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2-Chloro-quinoline-3-carboxylic acid.

ABSTRACT: The crystal structure of the title compound, C(10)H(6)ClNO(2), can be described by two types of crossed layers which are parallel to (110) and (10). The crystal packing is stabilized by inter-molecular C-H?O and O-H?N hydrogen bonds, resulting in the formation of a two-dimensional network and reinforcing the cohesion of the structure.

SUBMITTER: Ladraa S

PROVIDER: S-EPMC2983594 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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2-Chloro-quinoline-3-carboxylic acid.

Ladraa Souheila S Bouraiou Abdelmalek A Bouacida Sofiane S Roisnel Thierry T Belfaitah Ali A

Acta crystallographica. Section E, Structure reports online 20100227 Pt 3

The crystal structure of the title compound, C(10)H(6)ClNO(2), can be described by two types of crossed layers which are parallel to (110) and (10). The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯N hydrogen bonds, resulting in the formation of a two-dimensional network and reinforcing the cohesion of the structure. ...[more]

PMID: 21580434

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3,7-Dichloro-quinoline-8-carboxylic acid.

Project description:THE TITLE COMPOUND (TRADE NAME: quinclorac), C(10)H(5)Cl(2)NO(2), was crystallized from a dimethyl sulfoxide solution. Quinclorac mol-ecules are packed mainly via π-π stacking inter-actions between neighbouring heterocycles (interplanar distance: 3.31 Å) and via O-H⋯N hydrogen bonding.

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4-Chloro-benzoic acid-quinoline (1/1).

Project description:In the title compound, C(7)H(5)ClO(2)·C(9)H(7)N, the 4-chloro-benzoic acid mol-ecule is almost planar, with a dihedral angle of 2.9?(14)° between the carb-oxy group and the benzene ring. In the crystal, the two components are connected by an O-H?N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 44.75?(4)°. The two components are further linked by inter-molecular C-H?O hydrogen bonds, forming a layer parallel to the ab plane.

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2-Chloro-4-nitro-benzoic acid-quinoline (1/1).

Project description:In the title compound, C(7)H(4)ClNO(4)·C(9)H(7)N, the two components are connected by an O-H⋯N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of benzoic acid is 3.15 (7)°. In the crystal, units are linked by inter-molecular C-H⋯O hydrogen bonds, forming a tape along the c axis. The tapes are stacked along the b axis through a C-H⋯O hydrogen bond into a layer parallel to the bc plane.

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(Benzoato-κO,O')(quinoline-2-carboxyl-ato-κN,O)(quinoline-2-carboxylic acid-κN,O)copper(II).

Project description:The crystal structure of the title compound, [Cu(C(10)H(6)NO(2))(C(7)H(5)O(2))(C(10)H(7)NO(2))], contains copper(II) ions five-coordinated in a distorted trigonal-bipyramidal environment. The equatorial plane is occupied by three O atoms, one from the carboxyl-ate group of the benzoate ion considered as occupying a single coordination site, the other two from two carboxyl-ate groups of the quinaldic acid and quinaldate ligands. The axial positions are occupied by the N atoms of the quinoline ring system. The metal ion lies on a twofold axis that bisects the benzoate ion. The quinaldate and quinaldic acid ligands are equivalent by symmetry, and the carboxyl-ate/carboxyl groups are disordered. The disordered H atom is shared between the carboxyl-ate groups of adjacent quinaldic acid mol-ecules. Such hydrogen bonds delineate zigzag chains that run along the c axis. The structure is very similar to that of the Mn(II) analog.

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(Benzoato-κO,O')(quinoline-2-carboxyl-ato-κN,O)(quinoline-2-carboxylic acid-κN,O)manganese(II).

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Crystal structures of 3-chloro-2-nitro-benzoic acid with quinoline derivatives: 3-chloro-2-nitro-benzoic acid-5-nitro-quinoline (1/1), 3-chloro-2-nitro-benzoic acid-6-nitro-quinoline (1/1) and 8-hy-droxy-quinolinium 3-chloro-2-nitro-benzoate.

Project description:The structures of three compounds of 3-chloro-2-nitro-benzoic acid with 5-nitro-quinoline, (I), 6-nitro-quinoline, (II), and 8-hy-droxy-quinoline, (III), have been determined at 190 K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base mol-ecules are held together by O-H⋯N and C-H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 -, an acid-base inter-action involving H-atom transfer occurs and the H atom is located at the N site of the base mol-ecule. In the crystal of (I), the hydrogen-bonded acid-base units are linked by C-H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C-H⋯O hydrogen bond, forming wide ribbons parallel to the (03) plane. These ribbons are stacked via π-π inter-actions between the quinoline ring systems [centroid-centroid distances = 3.4935 (5)-3.7721 (6) Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid-base units are also linked into a tape structure along the b-axis direction via C-H⋯O hydrogen bonds. Inversion-related tapes are linked by further C-H⋯O hydrogen bonds to form wide ribbons parallel to the (08) plane. The ribbons are linked by weak π-π inter-actions [centroid-centroid distances = 3.8016 (8)-3.9247 (9) Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N-H⋯O and O-H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π-π inter-actions [centroid-centroid distances = 3.8016 (8)-3.9247 (9) Å], and the mol-ecular chains are linked into layers parallel to the ab plane through these inter-actions.

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Discovery of 2-(4-Acrylamidophenyl)-Quinoline-4-Carboxylic Acid Derivatives as Potent SIRT3 Inhibitors.

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2-(2-Chloro-phen-yl)-5-methyl-1,3-dioxane-5-carboxylic acid.

Project description:In the title compound, C(12)H(13)ClO(4), the 1,3-dioxane ring adopts a chair conformation and the 2-chloro-benzene and methyl substituents occupy equatorial sites. The carboxyl group is in an axial inclination. In the crystal, carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(8) loops.

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Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives.

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SAR Based Optimization of a 4-Quinoline Carboxylic Acid Analog with Potent Anti-Viral Activity.

Project description:It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein we report structure-activity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl)quinoline-4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC50 of 1 nM, and viral replication of VSV and WSN-Influenza with an EC50 of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogs of brequinar.

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