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4-[(2-Hydr-oxy-1-naphth-yl)(piperidin-1-yl)meth-yl]benzonitrile.

ABSTRACT: In the title compound, C(23)H(22)N(2)O, obtained from the condensation reaction of 4-formyl-benzonitrile, 2-naphthol and piperidine, the dihedral angle between the naphthalene ring system and the benzene ring is 75.31?(4)°. The piperidine ring adopts a chair conformation. The crystal structure is stabilized by inter-molecular C-H?N hydrogen bonds, which link the mol-ecules into centrosymmetric dimers. An intra-molecular O-H?N hydrogen bond is also present.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC2970085 | BioStudies | 2009-01-01T00:00:00Z

REPOSITORIES: biostudies

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3-[(2-Hy-droxy-1-naphth-yl)(pyrrolidin-1-yl)meth-yl]benzonitrile.

Project description:The title compound, C(22)H(20)N(2)O, was obtained from the condensation reaction of 3-formyl-benzonitrile, 2-naphthol and pyrrolidine. There are two mol-ecules in the asymmetric unit, having similar conformations. Intra-molecular O-H?N and C-H?O hydrogen bonds occur, with only van der Waals forces between mol-ecules. The dihedral angles between the naphthalene ring system and the phenyl ring in the two molecules are 75.28?(10) and 76.07?(11)°. The five-membered rings adopt half-chair conformations.

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1-[(2-Methyl-piperidin-1-yl)(phen-yl)meth-yl]naphthalen-2-ol.

Project description:In the title compound, C(23)H(25)NO, an intra-molecular O-H?N hydrogen bond defines the mol-ecular conformation; the naphthol mean plane and the benzene ring form a dihedral angle of 75.8?(2)°. The piperidine ring adopts a chair conformation. The crystal packing exhibits no short inter-molecular contacts.

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Project description:In the title compound, C(17)H(23)N(3), both piperidine rings adopt chair conformations. In the crystal packing, intermolecular C-H?N hydrogen bonds and C-H?? interactions are present.

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Crystal Structure of LSD1 in Complex with 4-[5-(Piperidin-4-ylmethoxy)-2-(p-tolyl)pyridin-3-yl]benzonitrile.

Project description:Because lysine-specific demethylase 1 (LSD1) regulates the maintenance of cancer stem cell properties, small-molecule inhibitors of LSD1 are expected to be useful for the treatment of several cancers. Reversible inhibitors of LSD1 with submicromolar inhibitory potency have recently been reported, but their exact binding modes are poorly understood. In this study, we synthesized a recently reported reversible inhibitor, 4-[5-(piperidin-4-ylmethoxy)-2-(p-tolyl)pyridin-3-yl]benzonitrile, which bears a 4-piperidinylmethoxy group, a 4-methylphenyl group, and a 4-cyanophenyl group on a pyridine ring, and determined the crystal structure of LSD1 in complex with this inhibitor at 2.96 Å. We observed strong electron density for the compound, showing that its cyano group forms a hydrogen bond with Lys661, which is a critical residue in the lysine demethylation reaction located deep in the catalytic center of LSD1. The piperidine ring interacts with the side chains of Asp555 and Asn540 in two conformations, and the 4-methylphenyl group is bound in a hydrophobic pocket in the catalytic center. Our elucidation of the binding mode of this compound can be expected to facilitate the rational design of more-potent reversible LSD1 inhibitors.

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4-(6-Quinolyl-oxymeth-yl)benzonitrile.

Project description:The title compound, C(17)H(12)N(2)O, was synthesized by an ether synthesis from quinolin-6-ol and 4-(bromo-meth-yl)benzonitrile. The phenyl ring of the benzonitrile group makes a dihedral angle of 47.52?(6)° with the plane of the quinoline fragment. The crystal structure is stabilized by inter-molecular C-H?? inter-actions between a benzene H atom of the benzonitrile group and the benzene ring of the quinoline fragment. In addition, the crystal structure also exhibits a weak inter-molecular C-H?N hydrogen bond.

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4-[(2-Hy-droxy-naphthalen-1-yl)(morpholin-4-yl)meth-yl]benzonitrile.

Project description:The title compound, C(22)H(20)N(2)O(2), was synthesized via a multicomponent reaction using naphthalen-2-ol, morpholine and 4-formyl-benzonitrile. The dihedral angle between the naphthalene ring system and the benzene ring is 81.25?(10)°. The morpholine ring adopts a chair conformation. The mol-ecular conformation is stabilized by intra-molecular O-H?N and C-H?O hydrogen bonds. In the crystal, inter-molecular C-H?N hydrogen bonds link mol-ecules into helical chains running parallel to the c axis.

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(2,6-Difluoro-phen-yl)(4-methyl-piperidin-1-yl)methanone.

Project description:In the title compound, C(13)H(15)F(2)NO, the piperidine ring adopts a chair conformation. The dihedral angle between the least-squares plane of the piperidine ring and the benzene ring is 48.75?(7)°. In the crystal structure, the mol-ecules are connected via C-H?O hydrogen bonds, forming a zigzag chain along the b axis.

1000-01-01 | S-EPMC3200831 | BioStudies

4-(Morpholin-4-yl)-3-(trifluoro-meth-yl)-benzonitrile.

Project description:In the title benzonitrile compound, C(12)H(11)F(3)N(2)O, an intra-molecular C-H?F hydrogen bond generates an S(7) ring motif. The trifluoro-methyl group is disordered over two orientations with a refined occupancy ratio of 0.549?(16):0.451?(16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04?(10)° with each other. In the crystal, mol-ecules are connected by inter-molecular C-H?F and C-H?O inter-actions to form R(2) (2)(8) ring motifs. These inter-actions also link the mol-ecules into chains parallel to the [10[Formula: see text]] direction.

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Crystal structure of the adduct (4-chloro-phen-yl)(4-hy-droxy-piperidin-1-yl)methanone-(4-chloro-phen-yl)(piperidin-1-yl)methanone (0.75/0.25).

Project description:In the title compound, 0.75C12H14ClNO2·0.25C12H14ClNO, which is an adduct comprising 0.75 4-hy-droxy-piperidin-1-yl or 0.25 4-piperidin-1-yl substituents on a common (4-chloro-phen-yl)methanone component; the dihedral angles between the benzene ring and the two piperidine rings are 51.6?(3) and 89.5?(7)°, respectively. The hy-droxy-piperidine ring is in a bis-ectional oriention (bi) with the phenyl ring. In the crystal, inter-molecular O-H?O hydrogen bonds between the hy-droxy-piperidine group and the keto O atom lead to the formation of chains extending along the c- axis direction.

2015-01-01 | S-EPMC4645011 | BioStudies

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