Synthesis of New 1-Aryl-4-(biarylmethylene)piperazine Ligands, Structurally Related to Adoprazine (SLV313)

Ullah, Nisar

doi:10.1515/znb-2012-0113

Cited by 3 publications

(1 citation statement)

References 7 publications

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“…In an ongoing effort to develop new antipsychotics 21,22 , we have synthesized a series of 5-piperidinyl-1H-benzo[d]imidazol-2(3H)-ones (5a-f) and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones (6a-f), which are structural analogs of bifeprunox (4) (Figure 2). Herein, we wish to disclose the synthesis, dual D 2 and 5-HT 1A receptor binding affinities and structure-activity relationship (SAR) of these compounds.…”

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confidence: 99%

Synthesis and dual D₂and 5-HT_1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Ullah

2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis and dual D₂and 5-HT_1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Ullah

2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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Crystal structure and Hirshfeld surface analysis of the hydrochloride salt of 8-{4-[(6-phenylpyridin-3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one

Ullah¹,

Stœckli-Evans²

2021

Acta Cryst E

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The amine 8-{4-[(6-phenylpyridin-3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one was crystallized as the hydrochloride salt, 4-(2-oxo-1,2,3,4-tetrahydroquinolin-8-yl)-1-[(6-phenylpyridin-3-yl)methyl]piperazin-1-ium chloride, C25H27N4 +·Cl− (I·HCl). The conformation of the organic cation is half-moon in shape enclosing the chloride anion. The piperidine ring of the 3,4-dihydroquinolin-2(1H)-one moiety has a screw-boat conformation, while the piperazine ring has a chair conformation. In the biaryl group, the pyridine ring is inclined to the phenyl ring by 40.17 (7) and by 36.86 (8)° to the aromatic ring of the quinoline moiety. In the crystal, the cations are linked by pairwise N—H...O hydrogen bonds, forming inversion dimers enclosing an R 2 2(8) ring motif. The Cl− anion is linked to the cation by an N—H...Cl hydrogen bond. These units are linked by a series of C—H...O, C—H...N and C—H...Cl hydrogen bonds, forming layers lying parallel to the ab plane.

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The crystal structures, Hirshfeld surface analyses and energy frameworks of 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2-methoxyquinoline and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline

Ullah

Stœckli-Evans

2021

Acta Cryst E

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The title compounds, 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2-methoxyquinoline, C27H30N2O (I), and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline, C26H29N3O (II), differ only in the nature of the central six-membered ring: piperidine in I and piperazine in II. They are isoelectronic (CH cf. N) and isotypic; they both crystallize in the triclinic space group P\overline{1} with very similar unit-cell parameters. Both molecules have a curved shape and very similar conformations. In the biaryl group, the phenyl ring is inclined to the cyclopentene mean plane (r.m.s. deviations = 0.089 Å for I and 0.082 Å for II) by 15.83 (9) and 13.82 (6)° in I and II, respectively, and by 67.68 (6) and 69.47 (10)°, respectively, to the mean plane of the quinoline moiety (r.m.s. deviations = 0.034 Å for I and 0.038 Å for II). The piperazine ring in I and the piperidine ring in II have chair conformations. In the crystals of both compounds, molecules are linked by C—H...π interactions, forming chains in I and ribbons in II, both propagating along the b-axis direction. The principal contributions to the overall Hirshfeld surfaces involve H...H contacts at 67.5 and 65.9% for I and II, respectively. The major contribution to the intermolecular interactions in the crystals is from dispersion forces (E dis), reflecting the absence of classical hydrogen bonds.

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Synthesis of New 1-Aryl-4-(biarylmethylene)piperazine Ligands, Structurally Related to Adoprazine (SLV313)

Cited by 3 publications

References 7 publications

Synthesis and dual D₂and 5-HT_1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Synthesis and dual D₂and 5-HT_1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Crystal structure and Hirshfeld surface analysis of the hydrochloride salt of 8-{4-[(6-phenylpyridin-3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one

The crystal structures, Hirshfeld surface analyses and energy frameworks of 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2-methoxyquinoline and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline

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Synthesis of New 1-Aryl-4-(biarylmethylene)piperazine Ligands, Structurally Related to Adoprazine (SLV313)

Cited by 3 publications

References 7 publications

Synthesis and dual D2and 5-HT1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Synthesis and dual D2and 5-HT1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Crystal structure and Hirshfeld surface analysis of the hydrochloride salt of 8-{4-[(6-phenylpyridin-3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one

The crystal structures, Hirshfeld surface analyses and energy frameworks of 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2-methoxyquinoline and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline

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Synthesis and dual D₂and 5-HT_1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

Synthesis and dual D₂and 5-HT_1Areceptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones