Synthesis of New 4-Aryl-1-(biarylmethylene)piperidines. Structural Analogs of Adoprazine (SLV313)

Ullah, Nisar; Al-Shaheri, Ali Ahmed Qaid

doi:10.1515/znb-2012-0312

Cited by 4 publications

(1 citation statement)

References 4 publications

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“…The main action of these two compounds is to combine dopamine D 2 receptor blockade with serotonin 5-HT 1A receptor activation rather than antagonism (Feenstra et al, 2001(Feenstra et al, , 2006. In continuing efforts in this field, Ullah and collaborators have synthesized a series of compounds that are structural analogues of Adoprazine # and Bifeprunox # (Ullah, 2012(Ullah, , 2014aUllah & Al-Shaheri, 2012). These include a number of 1-aryl-4-(biarylmethylene)piperazines (Ullah, 2012), such as 8-{4- [(6-phenylpyridin-3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one (I), and 8-(4-{[6-(4-fluorophenyl)pyridin-3-yl]methyl}piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one (II) Ghani et al (2014) have reported that the D 2 receptor binding affinity of compounds I and II are K i = 28.4 nM for I and 42.0 nM for II.…”

Section: Chemical Contextmentioning

confidence: 99%

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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Section: Chemical Contextmentioning

confidence: 99%

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 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 structural analogues of GGT1-DU40, a potent GGTase-1 inhibitor

Mansha¹,

Ullah

Alhooshani

2016

Zeitschrift Für Naturforschung B

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A series of new substituted pyrazoles 2-12 have been synthesized. The synthesized compounds are structural analogues of GGT1-DU40 1, a highly potent and selective inhibitor of protein geranylgeranyltransferase I (GGTase-I) both in vitro and in vivo. The implications of GGTase-I in oncogenesis have highlighted its potential as a cancer therapeutic target. Accordingly, the development of GGTase-I inhibitors has been a subject of much interest. The synthesis of 2-12 stemmed from the acetylation or acylation of N-function of amino acids to produce suitably modified amino acids. Meanwhile, the substituted pyrazole subunit originated from the reaction of ethyl nicotinate with γ-butyrolactone followed by condensation of the resultant β-keto lactone with (3,4-dichlorophenyl) hydrazine. The operations of O-alkylation and thioetherification on the resultant intermediate eventually produced the substituted pyrazole fragment. The amidation of the latter with amino acid derivatives finally rendered 2-12 in good to excellent yields.

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Synthesis of New 4-Aryl-1-(biarylmethylene)piperidines. Structural Analogs of Adoprazine (SLV313)

Cited by 4 publications

References 4 publications

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

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

Synthesis of structural analogues of GGT1-DU40, a potent GGTase-1 inhibitor

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