, C(10)H(10)N(2)O(2)S, is essentially planar, except for the ethyl group, which is twisted away from the carboxyl plane by -90.5?(3)°. In the crystal structure, mol-ecules are linked into a zigzag sheet propagating along the b axis by inter-molecular N-H?O and N-H?N hydrogen bonds.

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6-Amino-3,4-dimethyl-4-phenyl-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile.

Project description:In the title compound, C(15)H(14)N(4)O, the pyrazole ring is aligned at 88.23?(4)° with respect to the aromatic ring and at 3.75?(4)° with respect to the pyran ring. In the crystal, N-H?N hydrogen bonds link adjacent mol-ecules into a linear chain motif. C-H?N inter-actions are also observed.

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Project description:In the crystal structure of the title compound, C(6)H(10)N(3) (+)·H(2)PO(4) (-), the cations and anions are linked by inter-molecular O-H?O and N-H?O hydrogen bonds, forming a two-dimensional network. Additional stabilization is provided by weak inter-molecular C-H?O inter-actions. N-H?N inter-actions are also present.

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Project description:In the title compound, C(7)H(11)N(2) (+)·C(7)H(5)O(2) (-), the 2-amino-4,6-dimethyl-pyridinium cation and the benzoate anion are linked by two N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The H atoms in both the methyl groups are rotationally disordered, with fixed site occupancies of 0.50. In the crystal structure, the mol-ecules are stabilized by inter-molecular N-H⋯O hydrogen bonds. A π-π inter-action, with a centroid-centroid distance of 3.661 (2) Å, is also observed.

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GPCR Modulation of Thieno[2,3-b]pyridine Anti-Proliferative Agents.

Project description:A panel of docking scaffolds was developed for the known molecular targets of the anticancer agents, thieno[2,3-b]pyridines, in order to glean insight into their mechanism of action. The reported targets are the copper-trafficking antioxidant 1 protein, tyrosyl DNA phosphodiesterase 1, the colchicine binding site in tubulin, adenosine A2A receptor, and, finally, phospholipase C-?1. According to the panel, the A2A receptor showed the strongest binding, inferring it to be the most plausible target, closely followed by tubulin. To investigate whether the thieno[2,3-b]pyridines modulate G protein-coupled receptors (GPCRs) other than A2A, a screen against 168 GPCRs was conducted. According to the results, ligand 1 modulates five receptors in the low µM region, four as an antagonist; CRL-RAMP3 (IC50-11.9 µM), NPSR1B (IC50-1.0 µM), PRLHR (IC50-9.3 µM), and CXCR4 (IC50-6.9 µM). Finally, one agonist, GPRR35, was found (EC50 of 7.5 µM). Molecular modelling showed good binding to all of the receptors investigated; however, none of these surpass the A2A receptor. Furthermore, the newly-identified receptors are relatively modestly expressed in the cancer cell lines most affected by the thieno[2,3-b]pyridines, making them less likely to be the main targets of the mechanism of action for this compound class. Nevertheless, new modulators against GPCRs are of an interest as potential hits for further drug development.

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